The #1 question people ask me is this: How do you afford to travel so much?

While the question usually comes from strangers on the internet, friends and family members have started asking me, too, as if I’m harboring some closely-held secret. “How do you do it?“ they whisper. “Do you even work?” they half-laugh.

First of all, I probably don’t travel as much as you think I do. Second of all, my kind of budget travel isn’t glamorous — most of the time I’m literally sleeping in my car.

But I do manage to travel a lot, and here’s how: I work for myself. I’m a freelance writer, a digital nomad who can work from anywhere —and often does. My parents don’t pay my bills and neither does my (imaginary) rich boyfriend. I’m making it work on my own.

I’m not saying I have all the answers. Far from it: I took the leap to digital nomad just a few months ago. I’m building this plane as I’m flying it, so it feels strange telling other people how I got it off the ground. But since you asked, I’m answering.

My overnight success story

I didn’t become a digital nomad overnight. In fact, without really realizing it, I’ve been working towards this for over a decade.

I’ve been getting paid to write online since 2009, when I wrote the headlines for my college’s newspaper every Monday and Wednesday night for $7.25/hour. 10 years later, my clients pay me more than 13x that! (Technically my first paid writing gig was in 2006, when 15 year-old me won a cash prize in an essay contest about the Nanjing Massacre.)

I’ve always loved to write, but society and well-meaning mentors convinced me that I couldn’t make a living from it. So I did an English minor instead of a major and got a degree in Environmental Sustainability instead.

I don’t regret majoring in Sustainability. It taught me a lot about the world I wouldn’t have learned otherwise. My degree got me my first job, a 2-year part-time contract with NASA as a NASA Earth Ambassador. It also got me my first “real”, full-time job at Opower, an energy efficiency software company in Washington, D.C. I loved both jobs. I was saving the world with words! Eventually I took my ever-growing copywriting skills to Uber in San Francisco, where this sustainability nerd got to work on cool projects like Uber Bike and Uber Movement. (More on Uber later, if anyone is interested.)

While working as a copywriter at Opower and then at Uber, I was spoiled by the relaxed startup culture: free food, standup desks, dog-friendly offices, and flexible hours. Opower let us work from home around holidays or doctor’s appointments, while Uber let us work from home pretty much whenever we wanted. With colleagues spread out around the city, country, and world, most work happened via video call. As long as I did good work, met my deadlines and made myself available for calls, it was okay if I wasn’t always at my desk.

To escape the tyranny of Uber’s open-office floorplan (my desk was closest to the ping-pong table, which made matters even worse,) I began setting up office in the sunny courtyards and patios of San Francisco at large. Nobody really missed me as long as I was online, and I got more work done without the coworkers, commute, and ping-pong to distract me. Eventually, I stopped commuting to San Francisco altogether.

I quit my corporate job at Uber in July 2018 without another job lined up, planning to freelance. But before my 2 weeks’ notice were even up, an ex-coworker slid into my Instagram DMs with a job offer that was too good to pass up: a director-level role at a startup in Idaho that would let me work 100% remotely. I did that for 2 months before admitting it wasn’t a good fit, partially because it was incredibly stressful (hello, 5-person startup!) and partially because deep down, I didn’t want to sell baby toys: I wanted to be my own boss. Burned out and ready for a break, I used my savings to take the last 3 months of the year off to travel: 2 months in Europe, the rest with family. In January, I started freelancing in earnest.

Now, as of May 2019, 80% of my income comes from freelance copywriting. Another 10% comes from privately tutoring the SAT, while the last 10% comes from walking dogs via Wag. (Use my code REBECCA5834 for $50 in free credits!) I actually enjoy the dog walking, which pays me to be outside and meet cute new pups, but I soon hope to cut the tutoring and make at least 90% of my income from writing alone. Eventually I hope to add passive income from this blog, too, which right now fuels my bubble tea habit —I jokingly call it my “boba bucks”— and not much else. Maybe someday it’ll be more like “two-bedroom house bucks”? Hey, a girl can dream. 😉

The best and worst parts of being a digital nomad

Most days, freelancing is the FREAKIN’ BEST.

I don’t set a morning alarm, allowing myself to wake naturally after 8-9 hours of sleep. I eat a healthy breakfast, take my dog on a walk, and make the pleasant 30-second commute from my bedroom to my sunny backyard office.

That’s when I’m home in Oakland, at least, because I’m often traveling. So far this year I’ve spent 2 weeks in Colorado, 2 weeks in Utah, a week in Portland, 2 weeks in Kansas with my grandmother and 2 weeks in New Mexico with my parents, not to mention various shorter trips up, down, and all around the Southwest and the California coast.

I have plenty of time to see friends and loved ones. I haven’t been sick in over a year because I’m not stressed and have time to take care of myself. I can go on a hike in a popular National Park at 10am on a Tuesday and have the whole trail to myself, or to the grocery store at 1pm on a Thursday and enjoy empty aisles with a front-row parking spot.

Sound perfect? Like any life, it’s not.

Some days I work hard and make no money. I spend a lot of hours seeking work —emailing leads, fielding calls from potential clients, drafting proposals— that never materialize into payment. I try to account for that unpaid work in my hourly rate, since those are things I’d get paid for on salary (or have an HR or account department to handle,) but it can still be demoralizing to work a full 40-hour week without a paycheck at the end of it.

Some days, especially the days where I make no money, I feel like a lonely, depressed, fraudulent sack of potatoes. Without a team to cheer me on or pick up the slack, it’s easy to take every setback or stressful day as a reflection of my own personal failings. Client takes 4 days to send me feedback on a project? Well obviously they hate me, aren’t going to pay me for my work, and are secretly planning to blacklist me and tell all their business friends that I’m a miserable fraud!!! (Jk, they were just busy.)

I don’t get health insurance. I don’t get paid sick days or vacation time. Some days I crave the stability of a 9-5 and find myself trawling job boards, looking for a way out.

But most days, I absolutely love it. I’m not yet replacing the 6-figure income I was earning in Silicon Valley, but I’m richer in other kinds of green. 🙂 (And I’m paying my bills without going into credit card debt or wiping out my emergency fund.) I’m not saving for retirement in any meaningful way right now, which makes me anxious, but I’m betting on myself that I can increase my income to a savings-friendly level with just a little more time. For now, my old 401ks and IRAs from my time in the working world will sit there earning money for me while I invest in myself.

What does it take to be a digital nomad?

If you’re still sitting there thinking “Gee, I wish I could be a digital nomad,” you totally can! There are many ways to work from the road —coding, web design, photography, videography, teaching English, customer service— that I haven’t tried but that have enabled thousands of people to travel full-time. If you take one thing away from this post, though, it’s that becoming a digital nomad doesn’t happen overnight.

I’m able to be a digital nomad (and still, just barely,) because:

1. I have a reputation and professional network in place from my time in the corporate world that helps me find clients. I’m not starting from scratch.
2. I saved money from my previous corporate jobs that helps me weather the feast-or-famine nature of freelance.
3. I supplement my income with other short-term gigs like dog walking.

Without any of those three, I wouldn’t be able to do this. I feel grateful every day that I can live this life, but I don’t want to make it sound like it’s easy. Being a digital nomad is messy, beautiful, freeing, stressful…just like life. And right now, this is mine.

Is there anything else you want to know about freelance writing/being a digital nomad? I’m still figuring out but would love to share what I’ve learned so far. Are you a digital nomad yourself? Let me know in the comments!