New book from NYT bestselling author Lewis Howes is now available!

New book from NYT bestselling author Lewis Howes is now available!


Whitney Cummings

Loving Yourself, Addiction and Creative Success


We learn a lot of coping mechanisms growing up. They help us get through tough times. But we’re adults now, and so many of us are still carrying around coping mechanisms that are no longer needed. They can make us defensive, they can prevent us from developing healthy relationships, and they can hold us back from achieving our goals. 

It’s time to “update our software.” Our situation has changed. We’re adults, with the ability to protect ourselves and the freedom to make our own choices. Yet, our brain has stayed the same. 

Updating our software means working through our issues and not being afraid to change. In doing so, we can learn healthier ways to engage with the world and create a life we love. 

On today’s episode of The School of Greatness, I talk about letting go of the things that no longer serve us with world-famous comedian, Whitney Cummings. We also discuss codependency, reinventing yourself, and overcoming bad habits. Let’s get started!  

Who Is Whitney Cummings?

Whitney Cummings is a stand-up comedian, actress, writer, and producer. She created the CBS sitcom “2 Broke Girls,” the NBC sitcom “Whitney,” and the movie “The Female Brain.” She was also a producer and writer for the ABC revival of “Roseanne.” 

Her credits also include one comedy album, three Comedy Central Roasts, and four stand-up specials, including her latest special, “Can I Touch It?” which premiered on Netflix in July 2019. Whitney’s comedic memoir, I’m Fine, and Other Lies was released in 2017.  In it, she recalls stories and mistakes that are “way too embarrassing to tell on stage,” but that offer an honest perspective of the human experience.

Whitney grew up in Washington D.C. in a dysfunctional home with alcoholic family members, where she learned about codependency — a theme she brings up a lot in her book and stand-up. She was sent away at the age of 12 to Virginia to live with her aunt and returned to Washington D.C. to live with her parents when she was around 16. After high school, she studied acting at Washington D.C.’s Studio Theater and interned at Washington’s NBC-owned television station, WRC-TV. After graduating from the University of Pennsylvania, where she studied communications, she decided to depart from her journalistic aspirations and pursue a comedy career in Los Angeles.

The Comedy Rollercoaster

Whitney takes a lot of risks that don’t always get massive rewards, but that’s what has helped her grow, becoming braver, more curious, more exciting, and more adventurous throughout her career. For example, while her reboot of “Roseanne” got cut short without getting the full applause she was expecting, she never stopped creating. That resilience and risk-taking have gained her a lot of respect.

“I know that we’re all on this quest to solve insecurity and make it all go away. But insecurity sometimes drives us to do good things and get better and work harder, you know? So I think insecurity can be good fuel. It took me a long time to embrace the fact that in standup, you succeed by failing over and over again. It’s like going to the gym. You’re not always going to have the killer day that you want to put on Instagram. It’s not about saying the thing that’s the funniest, it’s saying the thing that’s the truest.” –Whitney Cummings

The key for Whitney, and for many comedians and creative people, is to just fail forward and keep persisting. It’s also important to understand the audience you are speaking to and to take lots of time to listen. Whitney explains the ups and downs of her chosen career. 

“It’s tricky because you think you’re great, and then you have a bad couple of months and then you think you suck. And then you have nothing to lose, so then all of the sudden you’re great one night just because you don’t give a crap anymore. And then you go, ‘Oh, whoa, I was trying too hard and that was repellent to people.’ So as soon as you stop giving a crap because you think you suck, is sometimes when you do your best work.” –Whitney Cummings

Whitney talks about how every city and venue is different, and every audience is also different, so you can’t ever go into autopilot doing standup. It’s a conversation, not a monologue. She equates it to boxing: if you’re a second ahead or a second behind, the joke’s not going to land. You need to listen and be aware. 

Whitney’s original career path was going to be journalism, which she says has some similarities to being a comedian, as both are “complaining snitches that are obsessed with justice.”

“I thought I was going to be a journalist because I was a seeker and I was curious and I was critical and I always wanted to get the dirt. And then, I was also a performer and I liked doing theater and plays. Then when I was with my friends, I would tell these really long, boring stories about how I hated that you can’t find your car in a parking lot, and I don’t like the ticketing system, and I didn’t realize what I was doing was standup. I was dancing around it and then someone one day — I think just to get me to shut up — was like, ‘You should try, stand up.’” –Whitney Cummings

What she loves about standup is that she believes we all have more commonalities than we do differences, and standup is all about putting a bunch of strangers in a room and having them agree on something. It’s a way for her to be a peacemaker. 

The Early Years

Finding a place of peace for her audience comes from searching for peace as a child. Whitney grew up in a very dysfunctional family with divorce, alcoholism, and mental health issues. She has had to do a lot of self-healing to overcome the unhealthy habits she learned as a child, like anxiety, addiction, and codependency. 

“I grew up in a home that was not harmonious, where there was a lot of discord and a lot of disagreement. And I always wanted to get everyone to agree and laugh. And it was always to sort of just manage tension. I thought if I could make this person laugh, maybe Christmas would be fun. You know? It was always just trying to manage people.” –Whitney Cummings

Whitney’s book title, I’m Fine, and Other Lies stems from these moments. Now, she says, there are so many more tools for parents, but back then there was a lot of passive-aggressive communication and parents saying “everything is fine,” followed by a huge explosion of resentment. 

Whitney’s mother worked a full-time career while taking care of the kids, so she was under a tremendous amount of stress. 

“I carried around a lot of weapons that worked great when I was younger, but I was ready to stop fighting.” @WhitneyCummings  

“[My mother] was up at 6:00 AM and she was home at 7:00 PM, and she brought me to work with her, but I just saw her trying to manage everything. And you know, it was always like, how do I just make things easier for everybody else? And the joke kind of, to me was like a magic trick. It was like, whoa, that was an easy way to get love; that was an easy way to cut some tension, so I learned how to make people laugh.” –Whitney Cummings

When Whitney was 12, she was acting out at home, so her parents sent her away to Virginia to live with her aunt for three years. There were some intense things happening at home with her parent’s divorce, and it began to be too much for her parents to handle. She would see them on the weekends, and that was interesting for her, but she reflects back on that hard time with a positive outlook overall.

“Looking back, I feel really lucky that I got to be exposed to so many different kinds of parents and caretakers and their flaws and their strengths. And you know, I grew up in D.C. and then I grew up in Virginia for a while, so I got the best of both worlds. And I think part of what makes me a good comedian is I’m not just from this elitist blue state. I got to see how people live that aren’t in metropolitan areas and see the value of that and learn about community and connecting with animals. And so I feel really lucky that I got to have a little bit of both.” –Whitney Cummings

As Whitney attended college and reached her twenties, much of her coping mechanisms from her younger years began to surface. Like most young people her age, she was trying to discover who she was apart from her family and her circumstances. 

“I wasted my twenties really, and nothing’s a waste, but unconsciously, I was trying so hard to control other people. My subconscious brain was working so hard to figure out ways to make myself feel safe and to avoid abandonment, rejection, and criticism. And as a result, I found that desperate energy is repellent. The more we want something, when we push something, we push it away.“ –Whitney Cummings

This realization came through many years of therapy, counseling, 12-step programs, and education on neurology that taught Whitney so much about herself, her habits, and the choices she can make each day in order to achieve greatness. This also inspired her to produce the movie, “The Female Brain.”

“I was really ready to release my character defects and put down all the weapons that I needed when I was a kid because I was carrying around a lot of armor and a lot of weapons that worked great then, but weren’t needed now.” –Whitney Cummings

Even though Whitney has succeeded greatly in her career, some of the biggest achievements to her are the “small things” in life, like learning how to handle a conflict with grace, listening to someone who is wrong, or trying not to control someone else’s behavior.

Now that she is a producer and has multiple employees, she has had to learn how to let go of those tendencies. 

“The hardest thing for me is to be able to be in a relationship with someone whether that’s a working or romantic relationship, and to not try to control their behavior, opinions, or neurology, and to be able to tolerate the discomfort of others.” –Whitney Cummings

She sees it as getting an inner “software update.” Circumstances may have changed, but her brain had stayed the same. That psychological software update was really just acclimating to her new life circumstances and allowing herself to be open to change and improvement. She just wants to be the best version of herself possible—and make people laugh in the process. 

Words of Wisdom

At the end of my interviews, I always ask my interviewees about their three biggest truths in life. If they could leave three pieces of wisdom behind, what would they be?

It was a hilarious and somewhat uncomfortable process for Whitney when I asked her this question, and we ended up with quite a few truths, so here’s her list. There are some great nuggets in here:

  1. No one owes you anything and you don’t owe anyone anything.
  2. Kindness and forgiveness can fix anything.
  3. The way you treat others is a reflection of how you feel about yourself. 
  4. You don’t forgive others because they deserve forgiveness, you forgive others because you deserve peace. 
  5. Mistakes can be where the magic is.
  6. You can be a mess and still have success.

Why You Should Listen to This Whitney Cummings Podcast Episode Right Now…

If you found value in what Whitney and I talked about today, please tag Whitney Cummings and me, Lewis Howes, on Instagram with your key takeaways. Please also go to Apple Podcasts, give it a five-star rating, and don’t forget to subscribe!

I always ask my guests about their definition of greatness at the end of each interview and this is what Whitney had to say:

“My definition of greatness would be excellence and authenticity. It’s about leaving an imprint on someone in a real way where they leave your presence a better person. Greatness isn’t martyrdom—it’s leading by example.” –Whitney Cummings

If you’re ready to learn about overcoming your past, staying creative, and having a lot of good laughs, you can check out the entire podcast here. You can also browse the entire library of podcasts on The School of Greatness! Until next time!

To Greatness,

Lewis Howes - Signature

“I don’t care if other people are interested in me, I just care if I’m interested.”@WhitneyCummings  

Some Questions I Ask:

  • When did you realize you were good at stand up? (6:30)
  • What are you most proud of? (29:00)
  • Who was more influential growing up- mom or dad? (51:00)
  • How do you deal with the Hollywood ups and downs? (1:06:00)

In this episode, you will learn:

  • Why we should forgive our parents (20:00)
  • How anxiety can help you (27:00)
  • How to change the type of people you’re attracted to (36:00)
  • Why your relationship needs to be “boring” (41:30)
  • The difference between interdependence and codependency (48:00)
  • Why financial freedom is important to Whitney (1:00:00)
  • About PC culture and stand up comedy (1:33:00)
  • Plus much more…
Connect with
Whitney Cummings

Transcript of this Episode

Episode number 832 with the inspirational Whitney Cummings.




LEWIS HOWES: Welcome to the School of Greatness. My name is Lewis Howes, a former pro-athlete turned lifestyle entrepreneur. Each week, we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now, let the class begin.




LEWIS HOWES: Mary Tyler Moore said, “Take chances, make mistakes. That’s how you grow. Pain nourishes your courage. You have to fail in order to practice being brave.” I hope you’re practicing being brave today because that’s the way you’re going to grow. That’s the way you’re going to build confidence within yourself. When you do those things that are a little bit risky, and the more risk you take, the more you’re going to build that confidence within and definitely grow.


I’m excited to talk about our guest today. What an incredible time. But before I dive in on our guest, I want to remind you that the Summit of Greatness, our annual event, is less than a month away. That’s right. We’ve got so many people flying in from all over the world. Everyone’s getting their tickets last minute. It’s how people do it, I guess, these days. So if you’re one of those last minute people, I do this as well. Make sure to go to Check out the incredible speakers we have. We’ve got some of the most inspiring speakers in the world. Workout leaders who are going to lead you with great workouts in the morning. And some special surprises like we always do. If you’ve been to one of our previous three annual events, then you know it’s always a time to remember. So go to right now and check it out. We are one month away. I want to high five you, I want to hug you, I want to say hi, I want to hear about your story so make sure to get there because there’s just going to be so many incredible people you will meet, and I don’t want you to miss out this year. So make sure to go to


Today we’ve got the hilarious and inspiring Whitney Cummings. You’ll hear a different side of Whitney in this interview. We really dive in to a lot things. I think she was a little shocked on some of the questions I asked her, and I was really moved by a lot of her responses. I really just enjoyed my time and my company with her. I saw her on stage one time, laughed my butt off, and really got to dive in to the work she’s done.


Now she’s a comedian, an actor, producer, an author who’s appeared in multiple TV shows and films as well as multiple stand-up specials. You’ve probably seen her either on Netflix or online or one of her movies. One of her stand-up specials was nominated for an American Comedy Award. She created also the sitcom, the massive megahit, Two Broke Girls. You probably watched that show. And the show Whitney, and her TV appearances have been on comedians of Chelsea Lately and Live Nude Comedy which she created, starred, and wrote for. And the Comedy Central Roast of Joan Rivers, David Hasselhoff, and Donald Trump. Her incredible book I’m Fine and Other Lies was out in 2017 and her film The Female Brain which I saw on a plane recently is now available for streaming. Her latest comedy special Can I Touch It? Is also on Netflix right now. It’s a funny one. Make sure you go watch Can I Touch It? on Netflix also.


In this interview, we’re talking about why desperate energy is repellent. It’s repellent. In her business, the Hollywood business is definitely repellent and it’s also in almost every career possible. When anxiety can be a good thing in life, the importance of loving yourself in a way that is also self-aware, the addiction of being a victim, and how Whitney broke free of all of it herself, and doing work for yourself and not for the reward. Whitney takes a lot of risks that don’t always get massive rewards, but that’s what helps her grow, that’s what makes her become more brave, more curious, more exciting, more adventurous, and that’s what makes people respect her more. It’s one of the reasons I respect her because of the risks she takes and the constant work she’s willing to do on herself.


So get ready for this one, I think you’re going to really love it. Make sure to share it with your friends, and just share it with one friend today. One friend that you think this will inspire. Text them the link Text one friend the link to the podcast that you’re listening to or just and spread the message of greatness, of inspiration, of learning, of knowledge. These tools can really help us grow when we apply just one principle from someone who’s been there, who’s done that, who’s achieved great things, who’s had big failures. And you can be someone’s hero and champion today by just texting them right now. So whoever’s on your mind right now that you really care about and think about, send them a text with a link to the podcast app that you’re listening to, or


And do me a favour while you’re listening, leave a review on Apple podcast and write a review. I don’t care how many stars you give me, just write a review of what this specific episode has done for you. I’d love to hear your thoughts, your specific thoughts. We share it with our team, we share it with our audience the impact that we make on other people. So I’d love to hear your thoughts. Just write a review. You can leave one star, five star—it doesn’t matter to me. But I just want to hear your thoughts, I want to hear from you.


