The Squiggly Career

The Squiggly Career Plot Summary

Introduction

The world of work has transformed dramatically over recent decades. Gone are the days of predictable, linear career paths where you could clearly see each rung of the ladder ahead. Today's careers are wonderfully squiggly - full of twists, turns, pivots, and possibilities that weren't available to previous generations. While this new landscape offers unprecedented freedom and opportunity, it also presents unique challenges. How do you navigate a path that isn't clearly marked? How do you make decisions when there's no obvious "next step"? And how do you find fulfillment in a world where jobs for life have been replaced by careers full of transitions? If you've ever felt overwhelmed by career options, uncertain about your next move, or simply curious about how to thrive in today's fluid workplace, you're not alone. The good news is that succeeding in a squiggly career isn't about luck or perfect planning – it's about developing specific skills that enable you to adapt, grow, and find opportunities in any environment. Throughout these pages, you'll discover a practical toolkit for navigating modern work life with confidence, purpose and joy. The journey ahead is an exciting one, and by embracing your unique squiggly career, you'll find greater fulfillment, impact, and possibility than you ever thought possible.

Chapter 1: Identify Your Super Strengths

Super strengths are the things you're brilliant at - the talents that make you stand out and that you can build a reputation around. Unlike just being "good" at something, super strengths represent your areas of true excellence. When you know and apply your super strengths, you not only perform better but also experience higher levels of happiness and satisfaction. Research by Gallup found that employees who use their strengths are six times more effective and engaged in their role. Helen's story perfectly illustrates how discovering unexpected strengths can transform your career. While working at Microsoft, Helen decided to ask both her oldest friend Kaye and a colleague Mike to describe her strengths. Surprisingly, both used similar metaphors - Kaye said Helen had "more energy than a kangaroo" while Mike described her as "like Tigger, entering a room with boundless energy and positivity, leaving everybody feeling better for having spent time with you." This feedback was eye-opening for Helen, who had never considered her natural energy as a professional strength. In fact, she had been trying to suppress this aspect of herself at work, believing it made her seem less "professional" and "serious" as a leader. This realization marked a turning point. Helen stopped trying to subdue her natural energy and instead embraced it as one of her super strengths. She noticed that her happiest and most successful moments at work were when she was using her positive energy to make a difference - whether in meetings, presentations, or one-on-one interactions. This self-awareness ultimately gave her the confidence to leave Microsoft and run Amazing If full-time, bringing her energy to growing the business. To discover your own super strengths, start with a four-step process. First, identify your natural talents - the things you do well without even trying. Second, recognize your learned strengths that you've developed through experience. Third, evaluate these strengths against four criteria: success (how effectively you use them), frequency (how often you apply them), openness (how visible they are to others), and happiness (how energized you feel when using them). Finally, select the strengths that score highest across these dimensions, particularly in happiness. Once you've identified your super strengths, take deliberate action to make them show up and stand out. This might involve job crafting (reshaping aspects of your role to better match your strengths), seeking strengths-based feedback ("When do you think I'm at my best?"), or pursuing side projects that showcase your talents. Remember that if you find yourself in a role where you can't regularly use your super strengths, it might be a sign that you're in the wrong job. Your super strengths are uniquely yours. They're the foundation of your career success and personal fulfillment. By investing time to discover them and creating opportunities to use them more frequently, you'll not only add greater value to your organization but also experience more enjoyment and satisfaction in your day-to-day work.

