
The Squiggly Career
12 minIntroduction
Narrator: Imagine two friends, both successful in their fields, meeting for coffee. They reflect on their careers, which look nothing like the straight, predictable ladder their parents climbed. One of them, Sarah Ellis, jokes that she’s had more roles than her dad had in his entire career. As they talk, she grabs a napkin and sketches two lines. The first is a straight, upward-climbing ladder. The second is a messy, unpredictable, looping line—a squiggle. In that moment, they realize the career ladder is gone, replaced by the squiggly career. This simple drawing captured a profound shift in the world of work, a shift that leaves many feeling lost and overwhelmed. The book, The Squiggly Career, by those two friends, Helen Tupper and Sarah Ellis, provides a new playbook for not just surviving but thriving in this new reality.
The Career Ladder is an Obsolete Relic
Key Insight 1
Narrator: The fundamental premise of The Squiggly Career is that the traditional model of work is dead. The idea of joining a company, working hard, and steadily climbing a predefined ladder of promotions until retirement is a concept from a bygone era. Today, the world of work is defined by constant change. Technology automates tasks, the gig economy offers flexibility, and people are living and working longer, often with multiple generations in the same workplace.
The authors point to clear evidence for this shift. A YouGov survey revealed that only 6% of people now work a traditional nine-to-five schedule. The promise of a "job for life" has evaporated. This uncertainty creates a gap between the promise of modern work—creativity, freedom, purpose—and the reality many people face. To navigate this landscape, individuals can no longer rely on their organizations to map out their future. The responsibility has shifted. Success in a squiggly career requires a new set of skills and, most importantly, a new mindset. It demands that individuals take ownership of their development, moving from a "know-it-all" attitude to what Microsoft CEO Satya Nadella calls a "learn-it-all" culture. The squiggle isn't a sign of failure or a lack of direction; it's the new normal, and learning to navigate it is the first step toward building a fulfilling professional life.
Your Super Strengths Are Your Greatest Asset
Key Insight 2
Narrator: In a world without a clear path, what you're uniquely good at becomes your primary currency. The authors distinguish between strengths—things you're good at—and "super strengths," which are the things you are brilliant at and that give you energy. These are the skills that make you valuable and lead to enjoyment at work. Research from Gallup supports this, showing that employees who use their strengths are six times more engaged and that strengths-focused teams are over 12% more productive.
The book advises spending 80% of your time amplifying these super strengths and only 20% mitigating critical weaknesses. To identify these, the authors offer a simple but powerful exercise. Co-author Helen Tupper tells a story of feeling uncertain about her next career move. She asked her oldest friend and a former colleague to describe her in three words. Her friend called her "super bendy" with "more energy than a kangaroo." Her colleague compared her to Tigger from Winnie-the-Pooh, saying she enters a room with "boundless energy and positivity." Helen realized that this high energy, something she had often tried to suppress in corporate settings, was actually one of her core strengths. By embracing it, she gained the confidence to leave her job and run her company, Amazing If, full-time. Owning your super strengths is not about arrogance; it's about understanding how you add the most value and finding roles where you can do that consistently.
Values Are Your Career Compass
Key Insight 3
Narrator: If super strengths are what you do best, values are the "why" behind your actions. They are the fundamental motivators and beliefs that guide your decisions. In a squiggly career, where "destinations" are no longer fixed, values act as an internal compass, helping you make choices that align with who you are. This alignment is critical for authenticity, empathy, and better decision-making.
However, identifying values isn't always straightforward. Co-author Sarah Ellis shares her own journey of discovery. When first asked to identify her values while working in the competitive financial district of Canary Wharf, she listed words like "achievement," "progression," and "rewards." But they didn't feel right. Her manager even noted they didn't sound like her. Later, she repeated the exercise in a creative coffee shop in Soho and came up with a completely different list: "learning," "curiosity," and "development." The experience taught her that context matters and that value discovery is an ongoing process of reflection, not a one-time task. By understanding her true drivers, she was able to make brave career decisions, like leaving a secure job to build her own business, that were right for her, not just what looked good on paper.
