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Freedom lifestyle

How a corporate engineer accidentally became a comedian loved by Barack Obama

Meet comedian Dan Nainan, a former senior engineer with Intel Corporation who now travels the world making people laugh. Welcome to “How I Escaped”. This Discovery Sessions interview series probes inspiring individuals who successfully ditched the rat race to inspire readers just like you. 

 

Where are you from or where do you feel local to?

Dan Nainan: I was originally born in Indiana to parents from India and Japan. I grew up in the DC area, spent some years in both Southern and Northern California, and now call New York City my home.

How did you escape the rat race? Tell us the backstory of your former profession.

DN: I was a senior engineer with Intel Corporation. It was my job to do technical demonstrations on stage with Intel executives, including the CEO, at events all over the world. Designing the demonstrations in the lab was easy, but the tough part was speaking on stage in front of thousands of people, or sometimes millions on television.

I took a comedy class to get over the fear, and I had some amazing beginner’s luck: in fact, my third performance ever was for 2,500 Intel employees at a sales convention. Even though I was an engineer pretending to be a comedian, many people thought I was a professional comedian pretending to be an engineer.

What advice would you give someone looking to become a traveling comedian? 

DN: Some people think they can leave their day job for a creative pursuit, but that’s not the way to approach it. In many creative jobs like mine, it’s very difficult to make any money in the beginning. So the key is to work on the craft in the evenings and weekends when everyone else is watching TV or getting wasted and hungover. Sure, it can mean the occasional Friday or Saturday night alone, but in the end, it will be well worth the sacrifice.

 

What does a typical day in the life look like for you (if you have one)? 

DN: If it’s a show day, typically I’ll fly in the night before, get to the hotel, and then relax. I go over my jokes during the day and then perform at night. Then, I meet and greet everyone after the show, handing out my business cards and selling my books, CDs, and DVDs. If I’m on tour overseas, I frequently have radio and television appearances every morning. I have performed in 28 countries, and the travel sounds grueling, but I truly enjoy it. As they say, half the fun is getting there.

What’s the biggest challenge of life as a traveling comedian

DN: I would say the biggest challenge is working out and eating right on the road. Sometimes, it can be difficult to find a gym, and if I’m not working out, then I’m more tempted to eat badly. There is so much junk food within easy reach on the road, especially at airports. Fortunately, at home, I am extremely disciplined about working out and eating right. I wake up at 4:30 AM, with no alarm and no coffee, and I’m at the gym at 5:00 AM.

 

What’s the biggest reward of life as a traveling comedian

DN: Making new friends (and girlfriends) has been the most rewarding part of my job. I meet people from all walks of life at my events, especially since a lot of them are corporate functions and charity galas. I’ve also gotten to meet a tremendous number of celebrities. I’ve performed for President Obama, Hillary Clinton, the last three mayors of New York, actors, athletes, you name it (you can see Kamala Harris say “Dan is funny” at the 3:55 mark of this testimonial reel). My favorite, of course, was getting to meet Steve Wozniak, co-founder of Apple. The next time I was in his town, I had the privilege of having dinner with him, and he was quite the prankster.

What does freedom mean to you? When do you feel freest?

DN: When I’m on stage in front of hundreds or maybe thousands of people, and everyone is laughing and applauding at a joke I thought of that afternoon in the shower or walking down the street, there is nothing that can quite match that feeling. Unlike most people in my profession, I’ve never done any kind of drugs and never been drunk, but as a famous comedian said, that must be what heroin feels like.

 

What advice would you give to someone wanting to become location-independent, work online, and maximize their freedom?

DN: I think it’s a great idea to have your goal in mind for the perfect job that allows you to work remotely, then work backward and write down exactly what actions you have to take to get there. One has to have a realistic time frame and set realistic goals, but sometimes it helps to set crazy goals as well. The night before I opened for one of the top comedians in the business, I told a friend I had a goal of being asked to tour with him as his opening act. My friend laughed at me and said I was crazy, but that’s exactly what ended up happening.

What do you wish you did differently (in work or life)? 

DN: I’ve been extraordinarily fortunate, but the one thing I would change is that I would have majored in music and theater in college instead of in business and computers. Then I could have been that much further along now. But I heard a great saying: You’re only old when regrets take the place of dreams.

Comedian Dan Nainan’s book “Accidentally Funny” is now available at www.comedybook.net. Use code FBFRIEND for a substantial discount.  

DIGITAL NOMAD RESOURCES

What is the best travel insurance for digital nomads?

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How can I find accommodation as a digital nomad?

There are great deals to be found for short and longer stays (of up to 30 days) anywhere in the world on Agoda, Trip.com, Expedia US, or Booking.com, where you can search for accommodations and filter according to criteria like desks, air conditioning, private bathrooms, and complimentary Wi-Fi.

How can I get an international SIM card when I’m traveling?

It’s quick and painless to get an eSIM (or digital SIM card) and data plan from Airalo that covers practically any country in the world before you get there, so you never have to bother going into a phone shop. With the Airalo app, you can keep track of your data usage and top up easily.

Where can I find useful travel resources for digital nomads?

You can find all my nomad-friendly resources right here on this page. These will help you out with everything from the best flight search tools to digital SIM cards. 

If you’d like ongoing reflections, frameworks, and interviews on navigating change, you can also subscribe to the Discovery Sessions newsletter on LinkedIn.