Making sure the Great Resignation does not become the Great Boomerang

Carin-Isabel Knoop
12 min readApr 13, 2022
The photo by Ellen Feldman shows five cows leaning into a barbed wire
If only… @Ellen Feldman

“Being an entrepreneur or freelancer is a painful and exhilarating experience. It’s a lot like having an invisible best friend that only you can see. The grit and perseverance that entrepreneurs speak of, is the willingness to continue pointing to that empty seat, until something is there.”

Work is what we do, but it’s not who we are. We spend time on paid work and invest time in unpaid work as a form of self-expression, in the eternal pursuit of an answer to the existential question of our meaning and purpose.

If we believe that we are born with a purpose in this life and given some tools to get started in finding it (natural talents, capabilities, etc.), then the game of life is not to “find” yourself (which implies a predestined design), but to “build” yourself (implies freedom) through the prism of work as we endeavor to live with a sense of balance.

Work is fundamental to human existence. Finding and keeping the right fit is therefore central to our well-being.

Today, many of us are on the professional move, either in real or imaginary ways, as we consider career transitions. The stress of enduring COVID-19, forced remote work, global instability, etc. caused people to reconsider what is meaningful in their lives.

As a result, many are searching for career opportunities that afford them new experiences or the flexibility to search for what’s missing instead of engaging in the sometimes difficult introspection that may be necessary to find it. Many resigners are switching jobs, but many of them are also moving to the Open Talent market and becoming independent workers.

Sure, there is hope that the grass is indeed greener — and hope is an alluring, intoxicating feeling — but it may not turn out the way many expect it to. In March 2022, we heard that nearly three-quarters of workers regretted quitting. And some 40% might be on the move again. That’s because we may unknowingly take our baggage with us. The Great Resignation will be followed by the Great Boomerang if we don’t do the work of knowing who we are, what we want, and how we want to live.

Resigning from Resignation

“Working 9 to 5, what a way to make a living
Barely getting by, it’s all taking and no giving
They just use your mind, and they never give you credit
It’s enough to drive you crazy if you let it.”

When we are employees, others define our career scope and responsibilities, such as annual goals and objectives, thus limiting our self-discovery. This arrangement worked well for a long time, in part thanks to Frances Perkins, President Franklin D. Roosevelt’s labor secretary for 12 years. She built the social safety net and constructs of work (8-hour day, 40-work week) still in use today. We got predictability, stability, security, and social networks — even someone else to blame when things went wrong, namely everyone else.

In exchange, we put up with long commutes, dreary offices, one-size-fits-all benefits, and sometimes toxic bosses and colleagues.

We were resigned. That was the great collective resignation.

Then came COVID, which sent us home, upended everything, and made us restless and anxious. We questioned personal and professional choices. We started not only flirting online with potential partners but also with potential employers — LinkedIn is the new Tinder where we check our attractiveness and create different narratives of who we could be. When we have a bad day at work, our professional eyes wander. The same is true for our teams and colleagues, and probably bosses.

Then we resigned — 47 million of us in 2021 in the U.S alone.

In May 2021, American psychologist and Texas A&M professor Anthony Klotz coined the term “Great resignation.” From the US, it extended to OECD countries and beyond. As Klotz put it, “who we are as an employee and as a worker is very central to who we are.” He saw it as the tipping point of decades of low worker engagement at work. Some workers left for other employers, and some left for good, reported McKinsey.

The current labor narrative is that for some, especially knowledge workers, the siren songs of change, freedom, and flexibility are too strong to resist. People can now fit work into their lives instead of having lives that squeeze into their work. In this context, work becomes a lifestyle choice:

Chart with options paycheck vs gig; limited freedom vs complete freedom; company resources vs business of one; team vs solo; shared responsibility vs personal responsibility…

Take stock before taking the leap.

Freedom = free + dom — being free (with respect to time and space) in your own kingdom (your life)

The authors of a March 2022 Harvard Business Review article reported that workers feel that traditional jobs are riskier than they used to. They see working independently as less risky and more secure than they used to.

As a result, educated white-collar workers are flocking to the possibility of being their own bosses — solopreneurs and freelancers — and embracing the Open Talent or “fluid economy” model.

The Open Talent market has three parts: the platforms, the companies, and the workers. As a utility function, the platforms serve as a matchmaker, a dating site for job seekers and job givers.

