Architectural terms are often used to describe careers and career growth: solid, foundational, a staircase, a ladder.
The Squiggly Career, by Helen Tupper and Sarah Ellis, offers a different, less stiff metaphor to express the more organic nature of how our work lives can unfold.
At the same time, they validate that adhering to a formulaic, cookier cutter trajectory can leave us feeling frustrated, stalled, or quietly disengaged when we don’t live up to our own expectations — which are heavily shaped by larger corporate structures and traditions.
Tupper and Ellis both have backgrounds spanning corporate leadership, learning design, and organizational development. Their book draws on years of coaching conversations rather than abstract theory.
Instead of offering a “right” career path, it accepts uncertainty as the default and focuses on building skills for navigating it. A term more widely accepted in the corporate world for that for that is “adaptable” — we know you hear it at least once a week.
The book is practical, sometimes uncomfortable, and refreshingly honest about how modern careers actually behave. It ditches the overused motivational slogans and productivity hacks in favour of practicality and self-discovery.
Here are five takeaways that capture what makes The Squiggly Career feel different and relevant long after you’ve closed the last page.
1. Career progress is about momentum
The book moves the conversation away from where you’re headed and instead focuses on whether you’re moving at all.
Traditional career advice obsesses over long-term clarity: five-year plans, fixed goals, definitive titles. The authors argue that this fixation often freezes people in place — or distract from even more personally and professionally meaningful opportunities.
Instead, they emphasize on momentum. Small experiments, lateral moves, temporary detours are all ways to stay engaged and learning.
A “sideways” project that stretches a skill, or a short-term role that exposes you to a new function, counts as progress even if it doesn’t fit a tidy narrative. There is less stress on explaining your path to others and more on staying in motion yourself.
2. Strengths are not static traits
Rather than treating strengths as permanent attributes, The Squiggly Career reframes them as skills that show up under specific conditions and can vary depending on context.
They argue that: you’re not just good at something. You’re good when something is true and when the environment, the challenge, or the context aligns.
This explains why people can feel competent in one role and drained in another, even when the work looks similar on paper.
The authors encourage readers to pay attention to energy patterns. When does work feels expansive and when is it depleting? Critically reflecting on these questions can offer valuable data about yourself and when or where you thrive.
Of course, every job will have a blend of energizing vs draining tasks. However, the authors encourage readers to assess what environmental factors outside of the task itself impact this.
For example, a fluid and functioning CRM makes a huge difference over a broken, clunky program that slows you down.
When pin-pointed, these behavioural patterns become more actionable than any personality test or strengths inventory.
3. Confidence is built through action
One of the book’s more grounded insights is its refusal to romanticize confidence.
Instead of treating it as a prerequisite for change, the authors describe confidence as a byproduct of doing hard things in small, repeatable ways.
They highlight “confidence loops”. These entail trying something slightly outside your comfort zone, reflecting on what worked, and carrying that learning forward.
This reframing removes the pressure to feel ready before acting. Confidence doesn’t arrive first; it accumulates quietly, and often incidentally, through experience.
4. Career communities vs a singular mentor
Rather than elevating the idea of a single all-knowing mentor, The Squiggly Career introduces celebrates the concept of a “career community.”
Different people offer a collage of valuable wisdom and teachings. No matter what, there is someone to challenge you, someone who opens doors, someone who listens without judgment, and someone who helps you see patterns you’re too close to notice.
This approach mirrors how careers grow through real-life, interpersonal connections. It doesn’t just happen in a mechanical, production line journey from A to B.
Overlapping conversations, informal guidance, and evolving relationships are all just as valuable as having a single, formally-dedicated mentor.
The social confidence this type of community creates can also lower barriers to asking for help — which is something that so many people deeply struggle with.
You don’t need just the mentor; you also need intentional, communal conversations. And most importantly, you need to trust your gut.
5. Reflection is a skill, not an afterthought
Many professional and personal development books tout the importance of reflection.
In The Squiggly Career, Tupper and Ellis treat reflection as an active practice — asking better questions, capturing insights while they’re fresh, and using reflection to inform the next decision rather than to justify the last one.
They introduce tools and prompts that turn everyday experiences into learning moments:
- What gave you energy this week
- What drained it
- What surprised you
- What felt off, etc.
Over time, this habit builds self-awareness that’s rooted in real work, not abstract self-analysis. It’s less about navel-gazing and more about pattern recognition.
Learning is not linear
The Squiggly Career removes the pressure to have it all figured out, but without lowering the bar for intentionality. It doesn’t promise certainty or success by a certain age. Instead, it offers a way to stay curious, capable, and resilient inside careers that refuse to behave predictably.
In a world where work changes faster than job titles can keep up, that might be the most practical promise a professional development book can make!
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