✶Explainer06:00
What a squiggly career actually is
Tupper defines a squiggly career as one where you can develop in different directions rather than being defined by the last job you did. A career, in her framing, is simply a collection of jobs — the journey of the jobs. A squiggly journey creates choice and freedom; a ladder-like journey goes in one direction and leaves you waiting for someone else to gift you a promotion. Once the ladder constraint goes, people stop looking outward at what success looks like on the surface and start looking inward at what they actually want from work.
“it is a career where people can develop in different directions so you don't have to be defined by the last job that you did”
“it's about not being limited by a ladder not thinking that the only way is up”
✶Explainer11:30
Where the career ladder came from — and why it no longer fits
The career ladder is over 100 years old, originating in the early-1900s financial services sector, largely for managers trying to create conformity across a rapidly growing clerical workforce so they could manage and motivate it. Tupper's objection is structural: conformity and control were never the ingredients of happy careers, and a model built for one narrow context has been extrapolated everywhere. The world it assumed — predictable, single-employer, clock-in and clock-out — no longer exists. People now do multiple roles in multiple companies, and identify with work far more, which raises questions about purpose and meaning the ladder was never designed to answer.
“it's over 100 years old as a concept and start in the financial services sector”
“are the ingredients for like happy careers but you know that ladder stuck around for a very long time”
✶Explainer20:30
Why people end up in jobs they don't enjoy
Tupper's diagnosis has three parts. First, lack of self-awareness: people bounce from one job to the next hoping they'll discover what makes them happy once they've arrived, instead of reflecting before they move. Second, shiny objects — grades, cars, salary above what you actually need — status symbols of ladder-like progression that are persuasive precisely when you haven't reflected. She admits taking a job for the company car and sitting in it wondering whether the job was making her happy. Third, other people's opinions and expectations: when you're unsure, you default to what your manager, partner or family thinks you should do.
“self-awareness and a lot of shiny objects”
“everyone has a base level of pay that they need for their life and then I think there's money beyond that that can become discretionary…”
✶Explainer1:05:30
Active rest sits between sleep and restlessness
Tupper cites Alex Pang's idea of a scale running from restful — deep sleep — to restless, the scrolling, over-full mind. You can't sleep during the working day and the restless end isn't working, so the useful zone is active rest in the middle: an activity that consumes your attention and gives energy back. It reframes rest as doing something you enjoy and find consuming rather than doing nothing, and it turns off the noise from work or home. Anything qualifies — puzzles, Scrabble — but if the activity also aligns with a strength you're trying to build, you get the recharge and the reps at once.
“Alex Pang always talks about kind of this active rest thing in the Middle where you're doing an activity that consumes your attention that gives…”
“it can mean doing something that you enjoy that you find consuming”
✶Explainer19:30
Democratise development — why Squiggly Careers exists
Tupper's origin story is a gap she noticed inside large organisations: career support is unlocked by seniority. Make director, get an executive coach, have your epiphany about your life and career. But the uncertainty isn't senior-specific — her friends, colleagues and everyone else were asking the same questions with none of the support. Her conclusion was to take the questions, tools and frameworks and give them to everybody, rather than limiting development by level. The business started as evening training sessions run alongside a five-day-a-week job; the material stuck, people shared it, and it became a book, a podcast and a training company.
“don't we take the questions and the tools and the Frameworks and just give them to everybody like democratize development don't limit it by level”