The Squiggly Career
Helen Tupper, Sarah Ellis · 2020
Editorial rating
- Evidence
- 5/10
- Actionability
- 8/10
- Originality
- 5/10
The thesis
Career ladders are dead. Modern careers are "squiggly" - full of sideways moves, pivots, and unexpected turns. To thrive in this new landscape, you need five skills: knowing your strengths, understanding your values, building confidence, expanding your network, and exploring possibilities.
Who this is for
Professionals navigating non-linear career paths, anyone feeling anxious about not having a "traditional" trajectory, and those who want practical tools for career development in an uncertain world.
My favorite quote
In a squiggly career, you are not climbing a ladder, you are exploring a jungle.
Why it matters
This metaphor reframes career anxiety as career opportunity. Jungles are messy but full of possibilities; ladders offer only one direction.
Do this
Map your last three career moves. Were they ladder-like (up) or squiggly (sideways, diagonal, unexpected)? What did the squiggly moves teach you?
Start here
Know Your Super Strengths: Not just what you're good at, but what you're distinctively good at AND enjoy. Super strengths are the intersection of capability and energy. Build your career around them, and squiggly moves become strategic rather than random.
Critical summary
Helen Tupper and Sarah Ellis, founders of career development company Amazing If, codify their popular approach to navigating modern careers. The book acknowledges that job-for-life is dead and provides a practical toolkit for thriving amid constant change.
The framework centers on five skills: Super Strengths (know what you're great at), Values (know what matters to you), Confidence (overcome your gremlins), Networks (build support systems), and Future Possibilities (explore what's next). Each chapter includes exercises and worksheets.
What it gets right
- Normalizes non-linear careers and reduces associated anxiety
- Practical, workbook-style approach with actionable exercises
- "Confidence gremlins" concept is relatable and useful
- Emphasis on networks as "solar systems" rather than contact lists
What it misses
- Core ideas aren't new (strengths, values, networking are career coaching staples)
- UK-centric examples may not translate globally
- Some exercises feel like generic career coaching
- Light on evidence; heavy on assertion
Evidence is primarily from their consulting practice and workshops. Practical wisdom rather than research-backed claims.
Key concepts
Squiggly Career
The non-linear, unpredictable career path that's becoming the norm. Embracing the squiggle means treating sideways moves as strategic.
Super Strengths
Skills you're both good at AND energized by. The foundation of differentiation in a squiggly world.
Confidence Gremlins
The internal voices that undermine your confidence. Naming them is the first step to managing them.
Support Solar System
Your network as concentric circles of support - close allies, broader connections, distant resources. Not just who you know, but who energizes you.
Future Possibilities
The range of potential next moves. In a squiggly career, you need many options, not one linear path.
Career Possibilities Wheel
A visual tool for mapping potential moves - not just "up" but sideways, down, out, or in.
Core insights
-
Squiggly is the new normal
Linear careers are increasingly rare. Stop comparing yourself to a model that no longer exists.
-
Energy matters as much as skill
Super strengths include what energizes you, not just what you're capable of. Skill without energy leads to burnout.
-
Confidence is a skill, not a trait
You can build confidence deliberately by naming gremlins, collecting evidence of success, and practicing action despite fear.
-
Networks are support systems, not contact lists
Think of your network as a solar system - different people serve different purposes at different distances.
-
Explore before committing
In a squiggly world, gathering options is more valuable than picking one path too early.
Implementation steps
Today
- List 3-5 super strengths: things you're good at AND enjoy
- Name one confidence gremlin that's currently limiting you
This week
- Complete a values audit: which values are being honored or violated in your current work?
- Map your support solar system: who's in your inner circle, middle ring, outer orbit?
This month
- Use the Career Possibilities Wheel to map 5+ potential next moves (not just "up")
- Have a career conversation with someone whose path you admire
Ongoing
- Monthly super-strength check: are you using yours?
- Quarterly network audit: are you nurturing your solar system?
Suggested 30-day practice plan
An editorial application plan created by Monolithic Vault - an interpretation of the book's ideas, not part of the original book.
- Day 1
List your top 5 super strengths (skill + energy)
- Day 2
Identify your top 5 values; rank them
- Day 3
Name your top 3 confidence gremlins
- Day 7
Map your support solar system - who's where?
- Day 14
Complete a Career Possibilities Wheel - what options exist?
- Day 21
Have a career conversation with someone outside your usual circle
- Day 30
Review: which skill (strengths, values, confidence, network, possibilities) needs most attention?
Free PDF summary
Take this analysis with you: a designed two-page field-notes sheet with the thesis, my favorite quote, the key concepts and core insights, and the full 30-day checklist. Print it or keep it - free, no signup.
Go deeper
If this analysis earned your attention, the full book goes further than any summary can. The original is always the primary source.
