The Squiggly Career
Ditch the Ladder, Embrace Opportunity and Carve Your Own Path Through the Squiggly World of Work
Book Edition Details
Summary
In a world where traditional career paths have become relics of the past, "The Squiggly Career" offers a dynamic blueprint for navigating the exhilarating and unpredictable landscape of modern work. Helen Tupper and Sarah Ellis, renowned for their insights into personal development, illuminate the art of thriving amidst chaos by honing five crucial skills. This isn’t just a guide—it's a revolution in how you perceive your professional journey. Learn to define what truly matters to you, unleash your unique talents, silence the inner doubts, cultivate powerful networks, and dream without limits. Brimming with wisdom, actionable exercises, and inspiration from trailblazers who’ve mastered the art of the squiggle, this book empowers you to harness the freedom of career fluidity and craft a future rich with possibility and fulfillment.
Introduction
The traditional career ladder is crumbling before our eyes. Gone are the days when success meant climbing rung by rung toward a predictable destination. Today's professionals face a fundamentally different reality where five generations work side by side, where jobs disappear overnight due to automation, and where the nine-to-five workday exists for only six percent of workers. This dramatic shift has given birth to something entirely new: the squiggly career. Rather than following a linear path upward, modern careers twist and turn through unexpected opportunities, requiring us to develop five essential skills that will determine our success. These skills aren't just nice-to-have additions to your professional toolkit; they're the foundation upon which fulfilling, resilient careers are built in our rapidly changing world.
Discover Your Super Strengths and Core Values
Your super strengths aren't just the things you're good at—they're the talents that make you absolutely brilliant and irreplaceable. Understanding these strengths begins with recognizing that they emerge from combining your natural talents with your learned experiences. Natural talents are the qualities that come effortlessly to you, often so naturally that you take them for granted. Consider the story of Helen, who discovered one of her most powerful strengths through unexpected feedback. When she asked her oldest friend Kaye and her colleague Mike to describe her, both independently used animal metaphors. Kaye described her as having "more energy than a kangaroo," while Mike compared her to "Tigger, entering a room with boundless energy and positivity, leaving everybody feeling better for having spent time with you." For years, Helen had actually tried to suppress this natural energy at work, believing it made her seem less professional. But this feedback revealed that her energy wasn't a quirk to hide—it was a superpower to embrace. This revelation transformed Helen's approach to her career entirely. Instead of dimming her natural enthusiasm, she began leveraging it consciously. She realized that all her happiest and most successful moments at work occurred when she was using her positive energy to make a difference. This insight gave her the confidence to leave her corporate role at Microsoft and commit fully to building Amazing If, where her energy could fuel both personal fulfillment and business success. To identify your own super strengths, start with the four-step discovery process. First, conduct a sixty-second burst exercise writing down twenty things you're great at. Next, ask one family member, one friend, and one colleague for three words that describe you—their perspectives often reveal strengths you've overlooked. Then catalog your learned strengths by listing both the "whats" you know and the "hows" you work. Finally, evaluate potential super strengths using four criteria: success, frequency, openness, and happiness. Score each strength out of ten for how well it delivers positive results, how often you use it, how visible it is to others, and how much joy it brings you. The strengths that score highest across these dimensions, especially happiness, become your super strengths to develop further. Remember that super strengths require intentional cultivation. Use job crafting to mold your role around these talents, seek side projects that let you apply them in new contexts, and ensure your strengths are visible across all your professional platforms.
Build Confidence and Meaningful Networks
Confidence isn't something you're born with—it's a skill you can develop by learning to cage your confidence gremlins and build a robust support system. Confidence gremlins are the limiting beliefs that hold you back from reaching your potential. Everyone has them, but how they manifest is uniquely personal. Sarah's confidence gremlin centered around a fear of conflict that was sabotaging her career ambitions. In her ideal world, everyone would get along perfectly without friction or disagreement. During challenging meetings, she would become physically uncomfortable, stop listening effectively, and miss opportunities to contribute valuable insights. This fear was preventing her from developing the gravitas needed for senior leadership roles. The breakthrough came when Sarah asked a trusted colleague to rate a particularly difficult meeting she had found excruciating. While she scored it an eight or nine on the conflict scale, he rated it just a three or four, commenting that he appreciated everyone expressing their views directly rather than having corridor conversations afterward. This feedback helped Sarah realize that her experience of conflict wasn't universal—she was interpreting healthy debate as threatening confrontation. By sharing her gremlin with trusted colleagues and analyzing her triggers, Sarah discovered that her fear was most activated by unexpected disagreement and direct communication styles. She learned to reframe "conflict" as "conversations with different points of view" and developed strategies like asking questions to stay engaged rather than withdrawing. To cage your own gremlins, start by identifying what you're most afraid of at work and what negative thoughts you have about yourself professionally. Draw your gremlin to make it tangible, then dig deeper by asking "why" at least three times to uncover the root cause. Test your gremlin by taking small, deliberate actions that challenge these limiting beliefs. Share your gremlin with trusted supporters who can encourage you and provide perspective. Most importantly, reward yourself for taking brave steps—behavior change requires celebrating small victories along the way. Building confidence also requires cultivating meaningful relationships through strategic networking, which is simply people helping people. Focus on creating diverse networks that support your current role, future possibilities, and personal development.
