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Ditch the Desk Job: How to Become Location-Independent

Becoming location independent clears the way for you to start working from anywhere in the world.

For anyone who’s ever considered long-term travel, location-independent income is a non-negotiable part of the process.

Getting started, though, can be stressful — and scary as hell.

Let me start by telling you how I made the transition out of the traditional workplace and into a role that allows me to make a living no matter where I am in the world. (Hello from Thailand!)

Afterward, I’ll go over several options for making a living from anywhere in the world.

My Departure from the 9-to-5

When I was in my early twenties, I moonlighted as a freelance web developer while keeping 9-to-5 jobs ranging from a night auditor at a hotel to a project manager at a Kinko’s to a graveyard shift cook at a bowling alley diner.

I knew I wanted to work for myself, but I had no idea where to start. I only had a few clients, and sometimes I would go a month between jobs. What if I couldn’t find work? What if I couldn’t pay my rent?

My last job — working at Kinko’s — was a huge help in building my resolve to avoid corporate culture. Kinko’s had just been acquired by FedEx, and I watched as all the things that Kinko’s used to do for employees that made them love their jobs were systematically stripped away and replaced with more aggressive performance goals and stricter punishments for missing them —all with little or no reward for meeting goals.

For a year I watched FedEx methodically dismantle employee morale. I kept my spirits up by working my off hours on web projects, repeating to myself over and over, This is just for now. Things will get better soon.

A Terrifying Glimmer of Hope

When I got my chance, it felt like a bad idea.

My good friend had introduced me to a guy named David, who was trying to start a company building simple websites for B-list-or-lower actors and performers. His budget wasn’t huge, but he could offer me $1,300/month for three months.

At the time, I was spending about $1,050/month on living expenses. If I took David’s offer, I’d have $250/month to pay my mobile phone bill, buy any necessities, and, y’know, eat.

And it was only three months of guaranteed income. What if he didn’t renew for a fourth month? What if I didn’t have any income?

The Siren Song of Security

The same week I started discussing David’s project, I got an unexpected offer from a local creative agency. They asked me to come in and interview with them — they’d heard of me because of my volunteer work with a local coders’ meetup.

I went through the interview process, which involved several days’ worth of meetings with different department heads.

Finally, they told me they were prepared to offer me a job as a web developer and designer. I would more or less be the entirety of their digital department.

At the meeting, we finally got down to heavy details.

“We’d want to bring you in at a mid-range salary to show you that we’re serious,” said the woman who made the hiring decisions. “We can offer you $30,000/year.”

I felt a rush of mixed emotions. On the one hand, $2,500/month was more than I’d ever made before, and it would provide me with significantly more spending money than the freelance gig. But on the other hand, $30K was a mid-range developer salary at this agency? I didn’t know what was normal, but this felt pretty low to me.

“Okay,” I started carefully, “so assuming this all goes well and I’m a good fit for the team. What’s my growth potential here? Would I be able to see an increase in that salary after proving I’m able to handle the workload here?”

She shifted uncomfortably. “Well, yes. I would say you have the potential to make up to $35,000 a year here, assuming everything goes well.”

I felt my heart sink. I had a vision of software development at an ad agency as a glamorous job, full of challenging work and long hours, but with high pay to make it all worth it. But this job was offering me less than my manager at Kinko’s made in a year, with virtually no growth potential.

But still…

A little voice1 nagged at me that this was security and stability and a steady paycheck. I wouldn’t have to worry.

Getting By on Ramen Noodles and Hope

I didn’t sleep much the next few days. I kept rolling around my options.

The logical part of me was convinced. Take the agency job. Sure, it’s not a lot of money, but it’s experience that you can use to trade up in a couple years. And it’s not like you’re taking a pay cut to move into a job you like.

But my gut didn’t feel right.

You’re only considering this agency job because you’re a chickenshit, it hissed at me. You’ve been telling everyone you know that you just need a chance to be self-employed, and now you have that chance. So are you going to take it? Or are you a liar and a coward?

I was right, I realized. I had been looking for this chance for over a year, and now it was in my hands. If I turned it down, I couldn’t be sure how long it would take to get another chance like it.

I called the agency and declined, citing my concerns about growth potential. They seemed miffed, but it also sounded like they were already expecting me to turn it down.

I called David and accepted the contract. He told me he’d drop the check in the mail that day.

I put in my two weeks’ notice at Kinko’s.

And then I bought a pallet of ramen noodles, sat down on my couch, and hyperventilated for the rest of the evening.

The Payoff

After leaving Kinko’s, a funny thing happened.

Leads I’d been talking to for months without any movement were suddenly ready to pull the trigger. I started getting new leads around town.

It was almost like people could smell that I’d started taking web development seriously. I was no longer doing web design on the side; I was a web developer, full stop.

Between receiving David’s first check and the end of our contract (five months later), I had built up enough business to be bringing in an average of $3,000/month. If I could keep this up, I’d make $36,000 or so for the year — more than the agency would have paid assuming they found me especially good.

I was terrified to leave the security of my day job. I was convinced that I had no hope of making a decent living on my own. I was sure that the concerns of my parents, past employers, teachers — basically every adult I’d ever met — were correct and that the only way to really make it was to get a “real” job: the kind with health insurance and paid vacation and annual reviews.

But my instincts said there was a better way. And I took a leap of faith, set myself on fire, and trusted myself to be okay.

And my life has never been the same since. I’m happier now, more confident in myself, less bothered by the unknown — every part of my life improved as a direct result of taking charge of my life and becoming self-employed.

how to become location independent and earn a living from anywhere

What Options Exist for Remote Work?