Open Talent provides complete autonomy and freedom of choice. As an independent contractor, you now have all that you had wanted. But how do we know that is really what we want? What does it mean to have complete freedom of choice? And what will we do with it, when we find it?

Below we suggest seven main questions to help you find out:

· What are you really looking for? A greater share of your value add? A job or new meaning in your life?

· Are you in the right emotional state for such a decision?

· Are you clear about the risks?

· How and how well will you get it all done?

· What support from work will you miss?

. What do you need to make after-tax, per-hour to cover fixed and variable expenses, sick time and time off?

· With whom, besides yourself, do you need to have a clear and honest conversation before making a seismic move?

What are you really looking for? A job, a change, new meaning?

Potential is the difference between what we were born to do and what we are doing. It’s what’s below the waterline. “If we don’t think of a ‘job’ as an end but as a means to get you closer to where you want to be,” suggests DOOIT CEO Mariana Ferrari, “job choice becomes not an objective but a strategy. One that must be considered with less emotion and a greater focus on what you really want, while at the same time ensuring that you don’t demand or expect from a job what that job cannot give you.” You may also be looking for a greater share of your value add, but the financial pay-off is often less than expected (more on that below), so the choice needs to be counter-balanced with other benefits and payoffs.

Are you in the right emotional state for such a decision?

There is rampant cognitive impairment given the global levels of anxiety and depression. We are often told that we should not make major decisions when stressed or grieving, which most have been in the past two years. This might also make it harder to deal with the rejection of not being picked for a particular project you bid for. In addition, being on your own can be mentally very challenging, and there is a lot of burnout in the passion economy — in the best of times. Reach out to others who made the shift, such as members of the Center for the Transformation of Work to which we belong.

Are you clear about the risks?

Many of us jump into freelance or entrepreneurship due to frustration with the corporate world. Some believe that the new path will be easy and great, but many businesses fail within five years, and many freelancers cannot make ends meet. They might also be more vulnerable to recession if companies tighten their contractor budgets to protect existing jobs.

Going out on one’s own can be a wonderful learning experience, Ferrari notes: “Starting your own business is “freedom”; yes, it entails a lot of new responsibilities; at the same time, you try, you risk, you will probably have a hard time; and yes, it’s not for everyone. It’s not easy; there’s no such freedom (or at least the one most people expect), and there’s even less recognition for your ‘great’ work… In addition, if you don’t work on the sources of your frustration before leaving, it might come back 10 times over.”

“One thing we suggest to people considering the switch to self-employment is, if possible, they start part-time while keeping their day job,” notes Emergent Research Partner Steve King. “This gives them time to build up the business a bit before leaving their predictable paycheck, and it also exposes them to all the issues they will face being self-employed. Of course, many don’t have the option to go part-time first. But for those who can, it’s a good idea.”

How and how well will you get it all done?

Engage in an honest reflection of your skills and aptitudes. Being a freelancer or entrepreneur requires being a Janet-of-all-trades — you need to be good at selling yourself and your idea, but also be good at running the back office, being your own IT administrator, managing human resources and payroll, and hopefully not being the legal department. Will these activities take too much time and extend your workday instead of shortening it? What does work-life balance look like when you are doing six jobs? What happens to freedom when 9am — 5pm becomes 5am-9pm? Are you ready to be your product?

What supports from work will you miss?

Being in a company can leave you feeling lonely, but usually, we develop friendships. One thing that workers often underappreciate is how much of their social lives come from work. Work is emerging as a lifestyle choice, and when we choose to work alone, we need to find a different community of peers. Loneliness is always one of the top three to five challenges reported by solopreneurs/freelancers. It’s also one of the reasons they return to a traditional job. How will you flip the fear of loss?

Company affiliations offer other payoffs, such as trading on the brand recognition of our employers and back-office resources and databases. Then there is paid time off and healthcare benefits, employee assistance programs, training and development, unemployment and disability insurance, and other mental health benefits. Are you ready to build these functions or forego them entirely? For example, as a freelancer you can set up a 401K to save for retirement but no one will be matching your contributions. Nor are you paying into social security.

What do you need to make after-tax, per-hour to cover fixed and variable expenses, sick time and time off?