Chapter 2: Live Your Core Values

Values are the unique attitudes and beliefs that motivate and drive you. Think of them as your career DNA – the fundamental principles that define what matters most to you. Unlike your strengths, which are about what you're good at, your values explain why certain activities and environments energize you while others drain you. Most people have between three and five core values that guide their decisions and influence their happiness both at work and in their personal lives. Sarah's story reveals how discovering your values is often a journey rather than a single moment of clarity. Sitting in a corporate office in Canary Wharf, Sarah attempted to identify her values in a one-hour exercise, coming up with achievement, progression, rewards and competition. When she proudly shared these with her manager, the response wasn't what she expected. Her manager suggested the list only captured "a bit of her" and encouraged her to think more deeply. Determined to get it right, Sarah repeated the exercise in a coffee shop in Soho and was surprised when completely different values emerged: learning, curiosity, development and coaching. This experience taught Sarah that understanding your values isn't a box-ticking exercise but an ongoing process of reflection. As she explains, "I've been working on my values for over eight years now and it's only in the last eighteen months that I've added 'variety' to the three core values I was confident in: achievement, ideas and learning." This deeper understanding has impacted every aspect of her career, from making brave decisions like requesting part-time work while being promoted, to how she introduces herself in new roles. To discover your own values, start by reflecting on your career highs and lows. Notice what was happening during your most fulfilling moments and your most frustrating times. Then, explore what's important to you about the people you work with, the work you do, the organizations you join, and your work environment. Scan through a list of value words and select those that resonate most strongly. Next, prioritize these values through a comparative process, asking yourself which matters more between each pair. Finally, define what each value means to you specifically, as the same value word can represent different things to different people. Once you've identified your core values, look for ways to live them more fully at work. This might involve job crafting to align your role with your values, using values as a filter when making career decisions, or sharing your values with your manager to find more fulfilling projects. Remember that understanding other people's values also helps build stronger working relationships through increased empathy and understanding. Living your values isn't always easy, but it's essential for career fulfillment. When your work and workplace align with what matters most to you, you'll experience greater authenticity, make better decisions, and find more meaning in what you do each day.

Chapter 3: Develop Unshakable Confidence

Confidence is having belief in yourself – the ability to recognize your successes, trust in your abilities, and bounce back from setbacks. It's not just about how you feel internally; when you're confident, others trust and believe in you too. The good news is that confidence is a skill that can be learned, practiced, and improved by anyone, regardless of whether you're naturally extroverted or introverted. Sarah's confidence journey centered around overcoming her fear of conflict. She describes her confidence gremlin as a deep discomfort with disagreement that would cause her to withdraw from challenging conversations. In meetings where disagreement arose, she would become physically uncomfortable, stop listening effectively, and miss opportunities to contribute valuable perspectives. This fear was holding her back from her ambition to lead teams and projects on a significant scale, as leadership requires the ability to constructively challenge others. A pivotal moment came when Sarah asked a colleague to rate the awkwardness of a particularly difficult meeting. While Sarah perceived the meeting as an eight or nine on the "conflict scale," her colleague rated it only a three or four, commenting that he was glad everyone had spoken openly rather than having corridor conversations afterward. This conversation helped Sarah realize that her experience of conflict wasn't universal – she had been projecting her own discomfort onto others and blaming them rather than taking responsibility for her reaction. To overcome your own confidence gremlins, start by identifying what holds you back. Draw your gremlin to bring it to life visually, then identify specific situations where it limits you and what triggers it. Test your assumptions by taking small actions that challenge your gremlin – for example, if you fear public speaking, volunteer to present at a small team meeting. With each step forward, recognize your progress and reward yourself for your bravery. Building confidence also requires recognizing and reflecting on your successes. Most of us are better at remembering our mistakes than our achievements, but confident people regularly acknowledge their daily wins. Try recording one success at the end of each day for a week, categorizing your successes across different areas of your life – work, home, and helping others. Finally, evaluate and strengthen your support system. Create a "Support Solar System" by mapping the people who give you support and those you support, noting the frequency and direction of these relationships. Aim for diversity in your support network, including people who "get" your context, ask challenging questions, and have relevant experience to share. Remember that developing confidence is an ongoing journey. With each small action you take to challenge your gremlins, celebrate your successes, and strengthen your support system, you'll build the resilience and self-belief needed to thrive in today's changing workplace.

