How I Freelance from Anywhere in the World: Audio Interview

A little while back, I got an email from an anonymous email address.

This guy — let’s call him “John” — had a lot of questions about how I was actually making my lifestyle work. Never mind the travel tips, he said, I want to know how you make money.

I asked John if he’d be willing to get on a call with me and let me record our conversation. He agreed, and we talked for about 50 minutes. John grilled me on how I got started, how long it took me to break even, and how I keep things moving now that I’m half a world away from the people I work with.

Note: The audio ends rather abruptly; John wanted to ask a couple questions off the record (that were very specific to his own situation), so I cut the audio off there.

Below, I’ve summarized what we talked about on the call. John’s questions are the headlines, and my (heavily paraphrased) responses are the text in each section.

How to freelance from anywhere in the world.

Credit:Tyler Dylan

What Is the Actual Nature of the Work You’re Doing?

Right now I work as a freelance web developer, but I have a single long-term contract with one client.

My day-to-day tasks center around software research and development: I build experimental apps quickly to test new ideas (kind of a one-man skunkworks). I try out something crazy on a small alpha audience, and if it proves viable, the project is handed off to the production team as a “real” project with dedicated resources and so on.1

How Did You Get to the Point of Feeling “Established”?

Within a year and a half of going full-time freelance, I was able to make about $30K/year. For me, who had no family, debt, or much overhead at all, was more than enough to get by.

How Did You Get Started?

I first got interested in web design when I was playing in a band. We couldn’t afford to hire help, so I volunteered myself to do design when we needed it. It stayed interesting, so I kept learning.

After the band broke up, I was still interested in web design. I built a website for a close friend of mine, which led to leads for a couple local websites.

One of those leads gave me the opportunity to quit my day job and freelance full-time. I took the plunge, and I’ve been my own boss ever since.

So Your Business Grew Organically?

At first I had to take work wherever I could find it, and I spent a lot of time chasing leads.

Over time, though, I started to get emails from people asking about websites. Most of them were health and fitness professionals.

Thanks to my work for Nate — the first website I ever built that wasn’t for me — and due largely in part to Nate’s incredible success in the health and fitness sector as a journalist, I was introduced to a few up-and-coming fitness pros who needed websites.

I built sites for John Romaniello, Tony Gentilcore, and Mike Robertson. They all had (or would soon have) enormous online presence, and their recommendations carried a lot of weight.

These guys were rising stars in the industry. They were speaking at conferences, writing articles, getting interviewed in major publications — they were the connectors, to put it into Gladwellian terms. Other people looking to make it as fitness pros asked my clients for advice, and when it came to web design, my name was dropped frequently.

This turned into a very strong referral network that became effective enough over time that I didn’t have to go looking for clients anymore; I had 3–5 new leads coming to me each week.

I had become “the guy for that” — this has been the ultimate secret to my success. I have become dependably excellent in my area of expertise: my clients could trust me to solve their problems effectively without requiring much of their time. That trust led them to continue working with me and referring me to others.

How Long Did It Take Before You Felt Comfortable?

It took about a year and a half to get to the point where I was making $30K/year. It wasn’t anything extravagant, but I was able to live comfortably.

Dealing with Dry Months

Where things were rough for me, starting out, was when I had a slow month. I didn’t think ahead and put money aside when I had good months, so the dry months were rough.

I could have solved that problem fast, had I been a little smarter about things, and it would have made me far more stable as a freelancer.

But I was dumb, so I’d have a good month and — instead of putting it away to cover a slow month later — I’d say, “Fuck yeah, let’s go to Hawaii!”

How Did You Gain the Technical Competency to Get Where You Are Now?

I’ve always been really curious about how things work, and I think that’s probably the single biggest advantage I have in life.2

In addition to being generally curious, I also had a need: my band needed a website if we were going to tour effectively, but we didn’t have any money.

So I learned to customize a MySpace page. Then I built a crappy website after a shitload of Googling. I built it again. And again.

I would come up against a problem that we needed to solve, and then I would find a way to solve it. It was fun for me.

The Hubris of Being 19

I was curious about how to make more powerful tools, and I needed to find a way to let my clients update their own websites without requiring me to go in and do it.

I wasn’t aware of the open source community at this time, or of WordPress. Plus, I was a cocky teenager who thought I could build something better than anything else that was out there — so I built a CMS.

