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

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


Emily Skye, Josh Shipp, Rupi Kaur & Joshua Fields Millburn

Overcome Emotional Obstacles

Our obstacles are opportunities to grow.

There’s so many times where we focus on what society tells us will make us happy, and that’s all we chase. Money, a nice car, a house, and material objects that show off our “success”.

We always end up overlooking ourselves. You avoid exercising until the doctor says you have to.  I’m sure you’ve experienced it plenty. You ignore your stress at work until you just can’t take it anymore.

Ultimately your emotional state should take a priority. Without it, you can’t be at your best. At the end of the day, happiness is an emotion. All of the material items in the world can’t get you there.

That’s why I wanted to do a mashup this week on overcoming emotional obstacles from some of the masters: Emily Skye, Josh Shipp, Rupi Kaur and Joshua Millburn.

“No one feels 100% confident in themselves all the time.” - Emily Skye  

On this episode, you’ll learn how to overcome emotional barriers that continue to hold us back.

If you take these lessons from people who have come from all walks of life, you’ll be able to achieve your true destiny.

Please, sit down with this one and take notes. I know it’s going to help you tremendously.

So learn how to keep your emotions in line to nail your goals, and feel fulfilled, on Episode 671.

“We don’t see you as a problem, we see you as an opportunity.” - Josh Shipp  

Some Questions I Ask:

  • Do you still go through times of being insecure? (5:40)
  • Why do you get insecure at times? (6:32)
  • If something isn’t working in your business, how do you handle the inner critic? (10:26)
  • How old were you (Shipp) when you met your final foster parents? (15:56)
  • Do you (Rupi) think your work would be as powerful without going through pain and suffering? (19:43)

In this episode, you will learn:

  • What everyone needs to be responsible for (5:04)
  • Tools you can use to overcome insecurities (7:48)
  • How Emily stays grounded when things are going well (11:38)
  • How Josh Shipp was emotionally removed from people who were trying to help him (14:02)
  • Shipp’s lesson from a night in jail as a teenager (16:38)
  • The danger of being your own worst enemy (18:41)
  • How Rupi continues to create new things (21:03)
  • What you need to focus on (22:34)
  • How Joshua Millburn knows what needs to be fixed (25:17)
  • Plus much more…
Connect with
Emily Skye, Josh Shipp, Rupi Kaur & Joshua Fields Millburn

Transcript of this Episode

Lewis Howes:                 This is episode number 671, Overcoming Emotional Obstacles.

Welcome to The School of Greatness. My name is Lewis Howes, former pro-athlete turned lifestyle entrepreneur and 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.

Napoleon Hill said, “Your big opportunity may be right where you are now.”

We’ve heard some amazing stories over the years on the podcast, of people overcoming massive challenges, to become incredible leaders and achieve greatness in their own industry and in their own life.

And I love these stories so much because they remind me that no challenge is too big to overcome, and I don’t care where you’re at in your life, or what challenge you are facing, or any type of emotional distress that you may have right now, we all face them and we can all get through them better and stronger.

And in this mash-up we’re featuring clips from the past episodes that inspire me to view obstacles as opportunities to grow. We’ve got incredible people on this. Some of you may have heard these episodes, but if you haven’t yet, these are huge reminders to help you overcome those emotional barriers that continue to hold all of us back from reaching our true destiny and our true greatness.

We’ve got Emily Skye in the house, Josh Shipp, Rupi Kaur, and Joshua Fields Millburn. This is going to be a powerful one! Make sure to share it with your friends,

And a big thank you to our Fan of the Week! This is from Eli Keiser who says, “Lewis, thank you for bringing your light into a place that needs it. This podcast is a beautiful reminder of the truest truths: To never give up on my dreams. To remember I am unceasingly, eternally, completely loved, and to perpetually train my mind, body, spirit, to recognise the greatness within! Let’s do this!”

Eli Keiser! You are the Fan of the Week! And that was a beautiful review. If you guys haven’t left a review yet, go over to iTunes or the podcast app that you’re on right now and leave us a review for your chance to be featured as the Fan of the Week.