Confidence Is a Skill, Not a Trait
Key Insight 4
Narrator: Confidence is often mistaken for an innate personality trait—something you either have or you don't. The authors argue this is a myth. Confidence is a skill that can be learned and developed through practice. It's the belief in your ability to handle challenges and bounce back from setbacks, which is essential for navigating the bumps of a squiggly career.
To illustrate this, Sarah Ellis recounts her time at the UK retailer Sainsbury's, where she observed its highly respected CEO, Justin King. She initially assumed his powerful, confident presence was natural. But when she moved into a role where she worked more closely with him, she saw the truth. Before major presentations, King would meticulously rehearse, practicing his delivery and content with a small team who gave him direct, honest feedback. He wasn't just winging it; he was preparing. This revealed a profound lesson: confidence is built through practice, preparation, and a willingness to learn. The book also introduces the concept of "confidence gremlins"—the inner voices of doubt that hold people back. By identifying these gremlins, understanding their triggers, and actively working to reframe them, anyone can build the self-belief needed to take risks and seize opportunities.
Networking Is Simply People Helping People
Key Insight 5
Narrator: The word "networking" often conjures images of transactional, awkward exchanges at stuffy corporate events. The authors seek to redefine it with a simple phrase: "people helping people." A strong network isn't about the quantity of your LinkedIn connections; it's about the quality of your relationships and your willingness to give without expecting an immediate return. An effective network should be discerning, deliberate, and diverse.
Helen Tupper shares a pivotal story from early in her career. After being rejected for a promotion, a senior director gave her some blunt advice: "You need to put yourself in a position where the jobs come to you." At first, she was dismissive, but the advice stuck. She began to intentionally build relationships, becoming curious about other people's work, offering help, and staying in touch with former colleagues. Over time, this focus on giving and connecting transformed her career. Opportunities started to find her. She got a role at BP through a headhunter recommended by someone in her network and later used that network to learn about Virgin before taking a job there. Her story shows that by focusing on generosity and genuine connection, a network becomes a powerful source of support, diverse perspectives, and unforeseen opportunities.
Ditch the Five-Year Plan and Explore Possibilities
Key Insight 6
Narrator: In a world that changes so quickly, a rigid five-year career plan is not only unrealistic but potentially limiting. The authors advocate for replacing long-term plans with the exploration of "future possibilities." This involves staying curious and open to different potential paths, categorized as obvious, ambitious, dream, and pivot possibilities. This mindset shift is supported by three future-proof skills: curiosity, the ability to seek and use feedback, and grit.
Sarah Ellis's personal story provides a compelling case study. Early in her career, she was a meticulous planner who created a detailed five-year plan to reach a senior leadership role. But life intervened. A corporate restructuring eliminated her role while she was on maternity leave. The plan was shattered. Instead of panicking, she used the moment to explore her possibilities. She considered consulting, working for a charity, and focusing on her side project, Amazing If. She ultimately found a path that combined part-time work with building her own business—a squiggly solution that was far more fulfilling than her original linear plan. Her journey demonstrates that letting go of a fixed destination and instead focusing on the journey of exploration can lead to a career that is better aligned with your strengths, values, and life.
Conclusion
Narrator: The single most important takeaway from The Squiggly Career is that you are the sole owner of your career development. The era of relying on a company to pave your way is over. Success and fulfillment now depend on your ability to proactively build a toolkit of five core skills: knowing your super strengths, being guided by your values, developing your confidence, nurturing your network, and exploring future possibilities.
This shift in responsibility can feel daunting, but it is also incredibly empowering. Instead of climbing a ladder designed by someone else, you get to draw your own map. The challenge, then, is to embrace the squiggle. Stop waiting for the perfect, linear path to appear and start taking small, deliberate actions. What is one strength you can lean into this week? Who is one person you can help? By starting to scribble, you begin to design a career that is uniquely, authentically, and successfully yours.