The Squiggly Career

Are you still trying to climb a ladder that no longer exists? In The Squiggly Career, Helen Tupper and Sarah Ellis challenge the outdated notion of a linear career path and invite you to embrace the reality of today’s world: careers aren’t ladders—they’re squiggles. The authors, both accomplished corporate leaders turned entrepreneurs, argue that work has changed in ways that demand adaptability, self-awareness, and continual learning. Success no longer comes from climbing in a straight line; it comes from knowing your strengths, growing your confidence, building meaningful networks, and exploring a variety of future possibilities.

The squiggly career reflects a world where you might change roles, industries, or even professions multiple times. In parallel, work itself has become more flexible, project-based, and purpose-driven. Tupper and Ellis contend that because organizations can no longer map out defined career ladders, you must own your own development. In their words, “No one cares about your career as much as you do.” This isn’t meant to be discouraging—it’s liberating. Taking charge of your own squiggly path opens up creative opportunities and personal growth that can lead to real fulfilment at work.

Why Ladders No Longer Work

Tupper and Ellis begin by contrasting the old idea of the corporate ladder with today’s dynamic professional reality. Once, “success” meant moving up through predictable rungs at a single company. Now, the ground beneath our careers has shifted. Jobs are vanishing due to automation, flexibility has replaced fixed hours, and more people define themselves by purpose rather than position. The 9-to-5 is dying, job descriptions are temporary, and lifelong employment with one firm is almost extinct. In short, the ladder model, built for stability and hierarchy, no longer fits a volatile, uncertain, complex, and ambiguous (VUCA) world.

Instead, every career now twists and loops in its own unique shape—a mix of progress, pauses, pivots, and setbacks. The authors’ metaphor of the “squiggle” vividly illustrates the unpredictable turns and creative opportunities of modern work. Unlike a climb, a squiggle rewards curiosity and experimentation. It’s an environment where personal growth, not linear titles, becomes the measure of progress.

The Five Essential Squiggly Skills

To thrive in this new landscape, Tupper and Ellis identify five foundational skills that empower you to take control of your own development:

• Super Strengths: Knowing what you’re naturally brilliant at and using those abilities every day.
• Values: Understanding the underlying beliefs that motivate you and guide your decisions.
• Confidence: Building self-belief by conquering “confidence gremlins” that hold you back.
• Networks: Viewing relationships as “people helping people,” built on generosity, not self-promotion.
• Future Possibilities: Replacing rigid career plans with curiosity and exploration of multiple directions.

Each of these five skills works in tandem. Your strengths generate energy, your values keep you grounded, confidence powers action, networks open access, and curiosity sustains momentum. Together, they form a repeatable toolkit—usable at every stage of your career, whether you’re just starting out, pivoting mid-career, or reinventing yourself later in life.

How the World of Work Has Changed

The authors map how five dimensions of work—the who, what, where, when, and why—have transformed. You now collaborate across five generations; tasks automate rapidly; remote and flexible arrangements dominate; smartphones blur work and life; and people increasingly seek meaning rather than mere money. This shift demands that you design your own “operating system”—your personal approach to when, where, and how you do your best work. As they put it, “Work in a way that works for you.”

Instead of expecting employers to proactively “develop” you, you must become what Microsoft’s Satya Nadella calls a “learn-it-all.” That means treating every experience—success or failure—as input for growth. A growth mindset (from Carol Dweck’s research) underpins this philosophy: you’re never done learning, and challenges are invitations to stretch further.

Why This Shift Matters

The squiggly career can feel intimidating, even chaotic. But the authors point out that it removes much of the ceiling that once restricted talented individuals. Ladders excluded those unwilling or unable to follow a narrow linear route. Squiggles, in contrast, create room for experimenters, side hustlers, parents returning from career breaks, and late bloomers. The reward for managing your squiggle isn’t just employability—it’s fulfilment, a sense that your work aligns with your strengths and values while adapting to life’s changes.

Ultimately, The Squiggly Career teaches that thriving now means becoming your own career designer. You can’t rely on corporate blueprints; you must redraw the map yourself. The book’s message is both practical and hopeful: if you invest in your own learning, reflect on what matters most, and build authentic connections, you can create a dynamic, purposeful, and adaptable career that’s truly your own shape of success.

Your career happiness doesn’t depend on fixing your weaknesses but on making your strengths even stronger. Helen Tupper and Sarah Ellis define strengths as the things you’re good at, while your super strengths are the things you’re brilliant at—the unique abilities that energize you and create outsized impact. Building a squiggly career begins by understanding what makes you exceptional.