And before we dive in, big thank you to our sponsor Blinkist. Now I’m a big fan of Blinkist. Blinkist is the only app—it takes thousands of the best non-selling non-fiction books and distils them down to their most impactful elements. So you can read or listen to them in under 15 minutes all on your phone. With Blinkist, you will expand your knowledge and learn more in just 15 minutes than you can in almost any other way. Plus you can listen anywhere. I love doing this and listening while I’m driving to the gym, while I’m driving to get groceries, or when I’m driving. Five million people are using Blinkist to expand their mind 15 minutes at a time. You can get started today for a limited time. Blinkist has a special offer just for you guys at School of Greatness. You can go to to start your free 7-day trial. So make sure to go there right now. That’s, spelled b-l-i-n-k-i-s-t. Again, to start your free 7-day trial at


And big thank you to our sponsor Candid Co. Now, did you know that your teeth move as you get older? I didn’t know this. I went to the orthodontist about a year ago and they told me this. My dentist told me this as well and I was like, “Really? I thought it was kind of just set in stone when you’re 18, 19, 20, and that’s pretty much it.” But nope, that’s not true. If you want to get your teeth fixed, the last thing you want to do is wear braces. I know I don’t want to wear braces because I do a lot of video and I just don’t want to wear them. That’s why I’m happy to tell you about Candid. It’s the clear alternative to braces. Candid has an orthodontist who is licensed in your state to create a treatment plan designed for you. And Candid only uses experienced orthodontists. They even create a 3D preview of what the final results are like. Once you approve your 3D preview, then Candid creates custom clear aligners that will be sent directly to you. Super simple. That means there’s no hassle of having to go into the orthodontist’s office all the time. And Candid costs 65% less than braces. So you can save thousands of dollars and have straighter, brighter teeth in an average of just 6 months. And you’re one step away from getting straighter, brighter teeth right now. You can learn more at Use the code “greatness” to get $75 off. So make sure to check that out right now, it’s going to help you with your confidence, and get straighter and brighter teeth. That’s Again, use the code greatness for $75 off.


Big thank you again to our sponsors and without further ado, let’s dive into this episode with the inspirational Whitney Cummings.




LEWIS HOWES: Welcome back everyone in the School of Greatness podcast. We’ve got the inspiring and hilarious Whitney Cummings in the house.




LEWIS HOWES: I’m super pumped you’re here.


WHITNEY CUMMINGS: Thank you. Thanks for having me.


LEWIS HOWES: I watched your movie on a plane like 8 months ago.




LEWIS HOWES: The Female Brain.


WHITNEY CUMMINGS: Yeah? Did not the other movies load or what was happening? What was it you’re having?


LEWIS HOWES: [inaudible]


WHITNEY CUMMINGS: I’m just curious.


LEWIS HOWES: No, because I wanted to learn more about you. I think I saw you at whatever Comedy Store, which one is it?


WHITNEY CUMMINGS: Oh really? Comedy Store?






LEWIS HOWES: I saw you there probably a year ago. I’ve only been there maybe four times since 7 years since I’ve been.




LEWIS HOWES: Maybe 4 or 5 times. I went there and you were performing and I was dying laughing.




LEWIS HOWES: You were so talented.


WHITNEY CUMMINGS: A year ago, I must have been working on new material.


LEWIS HOWES: A year and a half.




LEWIS HOWES: Yeah, it was pretty rough.


WHITNEY CUMMINGS: That seems like when I was just starting this new hour and it was probably only premises.


LEWIS HOWES: That was amazing.


WHITNEY CUMMINGS: Oh, thank you.


LEWIS HOWES: It was amazing. I was in the balcony watching you. I actually tweeted you afterwards, not that you saw it but I was just like, “Wow.” I really admired the way you worked the room, the way you tell amazing stories. I think you were even saying that I’m working on new materials so like, work with me here.




LEWIS HOWES: But you weren’t allowing any of it to show that you were insecure in any way. Which I think you were talking before and a lot of comedians are always insecure.


WHITNEY CUMMINGS: Yeah, which is what drives us. I know that we’re all in this quest to solve insecurity and make it all go away but insecurity sometimes drives us to do good things and get better and work harder. So I think insecurity can be a good fuel sometimes. It’s not good if that’s your default state, that’s something to work on. But definitely, it took me a long time to embrace the fact that in stand-up, you succeed by failing over and over again. It’s like going to the gym. You’re not always going to have the killer day that you want to put on Instagram.


LEWIS HOWES: Standing ovation, laughing out of their minds, snorting [inaudible].


WHITNEY CUMMINGS: Most people just see the—it’s like a sculpture. Most people just see when it’s done in the museum, right? You don’t see the chiselling and the messing up and the fixing and the repasting and the whack-a-mole. That’s stand-up when you come and see the comedians are cobbling together. You’re going to see comedians at every level sort of figuring it out.

LEWIS HOWES: I haven’t noticed [inaudible] be a comedian but I feel like you’d be the most incredible training for my personal growth.


WHITNEY CUMMINGS: I just think everyone should just do it once. Even once.


LEWIS HOWES: Fail miserably and get laughed at. In a bad way. Right?


WHITNEY CUMMINGS: I think you wouldn’t. I think that you’re so authentic and you know who you are. That’s the key to it, I think. It’s not about saying the thing that’s the funniest, it’s saying the thing that’s the truest and that matches people’s perception of you the most. You’ll find out right away how people perceive you which is kind of an interesting exercise.


LEWIS HOWES: Interesting. When was the time that you realized, “Okay, I’m actually not that bad?” You know what I mean? Because there’s probably of—or were you just always funny and it always—people laughed and just clapped and cheered?


WHITNEY CUMMINGS: I mean, no. It’s tricky because then you think you’re great and then you have a bad couple months and then you think you suck and then you have nothing to lose so all of a sudden, you’re great one night just because you don’t give a crap anymore.


LEWIS HOWES: You don’t care anymore.


WHITNEY CUMMINGS: Yeah. And then you go, “Oh, whoa.” It was the trying too hard that was repellent to people and—so as soon as you stop giving a crap because you think you suck, sometimes that’s when you do your best work. So I think that I’ve never got that right. There’s a dysmorphia involved in it.


LEWIS HOWES: So you still need to prepare and care about your material, but not care what people think about you?


WHITNEY CUMMINGS: In a way, yeah, you have to care a ton and then as soon as you get on stage, you can’t care at all.




WHITNEY CUMMINGS: It’s like this switch you have to turn on and off, but it’s also—you can do the same set, same jokes, same way two nights. One time you get a standing ovation, the next night you just bomb. 


LEWIS HOWES: Really, why is that? 


WHITNEY CUMMINGS: Depending on your energy, depending on how in the moment you are. I took some boxing classes a couple of years ago and I couldn’t believe how much like stand-up it was. If you’re a second ahead or you’re a second behind, the joke’s not going to land. Like you just have to be listening. It’s a conversation with the audience. A joke that worked the night before might not work tonight. You just can’t go into autopilot. You just have to be right there.


LEWIS HOWES: You gotta feel the energy.


WHITNEY CUMMINGS: Yeah. Every city is different, every venue is different, every group of people is different. There’s a bachelor party in the corner. Weed’s legal in California, it’s different pacing in LA now. It’s just kind of being flexible and detaching from your plan and detaching from the rote memorization or detaching from this work 50 times so I’m just going to do the same thing I’ve done. It’s just being willing to detach from all the things that worked for the past year and being flexible, I think.


LEWIS HOWES: Did you always want to be in comedy? In school, growing up?


WHITNEY CUMMINGS: Yeah, I don’t think I knew that’s what I was meant to do. I hit a couple different walls that I thought—like I thought I was going to be a journalist.




WHITNEY CUMMINGS: Because I was a seeker and I was curious and I was critical and I’ve always wanted to get the dirt. Like we’re—in comics, we’re kind of snitches at heart. We’re complainy snitches that are obsessed with justice and I thought I was going to be like an Upton Sinclair where I was going to go into factories and reveal that we’re obsessed with that stuff—we’re obsessed with secrets and lies and injustices. And then I was also a performer and I was also doing theatre and playing—


LEWIS HOWES: Like dance, singing—


WHITNEY CUMMINGS: No dancing, no singing. As a strong boundary. How dare you. No, not like a theatre kid. I was doing very serious plays.


LEWIS HOWES: Shakespeare.


WHITNEY CUMMINGS: Like A Doll’s House. It’s in the Doll’s House which was sort of about this woman in a bad relationship. So I kind of was like—and then when I was hanging out with my friends, I would tell these really long, boring stories about how I hated how you can’t find your car in a parking lot and I don’t like the ticketing system. I didn’t realize what I was doing with stand-up. I didn’t realize—


LEWIS HOWES: Those are the conversation that do the best in stand-up.


WHITNEY CUMMINGS: Totally. And I was just sort of like, “Oh, I have a huge complaint and I want to talk about it for 40 minutes.” This isn’t a date. This isn’t what you do on dates.


LEWIS HOWES: This is what [inaudible].


WHITNEY CUMMINGS: This is what you do in front of—


LEWIS HOWES: Or your girlfriends.


WHITNEY CUMMINGS: Totally. I was dancing around. I was dancing around and then someone one day—and I think just to get me to shut up—was like, “You should try stand-up.” It was the way of saying, like, “Get this out of here.”


LEWIS HOWES: There’s a couple of moments—I’m not obsessed with comedians, like studying it all and going to all the shows and watch everything, but I enjoy it. It’s fun for me. I watch different stuff when it’s on Netflix or I’ll go to the comic store once a year type of thing. But I remember—I don’t know if you’re friends with him—Dane Cook had a CD special like 15 years ago. [inaudible] joke that was still on my mind. There’s something like you talking about the parking ticket system and he was talking about when you’re in a parking garage and your tires squeal. And for some reason, this joke stayed with me. It’s nothing crazy funny or some out of the world—


WHITNEY CUMMINGS: It just resonated with you and you felt connected and I think that’s what stand-ups do. It’s like you put a bunch of strangers in a room and they all agree on something. They all connect on something. They vote differently, they have different interests in movies and women and men. Who knows?


LEWIS HOWES: Different races, different experiences, backgrounds—


WHITNEY CUMMINGS: All coming from different socioeconomics get together and go the wheels squealing in the park—we all have that universal experience. It’s finding the things that we could all kind of agree on. I think that always interested me. I grew up in a home that was not harmonious so there’s a lot of discord, a lot of disagreement, and I always kind of wanted to get everyone to agree and laugh. It was always like to try to sort of just manage tension. It was always like, “If I can make this person laugh, maybe Christmas will be fun.” It was always kind of just trying to manage people. Then as an adult—it’s almost like a hurting dog, a shepherd that wants to get everyone in one place. I just sort of have this instinct of trying to go like, “We actually have more in common than we don’t.” It’s something that it’s just—like a instinct that I don’t know if you could teach.


LEWIS HOWES: Are you a younger sibling?


WHITNEY CUMMINGS: I’m the youngest.


LEWIS HOWES: The youngest of three?


WHITNEY CUMMINGS: The peacemaker, always. Yes. I mean, we’ve got some illegitimate ones floating around, but three that we know of.


LEWIS HOWES: That you know of, okay. Something [inaudible] for some reason, I just knew that you had an older sibling just in the way you were talking there.




LEWIS HOWES: Youngest of three, what was the biggest discourse within the family?


WHITNEY CUMMINGS: I mean—this was not—I have no victim stuff about it or regret about it. There’s just the divorce and alcoholism and a lot of mental illness in my house growing up. A lot of—we’re very lucky, we’re in the generation that has podcast like yours and books like this. We didn’t—my parents didn’t have those tools. It was passive-aggressive communication, it was everything’s fine, everything’s fine, then a huge explosion of resentment. There was no talking about that. I also grew up with a  mother that I’m really proud that I had, but she was kind of first generation of women that was bouncing full time with career and kids.


So she was under a tremendous amount of stress and didn’t have child care and was just always so stressed out and exhausted. But taught me she was up at 6am and she was home at 7pm, and she brought me to work with her, but I just saw her trying to manage everything. It was always like, “How do I just make things easier for everybody else?” And the joke kind of—to me, it was like a magic trick. I was like, “Woah, that was easy. That was an easy way to get love. That was an easy way to cut some tension.” So I learned early on how to kind of tap dance. We all did. I think we all grew up in—we’re the first generation that isn’t turning to alcohol and anger and range and some kind of just quick dopamine hit.


LEWIS HOWES: Or doing other dopamine hits which is like meditation and working out, 8 hours of sleep, eating healthy.


WHITNEY CUMMINGS: False sense of control is our new addiction.


LEWIS HOWES: Exactly. It’s trying to optimize certain things that we can to ease the pain.


WHITNEY CUMMINGS: Maybe overcorrecting in a way.


LEWIS HOWES: This is crazy because—


WHITNEY CUMMINGS: Self-help ism is kind of the new “ism.”


LEWIS HOWES: It’s crazy because we’re very similar based on what you’re telling me. My parents were passive-aggressive, there was no love or affection. Zero. It was like they forced the love—they tried to show it. There should’ve been divorced before I was even born.


WHITNEY CUMMINGS: Was there a shame around getting a divorce or—


LEWIS HOWES: Yeah. They stayed together because of us, not because they loved each other. Maybe they loved each other in some sense but they were both working full-time jobs to pay for all four of us kids. And my mom—she was working full-time and then trying to take care of us. It’s almost like they went crazy in a sense.


WHITNEY CUMMINGS: And you’re watching, overwhelmed. You’re watching—


LEWIS HOWES: Stressed, overwhelmed, screaming, fighting, constantly leaving the house—uncertainty.


WHITNEY CUMMINGS: That’s right. Inconsistency, stormy. And it’s also I think, as a kid, because you don’t understand the emotional one plus one equals two so you’re just trying whatever you can, and the same thing you’re punished for one day you’re rewarded for the next day. It’s like, to me, I never understood what added up. So it was like, “Be funny, be loud, tap dance, come out and—” So I was always sort of experimenting with what worked. But I grew up in—and I wrote a book about codependence which is kind of a word we used to describe relationships where you spend a lot of time together which is not really what co—it can be codependence but I didn’t understand that I grew up in an alcoholic home, but also a very codependent home which where people did a lot of things out of obligation.


LEWIS HOWES: People pleased to feel—yeah.


WHITNEY CUMMINGS: Which is very—it’s part of tradition, I think, in our culture. I won’t speak for other cultures, but it is. You go to church on Sunday, you have to do this, you have to go to this bridal shower, you have to bring a gift, you have to go to this housewarming. There was a lot of sort of love that I now realize was obligation. Socializing that was obligation. We have to go to Christmas and so many people were divorced. It was like going to nine people’s houses for Christmas. I didn’t really learn “do what you want to do that makes you feel.” I just—force yourself to do things, white-knuckle through things. You do things out of obligations.


LEWIS HOWES: And be resentful the whole time.


WHITNEY CUMMINGS: That’s right, and codependence breeds resentment so I’m just going to be miserable and—socializing this joyless. I really had to work hard to make socializing joyful later because I just didn’t have a concept that it wasn’t work.


LEWIS HOWES: it’s interesting, I felt very similar. When I was 13, I begged my parents to send me away because I just didn’t want to be near the environment anymore. This is why I went to St. Louis. I went to a private boarding school. I’ve met some kids that were just more positive. I was like, “I want to be around these [inaudible] kids who are thinking differently, who are—just feel like they’re in better environments, better family environments.” And I begged them for a whole summer to send me to this school—it’s 7 hours away from Ohio where I was living. And it sounded like you tried to escape as well.


WHITNEY CUMMINGS: Yeah. I didn’t ask to be sent away. It wasn’t in [inaudible] Salisbury.


LEWIS HOWES: You just left.


WHITNEY CUMMINGS: Civilized. Yeah, I  kind of got sent.