And a big thank you to our sponsor today, LendingClub. Now, you guys know that life is crazy and there is never enough time, too many things to keep track of, and it’s hard to juggle all the bills and make sure you pay more than the minimum on your credit cards.

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They are the number one peer-to-peer lending platform with over 35 billion [dollars] in loans issued. Go to, check your rate in minutes and borrow up to $40,000. That’s All loans made by WebBank, member FDIC, equal housing lender.

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It’s time to overcome emotional obstacles! Let’s dive in to this powerful episode right now!

* * *

Emily Skye:                     You’ve got to be responsible for what you’re consuming, I think. And it’s hard to do, because young kids like looking at this sort of stuff. They like seeing ‘perfect’, they love that idea, it’s almost like a romantic movie, it’s romanticising it.

I think, if people can take more responsibility and if something’s making them feel bad, if a particular person’s making them feel bad about themselves and maybe question themselves, “Why are they, and do I need to have them on there? Can I get rid of them?” That’s hard.

I mean, you can only say to people, “Be responsible. Don’t do this,” but they’re still going to do it, because it’s an addiction, isn’t it? People love it.

Lewis Howes:                 Yeah. What about yourself, in terms of, you’ve got this massive audience, you have all these people that look up to you, and are inspired by your mindset, your body, your look, your muscles, whatever it is? Do you ever go through times of still being insecure, or comparing yourself?

Emily Skye:                     Yep!

Lewis Howes:                 Even though you have this, everyone wants to be you, but you’re like, “Well, I’m still not good enough.”

Emily Skye:                     I don’t think anyone feels 100% confident in themselves all the time. I think people always have times when they have a bad day, or they don’t feel like they’re as good as they can be. And I have those times. It’s nowhere near what it used to be, but I think now I have the tools to be able to get through it, and I know how to, and I’m aware of when I’m feeling down.

“Why am I feeling this way? What’s contributing to that? What can I remove to help myself move on and get past this?” So, being really, I guess, self-aware.

Lewis Howes:                 Why do you think you get insecure at times? What are the reasons?

Emily Skye:                     I don’t know whether it’s because I used to be a very insecure person, so it’s, I’m always fighting it.

Lewis Howes:                 It’s a habit.

Emily Skye:                     It’s always sort of coming back. I think that’s a huge thing, getting on top of that and knowing that’s the type of person I used to be as well, I’m not going back to that. But there’s a lot, like, social media’s insane, it’s competitive, there’s a lot of people out there, posting things that I could look at and then go, “Ah, I’m not this, or I’m not that.”

For instance, I’m pregnant at the moment, obviously, and I have gained fat.

Lewis Howes:                 Oh! Are you? I didn’t know.

Emily Skye:                     Yeah! That’s what this lump is, here. But I’ve gained fat and cellulite and I’ve changed and I’ve lost a lot of muscle.

Lewis Howes:                 Stretch marks and whatever, yeah.

Emily Skye:                     Yeah, all these things are happening, which I’m 100% embracing, I’m happy with. But I could look at these other people who are online, who are fit and pregnant, and they look amazing, and they’re on their own journey.

That’s the thing, everyone’s on their own journey and shouldn’t compare, but I could look at them and think, “Oh, how come this person’s got abs and she’s a few months ahead of me, and yet her abs are there, and she’s tiny and I’ve got all this cellulite and stuff going on?”

I could look at that and that could affect me, but I don’t. I think I’m at a really good place now, where I’m so happy and my baby’s obviously most important to me, so I don’t let those insignificant things affect me.

Lewis Howes:                 Yeah, that’s good! What are some of the tools that you use when you’re looking to overcome that insecurity or fear or comparison? Because I think this will be helpful for a lot of people who are constantly comparing. To see someone like you, with a massive audience, great body, great image, everything, on how you do that.

Emily Skye:                     I think you’ve got to work out what makes you happy in life, and what’s most important to you. Is it really trying to be perfect and worrying about what everyone else thinks of you? Especially on social media, if you put up a photo and people say, “Oh, you look great here!” Does that really make you happy?

Temporarily, yeah, you feel good, your ego’s getting fed, but, long term, I don’t think it really does. And I think you need to get to a point where you do know what makes you happy, and you’re aware of that and you don’t rely on that to keep feeding the happiness.

