The Squiggly Career

The Squiggly Career Summary

Ditch the Ladder, Discover Opportunity, Design Your Career

by Helen Tupper and Sarah Ellis

  • 15 min read
  • Published 2020
  • 9 takeaways

The career ladder looked reassuring because it was simple. The Squiggly Career hands you a messier, more honest map for work: one that survives sideways moves, surprise weather, and the occasional suspiciously shiny job title.

What you'll learn
  • Why the ladder stopped working
  • How values steer better choices
  • Strengths vs. useful old habits
  • How confidence collects evidence
  • Why weak ties reveal options

Key point 1

A folded map beats a polished ladder

A promotion used to look like proof that the road was straight.

Helen Tupper and Sarah Ellis have spent years helping people talk about work without the fake calm of corporate posters. Through their company Amazing If and the Squiggly Careers podcast, they treat career change as normal life, not a crisis with better shoes.

Their core claim is blunt and useful: modern careers need skills for movement, not just patience for promotion. You need to know your values, use your strengths, build confidence, grow a network, and keep spotting future options.

Careers now behave less like ladders and more like cities with bad signage.

The gift of The Squiggly Career is that it does not ask you to find one perfect path. It asks you to carry a better map, then update it while walking.

Key point 2

The straight climb hid too much

In a ladder career, everyone knows where to look. The next rung is above you, the person below wants your place, and success can be measured by neck strain.

Tupper and Ellis start from a different picture. Work no longer moves in one clean line for many people, even when companies still talk as if it does. The U.S. Bureau of Labor Statistics reported median worker tenure of about four years in 2024, which makes the forty-year single-employer career feel less like a plan and more like office folklore.

The old career ladder made sense only if the building stayed still.

The point is not that promotion has vanished. Titles, pay bands, and managers still matter. The point is that a single upward route is too narrow for the way people now build skill, meaning, and security. A sideways move can teach more than a promotion. A project can change your future faster than a new job title. A pause can be strategy rather than failure.

The ladder was tidy because it hid the person climbing it.

This matters because many career problems are misread as personal weakness. If the system is squiggly, then confusion is not proof that you are behind. It is a signal that the old tools are poor. Waiting for a manager to hand you the next step becomes risky, because managers often see only the job in front of them. Your wider options may sit in another team, another skill, or another version of work entirely.

The book turns career planning from prediction into navigation. You stop asking, “What is the one right role?” You start asking, “What information would help me choose the next useful direction?” That is a smaller question, and much kinder to real life.

Key takeaways

Key point 3

Values point before ambition runs

Key point 4

Strengths turn the lights on

Key point 5

Confidence is built by receipts

Key point 6

Networks make the city legible

Key point 7

The weather still gets a vote

Key point 8

Keep redrawing the route

Key point 9

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About the author

Helen Tupper and Sarah Ellis

Helen Tupper and Sarah Ellis are the co-founders of Amazing If and hosts of the Squiggly Careers podcast, where they help people navigate work without pretending careers still come with rails. Their authority comes from a mix of senior corporate experience, coaching, research-backed tools, and years of turning career development into something more useful than an annual appraisal form.

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