WHITNEY CUMMINGS: Yeah, I got sort of sent to Virginia.


LEWIS HOWES: Oh wait, how old were you?


WHITNEY CUMMINGS: Because I was acting out. I was 12.




WHITNEY CUMMINGS: I know, we have a similar thing. That’s a trip.

LEWIS HOWES: Holy cow. So you got sent away?


WHITNEY CUMMINGS: I got sent away because there was various family drama, hardcore. And it was like my parents kind of just—it was too much for them. So I went and lived with my aunts in Virginia for a while.


LEWIS HOWES: An hour and a half, four hours away.


WHITNEY CUMMINGS: Yeah, a little more. Like four hours away.


LEWIS HOWES: Four hours. For how long?


WHITNEY CUMMINGS: About three years.


LEWIS HOWES: So you went to middle school, high school for a little bit in Virginia away from your parents. You see them in summer?


WHITNEY CUMMINGS: I see them on weekends. You know what, I think that was okay. It was interesting. And I have all sorts of scars around that and character-building moments. Maybe it’s American, maybe it’s—I don’t know. You guys will correct me in the comments, I’m sure, but it’s just so odd to me that we’re raised by two people and that’s it. It’s like we’re kind of designed to be raised by many different people—




WHITNEY CUMMINGS: That’s right. As odd as it felt for my parents to go like, “We can’t take care of you, we’re leaving you here.” At the time, my brain was like, “You’re not good enough. You failed. You’re unlovable.” All those narratives that of course, my psyche was going to write. Because, my psyche—I know this is a common thing but I’ll speak for myself—is that when our parents fail, that’s too much for us to handle so we have to blame ourselves.


That was a really big part of the way I developed. But looking back, I feel really lucky that I got to be exposed to so many different kinds of parents and caretakers and their flaws and their strengths. I grew up in D.C. and then I grew up in Virginia for a while so I got to kind of get like—I think that’s part of what makes me a good comedian is I’m not just in this elitist, [inaudible]. I got to see how people lived that aren’t in the metropolitan areas and see the value of that and learn community and connect with animals. I feel really lucky that I got to have a little bit of both growing up.


LEWIS HOWES: You went back when you were 15, 16?


WHITNEY CUMMINGS: And then I went back to D.C. when I was 15, 16, yeah.


LEWIS HOWES: They were less exhausted?


WHITNEY CUMMINGS: I think so, yeah.


LEWIS HOWES: Your siblings were probably older, they were in college now and so.


WHITNEY CUMMINGS: Yeah. There was some scrapes. It was not ideal, but I don’t know where we get off as people expecting our parents to have any idea what they’re doing. I mean, when you look around and look at your friends that have a kid you’re like, “They’re having kids? Why?” Like you look at your friends and you’re like, “Oh my gosh. My parents—no one was ready for kids.”


LEWIS HOWES: No one. My parents had my brother when they were 19. They were in school. They don’t know yet who they are.


WHITNEY CUMMINGS: I just feel like for the most part—I mean, a lot of really tricky things happened to me as a kid, I have a lot of trauma, the whole thing, and I do EMDR, and I’m in a 12-step programs. A lot of people I think know about all the things I do to fix what happened but for the most part, I think we have incredibly high expectations for our parents that are just too high. If you study history or you study the timeline of—sort of what we know about neurology and psychology, it’s only in the last 20 years that anyone stood a chance.


LEWIS HOWES: And when we can learn to forgive and accept and have compassion for our parents, that’s when we can really heal these relationships and heal ourselves for not beating ourselves up or feeling like we’re less than or not good enough or not lovable.


WHITNEY CUMMINGS: Yeah, and they did the best they could. I truly don’t think my parents were like, “How are we going to mess up Whitney today?” They were literally just trying to keep their head above water given the tools that they had.


LEWIS HOWES: It sounds like if you had a perfect life, you wouldn’t be where you’re at. The adversity is what makes you stronger. It’s what you make more creative, and what makes you break out of your comfort zone and try things, probably.


WHITNEY CUMMINGS: And it just is what it is. There’s nothing you can do about it. I think we spend so much time in blame and that is just—to me, I have such economy of energy [inaudible] I just say, “[i] spending any time being mad at someone that—” I just don’t do it. I love what you said about forgiveness because I remind myself on a daily basis: We forgive others not because they deserve forgiveness, but because we deserve peace.


LEWIS HOWES: That’s it. It’s not about them.


WHITNEY CUMMINGS: No. Forgiveness is selfish.


LEWIS HOWES: For your inner peace.


WHITNEY CUMMINGS: It’s just taking things out of your backpack. It’s just like, “Why am I carrying this around? My mom has enough shame about what happened. I don’t have to be mad on top of it.” It just doesn’t work. If it worked, I’d do it. But it just doesn’t. Blame doesn’t work.


LEWIS HOWES: You’re not more connected, more loving with each other.


WHITNEY CUMMINGS: I don’t get a cheque everytime I get mad at my mom. It just doesn’t pay any bills.


LEWIS HOWES: Man, I’d be rich.


WHITNEY CUMMINGS: Totally. I just don’t.


LEWIS HOWES: I’m going to be rich, right?


WHITNEY CUMMINGS: I just don’t see the point. You might know this about me, but I’ve learned a lot about myself in about— sort of the error and the ideas I have by training animals. And even when I have the best intentions, I make mistakes and I screw up and I—it makes me have so much more compassion for my parents.


LEWIS HOWES: I’ve been watching your videos of you with your horses. How many horses do you have?


WHITNEY CUMMINGS: I have one. I only have one, but yeah.


LEWIS HOWES: It seems like there’s many because—


WHITNEY CUMMINGS: I know. I’ve worked with many but I only—


LEWIS HOWES: And I think there was one a couple of weeks ago of you walking away. It was just like your energy—she’s like, well, she’s going to walk or he or she—now [inaudible] she’s going to back off.


WHITNEY CUMMINGS: You know, I think I’ve spent so much time—I wasted my 20s, really. Nothing’s wasted but I really did was unconscious in my 20s because I was trying so hard to control other people and trying so hard—my subconscious brain was working so hard to figure out ways to make myself feel safe and to avoid abandonment and avoid rejection and avoid criticism. And equine therapy is really the only thing that helped me understand it besides al anon and 12-step programs and codependence recovery how desperate energy is repellent


LEWIS HOWES: So repellent.


WHITNEY CUMMINGS: And the more badly we want something—when we push something we pushed away.


LEWIS HOWES: When you have two desperate people that you can come together and be like, away and together, Whitney, [inaudible] codependent, right? 




LEWIS HOWES: Two desperate people.


WHITNEY CUMMINGS: That’s right. And just sort of the unhooking and the only way to win is to not play and to don’t just do something, sit there. Because to me, my drug is taking an action. My drug is—and it becomes this sort of the tighter you pull something, the knot just gets tighter and tighter. And that really is what I think about when I think of my 20s. it was just me trying so hard to be loved and respected and heard and seen that I was like—it’s just annoying. It’s repellent is the, I think, best way to put it. And working with prey animals really helps you understand. It really holds up a mirror to your energy and what you’re giving off, and what is needy energy and—so my horse has really helped me with that.


LEWIS HOWES: What are you most proud of about yourself that you’ve done in the last 10 years from your transition at 20s, at 30s, looking back?


WHITNEY CUMMINGS: That’s a really good question. And I have a couple. There’s the financial things I’m proud of like owning a home and having a 401(k) and just sort of—


LEWIS HOWES: Being independent, yeah.


WHITNEY CUMMINGS: The basic self care of that. I grew up poor. Just having health insurance is a big deal so I think time’s where I’m like, “I didn’t get this and I don’t have these many things and I don’t have this much money.” I’m just like, the fact that I have health insurance is a miracle with what I’ve come from. I think we forget our basic [gratitudeless?] our basic—if you have told me 15 years ago that I would have a 401(k). I would think you were on LSD. I think it’s important to also have gratitude about those little things. 


But for me, I would say it’s so simple for me—handling a conflict with grace is like the biggest achievement I can make at this point. Because achieving things and getting things and winning things and selling shows or making specials, that’s all—I know how to do that. But to me, the biggest challenges are sometimes just being able to shut my mouth for 20 minutes and listen to someone who’s wrong. That, to me, is one of the biggest accomplishments.


LEWIS HOWES: Listen to someone who’s wrong and not trying to make them right? Or?


WHITNEY CUMMINGS: Not trying to fix it and just go like, “That sounds hard.” And not try to change someone’s neurology in a conversation.


LEWIS HOWES: Not coach them or give them the solution.


WHITNEY CUMMINGS: No. “I’m sorry you feel that way.”


LEWIS HOWES: Now, try to be like a guy essentially, right.


WHITNEY CUMMINGS: How dare you, how dare you imply that I’m talking about the differences between men and women? That, to me, that’s what’s been the hardest thing for me. Is to be able to be in a relationship with someone—working relationship, romantic relationship, and not try to control their behaviour, opinions, neurology, and to be able to tolerate the discomfort of others and other people being wrong. Wrong is subjective so the hardest thing for me is becoming a boss and having employees and just going, “You’re not doing that the way I would do it.” And I’m just going to have to—


LEWIS HOWES: Accept it.


WHITNEY CUMMINGS: And I’m not going to spend the next hour obsessing over how I would have done it and then micromanaging the person. It’s just that kind of taking the hooks out for me has been a big one. Being able to tolerate the discomfort of others, the flaws of others—that’s my biggest thing.


LEWIS HOWES: [Essentially?] you say that because in the beginning before we have started recording, you said something about how we shouldn’t love ourselves. In like a cheeky way you’re like, “We shouldn’t just be all love yourself for who you are, because then you’re not going to work to improve yourself.” Is that right?


WHITNEY CUMMINGS: Yeah. I was driving over here and I was like, “God, I hope I’m a good fit for this show because I am so—” I see all these self-help stuff on Instagram and I just didn’t like—I don’t like generalizations. My brain just doesn’t do well with them. Like black and white— love yourself. I see this war on self-deprecation, I see this war on anxiety, that’s now all I hear about is “I have anxiety, I’ve got to get rid of anxiety.” Anxiety is great. It is why our species has proliferated. Anxiety is information. It tells us what situations to get out of, it tells us what people are not healthy for us. It’s our gut.


I know there’s anxiety disorders and I’ve struggled with it, but it usually is information telling me “do less of this thing, cut this person out of your life.” I think anxiety is important, so is adrenaline, so is cortisol. I think that we’re leaving neurology out of a lot of these conversations and we’re leaving sort of an evolutionary biology element on a lot of these conversations. So a lot of the things that made humans so successful we’re now trying to get rid of. And we have such a big problem with people self-medicating in our country, and I think a lot of it is that “we’ve got to get rid of our anxiety!” It’s like no human is allowed to be uncomfortable ever. Ever. I’m not pro-anxiety but I do think that anxiety is our gut sometimes telling us information we need to know.


LEWIS HOWES: I think if you look at it as intuition. Like if you’re starting to feel anxious about a moment or stressed or like something’s off. And you feel anxious. Okay, you don’t need to hold on to that for 30 days or for 3 years. You shouldn’t stay in that place, but listen to it and figure out a way to adjusting something in your life, right?


WHITNEY CUMMINGS: I think that we tend to pick and choose the pain and discomfort that we want. You don’t go to the gym and go like, “This hurts, I’m not doing it.” You go, “No, this is gonna—” I don’t know anything about exercising. I’m going to tear the muscle and get stronger. I think for me, this whole love yourself—I wrote a book on loving yourself and overcoming codependence and building self-esteem, but that term to me doesn’t honour neurology and how self-esteem or the frontal lobe works. And it also is just like—love yourself if you did something. What are the esteemable actions? If you want high self-esteem, you have to engage in esteemable actions. This idea of everyone just deserves to love themselves all the time—I don’t know. I mean, some people.


LEWIS HOWES: I think there’s something to be accepting yourself for where you’re at and how far you’ve come. “It’s okay, I accept and love where I’m at right now. But I also know there’s more available for me.”


WHITNEY CUMMINGS: I think, for me, I need an engine. I need—


LEWIS HOWES: [inaudible] and sitting around all day.


WHITNEY CUMMINGS: Yeah. For me, it’s not possible to just go, “Ah, I love myself,” out of nowhere. That’s just now how nature or nurture works. So I think for me, I’m really into achievable goals, but I do think there’s this sort of generation of people that maybe love themselves too much and haven’t—and that’s maybe my comedian brain kicking in and I think that their self acceptance or self love—this is just probably me trying to make a joke about it, but a lot of the people that I see saying like, “I’m going to love myself today.” I’m like, aren’t you the same person that just tweeted something nasty about it? I’m just like, why would you love yourself—I think that we just need to—I think self love coupled with self awareness is important. This radical “I’m perfect the way I am all the time” — look at our environment, look at our world catching on fire. Like we might love ourselves too much.


LEWIS HOWES: I think we’d build more confidence by the actions that we take. It’s by being our word consistently. Whether it’d be in a relationship or if you say you’re going to workout 5 days a week, and actually following through to your commitment. I think that’s what makes you feel like, “Okay, I love myself.” I’m like appreciating myself more from the actions that I took, and for being a good human being.


WHITNEY CUMMINGS: I guess for me—I don’t think I’m being clear. My problem with love yourself is I try not to set goals that are so unachievable and vague that I then feel disappointed that I couldn’t. So when I go, “I’m going to love myself in 5 minutes,” it’s just like, that’s not fair. I’m setting myself up to fail. I’m trying to change 36 years of neurology and God knows how many thousands of years of epigenetic imprinting I’m trying to overcome it because of an Instagram meme I saw that said: “Love yourself.” It just feels like a shortcut that is not attainable, and I’m just going to be more disappointed with myself when I can’t achieve it right away.


So I’d like to take bite-sized pieces of goals so that I don’t—a big thing we do in 12-step programs is you in order to honor word, you only set boundaries you can actually follow through with and you don’t make threats. So if you and I are in a relationship and you’re on your phone while we’re talking and I’m like, “If you ever do that again, I’m gone.” It’s like, nope, you cannot threaten something that you can’t follow through with. That’s not attainable because then of course you’re going to check your phone again. And then I’m not going to leave because I just made an impossible threat. It’s that I can’t follow through it and then it’s going to start to ruin my self-esteem because my word means nothing. You can’t take me seriously and I can’t take me seriously and then I don’t respect myself. So I just try to—


LEWIS HOWES: And then you resent everything.




LEWIS HOWES: Do you do this with many relationships that sounds like?


WHITNEY CUMMINGS: I don’t know what you’re talking about, no. I’ve heard that people do this.


LEWIS HOWES: Do you struggle on your current relationship? Because you’re engaged, right?


WHITNEY CUMMINGS: I am engaged. And I’m really lucky. By the time we started dating, I’d been in the 12-step program for almost 8 years. I’ve been doing EMDR for about 4.


LEWIS HOWES: I’ve been hearing EMDR is amazing, I hear from a lot of people.


WHITNEY CUMMINGS: It’s a game changer, it’s a game changer. Again, I’m not a “this is the [fantasy?] that’s going to fix everyone.” If you have—


LEWIS HOWES: Lots of tools. Or try different things.