But, yeah, when I feel down, and I’ve talked about this before, with my followers, but when I get in my down moments – and I haven’t had one for a while, which is a good thing – but last year I had a bit of a time, I think I had been travelling a lot and I just got really run down and everything just went to s**t pretty much.

Lewis Howes:                 It’s hard to keep your body healthy, and be consistent.

Emily Skye:                     Yeah, and then your mind goes, and eugh! I was feeling crappy, I wasn’t training, which is a big thing. Getting moving does incredible things for you and the endorphins that you get from it, it’s a real thing.

Lewis Howes:                 It’s a real thing!

Emily Skye:                     Yeah, and I hadn’t been doing it for a while and I just didn’t want to. I wasn’t motivated.

Lewis Howes:                 To move, to work out.

Emily Skye:                     Yeah, and I thought, “How can I get myself back there? I know that’s what changed my life, and yet here I am stuck, feeling s**ty again.” I thought, “Okay, well, I don’t want to go to the gym, because I’m not motivated to do that. How can I get myself there?”

And so I put music on and then danced around the house, and I started learning hiphop, I was putting tutorials on the big screen on YouTube and dancing around the lounge room, like an idiot. I was no good at it, but that’s not the point. I felt good, I felt happy, and the music lifted my mood.

And I started getting outdoors, outside in the sun and fresh air and just finding that balance again and I guess, grounding myself, in a way, so I could start to feel like, “Okay, what is it that makes me happy, again? What is it that gives me life, that makes me jump out of bed every day?”

So, I got back there, and I got back on track again. So, you’ve got to find what it is that does it for you. Maybe it’s reading a book, maybe it’s walking, I don’t know, ice-skating, rock-climbing, whatever. Do something that makes you feel good again, but you’ve got to find your creative, and my creative, for me, is training and getting outdoors and talking to people and helping people.

Lewis Howes:                 Yeah, it’s probably not sticking on your phone, looking at Instagram all day. Most probably not going to do it.

Emily Skye:                     No, and that can be quite poisonous. And you’ve got to set boundaries for yourself, and restrictions.

Lewis Howes:                 I know! Yeah, and when your following and your accounts is your business and your brand, and if something isn’t working, or isn’t getting the results you want, how do you deal with that inner voice? When, like, “Okay, I put a post out here, normally I get a certain amount of results,” whether comments, traction, sales, whatever, “and I didn’t get that!”

How do you handle that inner critic?

Emily Skye:                     It’s hard, because it is me! I’m the brand, it’s not someone else. So it’s hard not to take it personally, and I think you invest so much. I invest a lot into my business, and what I do, and I love it, but I do take things personally, because it is me.

And I know it’s a hard thing to do, so I’ve got to sort of sit back and go, “Okay, there’s a lot of things coming into play here, with algorithms and things. What could be the reason? Is it really my content that people aren’t liking? Or is it because they’re not actually seeing it because Instagram’s done an update and people who follow me aren’t actually seeing the post?

So you’ve got to step back and realise what’s going on here. So, it is hard to monitor what’s working and what’s not, and whether it is you or not. But you can test and there’s a lot of things you can do to find out what actually works and what people want to see and what your following really likes. But you’ve really got to think about maybe it is just the algorithm.

Lewis Howes:                 And how do you stay grounded if something’s taking off and doing really well? You’re on the cover of every magazine, you’re getting brand deals you’re getting all this stuff, it is all working for you. How do you stay grounded and also stay happy with it being enough?

Sometimes we look at these big marks, and then we’re like, “Ah, but it could be more! It could be this! It’s not enough!” So, how do you stay grounded in those times?

Emily Skye:                     Yeah, I think, because it’s taken a long time to get where I am, and you could say I started working on it when I was a teenager, because that’s when I started with modelling, and I use a lot of the things I learned with modelling, now.

So, I do a lot of things myself. I take my own photo’s on a tripod with a timer, I edit my own videos, I write my own content, I reply to people online. I do a lot of stuff myself, which I learned when I was doing modelling.

So, I think, in life, there’s a lot of things that you can use right now, I mean, down the track when you find what it is you want to do. Because I’ve gone through that and I’ve worked really hard, it hasn’t just happened overnight, I wasn’t just handed it, I have a lot of appreciation for what I’ve got.