From Strengths to Super Strengths

The authors emphasize that everyone has a combination of natural talents and learnt skills. Natural talents are things that come effortlessly—perhaps being empathetic, creative, or analytical. Learnt strengths are those developed through experience: managing projects, leading meetings, or solving technical problems. Together, these form your unique value equation: Natural Talent + Experience = Strength.

To move from generic strengths to super strengths, you must identify the few that make you stand out and consciously use them. Ellis and Tupper propose four criteria—success, frequency, openness, and happiness. A true super strength consistently brings success, you use it often, others recognize it, and it makes you happy. If a skill brings results but drains your energy, it’s not a super strength; it’s just competence.

“Spend 80 per cent of your time making your strengths stronger and 20 per cent mitigating specific weaknesses that hold you back.”

Exercises to Discover Your Strengths

The book includes a structured four-step process:

• First bursts: Write down twenty things you’re good at in one minute. Then reframe your weaknesses by identifying their opposite strengths—for instance, “not finishing things” reveals a strength in “idea generation.”
• Natural talents: Ask a family member, friend, and colleague to describe you in three words. These reflections often reveal invisible strengths you take for granted.
• Learnt strengths: Separate your whats (knowledge and expertise) from your hows (behaviours like curiosity or empathy) to appreciate the full range of your value.
• Super strength selection: Use the four criteria—success, frequency, openness, and happiness—to identify your top strengths and create an action plan to use them daily.

Helen’s Story: Turning Energy into Strength

Helen shares how feedback from two sources—her lifelong friend Kaye and a coworker Mike—helped her recognize her contagious energy as a hidden super strength. Both described her as a source of positivity (“like Tigger”), yet she had tried to suppress this side at work to seem more professional. Realizing that her enthusiasm actually inspired others, she reframed her energy as an asset rather than a liability. It became central to her leadership style and eventually gave her the confidence to leave Microsoft and grow her own company, Amazing If.

Her story underscores that what makes you unique might be the thing you’ve undervalued or concealed. When you align your career with the qualities that energize you, work becomes more fulfilling and you naturally attract opportunities aligned to your strengths.

Making Strengths Visible

Once identified, super strengths must be visible. Practical techniques include requesting strengths-based feedback (“When have I been at my best this week?”), engaging in super strengths speed dating where you share and practice explaining your strengths, or modifying your role through job crafting—adjusting tasks to align with what you do best. Visibility also means updating your social and professional profiles so your strengths are instantly recognizable.

Ultimately, Tupper and Ellis show that your super strengths represent your career’s renewable energy source. The more you operate from them, the more motivation, confidence, and resilience you’ll have to navigate the twists of your squiggly path.

Where do you find fulfilment in your work? According to Tupper and Ellis, your values—the deep beliefs that motivate and drive you—are the compass that keeps your career moving in the right direction. They describe values as your “career DNA,” the personal operating system that shapes motivation, relationships, and satisfaction. When your work aligns with your values, you perform at your best and feel genuine contentment. When it doesn’t, frustration and burnout follow.

Why Values Matter in a Squiggly Career

In a career landscape with no fixed destination, values replace plans as your ongoing career compass. Understanding them helps you in three ways: being your authentic self at work, deepening empathy for others, and making better decisions about roles and opportunities. When faced with uncertainty—such as deciding whether to switch industries or take on a new project—clarity on your values becomes a reliable filter for choices.

How Values Form

The authors trace the evolution of values across three developmental phases: the spongey phase (birth to age seven, when we absorb parents’ beliefs without question), the copy-cat phase (ages eight to thirteen, when we mimic peers and role models), and the rebel phase (teenage years, when we test ideas and assert independence). By early adulthood, our core values have stabilized—usually between three and five enduring principles that influence everything from motivation to decision-making.

The Discovery Process

Tupper and Ellis lay out a structured five-step process to uncover your values:

• Reflecting: Map your career highs and lows to identify what made you happy or dissatisfied at each stage. This reveals patterns behind what energizes or drains you.
• Spotting: Ask, “What’s important to me?” in relation to people, work, organization, and environment to clarify priorities.
• Scanning: Review a list of potential value words (like freedom, ambition, integrity, creativity) and mark those that resonate most.
• Prioritizing: Compare your top ten values in pairs (“Which is more important: freedom or learning?”) to identify your top four.
• Defining: Write personal definitions for each value to clarify what they mean to you—since “respect” or “success” might vary from person to person.

Sarah’s Story: The Power of Reflection

Sarah recalls trying to complete her values exercise in an hour while working in London’s financial district. Her initial list—achievement, progression, rewards—sounded good but felt shallow. Her manager challenged her: “Are these really your values?” Repeating the exercise in a different setting—a Soho café—produced a radically different set: learning, curiosity, and development. Over time, she realized that values reflection isn’t a one-off task but an ongoing relationship. For her, it later evolved to include variety—a value that drove her to balance consulting, writing, and entrepreneurship.