WHITNEY CUMMINGS: Yes. And I had also been in the 12-step program for whatever, 5 years by the time I got to EMDR so I think I had the tools to even receive what it was. I’m also a big fan of the Placebo Effect. It’s an effect that works—whether it’s psychosomatic, whether it’s scientific—I don’t care. I was in a place where I could really receive it and I was ready to change. So I think that there’s no point in doing it if you’re not ready to change or if you don’t buy it or whatever. But it was at a time where I was really ready to release my character defects and put down all the weapons that I needed when I was a kid because I was carrying around a lot of armor and a lot of weapons that worked great.


LEWIS HOWES: A lot of masks.


WHITNEY CUMMINGS: When I was younger. Yes. I had a mask on. I was just ready. I was ready to stop fighting. It was like something we say in Al Anon is, “The war is over, you lost.” And it’s like, you know.


LEWIS HOWES: Surrender.


WHITNEY CUMMINGS: Yeah, totally. We’re running around on the battlefield of a war we lost with our guns and our harpoons and our our canon and it’s like, no, we’re not—


LEWIS HOWES: The war is meaningless.


WHITNEY CUMMINGS: It has been over for 20 years and you’re running around like a maniac.


LEWIS HOWES: Yeah. Isn’t it interesting until we kill ourselves we can’t become something greater? Like we have to kill our old self, kill our ego—


WHITNEY CUMMINGS: It’s such a shame because—


LEWIS HOWES: Shed off these things, right?


WHITNEY CUMMINGS: Because I think in something that I talked about in codependent recovery stuff is like the person that grew up in the home that—that’s a superhero. I think we tend to look at our character defects as failures in some way or as that weirdo, that psycho. I was crazy. It’s like no, I was perfectly equipped to fight that emotional war. I was perfectly equipped to deal with mental illness and addiction and codependence and rage and whatever. I just don’t need to be The Hulk anymore.


LEWIS HOWES: No. It’s exhausting.


WHITNEY CUMMINGS: It’s exhausting and it’s just not useful or smart. It’s an energy drain. I’s the funhouse mirror. It’s just my perception. I just need to sort of update the software, that’s what I call it. It’s that things have changed and my brain stayed the same. It’s just really acclimating to my new circumstances.


LEWIS HOWES: How is this new relationship that you’ve been—I guess you’ve been in for a few years now? How is this—your partner now with all the work you’ve done, how do you feel like—what’s your rating? What’s your point card? “You’re like a D in all your relationships.” Are you a B+, an A-? [inaudible] the gold star everyday?


WHITNEY CUMMINGS: Oh, God. I give myself a B-, I would say.


LEWIS HOWES: There’s a lot of room to improve.


WHITNEY CUMMINGS: A lot of room to improve.


LEWIS HOWES: Okay, I was a C student so [inaudible].


WHITNEY CUMMINGS: It’s not so bad, I also am a perfectionist so I’m sure my version of a B- is probably another person’s A-. I feel like check for [inflation?]. I feel grateful. I also took this sort of course on how to kind of change the type of person you’re attracted to because I’m sort of obsessed with Harville Hendrix and how we’re attracted to people who have the negative qualities of our primary caretakers.


LEWIS HOWES: Isn’t that crazy?


WHITNEY CUMMINGS: Crazy. So I kept recreating my childhood circumstances over and over and dating my dad and dating my mom and dating my siblings. It was just like incest. At a certain point, you got to stop dating your dad, guys. And it would just trigger me. I had to do a lot of—I even did a lot of sort of like body trauma work because our bodies react before our brains.


LEWIS HOWES: [inaudible] keep score.


WHITNEY CUMMINGS: Totally. My favorite. So we are the same person, this is alarming.


LEWIS HOWES: You’re just much funnier than me.


WHITNEY CUMMINGS: As soon as—-[inaudible], but as soon as I would get into a defensive, I was gone. It was like I would just go offline and I would just turn into this robot who was just—and so, I found myself being attracted to people that I had to take care of, people that were a mess, people that were chaotic. It was just adrenaline. And I also identify as an addict. Adrenaline turns into dopamine so—dramatic situations are addictive.


LEWIS HOWES: They are.


WHITNEY CUMMINGS: Dramatic people are addictive.

LEWIS HOWES: Trauma is addictive.


WHITNEY CUMMINGS: Correct, correct.


LEWIS HOWES: Stress, trauma.


WHITNEY CUMMINGS: And being a victim is addictive. Being in a relationship where you’re like, “Well, he doesn’t do this and he doesn’t do this.” It makes you feel—


LEWIS HOWES: Feel responsibility.


WHITNEY CUMMINGS: It makes you feel interesting, it makes you feel bonded to other people. Complaining is addictive. I was in all of these really hectic relationships—secret relationships and cheating. You always feel like you’re on your own action movie and you feel important. So I found myself on that hamster wheel for a long time. And I was addicted to addicts and sick people. Malignant narcissists was my drug for quite a while. We called them Christmas trees. When you have not recovered your brain and the type of thing that you’re attracted to, you can walk into a room and it’s just like the most messed up person will just light up. It’s the only person that’s—


LEWIS HOWES: This is my person. I’m going to rescue you, they’re going to make me feel more important. They’re going to need me.


WHITNEY CUMMINGS: We call it passion, we call it chemistry, we call it butterflies when that’s really just your body saying stay away from this person. Anxiety. It’s helpful. We go, “Ugh, screw that anxiety.” No, screw the person that’s making you—well, don’t.


LEWIS HOWES: It’s really a reflection of us, though.




LEWIS HOWES: We attract what we are.


WHITNEY CUMMINGS: Vibrate. We just vibrate on a different frequency. [inaudible]


LEWIS HOWES: It might be a different level of messed up that we are.


WHITNEY CUMMINGS: It took me a long time to realize chemistry is a red flag. If I vibe with somebody, turn around, get in your car, and just leave the party.


LEWIS HOWES: So you just don’t vibe with the person you’re with?


WHITNEY CUMMINGS: You should get along. But if it’s like, [makes sound] something else is going on. And for me, personally. I found that if you mesh with someone right away and you’re like, “We spent five days together straight.” That is, for me, addictive, and I kept getting into these addictive [inaudible] things where you fall in love before you know the person. So it took me a long time because I kept being in these relationships with unrecovered codependence, unrecovered addicts, unrecovered narcissists. As if that’s something you can really recover from. My brain labelled it as chemistry, passion, soulmate. All these sort of things that we tend to romanticize. And it took me understanding neurology to really realize I was just kind of a puppet of this dopamine-oxytocin cycle. So that was really helpful for me. 


Learning neurology, I think, is the biggest game-changer when you said, “What are you proud of?” I think for me that’s the biggest one, to be able to just honor neurology and not make everything so romantic or personal or cinematic. It’s like, “Oh, that was just oxytocin, they’re not your soulmate. That’s all that was. It’s okay.” For me, it was really—I had to write lists. I wrote about it in my book. Like lists of what I wanted, what would be nice—it was like a list my therapist made me do. It was like—


LEWIS HOWES: Dream list.


WHITNEY CUMMINGS: Requirements with someone? Which is like requirements, like not [inaudible]


LEWIS HOWES: Not negotiable.


WHITNEY CUMMINGS: Not negotiable. My bottom line: “this is what I must have,” “this would be nice,” and “red flags.” And the red flags were like not negotiable. So that I really had to figure out [i]


LEWIS HOWES: They can’t be an addict, they can’t be whatever it is. Yeah.


WHITNEY CUMMINGS: Correct. Married. On Myspace, things like that.


LEWIS HOWES: You can’t be married right now.


WHITNEY CUMMINGS: Hard and fast rules. Because I think that the problem with chemistry clouds our frontal lobe. Dopamine clouds our judgement. For me, I had to get really self-aware about my judgement.


LEWIS HOWES: Yes. No list so it’s clear.


WHITNEY CUMMINGS: I had to really treat it like a business proposal [inaudible]. It’s non-romantic as that sounds because I found that my relationships were draining me and depleting me instead of energizing me. That’s a bottom line for me.


LEWIS HOWES: No stripper poles.


WHITNEY CUMMINGS: No stripper poles, no thank you. I’m good. My therapist said something to me that was really interesting. She basically went, “Your relationship needs to be boring.” And I was like, “No way, what do you mean? It has to be exciting and that and this.”


LEWIS HOWES: You’re going to bring the excitement.




LEWIS HOWES: You’ve got action and energy.


WHITNEY CUMMINGS: What she made me realize is what’s boring to you is really just serenity.




WHITNEY CUMMINGS: That’s right. 




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LEWIS HOWES: Because you don’t have peace in any relationship. And you need to have peace when you go home.


WHITNEY CUMMINGS: That’s right. Your home should be a sanctuary. I love that Flaubert quote which is like, “Isn’t it be boring in your personal life so you can be brave and violent in your professional life and take risks.” And a lot of the most successful people at least in my field are the ones that have been married for 35 years—Will Ferrell and Steve Carell and all these guys, they’re not out dating. It’s a time suck.


LEWIS HOWES: It’s so much energy.


WHITNEY CUMMINGS: It’s a full-time job. And I realize I was chasing people whose love I couldn’t get, that I could never get because of this addiction to—I think rejection and abandonment and this addiction to auditioning for approval. So I would be like—


LEWIS HOWES: Auditioning for approval, as you said.


WHITNEY CUMMINGS: I’d be magnetically attracted to people whose approval I could never get.


LEWIS HOWES: Like your dad.


WHITNEY CUMMINGS: Like my dad, or malignant narcissists who just can’t. Or I would need too much from somebody who couldn’t give. I was just really constantly in those relationships and I was in relationships where I would do 80 they would do 20 because to me—my workaholism, that was just my comfort zone.


LEWIS HOWES: To make it work, yeah.


WHITNEY CUMMINGS: It took me a long time to get out of that. To answer your question, it’s kind of a triumph, really. A victorious triumph that I’m in a relationship that’s healthy and—


LEWIS HOWES: Peaceful.


WHITNEY CUMMINGS: Peaceful and he’s just useful and calls me out of my shit and sets boundaries.


LEWIS HOWES: That’s good. He stands up for himself. He’s not just letting you walk all over him.


WHITNEY CUMMINGS: No. And I could be authentic with him. It’s really like—he has the tools to have these conversations which is really helpful. I think you have to date someone that has a similar toolbox in you.


LEWIS HOWES: He’s emotionally intelligent.

WHITNEY CUMMINGS: Or else, what are you doing. If he doesn’t, he’s able to say, express that he’s not in, so am I. And we’re really—this was something that I think was really helpful in this relationship. I didn’t throw all my crap at him right away. I used to think that my trauma was the only thing that was interesting about me.


LEWIS HOWES: Your heart is interesting.




LEWIS HOWES: Absolutely.




LEWIS HOWES: Of course.


WHITNEY CUMMINGS: But I didn’t sort of give it all at once. It started long distance, which I think was really helpful for an addictive brain. Because it was able to pace.


LEWIS HOWES: You can’t spend 24/7 for two weeks with them.


WHITNEY CUMMINGS: It’s not sustainable.


LEWIS HOWES: Obsess over like every little detail.


WHITNEY CUMMINGS: No, don’t do it.


LEWIS HOWES: I’m in a long distance right now and actually, it’s amazing because I miss her. And I’m like, “Oh my god, I wish she was here.” But I’m also like, “Wait. Let’s wait. Let’s give it more time, let’s reenjoy the process.” We’re communicating on the phone, we’re not obsessing over certain things. She’s independent, I’m independent. We’re building a foundation.


WHITNEY CUMMINGS: It’s really—I mean, this is just such a basic thing and we didn’t—I didn’t learn basic things like this when I was a kid. Get to know someone.


LEWIS HOWES: They’ll just fall in love [inaudible].


WHITNEY CUMMINGS: Don’t. Just get to know—it’s very simple. For me, I was just so sloppy about it. I think for me again, my biggest fear in life is being boring, believe it or not. So my thing was like, “Here’s all my trauma and here’s all the terrible things that happened to me and here’s all my—and it just—


LEWIS HOWES: “How interesting and complex I am.”


WHITNEY CUMMINGS: It gives you this false sense of emotional progress with the other person, this false sense of intimacy that’s just not real and you’re in this house of cards. So for me, it was really about kind of doling out my personal information with him. I mean, in a way that was—




WHITNEY CUMMINGS: Healthy. It wasn’t like I’m going to show all my victim, then now you’re attractive to a victim. And now we’re in this unhealthy thing. So it was really important to me to sort of curate and still be authentic, but kind of just curate and be boundaried about what I shared with him when. Because I was trauma bonding with people and wasting 6 months at a time.


LEWIS HOWES: What’s the thing you love about him the most?




LEWIS HOWES: Different type of podcast.


WHITNEY CUMMINGS: I love this. These are questions that nobody ever asks me. I love it. The thing that I love about him the most is—I think this is so obvious, maybe. He really is endeared by a lot of my—I don’t like when people call themselves crazy and I try not to do it to myself. I’m really careful about it.


LEWIS HOWES: You care about your words.




LEWIS HOWES: Become what you say.


WHITNEY CUMMINGS: My idiosyncrasies. He’s entertained—


LEWIS HOWES: The quirkiness.


WHITNEY CUMMINGS: Yeah, yeah. He understands recovery and he’s very like—he’s like, “I’m going to stay in my lane.” He doesn’t try to control me, he doesn’t try to fix me. My thing is I have enough notes for myself. I don’t need more notes. I want to hear your feedback and I want to improve. But he’s not—he’s entertained by it which I think is important. You need someone that is kind of your fan and isn’t disappointed when you do something—he doesn’t take personally my behaviour, how about that?


LEWIS HOWES: He doesn’t.


WHITNEY CUMMINGS: It’s not like everything I do—


LEWIS HOWES: [inaudible]


WHITNEY CUMMINGS: Yeah. If I don’t text him back, he’s just like, what happened? He’s not like, where have you—he’s just very like, “Did you lose your phone again?” He’s just like—


LEWIS HOWES: [inaudible] secure and [inaudible]


WHITNEY CUMMINGS: No. He’s just—exactly, he’s very just kind of endeared by—I have five everyday, come home with a new dog or a pig or a horse. He’s a very patient man, and I need that.


LEWIS HOWES: I interviewed a friend of mine named DeVon Franklin. Do you know this?


WHITNEY CUMMINGS: It’s familiar.


LEWIS HOWES: He’s produced different movies, written books. I don’t know if I want to [inaudible]. His wife is Meagan Good. Is that her name, Meagan Good? He’s like a pastor and speaker, he’s pretty inspiring.




LEWIS HOWES: He wrote a book called The Wait where he waited to have sex with his wife until they’re married, right? And he talks about relationships. And I said—I went through a break up the end of last year and I interviewed him afterwards, and I go, “When do you know you found the right partner? Maybe not like your soulmate, but the one who can be The One.” And he, without hesitation, said, “When you feel at peace.” I never thought about that before.




LEWIS HOWES: When you just mentioned this, how it’s like peace at home so you can be chaotic and take risks in the world.