There are many options for making a living without having to be physically present in a particular place. Three of the most common (and versatile) options are:

  1. Create a passive income stream
  2. Convince your boss to let you work remotely
  3. Work from anywhere as a freelancer

Create Passive Income

Passive income is the most alluring form of making money remotely. After all, who doesn’t want to make money while they sleep?

My personal experience with passive income has been generating it for other people; my own passive revenue streams are limited to affiliate sales on Amazon, book royalties, and whatever my investments earn — in short, it’s a very small part of my overall income.

For that reason, I won’t talk too much about generating passive income. There are other people more qualified to cover the subject — check out Chris Guillebeau’s $100 Startup for a good starting point.

Digital Products

The most successful passive revenue stream I’ve been able to reproduce for my clients has been digital products.

For example, my friend and client Jonathan Goodman runs a business from all over the world that sells digital products helping personal trainers become better at personal training, selling their services, and establishing additional revenue streams like online coaching. He has a small handful of products — most of which he created, built a marketing funnel for, and hasn’t had to touch (much) since — that earn him a comfortable living without a lot of weekly effort.

Online Services

Another friend and client, John “Roman” Romaniello, has built passive income by creating companies that he more or less only provides ideas for.

Roman’s created an online client management platform that he uses for his own online clients, but that he also sells to other coaches on a monthly basis.

He has a development team to keep it afloat, a management and marketing team to keep it running smoothly, and various other people on his team to take care of the day-to-day operation of the company — his only real job at the company is to give direction for what the team should focus on next.

“Passive” Is Kind of a Misnomer

It’s important, though, to note that while Jon doesn’t have to put a lot of effort into building the products themselves, and Roman doesn’t need to deal with much of the daily operations of his coaching platform, both of these guys spend a lot of time working on creating content and staying active on social media.

Passive income is very rarely completely passive, after all.

Find a Full-Time Job That Lets You Work Remotely

In some ways, this is a little bit like having your cake and eating it too.

If you can find full-time employment that’s entirely remote, you’ve effectively managed to hold on to the security of a 9-to-5 job while also gaining the freedom of working from anywhere in the world.

Hunt for Remote Jobs

These days, being a remote worker is no longer uncommon. Many notable companies, including Automattic (the company that built WordPress), Basecamp, and Buffer are almost entirely remote, and reports claim that 3.3 million full-time employees in the US workforce were able to telecommute at least part of the time as of 2013.

For anyone looking to start a new career, or move to a new job, there are a large number of job boards that specialize exclusively in listing remote jobs, such as:

There are quite a few other options — if you’re looking for remote work, you won’t have too much trouble finding companies willing to hire you.

Convince Your Boss to Let You Work Remotely

This is a little more challenging, but if you feel confident that you can do your existing job without going into the office, it’s worth trying to convince your boss that it’s possible.

Make a strong case for why the company would be better off with you telecommuting, and build trust in your ability to work from anywhere.

(For an in-depth strategy, read How to Convince Your Boss to Let You Work Remotely.)

Freelance Remotely

Simultaneously the simplest and most difficult way to make a living remotely, freelancing is one of the most common approaches taken by digital nomads.

It’s the riskiest prospect because there’s no guarantee of work, but with a little care and a lot of effort, you can build a strong referral network to keep your sales funnel full.

Position Yourself as an Expert

Find things that you’re very good at and interested in — the things you get excited talking about — and start teaching them: speak at local meetups, submit conference talk proposals, write tutorials, and do anything you can to publicly stake a claim that you “get” whatever arena you want to work in.

This makes you appear to be an authority, and people looking for freelancers want to hire the best available help.

As an added bonus, nothing will force you to really know your shit like trying to teach it to someone else. You can’t gloss over details when you’re explaining it to someone else.

Make Damn Sure You Get a Good Referral

When you’re working remotely, you may not get the chance to go out and meet your clients — especially in more remote locations — so you need to make sure that other people are doing your sales for you.

When you get a client, become their hero. They’ve come to you to solve a problem, so solve that problem completely, and make sure they know what’s going on at all times.

If you can A) solve your clients’ problems for them, and B) make sure they never felt like you had disappeared2 during the project, you’re almost ensured a good referral.

At the end of each successful project, it’s a good idea to ask your client to either send you a testimonial (you can use this for marketing, too) or ask them to complete a survey about your performance — in either case, they finish the project by reminding themselves all the things they liked about working with you. Later, when a friend mentions a problem that you can solve, your client will be eager to drop your name.

Remove the Anchor of Office-Bound Work

Removing the anchor of reporting to an office every day is an astonishingly liberating accomplishment, whether your goal is to sell everything and travel the world, or simply to cut your commute and eliminate the requirement to wear pants.

It’s also daunting, and it requires some legwork to make it happen. But don’t give up — I’ve yet to meet anyone who made the transition to remote work and regretted it.


  1. This voice sounded alarmingly similar to my mother’s.
  2. #protip: The window of time between your last communication and when the client will wonder what you’re doing is much shorter than you think. Daily communication is ideal — you don’t need to deliver something every day, but make sure they know you’re working on their project.

About the Author: Jason Lengstorf

I’m living Post-Hustle.

I don’t believe in extremes. You don’t have to make a choice between a successful career and a fulfilling life outside of work. I’m living proof that you can have both: I work 40 hours a week while traveling the world — all while saving money and feeling happier than ever.

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Jason Lengstorf in Tokyo