The Squiggly Career

Picture this: you're sitting in your cubicle on a Monday morning, staring at your computer screen, wondering if this is really what you want to be doing for the next thirty years. The traditional career ladder that your parents climbed seems to have vanished, replaced by something far more unpredictable and winding. You're not alone in feeling this uncertainty. Research shows that the average person will change careers five to seven times during their working life, and the concept of a "job for life" has become as outdated as a fax machine.

The world of work has transformed dramatically, and with it, our relationship with career development. We're now navigating what can only be described as "squiggly careers" - paths that twist, turn, and loop back on themselves in ways that would have seemed chaotic to previous generations. But here's the exciting truth: this apparent chaos actually represents unprecedented opportunity. When you understand how to navigate this new landscape, you can design a career that's not just successful by traditional measures, but deeply fulfilling and authentically yours.

Your journey to career fulfillment begins with two fundamental questions: What are you naturally brilliant at, and what drives you at your core? These aren't just nice-to-know details; they're the foundation upon which all meaningful career decisions should be built. Understanding your super strengths means moving beyond what you're merely good at to identify those unique talents that energize you and create genuine impact.

Sarah, one of the authors, discovered this principle powerfully during her time at a major bank. She had always been competent at her marketing role, but it wasn't until she took time to analyze her natural patterns that she realized her true super strength lay in strategic thinking and connecting disparate ideas. This revelation came through a simple exercise: tracking when she felt most energized and impactful at work. The pattern was clear - her best days were when she was synthesizing complex information and helping teams see the bigger picture.

The process of identifying your super strengths involves four key steps. First, conduct a rapid-fire assessment by listing twenty things you excel at in just sixty seconds. Second, gather feedback from people who know you in different contexts - family, friends, and colleagues. Third, distinguish between your natural talents and learned skills. Finally, evaluate your top strengths using four criteria: success, frequency, openness, and happiness. The strengths that score highly across all four dimensions are your super strengths.

Your values work hand-in-hand with your strengths to create your career compass. While strengths show you what you can do brilliantly, values reveal what you must do to feel fulfilled. When you align both, you don't just succeed - you thrive with authentic purpose and sustainable energy.

Confidence isn't about being the loudest person in the room or never experiencing doubt. It's about developing an unshakeable belief in your ability to navigate challenges, learn from setbacks, and continue moving forward. This type of confidence becomes your secret weapon in a squiggly career where uncertainty is the only constant.

Helen's transformation illustrates this beautifully. She had always been perceived as confident by others, but internally struggled with what she calls her "confidence gremlin" - the fear of not being liked. This fear was holding her back from giving direct feedback and making tough decisions. The breakthrough came when she realized her gremlin wasn't just affecting her own growth, but was actually preventing her team members from developing because she was being "ruinously empathetic" rather than constructively challenging.

The key to building lasting confidence lies in three areas. First, identify and cage your confidence gremlins - those internal voices that tell you you're not enough. Draw them, name them, and then systematically test the assumptions they're based on through small, brave actions. Second, develop a success mindset by recognizing, recording, and celebrating your achievements daily. Most people are far better at remembering their failures than their wins. Third, build a robust support system - your personal "solar system" of people who challenge you, champion you, and believe in you.

Parallel to confidence-building is the art of networking, which is simply people helping people. The most powerful networks aren't built on what you can get, but on what you can give. Focus on sharing your knowledge, connecting others, and solving problems, and opportunities will naturally flow back to you.

The traditional career plan is dead. In its place, you need to develop the ability to explore possibilities and continuously evolve your skills. This isn't about having a vague sense of "being open to opportunities" - it's about systematically identifying and investigating potential paths while building the capabilities that will make you invaluable regardless of which direction you choose.

Consider Sarah's experience when her marketing division was restructured while she was eight months pregnant. Instead of panic, she felt excitement because she had been cultivating multiple possibilities throughout her career. She had identified four types of possibilities: obvious (the natural next step), ambitious (roles that felt like a stretch), dream (work she'd do if there were no constraints), and pivot (applying existing skills in new contexts). When the unexpected change came, she had already been nurturing relationships and exploring options in consulting, social enterprises, and creative agencies.

To explore your own possibilities effectively, start by defining one possibility in each category. For each, identify what you need to know and who can help you learn it. Then take action - reach out to people, attend events, read industry publications, and volunteer for relevant projects. The key is to explore while you're still happy in your current role, not when you're desperate to leave.

Simultaneously, focus on developing three future-critical skills: curiosity, feedback, and grit. Curiosity keeps you relevant and innovative. Feedback helps you grow and adapt quickly. Grit ensures you can persist through the challenges that come with any meaningful change. These skills compound over time, making you increasingly valuable in an unpredictable world.

Every squiggly career comes with its share of dilemmas and decision points. Should you start a side project? How do you achieve work-life balance? When should you stay in a role versus making a move? These aren't just philosophical questions - they're practical challenges that require thoughtful frameworks for decision-making.

The most successful professionals learn to view these conundrums not as problems to be solved once, but as ongoing navigation challenges. Take the question of work-life balance, for instance. Rather than seeking a perfect equilibrium, focus on making conscious choices about how you spend your energy. Ask yourself regularly: How is my life feeling right now, and what choices am I making that either support or undermine the life I want?

When considering whether to stay in a role or move on, apply the two-question test: Are you happy, and are you learning? If the answer to both is yes, stay put and maximize the opportunity. If either answer is no, it's time to explore alternatives. But be honest about whether you're running toward something exciting or away from something uncomfortable - the motivation matters enormously for your long-term satisfaction.

For building your personal brand, focus on what you want people to say about you when you're not in the room. Your brand should be everywhere you are - in your work, your online presence, your side projects, and your interactions with others. Consistency and authenticity are far more valuable than perfection or trying to appeal to everyone.

The career ladder that once provided clear structure and predictable progression has been replaced by something far more dynamic and potentially rewarding - if you know how to navigate it. Your squiggly career isn't a bug in the system; it's a feature that allows for unprecedented customization, growth, and fulfillment. As the authors remind us, "No one cares about your career as much as you do," which means you have both the responsibility and the power to shape your professional journey.

The path forward requires developing five core skills: understanding your super strengths, clarifying your values, building confidence, nurturing networks, and exploring future possibilities. These aren't one-time exercises but ongoing practices that evolve as you do. When you master these skills, you stop being reactive to career changes and start being proactive in creating the opportunities you want.

Start today by completing just one exercise from this framework. Write down three things you're naturally excellent at, or identify one person you could help with something you know well. Small actions compound into significant changes, and the best time to begin designing your ideal career is right now, wherever you are in your journey.