WHITNEY CUMMINGS: I can’t walk into my house and—I mean, I can say to him. I mean, I feel really lucky that I can go, “I don’t have a lot to give this week.” I can say that. “I don’t have a lot to give today.” You need someone who’s able to get their internal needs met without you. Have their own friendships, have their own life, get their own—drive their own value from their job, at their work or family or whatever. And he also—I think for me, you’re never going to find the perfect—that’s not a thing. It’s like, are you with someone who’s willing to course-correct? Are you with someone who’s willing to grow for you, if that’s so what you need? So for me, there was like a couple of things. Like when we met, I was like, “This doesn’t work for me. Is that something you’re willing to change or not? And if you’re not, I just got to go.” It’s [inaudible] what your bottom lines are and seeing how flexible the person is. This is the first time I entered a relationship as a business deal. Here’s the things I need, here are the things that don’t work. Are you willing to change those? If not, I got to go. No love lost.


LEWIS HOWES: How many things did he have you change? I’m talking about 20 things, I’m gonna be like, “Damn, this guy’s—”


WHITNEY CUMMINGS: I had to change some things, too. And they made me better.


LEWIS HOWES: He had some non-negotiable, she was like, “All right, you’re—”


WHITNEY CUMMINGS: We made each other better. I think. And there’s some things I’m like, “That’s not going to change. I don’t have time to change that.” It’s a negotiation. It’s emotional negotiation that’s like, what’s tolerable. But I think to me, the thing that’s the most valuable is that we can be in the same space and not be talking or touching each other. That to me is a big deal because I used to think that intimacy was about proximity.


LEWIS HOWES: Always like touching and talking. [i]


WHITNEY CUMMINGS: Always. My horse taught me that. You can coexist with somebody and not be so close that you’re going to put each other in danger all the time. There’s this thing I love that we say in program is that if you are holding a handful of sand—if you hold it like this, you can hold it forever. But if you hold it like this, you’re going to lose it. The goal is to always hold it like this—anything.


LEWIS HOWES: It can leave at once.


WHITNEY CUMMINGS: That’s it. “I love you, keep going” is our saying. I love you, keep going. Go to your other thing—go have your—do that. Because this is just—you never want to be here, you want to be here.


LEWIS HOWES: I was thinking about being here like moving up together side-by-side. Progressing, yeah.


WHITNEY CUMMINGS: Well, that’s right. This is the other thing—


LEWIS HOWES: Forwarder, [inaudible]


WHITNEY CUMMINGS: I didn’t learn this as a kid.


LEWIS HOWES: They didn’t teach us in schools, right?


WHITNEY CUMMINGS: Your listeners are like—maybe this is so obvious, but something that someone explained to me, this neurologist, she was like, “If two trains are going like this, they can go forever. But as soon as you’re here…”


LEWIS HOWES: You crash.


WHITNEY CUMMINGS: Yeah. And you can crash in relationships. You’re just so—him and I can coexist in the same room. I can be on my phone, he can be reading a book. We’re not “What are you doing?” Him having a life is not a rejection, and me having a life and ambitions is not a rejection to him personally. And I’d only been in relationships where me going on a trip, he has to come and meet—if you, then I have to come with you. This sort of interdependence, not codependence was something that really took me a long time to learn.


LEWIS HOWES: Who was more influential for you growing up, mom or dad?


WHITNEY CUMMINGS: God, that’s such a good question. God damn it, you’re asking such good questions. I think it was—probably my—I don’t know. I don’t know. Probably my—influential in different ways. But yeah, maybe my dad.


LEWIS HOWES: What was the biggest lesson he taught you? Whether through actually him saying a lesson or just an example or what he didn’t do or?


WHITNEY CUMMINGS: He said something to me that—I didn’t understand how good his advice was until he passed. Because I had this narrative that I have a crappy dad, I have a crappy mom, and that’s all we focused on. Then you do a little work on yourself and you’re like, “Okay, there were some major gems in there.” He used to always say, “Ask other people questions, they just want to talk about themselves.” It took me so long to take that advice because I thought when you meet someone, you have to entertain them and you have to impress them and you have to show them all the things that you know. It didn’t occur to me like, “No, just ask the person about themselves, that’s how you connect with somebody.”


Like I thought everytime I met someone, I had to perform for them. I just thought that that was the arrangement. It took me a long time to understand that the easiest way to connect with someone is to just ask them questions about themselves. I know that sounds so obvious, but it’s such a life hack and it’s such a great way to me now in business to find out who I’m dealing with because I like to decide who somebody is, and then when they don’t match how I’ve cast them, I get confused. “I’m not interested in who you are, I’m interested in who I think you are, and then you’re disappointing me.” It’s just like the most backwards. I’ve made an assumption about you and then you didn’t match my assumption instead of actually just doing the fieldwork and finding out who somebody is and if it’s a good match.


That was really helpful for me. He also gave me some really good advice where he said, “Be careful with how independent you come off because it doesn’t occur to other people to help you or give you any kind of emotional support.” Because what I would do is, “I’m a strong woman, I’m independent, I’m fine. And, da da da and like, why isn’t anyone helping me? Why am I doing everything alone?” It’s like it would never occur to anyone. So just asking for help was a really big deal for me for a really long time. Just saying, “Can I get some help with this?” And then not it being a shame-y, gross, I owe you, you owe me, and now I’m keeping score. Because in my household, asking for help or involving an adult and a problem came with guilt or shame or you’re needy. Never just too much of an emotional aftermath.


LEWIS HOWES: You’re not good enough to do on your own. Or smart enough or whatever.


WHITNEY CUMMINGS: Totally, totally. Just little things like that that probably—but also, my dad was gone a lot. I definitely have been defined by the absence of a dad when I was a kid. It took me a really long time to not decide that all men were that way or to not let it frame the way that I saw the world.


LEWIS HOWES: How did the relationship end for you when he passed?




LEWIS HOWES: Were you in a good place, do you feel like or?


WHITNEY CUMMINGS: No, not really. I think that death is such a defining part. It’s interesting because—I don’t know if anyone wants to hear about death but all the things that I’ve been working on for so long kind of click into place when a death happens. I’m working so hard on boundaries, I’m working so hard on saying no. I’m working so hard at reducing the amount of things on my plate, working so hard to not do things out of obligation. I’ve spent so much time doing that. And as soon as I lost my dad, it was like, “I’m not doing that. No, I’m not going on a hike with that person.” Everything becomes so clear, what’s important and what’s not. It’s interesting.


LEWIS HOWES: It’s sad that it needs something like that to happen for us to course-correct our lives.


WHITNEY CUMMINGS: Or just me. It could be me and what I needed. I don’t know how that tool is helpful. Don’t kill your dad to emotionally make for the progress you need. But it was something that was a little bit like his passing kind of was just a really big part of things clicking into place. In a weird way, I think it’s the gift he would have wanted to give me, in a weird way. He had a stroke, both my parents had strokes, which is a big part of why I got so into neurology and how to understand it really quick because I was all of a sudden in ERs, looking at brain scans, and people talking about the prefrontal cortex and I’m like, “Oh my god, I have no idea what that means,” and finding out what part of the brain affects what. So I think that ultimately, he gave me this incredible gift as a side effect of something kind of tragic.


LEWIS HOWES: When did he pass?


WHITNEY CUMMINGS: About a year and a half ago. Almost two years ago. It was interesting because you really find out who the people are around you when someone in your life passes, because grief makes you boring and makes you unable to give anything. And you really find out the kind of people that can show up and tolerate you grieving, really calls out your circle because you realize like—


LEWIS HOWES: [inaudible] being the fun one, the entertaining one, and the—


WHITNEY CUMMINGS: Like, are you still my friend if I’m just staring at the wall like a zombie crying for 6 days? Am I still someone that you wanted to be around? The tectonic plates really shift in your life when something like that happens. And I had just started dating the person I’m with. The way he handled it, I think is really what made me understand.


LEWIS HOWES: What great partnership is.


WHITNEY CUMMINGS: He handled everything. He just went into “handle it mode,” and I was like, “Okay.” So I feel grateful that—I think a  lot of the damage that my dad—I feel like I got from him, him passing at the time that I had started dating Miles gave Miles the opportunity to step up and show me who he was. It was kind of kismet, it was sort of this weird, divine thing where I was able to sort of—him passing is how Miles was able to step up. I was able to kind of undo the cycle kind of thing through it. it was pretty surreal.


LEWIS HOWES: Do you feel like you got to say everything you wanted to say to him?


WHITNEY CUMMINGS: No, and that’s okay.


LEWIS HOWES: You felt at peace about everything or do you wish you would’ve—


WHITNEY CUMMINGS: I’m so not this person but I’m going to be this person. I did do ayahuasca a couple of months after he passed, like six months, because the grief was just—I didn’t know what to do with it.


LEWIS HOWES: Strong. Yeah.


WHITNEY CUMMINGS: Yeah. I think because I’m such a “keep moving to get out of your feelings anyway,” I really didn’t want to run from it. And for the grief to manifest in other ways, I didn’t want that energy to come out, and the workaholism or the codependence or whatever. I actually think what happened for me with ayahuasca and why I think it’s a helpful tool is I didn’t hallucinate on ayahuasca. I kind of realized that I was hallucinating every day. And on ayahuasca, I kind of saw things clearly. I was able to take on a lot of the things that I thought were weaknesses for my dad as strength. And I was allowed to sort of accept the things in me that I got from him and alchemize them into positives.


It’s like, he was always working and too much. I was just trying to find ways to use what I thought were weaknesses of his and make them strengths and accept the parts of him that were in me. “I don’t want to be like my dad, I want to be like my mom,” that’s what we say. Maybe there are good things about them, maybe we’re just seeing them wrong. Or maybe we’re just so wrapped up in our own judgment and blame that we can’t see it. My dad had a very sceptical take on people. He always called everyone liars, thieves, and worms, is what he would say. It’s so negative, but I don’t know. I found myself overcompensating and the pendulum swinging too hard and trusting too much and being—


LEWIS HOWES: Going all in.


WHITNEY CUMMINGS: All in, trusting everybody. “Yeah, sure, manage my money.” “Sure, come stay at my house.” I just didn’t have enough of that sort of what I call “healthy scepticism” and healthy boundaries, and a healthy sense of seeing red flags. I kind of—it helped me stop divorcing myself from the story that “my parents were so messed up and I want to be totally different than them.”


LEWIS HOWES: Do you feel like you do things to make your dad proud still?


WHITNEY CUMMINGS: Oh my god. Oh god. You’re so good at this. When my dad passed, I had somewhat of an existential crisis because I realized so much of my engine was to try to impress him.


LEWIS HOWES: [inaudible]


WHITNEY CUMMINGS: I think more of my dad. My mom, not so much. My mom was more like physical stuff. Like body, appearance stuff that I’ve had to sort of work through.


LEWIS HOWES: You’ve got a great combo.


WHITNEY CUMMINGS: It’s a whole other thing. Yeah, real doozy. Real [inaudible]. They were made for each other. I realized when my dad passed, I felt like I was sort of in a freefall because I was like, “Do I even wanna do comedy?” The person that I was trying to impress is gone, I don’t even know why I’m doing any of this. I cancelled a bunch of projects I was doing, I checked out of a lot of things, I had to sort of completely rebound my priorities and figure out what I wanted.


LEWIS HOWES: What’s the priorities now?


WHITNEY CUMMINGS: The priorities now are for me—this probably sounds gross but I am big on making money because it is freedom. I didn’t have that growing up so I do try to make decisions based on it being lucrative enough to be able to help a family member out if they have an issue. A lot of my family members don’t have health insurance and they didn’t go to college so for me, I take a lot of pride in being able to earn so that I can help people. I don’t have cars. That’s not my thing, and shoes, and clearly, clothes is not my thing. I like to be able to give people the ability to sleep at night because they’re not stressing about money. I do make a lot of decisions based on earning.


LEWIS HOWES: You’re not making millions at The Comedy Store every [inaudible]?


WHITNEY CUMMINGS: No. $15. The night you saw me, I made $15. I work for free a lot because stand-up is like bodybuilding. You’re in the gym for a year making nothing and then you get your special or whatever. So I definitely—once my dad died, I got a little more mercenary about the way that I spent my time because I worked for free for so long and continued to until my dad passed. And then just really high quality—like, “Is this going to move the needle or not?” After that, the first thing I did was Roseanne which did not end as planned.


LEWIS HOWES: God, isn’t that crazy? It was so big. Like the launch and the show was so big. Only one tweet ruins it all.


WHITNEY CUMMINGS: Yeah. I don’t think it was one.


LEWIS HOWES: It was other stuff. It seemed like one tweet was what ruined thousands of people’s—


WHITNEY CUMMINGS: Ostensibly, yes, exactly. It was the tweet that broke the camel’s back but there was definitely more before that I hadn’t seen, and that was my mistake. I didn’t follow her before. My dad said, “Ask people questions,” I didn’t ask enough questions and I didn’t do enough research. At the time, it was like, we’re going to reach a bunch of people that we wouldn’t reach normally. And I think that Hollywood, we forget we’re in this echo chamber and we are talking to such a small number of people and this is an opportunity to talk to more people. So I think since my dad passed, I’m just trying to be a little more big picture in the things that I take. I don’t take jobs anymore to impress people, I don’t take jobs anymore because there’s a celebrity involved whom I—this person might think is impressive. I don’t have those sticky motives anymore. It’s like, “Do I want to do it or not?” And the answer is usually no. Like, am I going to be proud of this? Am I going to get paid? And pride is a big thing for me now that my dad has passed.


LEWIS HOWES: [inaudible] pride [inaudible]


WHITNEY CUMMINGS: That’s right. Am I proud of it? Am I paid by it? That’s sort of the way that I live now because it used to be like, “Oh, whatever.” I’m trying to think of a celebrity. “Julia Roberts is a producer on this, I’ll be able to tell my dad that I’m working with Julia.” You know?


LEWIS HOWES: “He’ll love me more.”


WHITNEY CUMMINGS: Totally. It used to be that stuff. It’s kind of not like that anymore. It’s like, “Would I do it for free?”


LEWIS HOWES: Because you love it. 




LEWIS HOWES: But I wouldn’t make a lot of money.


WHITNEY CUMMINGS: I know that it’s [inaudible] to say that, but I think it’s important to know your value and to know your worth.


LEWIS HOWES: I think financial freedom is a powerful thing. Having resources, you can serve humanity in a bigger way. You can create the products you wanted, you can create the life you wanted, you can have the people around you so I don’t think it’s wrong if you know yourself. But you’re not buying it to freaking buy gaudy stuff and flashy. You’re buying [inaudible].


WHITNEY CUMMINGS: This shirt was $45


LEWIS HOWES: I love it.




LEWIS HOWES: This is $45 as well. We’re the same person. 


WHITNEY CUMMINGS: That is a very fancy shirt.


LEWIS HOWES: This is a blank t-shirt. 


WHITNEY CUMMINGS: In LA, those are a big deal.


LEWIS HOWES: They call it a basic tee, I think. 45 bucks.


WHITNEY CUMMINGS: Basic tee. It’s not a V so we’re good. I feel like you’re a deep-V guy. 


LEWIS HOWES: Not a deep-V, just like a simple V.


WHITNEY CUMMINGS: In Turkey, you’re going to have those V’s out.


LEWIS HOWES: [inaudible]. I mean, I do live in West Hollywood. There’s a lot of deep V’s, but it’s just like a little classy [inaudible].


