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How One Man Uses Humor To Travel The World (And Get Paid!)

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dan nainan Each week, I get readers writing me wondering how they can travel the world and still make money. While it’s easy for me to teach readers how to work as a digital nomad through blogging, the truth is there are many options for earning an income and seeing the world, some less obvious than others. Like being a stand-up comedian. Dan Nainan has always been interested in travel. And while his corporate job introduced him to his true passion of comedy — more on this below — it was when he left the 9-to-5 world that he was truly able to combine his love of hitting the road and humor. I caught up with Dan to learn more about his inspiring travel story.

1. What inspired you to want to travel?

I’ve always had a wanderlust, ever since the beginning. Some people want to travel the world, and others say that they prefer to sleep in their own bed and have no desire to travel. It’s very interesting to see how different people feel so differently about travel.

2. Your foray into travel started when you were a senior engineer with Intel Corporation. How did that lead to a gig in comedy, and how does that allow you to continue to travel?

I had to speak on stage presenting technical demos with Intel’s senior executives at events all over the world. I designed the demos — and that part was easy — but the tough part was presenting them on stage. The public speaking was terrifying. I decided I had to do something, so I took a comedy class to get over the fear and I discovered my true calling. My third show ever I was in front of 2,500 Intel employees at a sales convention doing comedy. A lot of people who I didn’t know came up and said they knew that I was really a professional comedian who had been hired to pretend he was an Intel employee. That’s when I first thought I could do comedy for a living. Since then I’ve done over 1,200 shows in 28 countries. For example, right now I’m on a tour of shows in Australia, Singapore, Sri Lanka, Malaysia and Pakistan. My last trip two months ago was 31 days, 12 countries, 43,000 miles, 12 shows. Sticking to clean comedy — with no profanity, vulgarity or picking on people in the audience — has enabled me to get hired for corporate shows, charity galas, private parties, cruise ships, casinos — even AA meetings, and I don’t drink and I never have.
dan nainan

Photo courtesy of Jay Wennington/Unsplash

3. What would you tell someone who believes working and traveling the world cannot go hand-in-hand?

In this day and age, I would say that that is becoming less and less true. In my travels, I have met many people from all walks of life who are “digital nomads” – people who can literally work from anywhere. For example, a programmer from Sweden who travels the world and does all of his work remotely. These days, all one needs to work from anywhere are a laptop, a phone and Internet connection.

4. What was the venue you were most nervous about performing in, why, and how did it go?

The two that I was the most nervous about were the Ritz-Carlton Washington DC, where I performed for President Obama, and Donald Trump’s golf course in Palm Beach, Florida. In the case of the Ritz-Carlton I knew the president was going to be there, but Donald Trump unexpectedly showed up while I was performing at a private party at the course in Palm Beach, and although I didn’t show it, I was really, really nervous. Fortunately, it went really well. Same goes for the president, that was amazing (and you can see President Obama’s testimonial on Dan Nainan’s performance in this video!).
dan nainan

Photo courtesy of Scott Webb/Unsplash

5. What have been some of the most important lessons you’ve learned from traveling?

One very important lesson I have learned is that sometimes, being in America can distort how we see the rest of the world. I’ve performed in 28 countries so far, among them Muslim countries such as United Arab Emirates, Qatar, Oman, Pakistan, Malaysia, as well as Tanzania, South Africa and other countries that many Americans would be afraid to go to. Surprisingly, I feel safer in many of these countries than I do in the States – when I return to America, I have to put my guard up and worry about someone stealing my phone or mugging me, getting shot, etc. I think humankind could understand each other much better if people traveled more. Also, there are many things they do in foreign countries that we could learn from in the States. For example, escalators that stop moving after no one has used them for a few minutes, and having to put your hotel card in a slot near the door in order for your air-conditioning and lights to work, and roundabouts, and dollar coins, and money that is different colors, and money that is different sizes so that the blind can tell the bills apart.

6. What’s your favorite travel joke?

If someone speaks many languages, they must be European. If someone speaks two languages, they could be Canadian or Mexican. And if they speak only one language, they must be American.

About Jessie Festa

Jessie Festa is a New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

Jessie Festa standing in front of grafitti wall

Hi, I’m Jessie on a journey!

I'm a conscious solo traveler on a mission to take you beyond the guidebook to inspire you to live your best life through travel. Come join me!

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