One thing I do struggle with is really, really appreciating and being grateful for what it is that I’ve got right now, and it being enough. Because I always want to be, I want to be the best, I want to reach more people, I want to do so much stuff, and I sometimes get frustrated, because I know that I’m not quite where I want to be, yet.

And it’s such a hard balance, to really appreciate and look back on what you’ve done and go, “Yeah, I’ve killed this, I’m doing well,” and still go, “Ah, there’s still more I want to do.” It’s quite hard and it’s something I do still struggle with a lot. And when I do, say, get a magazine cover, I’ve got to really make an effort to go, “I achieved this, because I deserve it.”

It’s difficult, and I think I get a bit mixed up with, “I don’t want to lose who I am through the whole thing, and I don’t want people to think,” and it’s funny, because I always say, “Don’t worry about what people think,” but I do, I care what people think, because I’m doing this for a reason, I want to help people.

So, I have to care what they think, otherwise I wouldn’t be doing this. I want to always stay relatable to people and never seem like I’m full of myself, which I’m not, and I’m far from it, actually. So, yeah, it’s finding that balance between being proud of yourself, looking at what you’ve achieved, where you’ve come from and then still being able to say, “Yeah, but I’ve still got room to grow and more to do. More goals to do.”

* * *

Josh Shipp:                      When I was fourteen, I moved into yet another home. And I thought, “Here we go, yet another home, and these people are going to talk big about how they’re going to love me unconditionally and all this crap, and you know, whatever, let’s just get this over with.”

Lewis, dude, I would literally keep a notebook of when I entered a home and of when I exited the home by getting kicked out, and I would try to beat my high score. And I would document what technique I used.

I mean, I was so emotionally removed from it, it was just this game for me, of “You act like you care, but I know you don’t. I know you’re going to eventually give up on me, so let’s just get it over.” But these final set of parents completely changed my life.

They were consistent, they backed up everything they said with their actions, and they backed up all their actions with their words. They were tough and tender, which is exactly what a kid like me needed, was sometimes to be hugged and sometimes to be kicked. And those two individuals, the Weidermeyers, in Oklahoma, completely transformed my life, completely changed my life.

And this is why this is one of my big things, that every kid is one caring adult away from being a success story, because the Weidermeyers were that for me, and that’s been my drive and my motivating factor to do the work that I do with kids and teens and parents, is to be that one caring adult for some kid.

Be it through a message, a book, a show, training other people to go out and do that sort of work. That’s really my heartbeat behind why I do what I do, is I had this insane childhood, and I remember how frustrating and confusing and alienating and just what a complete and total mess I felt like, and to have some caring adults who didn’t put on show, but were genuine and helped me at that critical time.

That’s what I want to do. It’s my way of saying thank you to the Weidermeyers and others like them that helped me.

Lewis Howes:                 How old were you when you met them?

Josh Shipp:                      Fourteen years old. And if you think about that, it’s like, here’s this fourteen-year-old showing up on you doorstep, with all this baggage, and garbage, and crap that you did not cause, that was not your fault, but now you’ve got to deal with it.

And even though, again, they are two of the finest people on the planet, I pushed them away, I tried to hold them at arm’s distance, I tried to get kicked out of there. I tried everything to, again, “Let’s just get this over with. I know you guys don’t really care, so let’s just accelerate this inevitable breakup.”

They just wouldn’t. I remember one night I went to jail, because I wrote a bunch of hot checks, as a teenager. They brought me home, and it was certainly a rock bottom moment for me. My mom made me stay the night in jail, although she could have bailed me out the night before, which, looking back, was very wise, making me feel the pain of my own stupidity.

And they brought me home that next morning, and I assumed they would yell or lecture, which was certainly in their right. And they just looked at me and very calmly said, “You can keep causing problems, you can keep pushing us away if you want, but,” and excuse my language, but they said, “Dammit, Josh! We don’t see you as a problem, we see you as an opportunity! Why don’t you start to see yourself like that?”