WHITNEY CUMMINGS: Yeah, little tiny V’s, slight suggestion of V. Just like a little—they have a  clavicle peeking out. A little flirting. “Oop, hey! Oop, uh-oh!”


LEWIS HOWES: Oh, man. So pride and pay.


WHITNEY CUMMINGS: It’s like my bar is higher lower, and the bar is changing. So for me, it’s like, 10 years ago, 5 years ago I’ve been like, “I’m not going to do it because that’s selling out.” I don’t have that anymore. It used to be like, I was trying to impress people. I was so worried that if I post this ad on Instagram of me performing at a casino, what are comics going to think. I just don’t have that anymore. I don’t have the same kind of shame around my choices. I get to be a little more selfish in a good way. A good kind of selfish.


LEWIS HOWES: I remember I talked to Steve Aoki when I had him on. I was like, what’s one of your biggest fears or concerns? Something like that question. He said, “Being irrelevant”. I think I see a lot of people in Hollywood who like, they get this special and then they don’t get picked up again for the next seasons. So they’re hot and then it’s just that they’re chasing to be hot again. There was so much excitement and expectation or hope that it’s going to work out. How do you face that because you had 2 Broke Girls, huge hit. Then you had your own show which was like 2 or 3 seasons, I think. So maybe it didn’t last as long as the show you were creating. How do you deal with that aspect of Hollywood with a career of hot, maybe not as hot. Really hot and then okay, swell.


WHITNEY CUMMINGS: The vicissitudes of the in and out.


LEWIS HOWES: How do you deal with that? Emotionally or—




LEWIS HOWES: Maybe you’re better now because you’re choosing things, you don’t really care what’s working [inaudible] but—


WHITNEY CUMMINGS: Yeah. I guess, to me, I think you put something out when it’s good and that’s how you stay relevant. No, it’s like—I just—I agree with Steve and I feel that a lot, too. But I also know feelings aren’t facts, and I know what feelings are valid and which aren’t. So it’s like to just put stuff out to stay in the zeitgeist is—I personally don’t know a lot of comics. It takes a year to put a good special together.


In order to make good art, you have to have a life and you have to make mistakes and you have to go out in the world. I found that when I was doing three shows, it was this whole thing. Everyone thought of me as this big success. I was in a writer’s room all day and I wasn’t having a life. In order for art to imitate life, you have to have a life. And I didn’t have one. So I was limited in how good of an artist I could be. Now I believe you make something and you go off and you live more and you grow and then you come back and make something else and hopefully, your work is actually evolving. If I just only kept putting things out, I would be putting the same thing out.  How could I improve? So I’m a big fan of going away, growing, restoring, living, coming back, and elevating. That’s just my process. I also do lots of different things. So I’ll go do a special and then I’ll do a show and then I’ll do a book. I’m also—


LEWIS HOWES: A robot that—


WHITNEY CUMMINGS: I did made robots. I just don’t care if people were interested in me. I just want to be interested.


LEWIS HOWES: In what you’re doing.


WHITNEY CUMMINGS: Because otherwise, it’s not going to be good.


LEWIS HOWES: This is what I like. I feel like we’re siblings or something because—


WHITNEY CUMMINGS: Past life twins or something.


LEWIS HOWES: I do a lot of things where my peers were like, “Why are you doing that?” I wrote a book a year and a half ago about masculine vulnerability. It’s called The Mask of Masculinity.




LEWIS HOWES: And everyone was like, “This is the worst business association. You should do something else based on your last book and keep building up on it.” I was just like, “This is what’s going to be interesting to me and what I felt like is needed right now in the world that I’m proud of.”


WHITNEY CUMMINGS: You’ve worked so hard and you’re not allowed to do—I’m being like, “This one’s for me and that one’s for you.” I do that with jokes sometimes. There’s a couple jokes, I’m like—


LEWIS HOWES: No one laughs.


WHITNEY CUMMINGS: I know this never—this one is just for me. I like this one. This gets like    70% of the reactions of the other ones but I like it. I think that we’re so afraid of being boring that we’re boring ourselves. I don’t know how to put out authentic work if the engine is just to keep putting out work. Who’s benefiting from that? I mean, there’s just so much to choose from now. And making something for the sake of making it, I’m always big on “why.” What’s the “why” on this? Why am I going to give this thing a year of my life or whatever. Like making the movie, for example. That was just an experiment. We made it in 15 days for not even a million dollars. It was like, I mean—the coverage, it was very—


LEWIS HOWES: [inaudible] everything and everything else, yeah.


WHITNEY CUMMINGS: Totally. Figuring out in post and fixing it in post. Doing that weird, little—I wanted to learn about neurology and I wanted to make a movie about—


LEWIS HOWES: That’s great. I loved it.


WHITNEY CUMMINGS: I just was like, “I wanted to make the thing that I wish it had existed. And no one else was going to make a movie—


LEWIS HOWES: Gosh, that’s what I always say. I’m creating what I would want—


WHITNEY CUMMINGS: I want a movie about neurology that I wish when I was 23, there was someone explaining to me oxytocin and dopamine and when you’re in a relationship for a certain amount of time that you start producing less oxytocin and it’s not personal and how cortisol works and how organizing things reduces cortisol, that’s why I’m so obsessed with how everything—for me, I would have saved so much time with taking things personally and overpathologizing myself and other people. I had been like, “He’s not mad, that’s just cortisol. I’m going to give him a couple of days for it to wear off and then we’ll talk about it.” I guess I just wanted that to exist. And then as far as the book, this one couldn’t have been—it came out the day of the Vegas shooting so there were some interesting cosmic thing where it was—the universe is knowing—“we’re making sure you’re doing this for you and for the right reasons” Because glory isn’t always going to be the reward. I think when something comes out based on the success of it, then you decide if it was worth it. That’s so unhealthy to me.


LEWIS HOWES: It should be like, it’s successful because I’m proud of the work I created. If one person reads it or a million people buy it, right?


WHITNEY CUMMINGS: Yes. The reaction is the only thing that matters anymore. I found that I was chasing a reaction, chasing a reception, and chasing a feedback.


LEWIS HOWES: And an applause.


WHITNEY CUMMINGS: And an applause, that’s exactly right. So for me, I just want to be able to look back and be proud of the choices that I’ve made instead of just like on a hamster wheel trying to stay in people’s timelines. Some of the people’s career that I respect the most—it’s like when we’re talking relationships. You want to miss someone a little bit.




WHITNEY CUMMINGS: I think that right now, we’re in such like, fatigue of people. I think that I also experienced being ubiquitous and having a—


LEWIS HOWES: You were everywhere.


WHITNEY CUMMINGS: And it didn’t go great. I think I’m good—


LEWIS HOWES: Financially, maybe it went okay. 


WHITNEY CUMMINGS: It went great. I’m good in small doses. I also know that about myself.


LEWIS HOWES: Cause you have what, you had a comedy tour, you had the creator of 2 Broke Girls, you had your own show “Whitney.” You had a bunch of stuff happening at once.


WHITNEY CUMMINGS: And I just think that—I don’t know, I think that the artists being ubiquitous is you don’t want to overwear your welcome.


LEWIS HOWES: What are your thoughts on like Steve Harvey or Kevin Hart who is always everywhere all the time?


WHITNEY CUMMINGS: Those were such weird people to pair together.


LEWIS HOWES: Both comedians, right?


WHITNEY CUMMINGS: Wait, Steve Harvey and Kevin Hart?


LEWIS HOWES: They’re both comedians, right?


WHITNEY CUMMINGS: Yeah. I mean, Kevin Hart—what he has done is amazing and he does it so brilliantly. It’s like he has what, a movie come out a year and then—


LEWIS HOWES: Then a comedy special a year.


WHITNEY CUMMINGS: Yeah, but I’m not sick of him. I don’t know why. I think he’s just so endearing and he’s so charismatic and maybe he’s the exception to the rule. But I don’t feel like a fatigue on Kevin.


LEWIS HOWES: Interesting. Because he’s real and also authentic. He’s not forcey, maybe.


WHITNEY CUMMINGS: Yeah. I don’t know why I don’t feel that. I’m not sure why.


LEWIS HOWES: I think if Steve Harvey—because he’s got multiple shows at once.


WHITNEY CUMMINGS: Yeah. Oh, god. Does he?


LEWIS HOWES: Hey. He’s got Family Feud, he’s got Steve Harvey Show, he’s got—


WHITNEY CUMMINGS: I’m behind on Steve Harvey, I don’t know why.


LEWIS HOWES: He had the kids show. Like the kids celebrity show. America’s Got Talent for kids.


WHITNEY CUMMINGS: Right, right, right.


LEWIS HOWES: That feels like three or four shows at once. And a radio show and—


WHITNEY CUMMINGS: That’s right. You’re right, you’re right. Okay, okay, that’s fair. I just can’t think that way. In desperation to be relevant—I don’t know, that feels like chasing that just feels like a motive. To me, I just try to be authentic if I can and honest with myself and to just try to keep up with everybody which is what I used to do, frankly. It didn’t yield the kind of work that I really felt like I could be proud of. I’d rather just be mindful about it, figure out what I want to put out in the world, and put it out when it’s ready.


LEWIS HOWES: What’s your biggest fear now then? 


WHITNEY CUMMINGS: I mean, being irrelevant is up there. I just know it’s an irrational fear. Because for me, the fear of being irrelevant triggers codependency, rush culture, get it out now instead of when it’s right. This chasing. And then it doesn’t get the reception you want and you feel worse. My biggest fear now, being boring is one that I struggle with. That’s a big one. Podcasts are helping me with that because I’m just like, “Is this interesting to anyone?”


LEWIS HOWES: You said the answer because I was always very insecure growing up because I didn’t think I was interesting enough to people. And I would say stupid stuff that people would be like, “Whatever.” It happened two or three times that it stuck in my mind that people didn’t want me around because I was just stupid or ignorant or whatever it was.


WHITNEY CUMMINGS: This youngest kid.


LEWIS HOWES: In high school and in college, I really shifted [inaudible] like, I’m going to ask amazing questions and just listen. I’m not going to try to say anything. I’m going to do the opposite. And someone told me later, they were like, “You do a really good job of asking and listening.” And—


WHITNEY CUMMINGS: You’re amazing at it.


LEWIS HOWES: Thank you. And you said the most interesting person is always the most interested person. That’s what you said. I think it’s something why the podcast does well because I just want to ask questions.


WHITNEY CUMMINGS: But you also ask questions that nobody else asks and you’re very thoughtful and mindful about it. And you also ask it and then let the person answer. There’s a lot of people that go like, “What’ scares you the most because what scares me the most—” And you’re like—you know what I mean? You really wait for the answer and it’s—


LEWIS HOWES: It’s a practice, though.


WHITNEY CUMMINGS: It’s actually jarring because I keep waiting for you to change the subject. I’m like, oh, he’s really—I really have to answer that. It’s actually kind of jarring.


LEWIS HOWES: It’s not a comedy podcast where everyone’s interrupting each other.


WHITNEY CUMMINGS: No. I’m like, “Is someone going to do a bit or prank me?” You land. You stick the landing.


LEWIS HOWES: Yeah, yeah. [inaudible].


WHITNEY CUMMINGS: You really are just—silence is your tool of success. Like you ask the question and you wait for the answer which is unbelievably—


LEWIS HOWES: Well, it’s called an interview for a reason.


WHITNEY CUMMINGS: I know, but it’s jarring because I’m usually good at squirming out of things, and not with you. But I think that that’s the skill that I’m so happy for all your listeners because if people just did that on dates, it would save them 5 years of bad, toxic relationship. If you actually just asked a question and listened to their answer, which is the advice my dad gave me that seemed so simple.


LEWIS HOWES: And not trying to be interesting or try to tell the joke all the time.


WHITNEY CUMMINGS: Or have your reaction—the joke—just to really listen and let people reveal themselves. And then once they do—


LEWIS HOWES: People want to be heard and seen. People always tell me, “Gosh, I didn’t even know what he said to me, but I talked to him for 20 minutes and he’s just like the coolest guy. He’s just such a nice guy. I didn’t even know what he said, but I want to help them.”


WHITNEY CUMMINGS: And I had spent so much time trying to get love indiscriminately from people whose love I had no business engaging with. I spent so much time going like, “I don’t even know if you’re the kind of quality a person I should be with but I’m going to get your love regardless.” It was always like how to beguile people, how to charm people, how to get them to like you, and you’re stuck in this relationship with someone. And you’re like, “Oh god, why did I get so hard to get your approval? You’re a nightmare.” So for me, it’s—I’m learning a lot from you because I don’t do this enough in my hiring decisions. I don’t get to know people enough in my hiring decisions. 


LEWIS HOWES: Hire slow [inaudible] fast.


WHITNEY CUMMINGS: And I get to know their character defects and their song and dance, and I don’t really ask mindful questions to find out what their character is.


LEWIS HOWES: As a business owner as well, we need to fill a spot because you’re doing too much of the work you don’t want to do or you’re suffering in a situation. You want to put someone that quickly, but that’s why you should wait.


WHITNEY CUMMINGS: And I don’t ask enough smart questions and listen to the answer.


LEWIS HOWES: You should let other people interview them first on your team.


WHITNEY CUMMINGS: Oh, that’s good.


LEWIS HOWES: I just brought a new assistant. My last assistant had been with me for 6 years, she’s transitioning to start a family. So I have my assistant interview people first. I was like, “They need to meet your requirements.” Then when she found a few people that she liked, they go to my COO, he interviews them, and they meet his standard. Am I going to like this person? Are they going to fit into our culture?


WHITNEY CUMMINGS: What’s the biggest thing you look for in somebody?


LEWIS HOWES: For me, it’s attitude. I can’t stand people that make excuses or don’t have the willingness to figure it out, you know what I mean?


WHITNEY CUMMINGS: I’m big on—you can make mistakes, you just have to admit you made one. If you can’t admit you made it, then we’re in insanity. You can make a mistake a day if you want, a huge mistake a day.


LEWIS HOWES: Just don’t do the same one over and over.


WHITNEY CUMMINGS: Correct. My bar is really low. And what’s wrong with that? No, but if you can’t admit I was wrong, that’s my biggest sort of bottom line and red flag with people.


LEWIS HOWES: Exactly. So attitude, effort. For me, I was never the best athlete but I was always the MVP because of my effort. And my willingness to have clear vision, and I was willing to get up early, work out. I never drank my whole life.




LEWIS HOWES: I’ve never had a sip of alcohol. In college I was just like, I need a superpower, and it’s going to be effort and my mindset. So effort, attitude, the desire and willingness to continue to learn. Somebody doesn’t need to me to hold their hand.


WHITNEY CUMMINGS: How would someone be able to construe that to you in an interview?


LEWIS HOWES: I would tell them this.




LEWIS HOWES: I would say, “This is what I’m looking for. I need an effort, I need an attitude.” So I would ask them questions like, “What would you say—” I don’t know, I’m just thinking for a question about— “If you made a big mistake and I got upset, how would you react? Or you knew messed up, how would you respond?” You just kind of have to feel it out. If they’re like, “Ah, well…”



LEWIS HOWES: If they’re like, “I would own it, I would take responsibility, and I would want to see how I can get better, I would want coaching.” Cool.