Chapter 4: Build Meaningful Networks

Networking is simply people helping people. This definition might sound straightforward, but it represents a powerful shift from viewing networking as a transactional activity to seeing it as a way to build meaningful relationships that benefit everyone involved. Effective networking isn't about collecting business cards or adding connections on LinkedIn; it's about creating genuine connections where you can give value and receive support in return. Helen's networking journey demonstrates how transformative this approach can be. Early in her career at Capital One, Helen applied for an Insight Manager role but was rejected despite her enthusiasm and transferable skills. A senior director gave her some blunt but valuable feedback: "You're going about this all wrong. You need to put yourself in a position where the jobs come to you." Though initially skeptical, Helen reflected on this advice and began paying more attention to her relationships at work and beyond. As Helen moved between companies – from Capital One to E.ON to BP – she invested time in maintaining relationships with people who had helped her. An inspiring manager became an ongoing mentor, a colleague became a sounding board for ideas, and an internal sponsor became an external advocate. She mentored others who reached out for support, spoke at events, and shared her perspectives through writing. Over time, her network transformed from job-specific connections to a career-enhancing web of relationships that opened new opportunities. The result? Opportunities began actively coming Helen's way. Her role at BP came through a headhunter recommended by someone in her network, and she used her connections to research Virgin's culture before taking a position there. What started as a directive to build better relationships had evolved into one of her defining professional strengths. To build your own meaningful network, focus on three key characteristics: be discerning (selective and intentional about who you connect with), deliberate (actively investing time in relationships), and diverse (including people with different expertise, experience, and thinking styles). Assess your current network by evaluating its strength across three dimensions: your current role network, future role network, and personal development network. Once you've identified gaps, take specific actions to strengthen each area. For your current role network, map key relationships both inside and outside your organization. For your future role network, share your interests widely, start a side project, or join existing communities in areas you're curious about. For your personal development network, build a portfolio of mentors, earn a sponsor through excellent work, and find a "learning tribe" of people interested in similar growth areas. Remember that effective networking is about creating "career karma" – focusing more on what you can give than what you hope to gain. Translate your strengths and passions into valuable offerings for others, whether that's writing a blog post sharing your expertise, mentoring someone new to your organization, or volunteering for an industry group. When you approach networking with generosity, the connections you build will become a powerful asset throughout your squiggly career.

Chapter 5: Explore Future Possibilities

Future possibilities are not rigid plans or fixed destinations; they're potential pathways that reflect the fluid, multi-directional nature of modern careers. Unlike the traditional career ladder with its predictable progression, today's workplace requires us to embrace uncertainty and explore multiple options simultaneously. This shift requires a fundamental change in mindset – from focusing on a predetermined destination to enjoying the journey and discovering opportunities along the way. Sarah's story illustrates this evolution perfectly. While working at Barclays in 2010, she created what she called a "masterpiece" career plan, detailing exactly what would happen in her career over the next five years. When she proudly shared it with her manager, she was asked a simple but profound question: "Why do you want to do each of these things on your plan?" Sarah realized she had listed steps she thought she needed to take to achieve a specific job title, without considering her strengths, interests, or what would bring her fulfillment. This realization led Sarah to shift from rigid career planning to exploring possibilities. Nine years later, this mindset proved invaluable when, eight months pregnant, she discovered her role was disappearing in a restructure. Rather than panicking, Sarah saw multiple possibilities: building Amazing If with Helen, exploring consulting work, or finding a role in a charity or social enterprise. This exploration led her to combine possibilities, working part-time as a managing director for a creative agency while developing Amazing If. What could have been a career crisis became an opportunity for growth. To identify your own future possibilities, consider four different types: your obvious possibility (the natural next step from your current position), your ambitious possibility (something you've thought about but dismissed with "but"), your dream possibility (what you'd do with no constraints), and your pivot possibility (applying your existing skills in a new context). For each possibility you identify, ask yourself what you need to know and who could help you learn more. Understanding your career "why" is equally important as exploring what you might do next. While future possibilities focus on your "what," your career why is about purpose and meaning. Create a vision board with images representing what matters to you, or write a personal manifesto that captures your beliefs, opinions, and intentions. Sarah's manifesto, for example, includes sections on achievement, learning, people, self-knowledge, and what happiness means to her. As you explore future possibilities, also invest in developing three key skills that will help you thrive: curiosity (staying open to new ideas and perspectives), feedback (giving and receiving insights that drive improvement), and grit (the sustained application of effort toward long-term goals). These skills will help you adapt to changing circumstances and continue growing throughout your career. Remember that exploring possibilities is not about finding the "right" answer but about staying open to multiple futures. By embracing this approach, you'll discover opportunities you might never have imagined and create a career that truly reflects your evolving strengths, values, and aspirations.

