5 Counterintuitive Ways to Prepare for the Upcoming Freelance Shift

By: Michael Youngblood, Unsettled Co-founder

The Freelance Revolution & What It Means

Day 0. This is what we’ll call the day when our economy shifts from one where most of us work for employers to one where the majority of us work for ourselves. It’s a day that’s on the horizon. It’s a shift in our economy that’s being talked about across business publications, books on the future of work, policymakers, and studied by academics. It’s probably the biggest structural change in the workforce since America’s New Deal legislation which has guided our workforce for the last 80 years. 

Yet, this shift  into a freelance market may be a bigger revolution than we realize. And Day 0 is right around the corner. 

In the United Kingdom, it’s predicted that in 2020, more people will be working in a freelance capacity, than in traditional single employment. In the US, 2027 is the tipping point where the workforce will shift from majority single employment to a new era where more workers will have multiple freelance positions from that point forward. 

This shift in productivity may be deeper than many economists had been predicting. It is sure to reshape every part of how we work and many ways in which we live. As individuals, we will need to do more with less by marketing ourselves, managing our own finances from multiple sources, practicing client management for multiple clients at once, and much more. This used to be the focus of entire departments at a company, but when the majority of workers are freelance, we will now have to pick it up and do it on our own. 

In the early days of this shift into a freelance economy, freelancers will need to work much like a startup — and most importantly, we will have to learn how to manage failure and that intimate struggle between our personal and work lives, more than we have in the past. 

No matter where you live or work, this shift will affect you in the coming years. 


Here are Five Counterintuitive Ways to Prepare for the Future of Work: 

Since this will be affecting nearly everyone in the workforce, our suggestion is to get ahead of the pack by not following the pack. If everyone is going to have to pick up new skills and find new ways of working, you need to be prepared to get ahead and to stand out.

  1. Manage Your Emotions

What do your emotions have to do with transitioning into the future of work you ask? Everything. 

This change in our economy will impact how we show up as individuals. Our ability to manage our emotions will be magnified in a freelance career when we need to be more self-reliant than ever. For example, when you work for yourself, personal time management becomes of critical importance to stay on tasks or to work when no one is asking you to work. Studies have shown that time management is often more about being aware of and managing key emotions and reactions to things. As Dr. Tim Pychyl says to The New York Times, “procrastination is an emotion regulation problem, not a time management problem.” We put things off that make us feel bored or insecure. If we practice resiliency and regulating our emotions, procrastination becomes much less of a problem.

  1. Join A Community Based on Lifelong Learning 

There are many communities specifically for freelance talent, work, and job opportunities. This is the obvious place to go, but as this shift happens, there’s going to be millions of freelancers in the same freelance networks looking for the same thing: new gigs. 

Instead of going to the obvious places, we recommend searching out a community of lifelong learners. 


  • People open to learning are open to helping.
  • These communities will be more collaborative in nature, a key characteristic in this new economy.
  • These communities will be more balanced — not 100% of the people will be looking for work like in other networks, but people will come with sources, ideas, relationships, and they (as well as you) should be willing to contribute to them.

You can always join the freelance talent agencies and ‘gig boards’ (job boards will be on the down), but finding opportunity comes in unexpected places. 

  1. Slowly Build Up; The Shift Doesn’t Have to be Sudden.

Have a good stable job now? 

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.

  1. A Shift in Mindset 

This shift in the economy will require a shift in our mindset. One that we haven’t been taught in school or by past generations in the workforce. 

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 choices 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. 

List three: What’s non-negotiable? For me, 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.

  1. It Can Be Methodologically Done

One might think that the freelance world is only for the risk takers, the entrepreneurs, and the creatives. There are people who have told themselves that they are, and can only be, employees. That they were born to be employees and shouldn’t work for themselves. This is a product of the cultural and economic norms of the last big phase in our economy, but that’s about to come crumbling down.

No matter what kind of worker you are, you can excel in the freelance economy that is approaching. 

In summary, 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. You don’t need to make a complete career overhaul all at once. 

Fourth, take the pressure off of 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.

Viva La Revolution!


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

Growth | Meaning | Adventure

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