And, dude, Lewis, they had probably said that sort of thing to me a hundred times. I know them, they’re just that sort of people, they probably said it to me a hundred times, but here I was in a moment where I was actually really ready to listen to it. And in that moment, it’s not fair to say in that moment my life changed, but in that moment I made the commitment that my life would change.

Lewis Howes:                 You started shifting.

Josh Shipp:                      Yeah, and, you know, I’ve done a lot of work with young people who are at risk, and my opinion is, you can’t change anyone’s life, but you can get someone to make that commitment to begin to accept help.

And so then came hundreds of hours of counselling, a big brother, through Big Brothers Big Sisters, being more open to my foster parents, to my social workers. All this sort of stuff, of beginning to wade through my own issues, that began that life change.

And I’m unbelievably grateful for it today, as a guy who is married, has kids and I’m certainly not perfect, I’m certainly flawed in many, many ways, but I’m so grateful to have figured that out and that the Weidermeyers didn’t walk away, because, man, it would have been so easy to.

* * *

Rupi Kaur:                       Once we experience something, and once we overcome it, we almost forget how difficult it was, when you put time with that gap. And especially because my mind has really just blocked out so many of those memories.

But I think we go through different versions of suffering, and one thing I really have seen in the last year or two, and I do write about it in The Sun And Her Flowers, is that idea of becoming your own enemy.

And me becoming that in the last little while, is almost more painful than any external factors trying to attack me. And I tried not to write about that, because I was like, “Who cares about that?” But I ended up writing an entire chapter about it, and it’s what I’ve really taught myself in the last two years.

I worked so hard on trying to really respond to these other negative factors, but then it came to a point where I became my own worst enemy and that was probably the most painful, and is the most painful thing of all.

Lewis Howes:                 Do you think you would be able to have as much impact without going through that much challenge, pain, suffering? Do you think your work would be as powerful?

Rupi Kaur:                       I don’t know. I don’t even know if I would be writing if it weren’t for those moments, right?

Lewis Howes:                 So, are you grateful for those experiences?

Rupi Kaur:                       I am. I would say I have no regrets. Like, even before that there’s been things, and after that there’s been things, but I’ve taught myself that there are no regrets and all things happen for a reason. And a wonderful thing that I do, I don’t know if it’s healthy or not, is any time something terrible happens, I always respond to it with art.

So, going through that and ending that, I responded to that by going to my first ever open mic night and starting to do this thing on a regular basis. I don’t know if I would have done that otherwise. And I remember there were other things that happened after that, and every time things went wrong, I would do something else.

Then I started a blog, and then something else went wrong, and then I was like, “Okay, whatever, I’m going to start doing this,” and then I started my Instagram, and then other things went wrong, and then it was like, life became so bad, that I was like, “Forget about it! I’m just going to publish this damn book!”

Because that’s how I kind of deal with stuff and work through things. I have to keep myself really busy.

Lewis Howes:                 Wow! It’s like your therapy, yeah.

Rupi Kaur:                       It is, yeah.

Lewis Howes:                 Do you feel like you have to go through challenges every single year to create then? Do you think you’ll be able to create from a place of love?

Rupi Kaur:                       I think so. And that was a challenge. Like, after the success of Milk And Honey, I gained a lot of stability that I didn’t have, that my family didn’t have.

Lewis Howes:                 Like financial stability?

Rupi Kaur:                       Financial stability, emotional stability. You know, it’s interesting, because I came to a place that there was lots of love and everything had settled, finally, after so long, and it was the moment that I had been looking forward to forever. It’s the moment that you would dream of, but then I was scared, because I was like, “Oh, my gosh, if I’m not suffering, then how will I write again?”

And then I would go out and search for suffering and create situations.

Lewis Howes:                 And sabotage yourself.

Rupi Kaur:                       I’d kind of like fight with my friends, just to be, like, “Yeah! It’s going to give me something, move me emotionally,” but what I realised was that’s so not true, and that’s working from a place of trauma and suffering, and we do not have to do that any more.

It is very possible to write from a place of love, we just have to teach ourselves how to do that. Because, for so long, what I did, like, we learned to teach ourselves to write through the suffering, because that’s what we were trying to write through. And now, I have to reprogram myself to write though a place of love or happiness or whatever that is.

