The Squiggly Career

In The Squiggly Career, Helen Tupper and co-author Sarah Ellis argue that the traditional ladder-like career path—steady promotion through a single hierarchy—no longer reflects how most people actually work. Instead, they propose the "squiggly career": a non-linear journey of lateral moves, pivots, breaks, and side steps, which individuals must actively steer rather than passively climb. Published in 2020 by Penguin Business, the book is structured around five core "skills" the authors say modern careers demand: curiosity, confidence, strengths, networks, and values. Each concept gets its own chapter. On curiosity, Tupper and Ellis encourage readers to experiment with small "curiosity conversations" and deliberate exploration rather than waiting for certainty. The confidence chapter challenges the idea that confidence is innate, presenting it as a practice built through action and evidence. For strengths, they offer a "strengths audit" and warn against over-focusing on fixing weaknesses at the expense of what you do well. The networks section distinguishes between "squads," "kitchen tables," and broader connections, urging readers to build relationships before they need them. The final chapter on values asks readers to identify what matters personally and use that as a filter for career decisions. The book draws on the authors' experience running the career development company Amazing If and its podcast, plus interviews and surveys with professionals. It includes exercises such as a "career manifesto" and "squiggly career quiz." Its central argument is that job titles and fixed five-year plans are less useful than adaptability, self-awareness, and ongoing reinvention. Rather than prescribing one route, Tupper and Ellis frame career success as personal, evolving, and rarely straight.