LEWIS HOWES: You set traps?


WHITNEY CUMMINGS: That’s healthy. I do. And it’s the same thing I’ve learned in relationships. This probably sounds manipulative—you have to sometimes. You got to test people. Your listeners might think that I’m off the grid on this, but I go like, “What was it like at your last job?” And if they say negative things about their boss, I can’t hire you. The same way if you’re dating someone and you say, “How did your last relationship end and?” and they say, “Well, she’s crazy or he was—” It’s like, I already know that you blamed people and I already know that the way you do anything is the way you do everything and it’s important when people reveal themselves to just—


LEWIS HOWES: Like when you take ownership for everything in your life and responsibility, that’s when you feel like, “Okay, I can trust this person.” Maybe they’re going to mess up, maybe they’re going to make mistakes. But they’re going to own stuff, and they’re willing to grow.


WHITNEY CUMMINGS: I think we have to really remember that we are wired to have a common enemy, it’s something we bond over. And I think it’s really important to know how we’re wired to just honor that. It’s the same with people with dog breeds. They want to say, “[inaudible].” But we can’t, and then people go, “Breed doesn’t matter.” It all matters. Nature and nurture both matter, and I think it’s important we just have to understand part of our nature sometimes. When you’re dating someone new and you both get to be mad at the person’s ex, we’re bonding over something because that’s what we’re wired to do.


LEWIS HOWES: Something negative.


WHITNEY CUMMINGS: Right. But then you go zoom out and it’s like, “Oh no, that’s a red flag.”


LEWIS HOWES: It’s not healthy. I want to ask you a couple of final questions, but I want to make sure people check out your book, I’m Fine and Other Lies. You guys can go get this book right now since it was such a big hit the day it dropped.


WHITNEY CUMMINGS: That was so wild.


LEWIS HOWES: Really funny stuff but powerful about anxiety, overcoming all the challenge you’ve gone through.


WHITNEY CUMMINGS: It’s about addiction, it’s about codependence, it’s about eating disorders, it’s about freezing your eggs. It’s about sort of—a lot of sexual assault. It’s about sort of everything we all have dealt with, and it was interesting because to come out the day of a tragedy, at least to go like, “You’re going to have to wait two weeks to promote it and we have to relaunch it.” Like so much of the book is about not trying to control what you can’t control. So for that to have happened for me to not surrender and surf that wave would have meant this book was for nothing. But yeah, and I have a new stand-up special.


LEWIS HOWES: It’s on Netflix, right?




LEWIS HOWES: [inaudible] hilarious.


WHITNEY CUMMINGS: It’s called Can I Touch It? and it has a robot in it.


LEWIS HOWES: Which I touched already.


WHITNEY CUMMINGS: You did, you touched, yep.


LEWIS HOWES: I touched it. You gave me a permission. I asked for permission.


WHITNEY CUMMINGS: It’s called Can I Touch It? for many reasons because I talk about all this sort of harassment stuff in the news. And in comedy we’re at this place where it’s like, “Can I touch this? Can I talk about this? Can we talk about this? Can I say this? Can I have this opinion?”


LEWIS HOWES: I feel like it’s sad that comedians are getting shamed for so much. In some ways, maybe there’s some crossing of lines but sometimes. And I feel like we’re just so wound up, like everything is personal.


WHITNEY CUMMINGS: There’s a lot of [inaudible] but comedy’s always been a democracy. It’s just that where people vote is changing—


LEWIS HOWES: It evolved with it.




LEWIS HOWES: [inaudible] gonna laugh and show up.


WHITNEY CUMMINGS: Yeah, it’s like funny’s funny. I don’t think there’s words that I don’t—there is a shift happening. I don’t think that people should be silenced, but if you don’t get a laugh, it—


LEWIS HOWES: I think it makes you be more creative.


WHITNEY CUMMINGS: It’s not because the audience was stupid, you know what I mean? Well, you guys are laughing because you’re [inaudible]. It’s like, no, I always give the audience the benefit of the doubt. And the audience is always right. I think that because taste is changing and like what you just said—what’s funny is changing. Because what we see in the news all the time, it’s so brutal that I think what people want to see on their night off is changing. It used to be like, We make fun of the president and then we say the things no one can say. We hear about that all day, every day now with Twitter. We’re constantly seeing negativity all day in the news. So I think what people want to see on their night off when they’re paying 80 bucks is just changing, and that’s okay.


LEWIS HOWES: 80 bucks a seat? I’m in the wrong business.


WHITNEY CUMMINGS: Well, not when you saw me, no. But yes, I think it’s just—to me, and your listeners are obviously about thriving and success. You cannot stick to the thing that worked a year ago if it doesn’t work anymore.


LEWIS HOWES: In your relationship, in your business, in your life.


WHITNEY CUMMINGS: In anything. How many times are you going to stub your toe on the table before you either move the table or go around the table? It’s 12-step 101, God help me to accept the things I cannot change. What can you change, what can’t you change? And then go from there.


LEWIS HOWES: I like it.


WHITNEY CUMMINGS: Because right now, we’re just going like, “This thing—the thing I did five years ago isn’t working.”


LEWIS HOWES: [inaudible]




LEWIS HOWES: Gotta grow. When’s the special about?




LEWIS HOWES: July 30th, Netflix. 




WHITNEY CUMMINGS: Watch it, post it, share it on Instagram stories when you’re watching it, tag you. It’s going to be amazing. The trailers are incredible on Instagram right now.


WHITNEY CUMMINGS: Yeah. I feel like it’s half-said, that serenity prayer. I was like, “Do I even say this?” I’m assuming everybody knows that for some reason God granted me this serenity to accept the things I cannot change, control the things I can, and the wisdom to know the difference.


LEWIS HOWES: Is there anything else we can—you’re hilarious on Instagram.




LEWIS HOWES: Whitney Cummings on Instagram. They can see you on tour in LA.


WHITNEY CUMMINGS: Yeah. I’m not touring for a while. It’s kind of my stand-up special, I’m working on a new show, we’ll see what happens with it, but I’ll start touring soon.


LEWIS HOWES: Whitney 2.0, is that the new show?


WHITNEY CUMMINGS: Yeah. Well, I’ve got a robot that I’m going to start sending out for me.


LEWIS HOWES: It’s amazing, I love it. I want to acknowledge you for a moment, Whitney. Because you have an amazing heart.


WHITNEY CUMMINGS: Oh, that’s so nice.


LEWIS HOWES: You really do have an amazing heart. I think that is a thing that people should recognize the most about you. Obviously, you’re extremely creative, talented, hilarious. All these things, and you tell incredible stories, but you have a powerful heart because you continue to desire to get better and you want to improve. I think that’s what’s really special about you. So I acknowledge you for your heart.




LEWIS HOWES: So my final question, [inaudible] there’s a pause is what’s your definition of—oh, actually, I have two final questions. This one is, so maybe it will pause for a second. This one is called “the three truths.” So I’m going to imagine that you are giving the last performance, stand-up of your life and the whole world is watching. Just imagine. It’s 50, 100 years from now, you still have all your capabilities of communication. But it’s—you’re like, “All right, this is my last farewell tour,” And soon after, you’re going to die. But you’ve created everything you want to create, all the specials, books, robots, whatever you wanted in the future. But you have one last tour and one last performance. And you do this amazing show, people are laughing, they’re crying, they’re enjoying, whatever you want it to be. But at the end, you get to leave people with three things you know to be true about your life and the lessons you will leave behind. It’s what I like to call “the three truths” that this is all people to have to kind of remember you by these three lessons. What would you say are yours?


WHITNEY CUMMINGS: And I say them and they believe them? Like it works? Whatever I say works?


LEWIS HOWES: You say them, this is your truth. This is a lesson that’s for me is like when I always live in gratitude, I have a better day. Like I want to leave that behind for you is like a truth, a lesson.


WHITNEY CUMMINGS: Okay, okay. When I’m in gratitude, that would be like yours would be that.


LEWIS HOWES: I’m just making something up. Or like, the health is the most important thing in your life. That’s the truth. So just give me examples. What are your truths? I don’t want to make something up for you. I’m saying, what do you think will be all the lessons you’ve learned up to now? Imagine it’s the last performance you get to give, but the world is watching.


WHITNEY CUMMINGS: Are these more emotional, are these more—


LEWIS HOWES: Any truth you want it to be. For me, it can be lessons of life. Not like when you see a dog and buy it or something, but like a lesson that you would want to leave behind. This is all people would have to remember you by. What would you want to leave behind, these truths, these lessons?


WHITNEY CUMMINGS: This is a nightmare question. This is hard. Can I have an example of one that you’ve liked?


LEWIS HOWES: Yes. Someone said, Sam Harris—he’s like, “Always tell the truth. It solves so many problems when you tell the truth.”


WHITNEY CUMMINGS: Totally disagree.


LEWIS HOWES: He said it might be hard—


WHITNEY CUMMINGS: Sometimes you have to lie to people to get them to leave you alone.


LEWIS HOWES: Okay. Well, now it can be your truth. 


WHITNEY CUMMINGS: No. I’m such a big fan of Sam Harris, I’m totally joking. I need to take that advice because I’m always like, “Sorry, can’t make it today. I can, but I’m not going to. I mean, I really need guidance to know how to—I really need walls to operate in because I get too—


LEWIS HOWES: Yeah. Imagine it’s your last day and you’ve created everything you want to create in the world. TV, movies, whatever—the family you want. But you’ve got to take it all with you. So no one access to any of the work you have anymore. So they don’t [inaudible] your content anymore. Social media’s all gone. But you get to write down three things to be true to you. You get to say a message in front of an audience that you can leave behind, and this is all they have. These lessons to live by. Kind of your commandments.


WHITNEY CUMMINGS: I should’ve prepared for this, I know everyone else does. 


LEWIS HOWES: No, they don’t.


WHITNEY CUMMINGS: Really? It always goes like this? Because you’re dealing with a bunch of perfectionists and I want to get it right. I want to win this one. I want to beat Sam Harris.


LEWIS HOWES: It’s better with what’s on your mind right now or what’s on your heart is even better.


WHITNEY CUMMINGS: It’s tricky. Now you’re getting an insight into the part of my brain I’m not proud of because I get really indecisive and I get really dichotomous in my thinking because my first instinct was you don’t owe anyone anything and no one owes you anything. That’s something that really helps me when I walk through [inaudible] because I’m like, “Nobody owes me, nobody owes me anything,” when my expectation starts getting too high. But at the same time, I want to say kindness fixes everything and forgiveness fixes everything but then I’m like, “But you don’t owe—” Do those contradict each other or am I a hypocrite?


LEWIS HOWES: Is that a truth or no?


WHITNEY CUMMINGS: No. None of these are good yet.


LEWIS HOWES: Okay. Number one, what would you say? What’s something that you could be proud of to leave behind as a truth?


WHITNEY CUMMINGS: But am I like trying to fix problems, am I trying to fix the world? I’m trying to make—what am I—


LEWIS HOWES: It’s your final message. You’re going to fix anything?


WHITNEY CUMMINGS: I wouldn’t do the show. How much am I getting paid for the show? If I only have one show left, I wouldn’t show up. I wouldn’t go.


LEWIS HOWES: What are you feeling right now? You can always tell me later, “Hey, I would add this as a truth.” It’s okay if you need 7 truths or 20. But if you have just three things and you feel like in the last few years that you’re like, “Yeah, those are good lessons. I’d want to share that.”


WHITNEY CUMMINGS: If you’ve met more than two assholes in one day, maybe you’re the asshole. I know it sounds like an ism, it’s just you have more power than you think in terms of—maybe it’s you. Because I think blame is such a drug and it’s tricky because we’re seekers and we’re people that are constantly proving ourselves, but it really made me feel power—the power I didn’t have. When someone’s like—when something’s your fault, at least I can do something about it. There’s something liberating in it being your fault. I love when things are my fault, I love when I’m wrong because at least I can fix it. When someone else is wrong, there’s nothing I can do.


LEWIS HOWES: You can yell at them, shame them—


WHITNEY CUMMINGS: Totally. There’s nothing you can do. Manipulate them, scream at them, and then you’re in insanity. So I think they’d probably be quotes that you’ve heard from other people that works for me. 


LEWIS HOWES: That’s fine.

WHITNEY CUMMINGS: Insanity is doing the same thing over and over again, expecting a different result. That helped me a lot, so I know that to be true.


LEWIS HOWES: Okay, that’s one.


WHITNEY CUMMINGS: This is going to sound like me being—having an agenda and this is a quote—there’s people. Like 50 people have said it and nobody knows who actually said it. It’s assigned to like 50 people, but I do think we are so disconnected from the other species on our planet. The way we treat animals is our legacy because animals are just what would have less power than us. So the way we treat our animals is the way we treat our women, the way we treat our children, the way we treat anyone who’s more—it’s how it keeps the next generation to abuse their power. So I think that is something that just the way we treat our women and children and animals is who we are ultimately. IThis comedy show is going to be awful. My last show is going to be terrible.


LEWIS HOWES: You’ve already made people laugh, now they just want to hear a message.


WHITNEY CUMMINGS: I’m going to be bombing. Like I think it’s mistreating people doesn’t make you powerful. Mistreating something with less power isn’t power. 


LEWIS HOWES: I love the quote or the meme that’s like, “My father always taught me to treat the janitor as the same as the CEO.” Or it’s like, always treat people with equal kindness.


WHITNEY CUMMINGS: The way you treat other people is a reflection of how you feel about yourself. I think that when you disrespect other people, you’re just ruining your reputation. You’re hurting yourself. So I think that that’s something that we don’t understand or something that maybe there’s a little bit of dissonance on. The way you treat other people is very much a reflection of who you are and how you feel about yourself. Are you choosing to toxify your environment or are you choosing to purify your environment?


LEWIS HOWES: [inaudible]. Okay, that’s two. Your final message for the world.


WHITNEY CUMMINGS: I don’t even like that last one.


LEWIS HOWES: I like it. How you treat other people is a reflection of you.


WHITNEY CUMMINGS: Yeah, but that’s so obvious. It’s obvious.


LEWIS HOWES: It’s [inaudible] simple. They can be simple. It doesn’t have to be something like—I think simple is profound. That’s going to be one of my truths.


WHITNEY CUMMINGS: That’s a good one. Okay, that’s a really good one.


LEWIS HOWES: Less is more.


WHITNEY CUMMINGS: I don’t know what to do. This is so hard. What’s another good one?


LEWIS HOWES: What’s in your heart right now?



LEWIS HOWES: Because you’re analysing and [inaudible].


WHITNEY CUMMINGS: I know. I just want to be good.


LEWIS HOWES: “Am I going to win this?” If you had a lesson that you could share with your heart, a lesson from your relationship maybe. Relationship with your parents, relationship with your fiancé [inaudible].


WHITNEY CUMMINGS: I’m too analytical for this question because I don’t like truisms. I don’t like [inaudible].


LEWIS HOWES: [inaudible]?

WHITNEY CUMMINGS: “Love yourself,” I don’t like that. We talked about this because it’s like—

LEWIS HOWES: This is going to be in the comedy special one day.

WHITNEY CUMMINGS: This is a nightmare. 

LEWIS HOWES: That’s like, “A guy asked me about what my three truths are, [inaudible].”