* * *

Joshua Fields Millburn: My mother died, and my marriage ended, both in the same month.

Lewis Howes:                 Holy cow!

Joshua Fields Millburn: And these two events forced me to look around and start to question what had become my life’s focus. And I realised I was so focused on so-called success and achievement, and especially on the accumulation of ‘stuff’. The ‘trophies’ of success.

Like, “Look at me, I have two Lexuses, and I have this, I have that, I have the bigger house and…”

Lewis Howes:                 The golf membership, or whatever, yeah.

Joshua Fields Millburn: Yeah, the racquet club membership, actually.

Lewis Howes:                 There you go!

Joshua Fields Millburn: And so, I had these things, and here’s the thing I want to get across: There’s nothing inherently wrong with ‘stuff’. We all need some ‘stuff’. The problem isn’t consumption. The problem is this [compulsive] consumption. Buying things because that’s what we think we’re supposed to do.

We’ve been sold this meme of the American Dream. If you get this, then you will be happy, as if there is a template for happiness. And, in fact, I think that’s one of the bigger problems. It’s that we are chasing happiness.

For the longest time that’s what I did. I chased happiness, and that forced me to really forsake what was important. In fact, I was at a point in my life, when I was very narrowly successful. I had the job title, but I wasn’t broadly successful.

And it’s because there wasn’t a lot of meaning in what was doing. We all have to earn a living, I understand that, but I was so focussed on just accumulating more money and status and identity. My whole life was wrapped up in that identity.

We hold on to a lot of stuff. We hold on to these supposed ‘memories’, and I know that’s what I was doing, it’s what my mom did when I went to deal with her stuff. And I realised that, you know what? Some of the stuff actually adds value to my life, but I don’t know what.

And so, I started small, because I had attachment to so many things in my life, I had given so much meaning to my ‘stuff’ and I said, “I need to try to get rid of some of this. Some of it’s in the way, I don’t know what’s actually adding value.”

And so, over the course of thirty days, I said, “I’m going to let go of one thing a day, one item a day, each day, for thirty days. What would happen if I did that?” My values aren’t different, and I think that’s what’s important, is identifying what is important in my life, what items, what material possessions are going to augment that experience and not get in the way?

And so, letting go allowed me to figure out the paradox of minimalism. I get far more value from the material items I own now, than by watering them down with hundreds of thousands of items. I always look back to those five values. If my health is lacking, I need to repair that.

Lewis Howes:                 That’s the first thing.

Joshua Fields Millburn: Yeah, and I think they’re all tied, though. My relationships are lacking, it means if I’m not giving to them, or if I’m not getting what I need from those relationships, then I have to question why. Right? And so, if I’m not creating, if I’m not passionate about this creativity or this craft, then I’m lacking. If I feel like I’m not growing, or if I’m not giving to the world in a meaningful way.

If any of those areas are empty, that’s the weak link. I need to go back and fix that. And it’s constant, every day I’m trying to look at, “How do I serve these values in my life?” And if I’m not serving them, then I need to be honest with myself and find a way to fix that.

* **

Lewis Howes:                 There you have it, my friends! I hope you enjoyed this episode! Again, don’t allow the emotional obstacles to consume you and control you and hold you back in your life. You are born to overcome these things. You have the power to withstand them, and you don’t need to hold on to them.

Move through the emotional challenges, move through the pain, move through the suffering and let it go! You were born and designed to express love and express your truest self right now.

If you enjoyed this, share with a friend, If you want to listen to any of the other clips and the full interviews with Emily Skye, Josh Shipp, Rupi Kaur, Joshua Fields Millburn, go to, and you’ll see the links for those episodes as well that you can click and listen to those full interviews which are extremely powerful in their own right.

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I hope you guys enjoyed this one! Made sure to share with your friends, let me know what you think! Tag me on Instagram, @LewisHowes, connect with me, let’s continue this conversation of greatness and keep spreading the message to be part of one of the most powerful movements in the podcast world. This is all about unlocking your greatness!

I love you so very much, and you know what time it is: It’s time to go out there and do something great!

Music Credits:

Music Credit:

We were Infinite by Inukshuk

Next Galaxy by Extan

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