Living Your Values at Work

Once identified, values should guide daily decisions. The authors suggest several ways to live them: “job crafting” (altering your role to emphasize value-aligned tasks), assessing new opportunities with a values-based scoring system, and initiating conversations about values with colleagues and managers to foster empathy and authentic collaboration. They emphasize that you don’t have separate sets of values for work and home—they’re consistent across life roles.

“Career destinations have disappeared. Your values are the continual compass guiding your decisions and actions.”

By defining and revisiting values regularly, you turn abstract ideas into practical anchors. Values bring clarity in chaos, reminding you who you are and helping you design a career that fits not just your skills—but your soul.

Confidence isn’t something you’re born with—it’s a skill you can build. In a squiggly career, where change is constant and direction uncertain, confidence provides the resilience to adapt and the courage to act. For Tupper and Ellis, confidence means believing in yourself and inspiring trust in others. But to build it, you must first tame the inner saboteurs they call confidence gremlins.

Meet Your Confidence Gremlins

Gremlins come in many forms: the fear of not being smart enough, of speaking up, of being disliked, or of failing publicly. They whisper “you can’t” in moments that matter most. The authors guide you through a process of identifying, testing, and ultimately caging these gremlins through self-awareness and action. Start by writing down what you fear most at work, what you avoid doing, and what negative thoughts replay in your mind. Then dig deeper by asking “Why?” three times to uncover the root belief beneath the fear.

Sarah’s gremlin, for example, was a fear of conflict. She realized she withdrew from debates to avoid discomfort, which hindered her growth as a leader. Through feedback and coaching, she reframed “conflict” as “constructive conversation” and built confidence by practising tough discussions step by step. Likewise, Helen’s gremlin was a fear of not being liked, which caused her to deliver overly gentle feedback—what leadership coach Kim Scott calls “ruinous empathy.” Recognizing how this limited her effectiveness helped her develop the confidence to be kindly direct, increasing her credibility and impact.

Building Resilient Confidence

Overcoming gremlins requires small, specific experiments—testing your assumptions in real life. Instead of avoiding presentations because “I’ll mess up,” practise in friendly environments and ask for constructive feedback. Tupper and Ellis also stress the importance of celebrating progress: reward yourself for bravery, not perfection. Confidence grows like a muscle—the more you stretch it, the stronger it becomes.

Their “three Rs of a success mindset”—Recognize, Record, and Run Your Own Race—help you cultivate self-belief by noticing daily wins, documenting them, and comparing yourself only to your past self, not others. This mindset prevents the toxic comparisons that modern social media amplifies.

The Support Solar System

Confidence is rarely built alone. The authors introduce the idea of a Support Solar System—a map of people who encourage, challenge, and inspire you. Diverse relationships matter: you need cheerleaders who energize you, wise “owl” mentors who offer perspective, and questioners who keep you honest. Surrounding yourself with the right mix of love, challenge, and experience ensures you never face your squiggle’s rough patches alone.

Confidence Boosters for the Moment

While long-term confidence comes from actions and mindset, the authors also offer practical “adrenaline moments” tools for when you need a short-term boost:

• Watch your words: Replace qualifiers (“I think,” “kind of,” “might”) with confident language (“I believe,” “I will”).
• Be in your body: Adjust your posture, breathe deeply, and practise expansive stances to project assurance (paralleling Amy Cuddy’s research on power poses).
• Practice makes perfect: Rehearse aloud before presentations—record yourself, self-review, and learn through repetition.

Confidence, Tupper and Ellis argue, doesn’t eliminate fear; it teaches you to act despite it. By confronting your gremlins, celebrating progress, drawing strength from your supporters, and practising courage regularly, you create an enduring sense of belief that fuels every future move in your squiggly career.

Forget dusty networking events with awkward handshakes and business cards. In the squiggly world, networking is simply people helping people. Tupper and Ellis redefine networks not as a numbers game but as meaningful, mutually beneficial relationships that accelerate learning, opportunity, and growth.

From Contacts to Connections

Traditional networking conjured images of schmoozing to get ahead. Instead, the authors advocate focusing on “career karma” — giving before you expect to receive. By helping others achieve their goals, you naturally build goodwill and credibility, which later translates into valuable introductions, mentorship, and roles. Helen’s career illustrates this well: once she began focusing on curiosity and contribution, jobs started finding her instead of the other way around.