Explore Future Possibilities and Essential Skills
The era of career plans is over. Instead of rigid destinations, successful professionals explore future possibilities while developing three essential skills: curiosity, feedback mastery, and grit. These capabilities will become increasingly valuable as change accelerates across all industries. Sarah's journey from masterplan to meaningful possibilities illustrates this shift perfectly. In 2010, she created what she called a "career masterpiece"—a detailed five-year plan mapping every step toward her ultimate job title. But when her manager asked why she wanted each role, Sarah realized she had simply listed what she thought she should do rather than what genuinely interested her. The plan had no connection to her strengths, values, or passions. A leadership conference speaker named Cilla Snowball changed Sarah's perspective entirely. Instead of advocating for detailed career plans, Snowball emphasized being clear about the value you add in any role and remaining open to opportunities that offered happiness and learning. This advice transformed Sarah's approach from rigid planning to possibility exploration. Years later, when Sarah was eight months pregnant and learned her role was disappearing due to restructuring, she felt excited rather than panicked. Having cultivated a possibilities mindset, she could see multiple options: expanding Amazing If with Helen, exploring consulting work that matched her strategic thinking strengths and need for variety, or pursuing opportunities in the charity sector. She ultimately chose a portfolio approach, working part-time as managing director of a creative agency while developing Amazing If. To develop your own possibilities thinking, identify four types of opportunities: your obvious possibility (the natural next step), your ambitious possibility (what you'd pursue without the "but" of self-doubt), your dream possibility (what you'd do with no constraints), and your pivot possibility (how you could apply existing strengths in new contexts). For each possibility, clarify what you need to learn and who can help you explore it further. Complement possibilities thinking by developing three future-critical skills. Curiosity can be cultivated through "meerkat moments"—regularly poking your head up to scan for trends and opportunities outside your immediate environment. Master feedback by making it relevant, real-time, and regular, using frameworks like "what went well/even better if" to create positive learning conversations. Build grit by connecting your daily efforts to fascinating questions and greater purposes that extend beyond yourself.
Navigate Career Conundrums with Wisdom
Modern careers present unique challenges that require nuanced thinking rather than one-size-fits-all solutions. Whether you're considering a career move, struggling with work-life balance, or wanting to demonstrate leadership without formal authority, success comes from applying core career principles to your specific situation. When facing the fundamental question "should I stay or should I go," apply Dame Cilla Snowball's elegant framework: ask yourself whether you're happy and learning in your current role. As long as both answers are yes, consider staying. If either element is missing, it may be time to explore new possibilities. This deceptively simple test cuts through the noise of salary comparisons and title upgrades to focus on what truly drives long-term career satisfaction. Work-life balance requires recognizing that everyone's version looks different and shifts over time. Rather than pursuing an impossible perfect balance, focus on two key elements: understanding how you're feeling in any given period and making conscious choices aligned with your priorities. Take control by identifying which current choices support your wellbeing and which work against it, then systematically adjust the latter while reinforcing the former. For building personal brand and demonstrating leadership without formal authority, focus on what you want people to say about you when you're not in the room. Your personal brand should authentically reflect your strengths and values while creating opportunities for meaningful impact. Develop leadership skills through volunteering, adopting organizational problems that need solving, mentoring others, and spotting opportunities to expand your influence and experience. Remember that every career conundrum is ultimately about alignment—ensuring your choices support your strengths, values, and desired impact while remaining flexible enough to adapt as circumstances change.
Summary
The squiggly career represents both unprecedented opportunity and increased personal responsibility for your professional development. As Helen and Sarah demonstrate throughout their journey, "no one cares about your career as much as you do"—making self-awareness and proactive skill development essential rather than optional. The five core skills of super strengths, values clarity, confidence building, strategic networking, and future possibilities thinking provide the foundation for navigating any career challenge or transition successfully. The path forward begins with a single step: choose one insight from these concepts and take action today, no matter how small. Whether that's asking three people to describe you in order to identify natural talents, scheduling a coffee with someone who can help you explore a future possibility, or simply starting to recognize and record your daily successes, the key is beginning immediately. Your squiggly career awaits, filled with opportunities to create meaningful work that energizes you and makes a positive impact on others.
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