How to Untether Your Life and Work From Anywhere

The biggest barrier to entry into the workationing lifestyle is being able to work from anywhere. There’s one thing all of us digital nomads have in common: we work remotely. But how do you get one of those sweet “work from anywhere” jobs?

If you have to clock into a desk job and sit in a cubicle from 9-5, five days per week, you’re too tethered to one location to be able to live the digital nomad lifestyle. And if becoming a workationing digital nomad is your goal, you’re going to need to cut that tie before you can catch that plane.

The good news is, we’ve already done it. Not only do we work remotely, but we’re going to teach you how you can untether your life and work from anywhere, too.

You can buy a ton of books on the subject, and each of them will tell you a different path to get to the ultimate destination: working from wherever you want. Some paths are easier than others.

If you’re Tim Ferriss, you just need a four hours, a muse and a good strategy for buying leftover ad space. And, you’ll get a hot beach bod along the way! Unfortunately, not everyone is Tim Ferriss (although we DO have a podcast detailing our adventures in Workationing – follow us on iTunes or SoundCloud). 

Here’s the step-by-step process for how we broke free of the 9-5 cubicle life, and how you can achieve the “work from anywhere” digital nomad lifestyle for yourself:

Work from anywhere

Step 1: You need to develop a skill that you can turn into a “work from anywhere” job.

First, you need to find something that you like to do and can be good at. Know that developing your skills is going to take some time, but that’s not to say that you can’t make money along the way as you learn. Good targets include:

  • Web content writing
  • Website design/development
  • Graphic design
  • Social media marketing
  • Tech stuff in general
  • Editing (content, video, whatever)
  • SEO
  • Translating

The idea here is that you need to find the kind of “work from anywhere” job that you can make a decent living at. There are plenty of smaller paying gigs in a variety of areas that you can piece together in order to make a paltry half-living, and you should avoid this. Instead, pick one area and specialize in it. Don’t do anything else until you get really, really good at that one job that you can do from anywhere.

Buy books on your industry, and then actually read them. Watch tutorials on YouTube. Read blog posts and sit in on webinars. Become as much of an expert as you can in your niche during the educational phase, because you don’t want to start off your work from anywhere career with a bunch of pissed off clients who aren’t satisfied with your work.

Once you’re confident that you’re competent (enough), proceed to Step 2.

Work from anywhere

Step 2: Source “work from anywhere” jobs on the side of your current job, until you’re able to make enough to quit.

Once you’ve identified the “work from anywhere” job that you want to have on an ongoing basis, start sourcing as much freelance work as you can. Craigslist is a great place to start.

Let’s say you want to become a professional web content writer. Good news: there’s plenty of work available, if you know what you’re doing and can write a good cover letter. Write that cover letter, and make it generic enough that you can copy/paste/slightly customize for each position that you apply for (after all, they’re all copywriting jobs, so it’s appropriate).

Next, go through Craigslist. Check the writing gigs and writing jobs for your city/state. Send your cover letter to every posting that seems relevant, going as far back as two weeks. Then, systematically do the same for every other city listed in Craigslist (check the right sidebar, then go by state as well so you can see some of the smaller metro areas, where the competition will be lower). Since you’re specifically trying to find remote jobs, don’t limit yourself to the job postings that are only in your area.

This is largely a numbers game, so you should be applying to 50+ writing jobs/gigs per day. By the time you finish the last city/state, a few days will have gone by, and you can repeat the process. By the time you send out your cover letter to 500 job postings, which you can accomplish in two weeks, you should have work requests starting to roll in. If not, you need to revise your cover letter.

Keep this process going, and between repeat clients, referrals, and your Craigslist numbers game, you’ll eventually have enough work to consider quitting your job. Kari followed this exact process, and it took her about three months to get to the quitting point.

Whether you decide to go the copywriting, video editing, translating or whatever, it’s important that you find a process for finding work that actually works for you. Then, refine that process along the way until you start to achieve optimal results.

Work from anywhere

Step 3: Stay where you are for a while, and make sure what you’re doing is sustainable.

By now you’re probably pretty busy, what with your day job and your new work from anywhere side gig. And you’ve probably got some extra money in the bank, as a result of the second job that you’re working.

It might be tempting to quit as soon as you see that you might be able to make a living at your work from anywhere side gig. RESIST THAT TEMPTATION. Before you quit, you need to make sure that what you’re doing is really sustainable.

What happens if your current clients decide to halt your projects? How long does it take for your leads to turn into paying clients? What’s the “slow season” for your industry, and do you even know what that looks like yet? If you couldn’t find any more work for an entire month, would you be in financial trouble?