The Three Ds: Discerning, Deliberate, Diverse

Tupper and Ellis distill successful networking into three principles:

• Discerning: Be intentional about whom you connect with. Seek people whose experiences or perspectives will challenge and stretch you. When asking for mentoring, be specific about what you’d like to learn, not just “Will you be my mentor?”
• Deliberate: Relationships require regular, active engagement. Schedule “connect” coffees, share helpful articles, or offer support on projects. Treat relationship building as part of your job, not a side task.
• Diverse: Avoid echo chambers. Include people from different industries, levels, ages, and cultures—including younger professionals whose fresh outlooks keep you learning. Diversity fuels innovation and empathy.

These habits shift networking from a transactional mindset to one of shared curiosity. Instead of hunting opportunities, you cultivate an ecosystem of people who help each other thrive.

Assess and Grow Your Network

The authors suggest mapping three types of networks: your current role network (who helps you succeed now), your future role network (who helps you explore possibilities), and your personal development network (who helps you grow). Scoring each from zero to five reveals gaps. Maybe you’re strong in present-focused relationships but lack contacts in other fields—an area to strengthen over the next year.

You can build these networks intentionally by joining professional communities, volunteering, or even launching your own groups or events. The authors describe four network roles—consumer (learning from a network), contributor (adding value), connector (linking others), and creator (building new communities). Over time, you should move through all four to amplify your influence.

Give and Get

The “Give Generator” exercise asks you to list three strengths or passions and brainstorm how they could be useful to others, such as mentoring, sharing insights online, or hosting skill sessions. Then write down what you’d like to get—three things you want to learn in the next year—and identify who might help. This simple structure transforms abstract networking into actionable generosity and learning.

In essence, networking becomes a lifelong habit of curiosity and kindness. Whether connecting over coffee or through digital communities, the key is to approach every relationship asking, “What can we learn from each other?” The more you give, the more unexpected opportunities flow your way—proof that in the squiggly career, your network really is your net worth.

If yesterday’s wisdom was “stick to the plan,” today’s secret is “stay curious.” In the final skill of a squiggly career, Tupper and Ellis urge you to ditch rigid five-year plans and explore many future possibilities instead. A squiggly career isn’t about plotting one path—it’s about discovering new ones.

Why Plans Fail

Linear careers assumed predictability: stable industries, long tenures, and clear promotions. But as Lynda Gratton argues in The 100-Year Life, our working lives are lengthening and diversifying. Today, you may have five distinct careers by retirement. Planning your entire trajectory upfront makes as little sense as mapping a city you’ve never visited. Instead, the authors advocate “possibility thinking”—an openness to experiment based on self-knowledge and continuous learning.

They promise that curiosity and reflection—not control—lead to purpose. Echoing psychologist Shawn Achor’s research from The Happiness Advantage, they remind us that happiness fuels success, not the other way around.

Four Types of Possibilities

To spark creativity without chaos, the authors introduce four categories of career possibilities:

• Obvious: The natural next step from your current role.
• Ambitious: A stretch goal that excites you but feels slightly beyond reach.
• Dream: The “if anything were possible” vision that taps into deep passion.
• Pivot: Using your existing skills in a new setting or industry.

Once identified, explore them with two questions: “What do I need to know?” and “Who can help me?” This transforms abstract dreams into practical research projects, using your network as a source of insight rather than only opportunity.

Vision Boards and Manifestos

To visualize your “why,” the authors encourage creating a vision board—a collage of images representing what motivates you—or writing a personal manifesto that articulates your beliefs and goals. Sarah’s manifesto, for example, revolves around achievement, learning, creativity, and the people who energize her. She keeps it visible as a reminder of what matters most, updating it as her life evolves. These creative exercises shift focus from external expectations to internal clarity.

Futureproofing Skills: Curiosity, Feedback, and Grit

To sustain exploration, you must develop what the authors call “up-and-coming” skills:

• Curiosity: The habit of asking questions, experimenting, and exploring diverse perspectives (“meerkat moments”).
• Feedback: Seeking relevant, real-time, regular input using simple frameworks like “What went well / Even better if.”
• Grit: Sustained effort and passion for long-term goals (echoing Angela Duckworth’s research that perseverance outperforms raw talent).

Each of these skills helps you futureproof your career in uncertain times. Curiosity keeps you open, feedback fuels improvement, and grit ensures you stay the course even when the path squiggles.

“Ditch the destination. Explore possibilities, and you’ll have a career that works for you.”

By shifting from certainty to curiosity, you release the pressure to have everything figured out. Instead, each possibility—whether it turns into a reality or not—becomes a step toward designing a more meaningful, adaptable, and fulfilling career.