10 Ways to Go Remote

By: Michael Youngblood, Co-founder, Unsettled  

To “go remote” is a way of life. It’ll require dedication, sacrifices, and lifestyle change, but if your dream is to have the freedom to choose where you live when you go into the office, and how you spend your days, then it’s worth it. For the record, if your dream is stability or a grounded life with a white picket fence and a good, predictable job that you go into every day, then there’s nothing wrong with that. We congratulate you on knowing exactly what you want because that is no easy feat.

For those of you who are a bit more unsettled and feeling the pull to go remote, read on…

1) Start Consulting on the Side

Start small. Don’t expect to rebuild your career overnight. Find your first client — maybe even volunteer for a nonprofit (but treat it seriously with a contract and a documented pro bono rate) — and just get started. You can achieve a lot in a year. You might surprise yourself, find a niche, and be able to replace your income in 12 months! In the meantime, don’t quit your day job until you can live off your new income stream.

2) Publish Your First Book

You don’t need a book contract or three years of time. Your first book should be fun and a very small step to your future. Self-publish it, but treat it as a professional project. Promote it. Speak about it. You are an expert. Alison Sher, author The Millennial’s Guide to Changing the World: A New Generation’s Handbook to Being Yourself and Living with Purpose, wrote her first book while road tripping around the United States — living remotely and building a personal brand for her future.

3) Quit Your job; Have them Rehire You as a Consultant

Does your workplace truly need you?  If the answer is yes, it’s a fortunate position to be in, and you should take advantage of it. You know the internal hiring needs, opportunities, and the future of your role better than anyone. Approach your boss and have a frank conversation with her. You may share that the company’s culture is no longer aligned with your personal needs and you need to go remote. Tell her that you’re planning to quit and find remote work, and you want to consider staying on in a remote position. We can count more than a dozen Unsettled alumni who have successfully taken this tactic.

4) Downsize Your Life

If you’re mid-career, you’ve likely accumulated some things. Consider downsizing. Can you sell your home (while the market is still up) and use that cash to buy a smaller home and have some savings leftover? Can you sell a car? Or better yet, re-organize your entire life to downsize everything? If you can earn some extra cash on the side, use it as a startup fund to invest in one of the other ideas on this list. Use it to live in your new tiny home and write your first book, land your first client, or start a new business.

5) Ponder This: What’s your Underachiever Dream Job?

This one should come with a warning that it might lead to people giving you the old midlife crisis talk, but have you ever thought of this?: What is the dreamiest, most underachieving job you could ever have?

Think about this question. Write about it. It’s a thought experiment for the ages because it forces you to:

  • Consider what makes you truly happy when you remove money, status, and importance.
  • Ponder what’s a fun and creative way for you to make money.
  • Give yourself permission to put your happiness above your ambitions (ambitions are often society’s creations, not your own).
  • Be imaginative in finding solutions.

Seriously though, you can work on vineyards in New Zealand. Bartend in a high scotch bar in Scotland. Spend a winter being a ski bum. And despite what people will tell you, it doesn’t have to be career suicide (again, people inserting their fucking judgments). Frame it as a sabbatical. As ethnographic research. As a creative endeavor. Or a failed startup. Make people respect it, you’ve earned it.

As a thought experiment, this forces you to make tough choices about your values and your happiness. It makes you let go of grand visions of changing the world and allows you to focus on being present, in the work at hand.

6)  Practice Creating

Start creating. Ideally, create things of value. There are larger and larger economies for niche creations — handmade children’s toys, furniture, phone covers, woodwork, and many more markets are being created as our society’s values shift from corporate, mass production to independent, small scale products. Practice creating as much as you can whether or not you plan to make a job out of it. It will bring fulfillment to your life, and if you think of it over the long tail, the more you practice it, the better you’ll get and eventually it may lead to an independent career for yourself.

7) Work for a Remote Company or Join a Freelance Talent Agency

There are dozens of job boards dedicated to remote work and hundreds of companies who hire remotely.

A few of them are: FlexJobs, We Work Remotely and Working Nomads.  Or check out this list of online job boards by Small Revolution

You’ll be better served, however, if you can get more specific than just “remote jobs” in your search. What’s your unique skill set and how might you find remote work?

Enter, an entirely new category of ways to find independent work: freelance talent agencies. Agencies, such as TopTal or Gun.io (for developers), are talent agencies for the leading independents within a sector, such as development, design, product, and more. If you have a CV that puts you in the top percentile in your field, consider joining one of these agencies and they’ll help you find work.

8) Start a Business; Not a Startup

Startups are having a moment, and they’ll always have a place in our economy, but if your goal is to be remote, don’t be so damn ambitious. Startups, defined here as new ventures with high-growth potential, are extremely difficult. The odds are stacked way against you. A savvy entrepreneur would never recommend someone choose the startup path. But not all businesses are startups. What kind of small business might help you live remotely? Have you considered a franchise? Or perhaps approaching a business owner you know about partnering up to grow or franchise their business? Look for low-risk ways to enter markets, and think like a small business owner, not a hotshot high growth entrepreneur.

9) Take a Sabbatical; Even if You use Your Savings

If you’ve worked for 10-15 years and have nice savings, chances are you’ve also figured some things out along the way about how to work and make money. Instead of buying that car or a new house, consider taking a sabbatical, but don’t define your sabbatical as a time to not work. Make it explicitly about growth, learning, and building your future. Spend as much of it as you can building something, asking others how they did it, and meeting people who took a different path than you. Even if you have to put off some financial gain, you use it to invest in yourself, as long as you take that investment seriously.

10) Change Your Mindset

We live in a world where our careers, ambitions, and status define our identity. That is, we let others define who we are. If you are interested in going remote and building ultimate freedom into your life, you have to realize that you can’t have your cake and eat it too. You’re going to have to shift your mindset and understand that the career is not an end in itself, but the lifestyle is. You’re going to have to go against the strong currents of society and you’re going to have to adapt the world to your lifestyle, rather than adapting your lifestyle to a set career path. As you consider making this shift, we recommend making three lists:

List one: Make a list of things you’re willing to give up. Do you need an important job? Do you need a traditional full-time job? Is six-figures in an expensive city necessary or could you cut your salary by 20% and move to one of the hundreds of smaller cities? The goal is to take control and realize that you have more choice than you previously thought.

List two: Write down your values. Maybe you value growth, meaningful work, or helping others. What have you found fulfilling in your jobs to date? Are those at the top of your list when you consider a career move? They may be more important than you’ve realized. Write them down.

List three: What’s non-negotiable? I will always need work that is intellectually stimulating, that allows me to bring my imagination to my job and gives me the time and space to be creative. That’s my non-negotiable. However, I’m willing to sacrifice a lot. I don’t need stability as I’ve kept my personal overhead low. I can take risks for a few months and not have an income. Whatever you do, define these on your own terms.

Once you’ve made these three lists and your perspective is beginning to change, don’t limit yourself. There are endless ways to make an income. By choosing to not conform to most career paths, you’ve already chosen the harder path. The harder path is full of growth, and that’s what leads to success — in how we define it — in the end.

It Starts with Your Biggest Obstacle: You

If a methodology were to be written, it might say this. First, start small, but most importantly start — action is key. Second, identify your passion, and let that guide you (to writing a book for example). Third, figure out what you are uniquely good at, and start earning an income on the side. Fourth, take pressure off yourself, you’ll get there and your negative emotions (fear, doubt, insecurity, etc.) will slow you down more than anything or anyone else. You’ll have to be brave to overcome society’s expectations of you. Fifth, shift your mindset and everything else will follow into place.


Unsettled is a global community for those who live and work differently. 

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