Chapter 6: Overcome Career Challenges

Navigating a squiggly career inevitably means facing common challenges that can feel overwhelming if you don't have the right tools and mindset. From deciding whether to start a side project to finding a mentor, balancing work and life, or building your personal brand, these career conundrums require thoughtful approaches tailored to today's workplace realities. The question of whether to stay in your current role or move on is perhaps one of the most common career dilemmas. Cilla Snowball, who served as Group Chairman and CEO at Abbott Mead Vickers for twenty-six years, offers a simple but powerful framework: ask yourself if you are happy and learning. If the answer is yes to both questions, consider staying put. If one element is missing, it might be time to make a move. However, be cautious about being distracted by "shiny objects" like job titles or salaries. Research by psychologist Daniel Kahneman and economist Angus Deaton found that once you earn enough to meet your basic needs (approximately £50,000), additional money has little impact on happiness. When dealing with work-life balance challenges, remember that everyone's version of balance is different and evolves over time. Rather than seeking a universal blueprint, focus on making conscious choices that work for you. Kate Rand, Director of People and Operations at Beyond, advises: "Always communicate your progress and avoid over-promising. If you say yes to everything and deliver nothing, you will be seen as less reliable than the person who says nothing and delivers the same." Small changes can make a big difference – getting enough sleep (seven to eight hours is optimal), taking regular breaks, making workplace friendships, and stopping unnecessary apologies for your boundaries. For those wondering how to demonstrate leadership without a team, think laterally rather than literally. Leadership today is increasingly defined by skills like self-awareness, curiosity, and adaptability rather than position on an organizational chart. Look for opportunities to volunteer for causes you're passionate about, adopt a problem no one else is solving, become a mentor, or take on additional responsibilities when colleagues are away. As Rob O'Donovan, Co-founder and CEO of CharlieHR suggests: "The best decision I ever made was to optimize my career for learning... I have simply flown in the direction of the steepest, most vigorous learning curve I could find and attacked it with everything I had." If your organization doesn't invest in training, take ownership of your development. Create your own curriculum using resources like Coursera, Skillshare, or LinkedIn Learning. Apply for grants or bursaries that could fund your learning, or become a learning advocate within your organization by sharing resources and organizing skill-sharing sessions. Remember IBM's research finding that employees who don't feel they are developing are twelve times more likely to leave a company. When building your personal brand, start with your strengths and values – what do you want people to say about you when you're not in the room? As Amelia Torode, Founder of The Fawnbrake Collective, plainly states: "No one cares as much about your career as you." By taking ownership of your challenges and approaching them with creativity and persistence, you'll develop the resilience and adaptability essential for thriving in today's workplace.

Summary

Throughout this journey into the world of squiggly careers, we've explored the essential skills that will help you navigate today's fluid workplace with confidence and purpose. From identifying your super strengths and living your core values to developing unshakable confidence, building meaningful networks, exploring future possibilities, and overcoming common career challenges, you now have a toolkit for creating a career that truly works for you. As Bruce Daisley wisely notes, "When I started working at Google all I wanted to do was work on YouTube. There was no YouTube team so I started helping out in my lunchtimes. Sharing facts, gathering information, sending round interesting research that I found. When a job came up the UK boss of Google said, 'It seems to make sense that Bruce does this'." The path ahead may not be linear, but that's precisely what makes it so full of possibility. Your career is not a ladder to climb but a landscape to explore, with each twist and turn offering new opportunities for growth and fulfillment. Start today by taking one small action that moves you toward greater self-awareness or connection. Perhaps revisit your strengths assessment, schedule a conversation with a potential mentor, or set aside time to reflect on your values. Remember that no one cares about your career as much as you do, and the magic happens when you take ownership of your journey. The squiggly path awaits – embrace it with curiosity, courage, and the confidence that you now have the skills to thrive wherever it leads.

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Helen Tupper

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