How To Pursue Your Dream & Make a Living As An Artist with Derek Hough

Text "GREATNESS" to Lewis at 614-350-3960


When people ask me, “are you flying for business or pleasure” I always seem to answer with, “both”.

I love to travel when I speak on the road because I never think of it as a “business trip”.  Even if I only travel for a short weekend or one day event, I make sure to set up something outside of the business activity to enjoy my time.

For me, most of my speaking gigs are about 60-90 minutes at most, with some additional schmoozing time before and after.  However, the total amount of time is usually only a few hours.  I like to make the most out of my time on the road if I’m going to pack my bags, hop on a flight, and take time away from my comfortable king sized bed.

During a recent two week business trip, I had an event or speaking gig in five different cities including Las Vegas, San Francisco, Dallas, L.A., and San Diego.  I made sure to balance my days on the road as I believe its essential to personal growth, and keeping myself sane.

There were many amazing “non business” related highlights during my trip, but I want to point out 13 things I did to make it more fun, fulfilling, and exciting below.

1.  Playing Roulette

While in Vegas during Ali Brown’s amazing Shine Event, I took some time to hang out with some good friends I hadn’t seen in a while (my man David from The Rise to The Top included).  I spent a few nights playing roulette with them because I think of it as a fun experience where we can do an activity together, share stories, laugh, and get behind each other in the game.

Let me just say that I don’t endorse gambling per say, but I do think of it as entertainment.  I’ll only go in with a small amount of money and take with me what I’m willing to lose.  I look at this as a similar experience as going to the movies.  Movies for 2 costs anywhere from $50 or more, and you lose your money to gain an experience of watching the movie.  This is how I look at roulette as I usually lose, but on this trip I won 🙂

2.  Watching Movies

I took the weekend trip to San Francisco to connect with some start up companies, but also spent time with some close friends.  During this time we went to see a hilarious comedy that almost made me snort milk out of my eye balls.  Make sure to enjoy your trips and take time to laugh a little… a good comedy flick will do that to you.

3.  Shopping

To be honest, I’m not a big shopper.  I still have t-shirts from 10 years ago that I wear when I workout, and I’m one of those guys that doesn’t like to try things on, I just hold it up and say “that should fit me”.  That being said, I enjoy window shopping, looking at the latest trends, and seeing whats happening in the stores.  I got a chance to do this in Vegas and San Francisco and even picked up a few new articles of clothing along the way.

4.  Eating Sushi, Pad Thai, and Steak

I recently started on a gluten free kick which basically cuts out everything I love to eat.  This was inspired by a few friends who had seen an amazing change in their daily mental performance and a healthier body.  Although it was a challenge to not eat all of those pastas and breads, I got creative and tried new things.  I also ate a lot of sushi, pad thai, and steak.  Mmmmm, Steak!

5.  Go to SoHo House in L.A.

I’d been to Soho House in NYC compliments of good friend Jonathan Fields, but the one in L.A. had a completely different vibe to it.  My friend Joanna Garzill had been a member for nearly ten years back in London, and invited myself and Sean to the L.A. one now that she was living in the area.  You can’t take pictures inside due to privacy of the celebrities inside, but lets just say everything about the Soho House is a fun time.

6.  Be On a Reality Web Show

When I went to L.A. I had the opportunity to be on a web reality show called ControlTV.  It was a lot of fun connecting with the star of the show Tristan and getting to learn more about where he is headed in his career.  Although part of it was hosting a sports networking event, I really consider most of them more like a party to help bring sports professionals together.  Feel free to watch the episode I was in with Tristan here.

7.  Spend Time With Quality Friends

I got to connect with so many great friends during my trip.  One of my favorite things about traveling is connecting with all of my old friends I haven’t seen in a while.  There are number of people I’d leave out if I tried to name them all off here, but lets just say it’s one of the best feelings in the world to take things off of social media and get back to genuine human interaction with all of my friends.  I miss spending time with them, and I do my best to enjoy every second when I see those I don’t see very often.

8.  Dance in the Car

This video of me and Sean Malarkey dancing in the car should say it all.

9.  Relax in a Hot Tub or Pool

Ahh yes.  The good ole hotel hot tub and pool.  It’s a shame I don’t take advantage of this more often as I don’t have easy access to either at my home.  Before my speech in Dallas I took the time to work out and jump in the hotel hot tub.  It’s such a nice way to loosen up your muscles from the long cramped flights and different hotel beds.  Enjoy them on your next trip.

10.  Play Ping Pong Against the Robo Pong Machine

I went to speak in San Diego at an online marketing event that super star Than Merrill was hosting.  About a week prior to the event Than told me that he could beat me in ping pong.  I’m always up for a challenge and hate to lose at anything, so I was pumped to play him.  After we played 4 games (which ended in a 2-2 tie) I noticed he had a device called Robo Pong.  It looked like a blast and I had to try it out.  How much fun does this look to you?

11.  Compete in Flag Football

One of the things I’m extremely passionate about it football.  I used to play in college and for a year in the Arena Football League, but I hadn’t run a route since after my surgery about three years ago.

When Than told me, “Lewis, you gotta change your flight and stay an extra day in San Diego because we need you for our flag football game.”  I felt an sense of passionate energy I hadn’t had in a while.

Even though my hands were rusty (I dropped a bunch of balls… sorry Than), I was out of shape (ran about 100 fade routes and got winded after 10th one), and I didn’t play as well as I wanted to, I still had an amazing time getting back on the football field and playing a game I used to literally live for.  It was a blast and I look forward to playing more football in the future.

12.  Give to a Charity

The more income I earn, the more I want to give back.  I feel extremely blessed to be in the situation I am.  I’m able to go anywhere, do anything, and live the way I want at all times because of the businesses I’m a part of.  I was able to give to two charities on this trip because I have more than enough to meet my basic needs.   It wasn’t any huge donations like how Mark Zuckerberg does it, but I hope to do more of this on my business trips as much as possible.

13.  Watch the Sunset on the Beach

Sometimes I get caught up in my business, in making sales, in results, etc… and I forget to just sit and watch the sky.  My friend and extremely giving individual, Eli Call, lives on the beach in San Diego.  Every night about 30 minutes before the sun sets, he gets out his chair, turns on some smooth Sublime’s “Summertime” tune, and watches the sun set.  He just enjoys the moment each and every night and stops everything else he is working on.

I almost missed the sunset one night because I was working on sending out some emails.  Eli insisted I stopped for a few moments to join him.  I’m glad he did as this was the result.

Enjoying The Business of Fun

Business, like social media, should be fun.  Of course some times should be focused on being more professional than others, but once the business part of your trip is over you should plan the rest of your moments having a good time.

These were just a few of the things I did to have fun during a recent business trip.  I still achieved my goals and did what I needed to do in business, but also enjoyed myself.

What are some things you like to do on trips to make them more fun, fulfilling and exciting?  I’d love to hear your stories in the comments section below.


Image credit: John Wardell

Comment below

let us know your thoughts

join thousands of
greatness subscribers
on your favorite platform