It was a terrible business plan, but an excellent learning tool. As a result I understand a lot of what happens behind the scenes in a tool like WordPress or Ghost, and when those tools don’t do what I need them to do, I can usually figure out a way to build something new to solve my problem.

How Did You Get Marketing Skills in Combination with the Tech Skills?

I have this delusional belief that — if I continue to study — eventually I’ll understand everything.

Since a lot of my clients work in the same industry, I saw them all running up against the same kinds of problems. I also saw what was working for my more successful clients, and what wasn’t for the clients who were struggling.

And since I love learning how things work, I started to dig into the “why” of it all. I saw patterns emerging, and I learned how to apply what I learned to new clients in a way that helped them grow their businesses.

I also had marketing experience out of the necessity of being a broke musician. I had to figure out a way to convince high school kids to come pay $5 to watch a band they’d never heard of before from Montana — it was a good primer on marketing.

Later, on bigger projects, I’d hire experts to come in and set up complicated marketing efforts, and I’d watch what they did and keep asking why they were doing it. So even when I didn’t do the work myself, I tried to continue learning.

How Would You Design Your Own Curriculum for Getting a Skill Set?

The technical side is the biggest job pool, but you can find non-technical jobs as well: customer support, executive assistants, writers, accountants, lawyers — the world is set up to make most knowledge work possible remotely.

If you want to go the tech route, you’ll need to figure out how you learn best: some people get the most out of reading tutorials and documentation; others have better luck with video instruction like Treehouse; and then there’s always something to be said for learning in an in-person, hands-on environment.3

For hands-on training, there are a lot of new bootcamps popping up all over. In Portland, for example, you can take a four-month course through Epicodus that guarantees real-world job experience through an internship.

For non-technical careers, start looking for jobs on the many job boards out there, including remoteok.io, weworkremotely.com, and wfh.io. Many of the listings are for tech jobs, but there are a good number of support, content, marketing, and human resources jobs posted as well.

What Are the Hurdles?

Easily the biggest hurdle to making it as a freelancer is your own temperament. Are you excited about your work and eager to get tasks knocked out? Or are you more likely to need someone cracking the whip over you before you’ll get things done?

(Further reading: Get More Done Faster — Scheduling for Maximum Productivity)

Breaking into the Industry

Just keep doing projects in the industry. If you have to start out doing free work, do it. But try to get paid every time — you’re providing a service, after all.

If I wanted to learn cars, I’d buy books, hang out with my more mechanically inclined friends, bother my mechanic with questions about what he was doing and why.

I’d start with small projects: changing my own oil or changing the tires. Then I’d graduate up to more difficult tasks — my ultimate aim would be to know enough to take the car apart and put it back together again, and I’d get there one step at a time.

Find a project that’s about 10% above your skill level and take it. Set yourself on fire to learn the new skill.

At 10% beyond your skill set, there’s very little risk that you’ll be unable to figure it out; where the risk comes in is if you get too ambitious and do something that requires learning several layers of skills to complete — taking a job as a lifeguard before you’ve learned to swim, for example.

Find a balance between challenging and “in way over my head”.

How Mutually Intelligible Are Programming Languages

Most programming languages share ideas. JavaScript and PHP have different syntax, but a lot of the concepts carry through. Each programming language is usually created by taking a programmer’s idea of the “best” features of any number of existing programming languages, and adding or removing features as they see fit.4

You have to build the mental models at first, which is the hard part. After that you’ll start to see patterns emerge. It starts out feeling like total nonsense, but similarities show up, and concepts cross languages. You’ll find that each new language you learn takes a lot less time than the one before it did.5

What Do You See in the Future, and How Are You Positioning Yourself? What’s Your Relationship with New Tools?

You have to find a balance between using tools that solve problems (WordPress will solve many of your problems very quickly) and learning how things work (understand that WordPress is built in PHP, and if you know PHP you can get WordPress to do anything rather than being limited by WordPress plugins).

How Do You Approach Data Security?

I’m fortunate in that most of what I do isn’t sensitive. (The most sensitive data I deal with is email addresses — and I try to avoid even dealing with those.)

I use TunnelBear as a simple, cheap VPN. It’s a simple solution that will do a pretty good job of protecting my data without making security an additional job for me.

I also use Dropbox (disclosure: if you sign up with that link, I get bonus storage) to make sure I don’t lose any data — I could drop my computer off a cliff and I wouldn’t lose any of my files.