WHITNEY CUMMINGS: And I jumped out the window. Because I don’t like things, if there’s even one way to disprove it, debunk it. I don’t like it. I just go, “Well, if it’s not true once, it’s not true.”

LEWIS HOWES: [inaudible] lesson. A good lesson then.

WHITNEY CUMMINGS: I feel bad about that love yourself thing. I think people are using the self-love thing to not take responsibility for their behaviour— “But I’m going to love myself.” You still should process your consequences and ramifications. There is this new radical self-love thing that is giving people permission to be jerks.

LEWIS HOWES: Or unhealthy.

WHITNEY CUMMINGS: Yeah. “I’m going to just love myself. I drink four glasses of wine a day, but I love myself.” And you’re like, “No, that’s—”

LEWIS HOWES: There’s consequences to loving yourself that way.

WHITNEY CUMMINGS: It doesn’t mean radically just be irresponsible and don’t take inventory of your behaviour. Like look at the ruckus you’re causing around you and the damage you’re doing as well. If so, we don’t forgive others because they deserve forgiveness, we forgive others because we deserve peace. That’s a good one.

LEWIS HOWES: That’s a great truth. That might be the most powerful one, no one’s ever said that.

WHITNEY CUMMINGS: That’s the best one. That is a banger. It’s a banger.

LEWIS HOWES: Because resentment is a disease.

WHITNEY CUMMINGS: Correct. It crystalizes in your heart.

LEWIS HOWES: Rat poison. You’re drinking and you’re trying to give it to someone else.

WHITNEY CUMMINGS: Yes, and it just calcifies and you project it all [inaudible].

LEWIS HOWES: You created an energetic cancer in the world. Yeah, I like this one. So you won with that.

WHITNEY CUMMINGS: I agree. Sam, take that. This is a good one, and I don’t think I’m going to phrase it eloquently first, but I do like it and I’m sure someone’s said it in some way, but just that it’s a big thing we say in program. It’s just like, “You’re not your story. You’re not the story you wrote about yourself.”

LEWIS HOWES: Or you can be a new—sorry, I interrupted you there.


LEWIS HOWES: New story. You can be the new story, right? You’re not the old story but you can create a new story.

WHITNEY CUMMINGS: You cast yourself in the wrong movie, yeah. I think that most of your thoughts are science fiction. I mean, that’s the other thing. A lot of your thoughts and beliefs just aren’t true. And that doesn’t mean you’re an idiot, that doesn’t mean you’re stupid. It’s just “that person’s mad at me, that person doesn’t like me.” They’re not thinking about you at all. In fact, they don’t care. They’re in their own insecurity. They’re worried if you like them. They’re obsessed about their selfie. You know, whatever. We obsess about what other people think about us to really realize they’re just not thinking about us at all. Good news, bad news. I think that a lot of our beliefs being science fiction is really helpful to me. A lot of the things that I—I think that a lot of people don’t like that because they’re like, “What do you mean? Are you calling me dumb?” No, that’s a relief. A lot of the things that the voices in your head aren’t yours.

LEWIS HOWES: [inaudible]

WHITNEY CUMMINGS: They’re voices that developed when you were a kid under different circumstances. Is that two?

LEWIS HOWES: That’s three.

WHITNEY CUMMINGS: Are you sure? I bombed this part.

LEWIS HOWES: The forgiveness one?

WHITNEY CUMMINGS: Yeah. That’s a good one.

LEWIS HOWES: This one that you just said? The story?

WHITNEY CUMMINGS: The way you treat others—no difference between the way that you treat other people.

LEWIS HOWES: And the story.

WHITNEY CUMMINGS: And then you’re not your story.

LEWIS HOWES: I like these three a lot. I don’t think I’ve ever heard of those three. It’s a combination. I think I have heard two of the three, I don’t think I’ve heard, so.


LEWIS HOWES: I’m not. I can’t remember if it happened. They’ve very  powerful. 

WHITNEY CUMMINGS: Your inner monologue’s just not true. That’s kind of helpful sometimes, sorry.

LEWIS HOWES: You got like 7 and a half in here. I like it, yeah.

WHITNEY CUMMINGS: That’s like solid, solild C-.

LEWIS HOWES: This is all good, it’s not a competition.

WHITNEY CUMMINGS: Yes, it is. Let’s be honest.

LEWIS HOWES: Life is a game.

WHITNEY CUMMINGS: I’m looking at this [inaudible] and I’m like, “Okay, I’m failing this.”

LEWIS HOWES: These are perfect. I mean, they’re beautiful.

WHITNEY CUMMINGS: Maybe this is so stupid, but I think as an artist, mistakes sometimes are the best part of anything except for the section of this. Mistakes are always where the magic is and everything. I think that’s what’s taken me a long time to learn.


LEWIS HOWES: I love it. This is amazing. I really acknowledge you for stating this. Through the construction, through the analytical brain, through the robot deformity, everything’s happening. But I really am glad that I got to know you because I’ve just seen you on your show or a special, at The Comedy Store once or twice. But getting to know your heart is really inspiring so I’m really glad we connected right now at this moment in time and I hope we get to do more stuff. If I can support you in any way, just let me know.

WHITNEY CUMMINGS: If anything, look. Your listeners, I have no idea what their takeaway from this is but if anything, it’s like I’m not—I’m looking at your wall of all these people who are experts that success in branding and I’m not. If anything, I’m a big mess and I have success. You can be a mess and have success. I’m looking at your wall and it’s all these overachieving A+ incredible people. I make mistakes and I’m an addict and I had eating disorders and I had—I’m still—I have not fixed everything about me and I still have success. So maybe that’s a good takeaway. You can just be a trainwreck and still have success. You don’t have to have read every single book, you don’t have to be giving inspirational seminars in order to have success. Maybe that imperfection is also okay.

LEWIS HOWES: It’s perfect.

WHITNEY CUMMINGS: God, this wall is really intense. It’s like all professional healers.

LEWIS HOWES: You know some of these healers?

WHITNEY CUMMINGS: Yeah, I know a lot of these people. Been through it all. You don’t have to meditate everyday to be a success. I’m about to totally ruin—I’m about to debunk everything. You don’t have to have rituals, you don’t have to write in a journal.

LEWIS HOWES: You don’t have to wake up at 5 a.m.

WHITNEY CUMMINGS: You don’t have to wake up at 5 a.m., you don’t have to work out, you don’t have to be keto or paleo.


WHITNEY CUMMINGS: I don’t even know what I’m saying. You don’t have to do any of that stuff. You don’t have to take vitamins—you can still be successful even if you’re not—


WHITNEY CUMMINGS: Yeah. Doing all the things that

LEWIS HOWES: Life hacking [inaudible].

WHITNEY CUMMINGS: Yeah, whatever.

LEWIS HOWES: That’s good.

WHITNEY CUMMINGS: You can be a hot mess.

LEWIS HOWES: I love it. I got to come to your show. You do it every week down here [inaudible].

WHITNEY CUMMINGS: Yeah, yeah. I’m there a couple nights a week.

LEWIS HOWES: I got to come more often, then. You’ve inspired me to want to come out more so I’m going to come out and bug you and heckle at you.

WHITNEY CUMMINGS: Sometimes I cancel, sometimes I flake. Sometimes I’m not—I’m imperfect. I’m a flaming mess.

LEWIS HOWES: I love it. This is my final question for you for this interview and I hope I do more with you in the future. But final question is what’s your definition of greatness?

WHITNEY CUMMINGS: My definition of greatness is I don’t know, I’m pretty rough about this. It’s excellence and authenticity in the same—do you know what I mean? For someone else’s version of great, that’s kind of whoops. I think , and this is maybe because I’m a comic and an artist, I think its greatness is like—at least in what I do in my personal life—I don’t even think I can really speak to that because I think greatness in your personal life is more about your behaviour instead of other people’s behaviour. What you don’t do instead of what you do do. 

Greatness is about shutting your mouth and not saying that thing or not giving that criticism or not losing your temper. Greatness is more about being stoic. But I think for what I do for a living professionally, it’s about making sure someone—before they see you and after they see you, they’re changed in some way. Leaving some kind of impact. Like making them think differently, see something differently, laugh at something they never thought was funny. At least it’s what I do. The movie I made—if you don’t leave that movie knowing more about neurology than you did then I failed. There’s no greatness in that. If you leave a comedy show that I did knowing less or not having tweaked to your perception of something, I failed. There’s no greatness there. So I think it’s like greatness and what I do is just leaving an imprint on somebody in some real way. Otherwise, what are you doing? You’re just wasting everyone’s time. It’s just [inaudible]. But that’s really specific. Yeah.

LEWIS HOWES: I like it.

WHITNEY CUMMINGS: [inaudible] mind about something, I guess.

LEWIS HOWES: I think so. That’s what we try to do here. That’s why I told you I wanted to do with this interview. I was like, “I want people to leave better than this. That they feel inspired to make an impact. They want to take an action, think differently, share with a friend.”

WHITNEY CUMMINGS: Because I just get a little bit—I get stuck in that. Sorry now I’m rambling. I get a little bit stuck in the whole “affect people” because that sometimes goes into my codependence. It’s not your job to fix people, it’s their job to fix themselves. Greatness isn’t martyrdom. You don’t go around to martyr yourself on people and rescue people emotionally, caretake people. That’s when I get a little bit like, “Wait a second.” Greatness is staying in your lane and fixing yourself because you’re the best way to—is to lead by example. So that’s why I’m kind of tripping up on it.

LEWIS HOWES: What I’m hearing you say is creating a piece of art through your work that empowers people to think in a way to improve their life.

WHITNEY CUMMINGS: Yeah, and have conversations they wouldn’t have normally or change the way that they think for the better, change their mind about something. Or even if it’s as simple as like, “Oh, women are funny.” Even if it’s that simple. Even if I’m setting an example or a woman go and like, “Oh, maybe I can do that thing I was scared of doing.” I think leading by example is important so I think greatness starts with making yourself instead of focusing on how can I help other people. Like get your shit together and then we’ll talk about what you can do for other people.

LEWIS HOWES: You’re a mess.

WHITNEY CUMMINGS: Clean up your mess and then we’ll talk about—so I try to sort of stay in that space. I also think there’s just a simple greatness like when I make a better decision today than I would yesterday, I think also there’s that. And you’re such a big picture healer that I think sometimes there’s this pressure to do something so—sometimes greatness can be tiny and incremental. And just like, today I didn’t text that person back. That can be greatness. Because sometimes that’s the hard—

LEWIS HOWES: Small acts every single day are great.

WHITNEY CUMMINGS: Yeah, I think to me I get so—

LEWIS HOWES: [inaudible] smiling at someone on the street.

WHITNEY CUMMINGS: That’s why I’m getting so daunted because I’m like, greatness! This is such a big—I think greatness can be really tiny.

LEWIS HOWES: My definition used to be something like, “Go be the best in the world in what you do.” But then it shifted to “discover your unique talents,” pursue your dreams which you enjoy, and make an impact on people on the way while you’re pursuing that thing you love.” For me, there’s knowing that being number one in the world and make a billion dollars or be so successful that everyone loves you—it’s do the thing you love and help people along the way by being positive.

WHITNEY CUMMINGS: Because I think that we always forget about the lead by example thing. It’s like people can look to you and go, “I might not have a podcast and be a brand like him but I’m a teacher and if I just teach these five kids—

LEWIS HOWES: Impact these people.

WHITNEY CUMMINGS: Yeah, yeah. I like that. Like what’s your version of greatness.

LEWIS HOWES: That’s it. That’s it.

WHITNEY CUMMINGS: God, these questions are really stressing me out. I’m stressed.

LEWIS HOWES: I told you. Well, this is the last question so I appreciate it. Again, thank you for your heart. I really like [inaudible]—I want to say I like [inaudible] someone I really like you [inaudible] I feel weird [inaudible].

WHITNEY CUMMINGS: Does he do this all the time?

LEWIS HOWES: I feel weird I’m saying I like you. I just think—

WHITNEY CUMMINGS: Why not? I hope so.

LEWIS HOWES: I don’t know, I just enjoy the level of work that you’ve done with yourself and continue to do and acknowledging of it and processing constantly. I think it’s rare to see someone in your position do this much work.


LEWIS HOWES: And talk about it openly and be proud of it and not shaming yourself.

WHITNEY CUMMINGS: I don’t know. For me, I like to lead with my failures and mistakes and flaws because I think right now, there’s this perfectionism culture and this brag about only your wins and don’t talk about any of your losses culture. I think it’s no good, but I appreciate that you say that.

LEWIS HOWES: Well, you’re amazing. I appreciated you being here. Thank you. 

WHITNEY CUMMINGS: Thank you, sir. I hope that was—

LEWIS HOWES: Perfectly imperfect.


A big thank you, my friend, for being here and listening to this episode. If you enjoyed this, you know what to do. Spread the love. Send a text to one friend. I don’t care if you’re using WhatsApp or you’re DM-ing a friend or you text them, Facebook Messenger. Just message one friend this link: or take the link on the podcast app where you’re listening to this on Apple podcast or Spotify. Wherever you’re listening to, take the link and message one friend. Be a champion, be a hero, be a leader, an inspiring person in someone’s life today by sending them this interview and recommending them to check it out.

Whitney has had an incredible life experience. So many things she’s been up to, so many mistakes and failures and lessons and successes that you can learn from, and your friends can learn from too. So make sure you share that out with your friends. And do me a favour and leave a review. I don’t care if you leave one star, three star, or  go five stars like most people do. But just write your thoughts. I want to hear your thoughts. I want to hear how I can make this better, I want to hear if you enjoyed this interview or not. What you gained from Whitney and what you’d like to learn more of. So share your thoughts, write it down. We share this with our audience, we share it with our team and it really helps us continue to spread the message of greatness.

Again, a big thank you to our sponsor, Blinkist. If you haven’t checked them out, go to Just start your 7-day free trial. They’re offering 7-day free trial for School  of Greatness listeners where you can get incredible non-fiction books and really get the Cliffnotes of those books in 15 minutes on your phone. Whether you’re driving, whether you’re in the gym, waking up in the morning, 15 minutes to get the whole book at Check it out right now.

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And big thank you to our ex professional athlete friends and entrepreneurs over at Beam, Beam TLC. They have incredible products to help you relieve stress, relieve soreness and elevate your everyday. I’m a big fan of the CBD-infused salve. This is like the cream that you put on your soreness, your joints, your body, and everything else relax the pain in your body, so make sure to check it out. For your path to better, visit and use the promo code greatness. That’s b-e-a-m-t-l-c dot com

In the beginning in here, we got a quote from Mary Tyler Moore who said, “Take chances, make mistakes. That’s how you grow. Pain nourishes your courage. And you have to fail in order to practice being brave.” I hope you’re doing something that scares you today, every single day. I hope you’re doing something that cultivates your courage that allows you to be brave. It’s hard to be brave if you’re just sitting on the couch and not doing anything that scares you if you’re not taking any risks, but you become more brave. You build the muscle of bravery when you take risks and chances and do things that risk being embarrassed, that risk failure, that risk of being judged. Put yourself out there and continue to step into who you were born to be.As always, I love you. You know what time it is. It’s time to go out there and do something great.

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