In this exercise, you budget a certain number of sick and vacation days at the outset to figure out what you need to earn on average on the days you plan on working. You also have to remember that billable days or working days will not be all earning hours — you will be in meetings to build business, answer emails and calls, etc. Multiply the leftover hours by a reasonable hourly rate.

Then add up expenses. You will have administrative costs (billing, invoicing, documenting expenses), as well as likely travel and transport costs to see clients. You might be able to work from home but also need a space to meet clients more professionally, such as a coworking space or daily office rentals. Consider sharing space with another freelancer to reduce costs and isolation.

These days more of our office supplies are digital — when they break or fail, you don’t have IT support. Hardware will not be enough, and you will need to think about licensing for software, anti-virus software, databases, design sites like Canva, etc. If there are several of you in a small business you might need multiple licenses. And electricity, higher cell phone bills, heat, toner, and business cards can be expensive, too, of course.

Other expenses relate to promoting yourself — here, the most significant cost will be your precious time on social media, selling yourself, engaging in business development, having people pick your brain without being willing to pay for your expertise, etc. However, some of the sites, like LinkedIn, also have expensive monthly subscriptions. You might also have to budget for Pay-Per-Click on Google, etc. Being part of a platform can help offset some of these costs but you still have your own website, which will cost to set up.

Finally, you will need to set aside money to pay taxes at the end of the year. Taxes are not taken out of your invoice as they are from your paycheck. Of course, there will be more deductions, which should lower the burden. But don’t be caught at tax time with the realization that you have lived over-estimating your take-home pay.

With whom, besides yourself, do you need to have a clear and honest conversation?

As more and more people turn to independent work, you likely have a friend or acquaintance that is a freelancer which makes the choice more socially acceptable. Rightly or wrongly, this may lead people to think that the path isn’t that risky, King suggests, and we don’t really have good data about what fraction of solopreneurs fail to be able to make a living. These friends and former colleagues, however, can be a wonderful source of information if they and we are willing to discuss the challenges of this path. Make sure to also talk to people for whom independent work was not a good fit. A wise decision is an informed one.

Finally, talk with your close circle of friends and family. They know you and will be impacted by your decision — practically, emotionally, and financially.

Should I stay or should I go now? If I go, there will be trouble… And if I stay it will be double…[1]

These questions really boil down to two related ones: Are you running towards or away from something? And, are you as clear as you can be about what you are leaving and what you are joining?

When we answer these questions honestly, we may decide to take the leap. This might require the professional help of someone who knows what questions to ask. “Many individuals I have coached,” said Sylvie Maury of Selfpath Coaching, “who have changed their jobs are doing so much better now. From others, I have also heard that people who made the jump increased their salary, responsibility levels, challenges, and recognition.”

We also blend our worlds. In early 2019 Brouder came across the term “Future of Work” and was immediately captivated. “In a (literal) lightbulb moment, I was struck by the enormity of the opportunity to re-write the rules of how we work in a way that could potentially (and finally) level the playing field in the world of work,” she recalled. “Adopting hybrid work is a little shimmy to the left or a little shimmy to the right — it’s not a monumental change to adopt — but it has a monumental impact. Hybrid done well has the potential to create a massive sense of freedom in the way we work. It can allow us to find freedom, right where we are.”

Or we may take a detour and return. “There used to be a fear that if a person left traditional employment for self-employment it would be hard to go back to a traditional job,” King noted. “Now most new independent workers report they think spending time as a freelancer or starting a business is additive to their resumes. They feel this lowers the risk of being independent.”

Finally, some of us will wind up staying right how and where we are, with no major changes, but with a clearer sense of what makes us happier. We might become better at advocating for our needs in our current work environment and with our current work partners. And in doing so, perhaps fall in love again.

Or in the words of T.S. Elliot, “We shall not cease from exploration, and the end of all our exploring will be to arrive where we started and know the place for the first time.”


We would love to chat with you about the points we made and be of assistance. Please reach out to us via LinkedIn (at Denise Brouder and Carin-Isabel Knoop). Also, consider joining our semi-monthly calls with our wonderful Center for the Transformation of Work community and visit SWAYworkplace to learn more about building happy hybrid teams.

Thank you to Mel Martin and Steve King for their inputs.

[1] Homage to The Clash (, accessed April 2022.

Carin-Isabel Knoop

Harvard Business School Executive Director, passionate about human sustainability@work. Pragmatic optimist devoted to helping those who care for others.