There are a lot of questions that you need to be able to answer before you should even think about quitting your day job and start living the “I work from anywhere” life. Stay where you’re at until you’re as sure as you need to be that you can work from anywhere – and actually make it work for you.

Work from anywhere

Step 4: Make a plan (and ideally, find a friend to be a digital nomad with you).

If you’ve gotten through the previous four steps and are ready to quit your “real” job in order to become a digital nomad and get your workation on, you still shouldn’t quit just yet. Instead, take another month or so to outline your plan. Things you should know:

  • The goals you want to accomplish, outlined by personal, career and family. Write them down, map out the steps you’ll need to take to accomplish these goals. Get granular with it, and really set your hopes and dreams down on paper.
  • Where you want to go, and when. Digital nomads have to make a lot of decisions, and what you gain in freedom you often lose in convenience. Do you want to stay where it’s warm in the winter? Or do you want to bounce around between climates? That impacts what you’ll pack, and how much you’ll pay for lodging and airfare.
  • Who you’re workationing with. Are you traveling solo, or with a partner? Is it a romantic partner, or a friend? How will you get along as you travel, when you haven’t slept in 22 hours because flights got delayed and got forced onto a red-eye?
  • What you’re going to do with your stuff. What’re you going to do with your mail? And your dog? And your car? And your lease? What about health insurance? Will you need US-based and international coverage?
  • How much you want to spend per month, and how frequently you want to bounce around places. You can get HUGE discounts on Airbnbs if you book for a month or longer, and if you time your flights right you can save hundreds of dollars on each leg of the trip. Planning ahead takes time and effort, but it usually pays off.

Before you quit your job and hop on a plane, you should have all of the details worked out. In fact, before you even book your first leg of an extended trip, you should have at least the first three months planned out.

Work from anywhere

Step 5: Make sure you actually like what you’re doing, then quit.

If you’re still rolling in freelance “work from anywhere” gigs, you’ve got some money saved up and you’ve got a plan, then it’s probably time for you to finally quit your day job. We work remotely, and we love it, but we cannot encourage you to quit your “real” job until you’re absolutely certain that you can sustain yourself exclusively on remote work.

Do not be too hasty when it comes to quitting your day job. You’ll find that some weeks, and months, work comes slower than others. You DO NOT want to find out that you can’t hack the “work from anywhere” lifestyle after you’ve already given up your primary source of income.

Additionally, at this point you should have a firm grasp on whether or not you like the work from home lifestyle. To be sure, it ain’t for everyone. Many people prefer office environments, socializing with coworkers, and having a defined beginning and end to their work day. Just because you can work from anywhere in the world, doesn’t mean you’re actually going to like it. Figure out if the work from home lifestyle is for you, and do it before you quit.

Beyond just deciding whether or not you like working from home (or anywhere – no matter where you are, it can be isolating at times), you also need to figure out of the job specialization you picked in Step 1 is interesting and rewarding. Do you like web content writing? Can you see yourself doing it for the next few years?

No? You hate it? Then pick something else and restart the process. If you ditch a job you don’t like so that you can take on another job you don’t like, albeit with more flexibility, you’re not setting yourself up for maximum happiness down the road.

In fact, you’re probably setting yourself up for disaster. When you hate the work you do, you tend not to do it (and when you do, you don’t do it well). That doesn’t sound very sustainable.

It’s not easy to find a work from anywhere job that you also genuinely like, but this is a goal you should achieve before you quit your day job. Otherwise, you may find yourself stranded in some foreign country, unable to source enough work to buy a plane ticket back home.

Work from anywhere

Step 6: Untether the rest of your life as much as possible.

So you’ve quit your job, you’re now able to work from anywhere (and you’ve probably tested out this new capability in coffee shops and on mini-workations). Before you celebrate your digital nomad status with a going away party, you’ll need to untether yourself from other aspects of your life that hold you to one location.

Quitting your day job and finding work from anywhere jobs is just the first step. Next, you need to execute the plan you laid out in Step 4. It’s one thing to recognize that you need to find a new home for your cat, and another thing to actually do it. Ditto: selling your stuff, moving out, and putting the rest of what you own in some storage facility.

As you’re untethering, focus on reducing your monthly expenses “back home” as much as possible so that you have more money – or need to make less money – as you travel the world. A larger storage facility is going to cost more money, and when you run the cost of storing vs. the cost of replacing (and who knows if you’re even going to want to!), you might find yourself downsizing more than you’d planned. That’s okay.

