Once upon a time, careers were ladders. You picked a path, climbed diligently, and - if you played your cards right - reached the top.
Stability was the goal. Predictability was the prize.
But some of us? We weren’t built for ladders. We were built for winding paths, unexpected pivots, and careers that look more like a Jackson Pollock painting than a corporate roadmap (hi! It’s me!).
I’ve been a marketer in publishing. A journalist with a column in The Telegraph. An influencer. A published author. A business owner – three times over. I’ve zigged, I’ve zagged, I’ve reinvented myself more times than Madonna. And I have never been happier.
Welcome to the squiggly career. It’s not a failure to commit – it’s a refusal to settle (and let’s be honest, a little bit of undiagnosed ADHD). And for many of us, especially women returning to work after caregiving and those neurodivergent brains, it’s the future of professional success.
The Death of the Linear Career (Good Riddance, TBH)
The old model of career progression was built for a different time—one where men worked while women stayed home, where promotions were a reward for years of loyal service, where job-hopping was seen as a red flag rather than a sign of adaptability.
But things have changed. A LinkedIn report found that today’s career paths are far more fluid, with 64% of executives having worked across multiple industries—a stark contrast to the 89% who stuck to a single field just a few years ago. The idea of a “dream job” has been replaced with a “dream life,” one that prioritizes learning, flexibility, and fulfillment over rigid career ladders.
The Power of Reinvention
A squiggly career is about trusting your instincts over tradition. It’s about embracing change, even when it’s terrifying. It’s about understanding that pivoting isn’t a sign of failure – it’s a mark of evolution.
Take Vera Wang. She designed her first wedding dress at 40, after careers in competitive figure skating and journalism. Or Julia Child (my hero), who worked in intelligence during World War II before becoming a world-famous chef in her 50s.
Reinvention isn’t just possible – it’s powerful. And sometimes, it’s necessary.
The expectation has long been that a career should be uninterrupted, linear, and unwavering. But life doesn’t work that way - especially when you’re raising humans.
Why Women (Especially Mothers) Need This Shift
For women, especially those returning to work after caregiving, the squiggly career isn’t just a trend—it’s a survival mechanism.
Traditional career paths weren’t designed with caregiving gaps in mind. The expectation has long been that a career should be uninterrupted, linear, and unwavering. But life doesn’t work that way – especially when you’re raising humans.
A woman I spoke to about squiggles shared how she shifted from being a chef to earning a master’s degree in psychology in her 40s after realizing she needed more stability. Another went back to school post-baby parenting for computer science and now makes six figures. Their careers didn’t follow a straight path – they followed their needs.
Returning to work after a break can feel daunting. But here’s the truth: The workforce isn’t just looking for experience – it’s looking for adaptability. Employers today recognize the value of resilience, transferable skills, and fresh perspectives. That gap in your CV? It’s not a weakness. It’s a testament to everything you’ve learned along the way.
How to Embrace the Squiggly Career Mindset
Let go of the guilt. You’re not behind. There is no “behind.” Every experience—whether professional or personal—has shaped your skill set.
Lean into your transferable skills. Your ability to multitask, manage crises, and navigate complex emotional situations? That’s leadership. That’s project management. That’s value.
Say yes to opportunities that excite you, even if they don’t “make sense.” The best career moves often come from the unexpected.
Keep learning. Whether it’s online courses, mentorships, or hands-on experience, every new skill opens a new door.
Build your own definition of success. Not everyone’s goal is a C-suite role. Maybe yours is flexibility. Maybe it’s creativity. Maybe it’s control over your own time. Own it.
The Future Is Squiggly
A career is no longer a job title – it’s a journey. It’s a story you get to rewrite as many times as you want. And if you’re worried that yours looks a little unconventional, remember this: straight lines are overrated.
The most interesting, fulfilled, and successful people didn’t get there by following a map. They created their own. And you can, too.