How Long Do You Intend to Travel?

I don’t have a definite answer to this question. I intend to travel for as long as travel seems like the right thing to do.

I’m always checking in with myself: am I doing this because I’ve convinced myself that I’m the type of person that travels, or because it actually makes me happy?

A time may come in a decade, a year, a month — or tomorrow — when I decide that I’d be happier if I was in one place instead of moving every few months.

However, for right now, I don’t see an end in sight. I expect I’ll be traveling for at least the next couple years unless something unexpected happens.

How Do You Overcome the Absence of In-Person Interaction?

John asks, “How do you make sure people remember you when you’re not in the room? If your best impression is face-to-face, how do you preserve that?”

I build my business as a “remote first” workplace. I’ve always worked with people without regard for geographical constraints.

At first, I would only correspond with my clients by email, but there were drawbacks to this: my relationships were weak and strictly business, and it can be hard to communicate tone effectively. Sometimes I’d think I was making a silly joke, and my client would think I was being a dick; other times, I’d think my client was unhappy, but they’d just responded in a hurry.

Now I require phone calls (preferably video calls) for big deliverables and check-ins. This allows me to walk through what I did and why, and gather feedback in realtime. It also allows discussion, just like a face-to-face meeting would. You lose the stiffness of email, and you build a real connection with your clients. This has resolved a lot of conflicts before they had a chance to start — it’s easy to yell in an email; it’s hard to yell at someone who’s right in front of you.

That being said, I do try to show up where my clients are from time to time. If I know I’ll be somewhere that a client lives, I’ll try to meet them for dinner or coffee. When a conference is happening where a good group of my clients is planning to show up, I’ll see if I can make it work. Even with video calls, there’s a huge amount of added value in just spending time with people, in person, without any agenda.

Make Yourself Useful

When I meet a potential client, I don’t try to sell them something. I just share a solution if I have one.6 This establishes me as an expert and — even if they don’t hire me — they’ll remember that I was able to help them out. If they meet someone who needs help in the future, you’ll get a referral, and if they need to hire help in the future they’ll think of you.


  1. For the technically inclined, I’m working heavily in realtime video right now: Node.js, Socket.IO, WebRTC powering the back-end, and a plain vanilla HTML/CSS/JS UI.
  2. My dad would play the “why” game in reverse when I was growing up. Whenever I had a chore, or a homework assignment, or anything at all, really, my dad would ask me how it was done. I didn’t get away with cop-out answers: I needed to have a thorough understanding of why priming a lawn mower helped it start; or why it was faster to sweep out the garage if I followed a pattern instead of whisking the dirt around haphazardly; why the lights turned on when I flipped the switch. As a kid, it was fucking infuriating; as an adult, I don’t think any other single factor has contributed as much to my success as my ingrained habit of asking why something works (or doesn’t) instead of shrugging and continuing about my business.
  3. In the audio, I refer to “Code School” in Portland as a bootcamp. It’s actually called Epicodus.
  4. I had some of my facts wrong in the audio interview. I talked about languages having ancestors, which isn’t correct. PHP was written in C. JavaScript is a standard of its own, with interpreters that are written in C, C++, Java, or even — in truly meta fashion — JavaScript.
  5. I haven’t tested this theory, but I have a hunch this applies to spoken language as well. I’m getting better at Spanish, and just barely starting to learn French; it doesn’t necessarily feel easier to learn French, but I have some strategies and constructs in place that are definitely helpful.
  6. Sharing a solution is very different from doing actual work. If we’re talking and I can help you out by just rattling off some knowledge I have that applies to your situation, then I’ll do that. But I won’t pull out my laptop and solve the problem for you unless we work out a budget and scope first.

What to do next.

If you’re like me, the idea of traveling permanently while making a living probably seems like a dream — but you don’t think you can pull it off.

I felt that way right up until I actually boarded a flight to leave the United States back in 2014 — and now I can’t believe I didn’t start living this life sooner.

The secret to a life on your terms — work where and when you want, living anywhere in the world — is remote work. And there’s good news: it’s easier than ever before to join the ranks of location-independent workers around the world.

I want to help you. The best remote workers all have a set of non-technical skills, and I’ve put together a free 6-point checklist to help you master them — and ultimately master your time and ability to work anywhere in the world.

Click here to get the free checklist now.