As you dig into the untethering process, you’re going to be confronted with bad decisions you’ve made along the way. How many pairs of jeans do you have? How many dresses have been hanging in your closet, for years, with the tags still on? Did you really need all of those kitchen gadgets from late-night infomercials? What is all this crap, and why did you spend so much money on it? This is painful, and sneaks up on you in ways you might not expect.

What about your relationships? While you’re gone, friends might get married and have babies. At the risk of sounding morbid, people you know might die while you’re away. Do you have a girlfriend or boyfriend? Are they coming with you? If not, you might want to consider ripping off the Band-Aid and breaking up before you go.

The point is, part of the cost of admission to the digital nomad lifestyle is leaving people at home behind. It can be a high price to pay – for some, it’s too high.

There are decisions that you’re going to have to make before you can embark on your new life as a digital nomad, and these choices are difficult to make. Emotionally prepare yourself, because almost none of this is easy.

Work from anywhere

Step 7: Follow through.

Every step in this process is going to require follow through. If you quit after applying to 50 work from anywhere jobs on Craigslist, you’re never going to get your new career off of the ground. If you can’t get rid of your cat, you can’t get on the plane. If you aren’t absolutely sure that you can sustain yourself solely via work from anywhere jobs, you risk financial ruin if you quit your job and aren’t able to make it work.

Listen: if the digital nomad lifestyle were easy, everyone would be doing it. It’s not easy, and you’re going to encounter a lot of roadblocks along the way to fully untethering your lifestyle.

But we’ve got to tell you, we work remotely and the grass on this side of the fence is pretty damn green. It’s a lot of hard work to build up your skills to the point where you can find a sustainable job that lets you work from anywhere in the world. But if you can do it, you’ll be rewarded with the freedom and flexibility to go wherever you want. And that’s borderline magical.


  • Good news! Depending on where you’ll be landing, you CAN keep your cat or dog. I brought my cat with me to South America. Not every country is as good about cats, so do your homework first.

  • Really nice and motivating post. Thanks for sharing. Two years ago I started traveling solo(spent a year in Asia) and it’s when I got an idea about getting my own travel blog. I didn’t have any idea about blogging, making webs or digital nomads. So, I’ve been putting all together for the last year. I know I’m not quite ready to leave but can’t wait more haha

  • Hi Kari!
    While planning our own adventure, my husband and I came across your blog and podcasts. It’s been a great source of entertainment and help. We’ve leased our house, and leave in July for 10 counties in 10 months with our 1 yr old girl. Do you have any recommendations for cell phone plans and travel insurance? My husband, like y’all, will be working (doing computer programming). Any help is appreciated!
    Thanks a million!

    • Hi Anne,

      So excited to hear you’re coming “out here” with us – and I’m so happy you enjoy the podcast! (Tell your friends, we need the downloads! Hahah).

      As for travel insurance and phone plans, it depends on where you’re going. The prices for travel insurance vary wildly depending on where you’re going (the North American packages that cover Mexico, the US and Canada are most expensive, and you’ll usually get the greatest savings if you go for the Central/South America with Europe…but as with all things, your mileage may vary). Same deal with the cell phones.

      Where are you going? Are you Airbnbing it? By the way, high five and props to you for doing it with a 1 year old!

      • Thanks Kari! We’re nervous and excited. Our list is flexible, but we really are hoping to get to each of these places. We are also being a perhaps a little less daring, due to our little one.
        London, Dublin, Stockholm, Prague, Nice, Florence, Alicante, Bali, Brisbane, Auckland.
        Yes, we’re definitely using Airbnb and staying 1 month in each spot to take advantage of ppl with those discounts!
        Packing all that is needed for 2 adults and a babe does make our travel bags heavier and the need for travel routes to be more direct (expensive), but we’re up for the challenge! Any advice is gold!

        • That sounds like quite the trip! The #1 tip I have for Airbnb is to always try to negotiate further discounts directly with the hosts. Often you can at least get the cleaning fee waived, if you offer to leave the place as clean as you found it.

          In more than 50% of cases, I’ve been able to get another 10%+ off just by asking. The worst they can say is no, but if you make this part of your strategy on an ongoing basis you can save a lot of money over time.

    • Hi Chelsea,

      Thanks for the feedback – it definitely takes some time, and if you’re building a new skill from scratch it’ll take longer to create or find a remote job for yourself that enables you to untether your life. Thanks for linking to the jobs post – I’m sure a lot of our readers will find that to be useful!


    • – Ok, I’m sitting here getting all choked up. I love this story. Hello love on so many amazing levels. I don’t cry over this stuff – girl, yo8u1&2#7;ve got something and it’s dang good. Love each and every one of these images.

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