What it’s like to go through a dramatic career change

One answer to lifelong fulfillment? A spicier, more varied professional life

Rebecca Kacaba spent a decade chasing the highflier lawyer life.

What it’s like to go through a dramatic career change

Being an M&A attorney in Canada’s financial district felt important — and it came with all the perks she’d dreamed of: A fancy office, assistants, fresh lattes, powerful clients, and a salary to match the stakes. 

But in early 2018, a sense of restlessness kicked in and Kacaba began to question the career she had spent years training for.

So, she left the legal profession and launched a cloud-based software company to help streamline the fundraising process for startups.

Kacaba’s yearning for something new is common: She is one of over 600 Hustle readers we surveyed who have undergone dramatic career shifts.

In recent decades, shifts in work culture have led to a more transient workforce. At the same time, advancements in modern medicine mean we are living — and working — longer, testing the virtues of professional monogamy.

What leads people like Rebecca to make dramatic career shifts? What’s it like to take the leap? And is it time to re-examine the notion that we’re only meant to have one career for life?

To find out, we spoke with workplace psychologists, career experts, and dozens of folks who had dramatic job shifts.

The case for generalism

For generations, committing to a single profession has been deemed to offer a competitive advantage and a safer income. 

But over the past decade or so, specializing in a single profession has quietly come under attack by proponents of generalism, which encourages professional “range.”

Zachary Crockett / The Hustle

Leading the movement are London professors Lynda Gratton and Andrew Scott. In 2016, they published the results of a 10k-person study on work and aging, which showed mass dissatisfaction in traditional labor patterns.

“Simply following the herd is not going to work,” they write in The 100-Year Life: Living and Working in an Age of Longevity, calling for an end to the linear trajectory of education, work, and retirement.

“If you now work into your 70s or 80s in a rapidly changing job market, then… [we must set] time aside to make fundamental investments in re-learning and re-skilling,” the professors argue, adding that technological disruption is making the multi-career pathway inevitable.

Similarly, researchers like David Epstein argue that the dogma of specialism is a farce. In his 2019 book Range: Why Generalists Triumph in a Specialized World, Epstein demonstrates how star athletes, scientists, and business gurus all actually nurture several interests and skills, rather than a single niche.

Many experts argue that we can — and should — excel in multiple professions across a lifetime.

But what’s it really like to take that advice to heart? 

Taking the plunge

To put multi-careerism to the test, we asked readers of The Hustle to share their stories of dramatic career changes.

We received over 600 responses. Among them:

  • A pastry maker who became a web developer
  • A COO who became a shaman
  • An accountant who became a dance teacher
  • A musician who became a pastor
  • A bond trader who joined a charity
  • A nurse who became a DJ

Others shared tales of going freelance or setting up their own businesses, often in their 40s — incidentally, the age at which founders are statistically the most successful.

The bulk of these respondents reported making the change 10 years or more into their career:

Zachary Crockett / The Hustle

The reasons for these changes were varied.

Some people craved creativity, while many sought the adrenaline rush of adventure and exploring their passions. Some were burned-out, others had simply lost their jobs or needed more money — only worsened by the train wreck of a year that was 2020.

Zachary Crockett / The Hustle

And most importantly, at the end of the day, most of these folks didn’t regret their decision to shake things up.

Some 97% of our respondents felt they made the right decision to change careers. This applied regardless of which sector they had moved into, or what the motivation was for swapping.

“I have now been here 10 years and wouldn’t change a thing,” writes Stacey Martin, who was let go as a medical aesthetician and used it as an opportunity for a professional reboot –– joining the sales team at a cruise ship.

Meanwhile, after many years in the financial advising world, Andrew Rotz says he’s “found [his] calling” teaching personal finance. 

“I won’t make nearly as much money as the corporate world but the quality of life is better,” he tells us.

Zachary Crockett / The Hustle

Dozens of other corporate types — investment bankers, lawyers, etc. — who left their careers due to “burnout” now report improved physical health.

“[Don’t] waste time saying ‘one day’ –– one day might not come,” says Carson Sweezy, who left real estate to start his own catering and treats business.

This sentiment was even echoed by those who switched careers for practical reasons, like wanting more money.

“Increasing my salary was a huge relief… There’s a simple delight in no longer berating myself for buying a coffee from the local coffee shop,” says Tim Hughes, who left teaching to find financial security. He now works in sales engineering.

What we want vs. what we do

The desire to have multiple careers is widespread. In a 2019 survey of US workers, 58% said they wanted to dramatically change careers, even if it involved a pay cut. Yet government data seems to suggest big career changes are unusual.

