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The Squiggle That Led Somewhere: How Professionals Are Reinventing Careers in Their 40s

8 min read
Olivia Bennett
Olivia Bennett Leadership Development Expert & Work-Life Balance Advocate

Helen Tupper had the kind of CV that makes other people’s heads tilt with polite envy.

She had come up through a graduate scheme, risen through the corporate ranks, and arrived at commercial marketing director — the sort of milestone that gets announced in team emails and earns a round of congratulations from people who know exactly what it means. By every conventional measure, the ladder was working.

And that, of course, was the problem.

For six years, Tupper spent her evenings and weekends quietly building a different life alongside her day job: a company called Amazing If, which she co-founded with her partner Sarah Ellis to show people that careers do not have to be linear. She called the alternative the “career squiggle.” She would eventually leave the corporate path to pursue it full-time.

“For a lot of people, it’s fear that holds them back,” Tupper told Newsweek in 2025. “Confidence gremlins tell them that they might fail, they don’t know enough, they’re too old to change, or not good enough to pivot into a new profession.”

Tupper is 41 now. Amazing If works with organizations including Microsoft and Levi’s. Her story — a decade of building what she wanted while managing the fear of losing what she had — is an unusually honest account of how professional reinvention actually happens. Not in a flash of clarity. In years of patient, quiet preparation.

A formal stone staircase gradually transforms into an organic winding path through a warm landscape, with the transition point sharply lit — cool blue tones on the rigid staircase left, warm amber on the living path right, a single human silhouette standing at the threshold
The squiggle is not the detour. It is often the actual route.

This Is No Longer Unusual
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The remarkable thing about Tupper’s story is how ordinary it has become.

According to data from an Aon Employee Sentiment Study covering more than 9,200 professionals across 23 countries, 60% of employees are either in the process of changing employers or are likely to seek new employment within the next twelve months — a number that reflects not just dissatisfaction, but a fundamental shift in how people relate to the idea of a fixed professional identity. Separate survey data cited in an ETHRWorld analysis in March 2025 is even more direct: nearly half of working professionals globally have already made a career shift, and among those who haven’t, 65% are either actively considering or currently planning one.

Antal International’s workforce analysis describes mid-career pivots as “one of the most overlooked workforce trends” of this moment — not because the numbers are small, but because the infrastructure around career reinvention has not caught up. Most reskilling programs still target entry-level workers. The professionals navigating these transitions in their late 30s, 40s, and 50s are largely doing so without institutional support, on the strength of their own resourcefulness and, if they are lucky, a network that believes in what they are building.

What Actually Drives the Move
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Burnout explains some of it. That I know from my own experience.

But the research points to something more layered than exhaustion. Professionals pivot mid-career for a complex mix of reasons: the desire for work that aligns with values that have evolved over fifteen or twenty years in the field; organizational structures too rigid to accommodate lateral ambition; the accelerating pace at which entire industries are being reshaped; and the quiet arithmetic of a working life that, at forty-five, still has twenty-five or thirty years ahead of it.

The early-career bargain — pick a path, commit, climb — was designed for a labor market and a life expectancy that no longer define the reality most professionals are living. The World Economic Forum’s Future of Jobs Report 2025 projects that nearly 60% of the global workforce will require significant reskilling by 2030, with technological change driving the largest share of that disruption. That number is not a distant forecast. It is the backdrop against which millions of professionals are already making decisions about whether the path they are on will still make sense in a decade.

Forbes contributor Cheryl Robinson, in her October 2025 analysis of career reinvention, framed the shift with precision: “Careers today are less like ladders and more like constellations: collections of experiences that, when viewed together, reveal the shape of who you’ve become.”

That reframing is not rhetorical decoration. It is functionally important. Because if the career is a constellation, then no single role is the destination — and changing direction is not a step backward. It is how the picture comes into focus.

The Sunk-Cost Trap
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The hardest part of a pivot, for most professionals, is not the logistics. It is the identity shift.

Damien Jordan, a podcast host who has interviewed dozens of mid-career pivoters, put it plainly to Newsweek: “There’s a perception that changing direction later in life equates to failure. We should be telling people in their 20s to try lots of things and quit if they don’t like them. Sticking it out is terrible advice when you have no idea what you enjoy.”

The professionals I have worked with through Balanced Leadership Institute describe the same internal standoff. There is the career they built — its titles, its accumulated credibility, the LinkedIn headline that summarizes twenty years of effort in eight words — and then there is the work they actually want to be doing. The distance between those two things grows quietly for years before anyone does anything about it. And every year of distance makes the sunk-cost calculation feel heavier.

What the research consistently shows, however, is that successful mid-career pivoters are not discarding their early careers. They are reframing them. A marketing director moves into nonprofit brand strategy. A finance manager shifts into impact investing. A corporate lawyer becomes an executive coach. The skills do not disappear — they translate. The second-act careers research from Davron summarizes the pattern well: professionals who pivot successfully are not starting at zero. They are starting from strength.

There is also a compelling counter-case to the “you’ll earn less” assumption. Tupper’s research suggests that professionals who take a career squiggle in their 40s and 50s often end up both healthier and wealthier in the longer term — because they are bringing full energy and commitment to work that actually fits, rather than performing commitment to work that quietly drains it.

How Pivots Actually Succeed
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Helen Tupper’s six-year bridge-building period before she left her corporate role is not the exception among successful pivoters. It is, increasingly, the model.

The professionals who navigate reinvention most effectively do not leap. They prototype. They start a consulting practice on weekends. They take on a rotational assignment that tests a new skill set with no permanent risk attached. They enroll in a course not to add a credential but to test genuine interest before it becomes a life-organizing commitment. They update their professional narrative incrementally — so that by the time they move, they are already credible in two worlds, not scrambling to build credibility in one.

Robinson’s three-phase framework maps this with clarity: disruption (the catalyst that forces honest self-assessment), design (where strategy replaces emotion and the pivot starts to take practical shape), and expansion (where connection and mentorship build the network that sustains momentum). Her framing of the disruption phase is worth sitting with: the research she cites on stress mindset shows that framing upheaval as a challenge rather than a threat consistently produces better outcomes — better focus, stronger emotional regulation, higher performance under pressure.

The pivot starts with how you interpret the moment, not with the résumé you send.

What I Know From the Inside
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I left my CMO role after a hospital stay that arrived instead of the next promotion. I did not have six years of careful preparation behind me. I had a collapse and, eventually, clarity.

What I built afterward — and what I have watched hundreds of clients build in the years since — does not look like any of the career stories I was told to admire when I was climbing the ladder. It looks like a squiggle. It looks like a set of experiences that, viewed together, reveal something coherent that none of them could have revealed alone.

The professionals who land well after a pivot are not the ones who avoided fear. They are the ones who recognized that the confidence gremlins Tupper describes are loudest precisely when the change is right. Fear is not a stop sign. It is, often, a compass.

You are not starting over. You are starting from everything you have learned.

And the squiggle, it turns out, is frequently how you find where you were always going.

References
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#career pivot #mid-career change #professional reinvention #career squiggle #second act