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Thoughts on my First Year as a Nomadic Entrepreneur


This blog post was originally posted on The Worldly Blend. Check it out for more great insights about entrepreneurship and travel.


At this time one year ago, I had a big decision to make: I needed to decide between admitting that it was finally time to enter the real world or refusing to believe I had to.

A year and a few months ago, I was in a hotel room in Missouri for a friend’s wedding. I was talking to one of my best college friends about 2 possible paths I could take when I returned home to Tucson.

The first was to transition to working full-time (from my current part-time position) at my awesome job with a marketing company. I had an incredible boss, flexible hours, and perks from our clients all over the city. I was a VIP at a trendy wine bar downtown (our client); I frequently went to business lunches where my $30 steak meal was comped by the company; I loved the work I was doing; and I never had to worry about where money was going to come from.

The second option was to take a chance and do what I really wanted to do – to start freelance blogging, making money on my own, and beginning a life of freedom to live and work from anywhere.

The only catch was I had no clients and no idea what I was doing.

I knew that if I chose the second option, I’d be choosing a road of uncertainty and hard work. I probably wouldn’t match my friends’ salaries for another few years at least. I knew I’d be working 70 hours a week and have sleepless nights wondering how I’d pay my rent that month. I knew that I had student loans to pay. And there was a chance of failure. Sure, failure has monetary consequences, but it’s way harder on your spirit than your bank account.

As I went over these options with my close friend in that hotel room, I already knew what I had to do. I had to try my hand at making money on my own and see where it took me.

If it didn’t work, I wouldn’t have to live with the regret of not knowing what would have happened. Plus, I had friends who’d spent months looking for a job. Might as well spend a few months trying this out instead. If it didn’t work, I could always find a job later. But if it worked, I’d feel like the luckiest person alive.

In the past year, the unimaginable has happened. While I still have a long way to go, I’ve accomplished more than I ever thought possible:

  • I started a company.
  • My team has grown from one (me) to three and is still growing.
  • I am connected to hundreds of entrepreneurs around the world through the DC and other links I’ve made abroad.
  • I lived on a tropical island at a resort in the Philippines for 5 months.
  • I backpacked through Southeast Asia for a month, including a completely spur-of-the-moment trip to Bali.
  • I get personal business advice and help from my business inspirations like Dan Andrews and Ian Schoen of Tropical MBA, and plenty of others.
  • I learned to scuba dive.
  • I moved to a city where I didn’t know anyone – twice in less than 6 months.

I’ve learned more about business, life, and myself in the last year than I ever have before. Here are a few things I absorbed my first year as an entrepreneur.

1. The ubiquitous “entrepreneurial loneliness”? That’s a real thing.

This is the first thing on everyone’s “what I learned” list, but there’s a reason for that. I have experienced loneliness in the last year like I never had before. I’ve never before had to confront such a raw feeling of being alone. If my business failed, no one would be affected by it like I would. All the tough decisions were mine and mine alone to make. I could ask for advice, but in the end, it was my decision.

When things were great, there was no one to celebrate with. When things were bad, there was no one who understood how I felt. Sure, I now have a lot of entrepreneur friends whom I can talk to and I’m so thankful for that. But at the end of the day, it’s all on me. And that can be a lonely feeling.

2. You don’t have to know everything to start a business.

One of the best things I learned this year is that no one has it all figured out. That goes for everything: life, love, traveling, career, and entrepreneurship. Once I started working with other businesses at my marketing job back in Tucson, I realized this. And it made owning a business a much more realistic goal.

You can make money without having a perfect company. You can be successful without having a perfect company. And you can help people without having a perfect company.

If you have something that can help others and that people are willing to pay for, then it’s not just your prerogative to share it with the world. It may be your obligation to share it with the world. And when you limit yourself based on your feelings of inadequacy, you’re not just hurting yourself. You’re withholding your help from those who could benefit from it.

When I started to think of business this way, it was a total game changer.

3. Starting a business is the hardest I’ve ever worked.

In 2009, I was practicing piano 4 hours a day with a full course load and in my free time, writing music history research papers that I planned to use to get into graduate school.

In 2013, I was writing a 100-page masters thesis of original research on American religious music.

Building a business was still more work than both of those – put together.

Though it may seem like I was living the dream life (and don’t get me wrong, I feel very fortunate), most of the last year was spent over a laptop for 60+ hours a week, grinding away and hustling to get clients. I often worked really late because I’d gotten started on something exciting or had a deadline. I often woke up at 5:30 AM to take calls with prospects in the US. I probably put in more work hours in the last year than I did in the 3 or 4 previous years combined.

4. There’s always more money where that came from.

Money went from being a finite resource to being an infinite one. There is always money changing hands, being exchanged for value. All you have to do is get in on it. Business owners have a very different view of money than most employees do.

It’s all about ROI. For many people, $1000 is $1000. Most people don’t want to spend $1000 because then they have $1000 less than they started with. An employee doesn’t want to spend $1000. But a business person is happy to spend $1000 – as long as they can make $2000 on it.

5. Being an entrepreneur means confronting your personal faults and weaknesses… all the time.

My one year in entrepreneurship promptly brought personal development issues to the surface that had been there all my life. I think it’s similar to being in a relationship: when you are growing as a person and working with others, there will inevitably be times when you make mistakes and have to apologize for them. It’s all about how you learn from those mistakes and change accordingly.

6. I couldn’t get by without the help of others.

I would absolutely not be here writing this today were it not for the help of so many people along the way. Friends, family, fellow entrepreneurs, mentors, and most of all, my parents helped me make the decisions I needed to make and choose the tough road when I just wanted to give up. When I think of all that has been given to me and shared with me over the last year, it just makes me want to pay it forward.

No other experience has ever humbled me so much; made me ask for help; made me accept support; and made me give support.

I look back on this post that I wrote a year ago when I first found out I was going to move to the Philippines. This excerpt is from that post, written almost exactly a year ago, but before I really got started. It’s still just as true today as it was then:

Life is not about remaining in the safe bubble of certainty. It’s about getting out of your comfort zone and doing what excites you. As Tim Ferriss says,

What is the opposite of happiness? Sadness? No. Just as love and hate are two sides of the same coin, so are happiness and sadness. Crying out of happiness is a perfect illustration of this. The opposite of love is indifference, and the opposite of happiness is—here’s the clincher—boredom.

So after all of that… am I ready for year 2?

Hell yeah.


About the Author

Anna Wickham is owner of Charm House, a remote content marketing agency. She is a digital nomad currently based in Saigon Vietnam and she blogs at The Worldly Blend. As a coworking enthusiast, she is always looking for awesome places to be productive around the world. Follow her on Twitter.


  • Thank you for sharing this story.. Especially the parts about always learning and facing loneliness. Sometimes its so hard being alone and facing all these challenges alone. So proud of you for all you achieved Anna!

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