Why are we still so hesitant to embrace a new philosophy of work?

Charles Ponti, one of hundreds of readers who responded to our November survey, says that’s because our careers and identities are so closely connected.

“I spent several years in finance and sales that were not fulfilling in any way,” he tells The Hustle. “That lack of fulfillment, however, was not enough to overcome the feeling that I had already invested too much time into this particular career.” 

“I had begun to identify with the roles I disliked doing, which made me feel trapped,” he adds. “It felt impossible to start over.”

Still, Ponti took the plunge, moving from sales to art, before switching again to engineering and to product management.

“It [actually] took 3-5 months to start over, and I essentially succeeded within the first month,” he says.

Zachary Crockett / The Hustle

Still, Ponti’s reservations aren’t entirely misguided. Success isn’t guaranteed. Major change can bring instability, while learning new skills can be a slow game.

Take Doug Johnson, who gave up his job in real estate to become a golf pro, before realizing he was not cut out for it. He then swapped to sales, but says it was an equally unsatisfying move.

“I convinced myself I had a goal of getting involved in sales analytics… but I was not fond of sales… I was lazy in seeking that position — I wanted out from golf… it was a mistake for me to take the job and skip addressing what I wanted long-term,” he says. 

Others warn of the dangers of moving jobs to pursue a passion, or out of a desire to “give back.”

Brandon Lee quit his job in real estate to join an education company –– in pursuit of “meaning.” But he burned out after a decade, and had to settle on a job in tech to find a “middle ground with stability/meaning.”

To succeed, he says, you must “set aside your ego to become a ‘nobody’ again” (he recommends reading this comic first).

Several career changers told us that it was tough finding themselves back at school, or in junior positions. 

The Hustle

Occasionally, giving up a career can bring increased financial strain too.

Trevor Frauhiger left insurance in early 2020 “to chase a dream” of starting a travel agency. But “COVID killed it,” he says, and “now I need a job that provides health care.”

Another Hustle reader, who asked to stay anonymous, said they regretted giving up a job in sales to work in the wine industry.

“My desperation [to leave] clouded my judgment, and the creative job (with its shitty salary) seemed much more attractive and glamorous than it really was,” they told us. 

As a result, several respondents, having been laid off from their new jobs, advise “vetting” employers or co-founders about their business plans before taking a career leap.

Others suggest having sufficient savings or “other sources of income” before moving.

Mindset is key 

Given the obvious obstacles, how do we know when it’s time to try changing careers?  

Most often, people choose to switch careers in their 20s or 30s.

Many bolt straight out of college and settle on attainable but undesirable professions, prompting career switches early in life.

Zachary Crockett / The Hustle

But it isn’t just millennials — the over-40s swap careers too. 

Ron Ward spent 24 years in banking before deciding to say “adios, Brooks Brothers 2-piece suits.” At 49, he was too young to retire, and was lured by a friend’s invitation to become a sales director at a startup.

Of course, changing careers as a youngster has fewer risks and costs.

“Sometimes I regret not starting or owning a business earlier in life. I continue to think about how much more productive or quicker we could grow if only I were still in my 30s,” says Seth Eisman, who left a career in TV to set up a craft cookie company with his girlfriend (now fiance).

But Sarah Ellis, co-host of the Squiggly Careers podcast, says age is less important than we think.

“There is no such thing as a perfect point to change jobs,” she tells The Hustle. “In our experience it’s a person’s mindset that determines whether someone can successfully change careers rather than their age or experience.”

“People that are adaptable, have a beginner’s mindset, and are curious… experience the most positive career changes.”

Sarah Ellis, co-host of the Squiggly Careers podcast (Sarah Ellis)

On a practical level, government support schemes (like retraining programs for people over 50) are also encouraging career-shifting later in life in some countries. 

Meanwhile, detailed manuals — including Ellis’ The Squiggly Career — offer practical, firsthand guidance on how to ditch a high-paced job, whether you’re 25 or 55. 

A new world of work?

Multi-careerism won’t work for everyone, but the theory does offer a thought-provoking reassessment of work.

  • What if we don’t allow ourselves to be neatly categorized by a 40- or 50-year career, and instead compete to be intellectually curious and professionally diverse?
  • What if we use challenging moments — redundancy, aging, COVID-19, divorce — as a trigger to swap careers?
  • Should we reframe how we talk to youngsters about work? Does a dream job really exist? 

“Two careers are better than one,” the actor and composer Kabir Sehgal writes in a 2017 Harvard Business Review piece. “You can learn new skills, broaden your network, and discover truly creative new solutions by committing to two (or more) wildly divergent careers.”

And it’s never too late to start again.

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