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The Squiggly Career

The Squiggly Career

The No.1 Sunday Times Business Bestseller - Ditch the Ladder, Discover Opportunity, Design Your Career
by Helen Tupper 2020 228 pages
3.95
500+ ratings
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Key Takeaways

1. Embrace the "Squiggly Career": Ditch the ladder, discover opportunities

Squiggly careers are fluid, not fixed.

The new career reality. Traditional career ladders are obsolete in today's rapidly changing work environment. Instead, careers have become "squiggly" – non-linear, unpredictable, and full of diverse opportunities. This shift requires a new mindset and skillset to navigate successfully.

Five essential skills. To thrive in a squiggly career, focus on developing:

  • Super Strengths: Identify and leverage your unique talents
  • Values: Understand what drives and motivates you
  • Confidence: Build self-belief and resilience
  • Networks: Cultivate diverse relationships
  • Future Possibilities: Explore potential career paths and opportunities

Adaptability is key. Embrace change, continuous learning, and self-reflection to stay agile in your career journey. Be open to lateral moves, new industries, and unexpected opportunities that align with your strengths and values.

2. Identify and leverage your "Super Strengths" for career success

Your strengths are the things you are good at, super strengths are the things you are brilliant at.

Discover your strengths. Use a four-step process to uncover your natural talents and learned skills:

  1. First bursts: Quickly list things you're great at
  2. Natural talents: Identify innate abilities
  3. Learned strengths: Recognize skills developed through experience
  4. Super strengths: Determine your standout capabilities

Maximize impact. Once identified, focus on making your strengths "show up and stand out" at work:

  • Job crafting: Shape your role to use strengths more often
  • Strengths-based feedback: Ask for input on when you're at your best
  • Side projects: Use strengths in new contexts
  • Social media: Showcase your strengths online

Career satisfaction. Aligning your work with your super strengths leads to greater enjoyment, productivity, and career opportunities. Regularly reassess and refine your understanding of your strengths as you grow and develop.

3. Discover and align your core values with your work

Values are what make you 'you'. They are the things that motivate and drive you.

Uncover your values. Use reflection exercises to identify your core values:

  • Career highs and lows: Analyze past experiences
  • Important aspects: Consider what matters in work environments
  • Prioritization: Narrow down to 3-5 core values

Live your values at work. Aligning your career with your values leads to:

  • Authenticity: Being yourself at work
  • Better decision-making: Using values as a career compass
  • Increased empathy: Understanding others' motivations

Continuous process. Regularly revisit and refine your understanding of your values. Share them with others to build stronger relationships and create opportunities that align with what's most important to you.

4. Build confidence by caging your "gremlins" and recognizing success

Confidence gremlins are the things that hold you back from reaching your potential. Everyone has them, but how you experience them is unique to you.

Identify and cage your gremlins. Follow these steps:

  1. Discover your specific confidence gremlins
  2. Understand how they hold you back
  3. Identify triggers
  4. Test and challenge your gremlin assumptions
  5. Take small, consistent actions to overcome them

Cultivate a success mindset. Use the three Rs:

  • Recognize: Acknowledge daily successes in various areas
  • Record: Document your achievements regularly
  • Run your own race: Define personal success criteria

Build a support system. Create a "Support Solar System" of people who:

  • Provide different types of support (e.g., empathy, challenge, wisdom)
  • Balance giving and receiving support
  • Offer diverse perspectives and experiences

5. Develop a diverse, deliberate network to fuel career growth

Networking is simply people helping people.

The three Ds of networking:

  • Discerning: Be intentional about who you connect with
  • Deliberate: Actively invest time in building relationships
  • Diverse: Seek out varied perspectives and experiences

Assess your network. Evaluate the strength of your:

  • Current role network
  • Future role network
  • Personal development network

Create career karma. Focus on what you can give rather than gain:

  • Identify your "gives" based on strengths and passions
  • Be specific about what help you need from others
  • Ask for support thoughtfully and make it easy for others to help

Choose your network role. Engage as a:

  • Consumer: Learn from existing networks
  • Contributor: Actively participate and add value
  • Connector: Link people with shared interests
  • Creator: Start your own network or community

6. Explore future possibilities and cultivate curiosity, feedback, and grit

Careers are becoming multi-directional as we move back and forth, in and out of organizations and professions.

Embrace possibilities. Instead of rigid career plans, focus on:

  • Obvious possibilities: Natural next steps
  • Ambitious possibilities: Stretch goals
  • Dream possibilities: Ideal scenarios without constraints
  • Pivot possibilities: New applications for existing skills

Develop your "career why." Use tools like vision boards or personal manifestos to clarify your long-term motivations and goals.

Cultivate future-proof skills:

  • Curiosity: Stay open to new ideas and continuous learning
  • Feedback: Give and receive regular, real-time, relevant feedback
  • Grit: Develop perseverance and passion for long-term goals

Take action. Regularly explore and reassess your possibilities, connecting them to your strengths, values, and evolving interests.

7. Navigate common career conundrums with strategic approaches

You don't need to develop every skill simultaneously and at the same pace. You can choose what feels most important for you to prioritize at the moment and start taking small steps straight away.

Address key career challenges:

  1. Starting a side project: Balance passion, problem-solving, and idea-testing
  2. Finding a mentor: Debunk mentoring myths and ask strategically
  3. Investing in training: Self-fund, create your curriculum, or advocate for change
  4. Achieving work-life balance: Make conscious choices aligned with your values
  5. Deciding to stay or go: Assess happiness, learning, and future potential
  6. Building a personal brand: Start with strengths and values, maintain consistency
  7. Demonstrating leadership: Seek opportunities beyond formal roles

Take ownership. Proactively address these challenges rather than waiting for perfect circumstances or external solutions.

8. Learn from expert advice to shape your unique career path

Listen to all the advice you can, but your most powerful tool is your own filter for that advice. You know the situation better than anyone. Take counsel, take as much as you can – but then trust your own judgement.

Key themes from expert advice:

  • Stay true to yourself: Develop self-awareness and authenticity
  • Trust your gut: Value intuition alongside rational decision-making
  • Focus on how you work: Cultivate a strong work ethic and positive attitude
  • Invest in relationships: Build meaningful connections and support networks
  • Have courage: Take calculated risks and embrace uncertainty

Apply wisely. Consider expert advice in the context of your unique situation, strengths, and values. Use it as inspiration and guidance, not rigid rules.

Continuous growth. Regularly seek out new perspectives and advice, but always filter it through your personal lens and experiences.

Last updated:

Review Summary

3.95 out of 5
Average of 500+ ratings from Goodreads and Amazon.

The Squiggly Career receives largely positive reviews for its practical approach to modern career development. Readers appreciate its focus on identifying personal strengths, values, and building confidence. Many find the exercises and activities helpful for self-reflection and career planning. Some criticize it for lacking depth or offering limited new information. The book is particularly recommended for those early in their careers or feeling stuck. Several reviewers wish they had read it earlier in their professional lives, while others find it valuable even late in their careers.

Your rating:

About the Author

Helen Tupper is a British author and career development expert. She co-wrote "The Squiggly Career" with Sarah Ellis, which became a Sunday Times Business bestseller. Tupper has experience in corporate roles and now focuses on helping individuals navigate modern career paths. She advocates for embracing non-linear career trajectories and developing key skills like identifying strengths, understanding personal values, and building networks. Tupper co-hosts the "Squiggly Careers" podcast and conducts training sessions on career development. Her work emphasizes the importance of continuous learning and adapting to changes in the job market.

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