5 Lessons from Helen Tupper on Building a Squiggly Career Culture

On this episode of the Future of Work Podcast, author and Squiggly Careers podcast host Helen Tupper talks lobsters, ladders, and how to create a career culture fit for the AI age.

Patrick Evenden

Head of Thought Leadership, EMEA

Workday

In this article we discuss:

Audio also available on Apple Podcasts and Spotify.

We humans have an odd obsession with straight lines. We like train tracks, orderly queues (especially if we’re British), and, when it comes to our careers, ladders.

For years, we’ve told ourselves that work is one long climb straight up—step by step, rung by rung, hoping eventually to reach the top. As a metaphor it works, if you ignore one simple fact. Life is incredibly messy and full of unexpected turns.

At Elevate London, Workday’s Vicky McNamara sat down with Helen Tupper, author, podcast host, and champion of all things squiggly, to talk about what happens when technology, human beings, and work all collide.

As AI changes the very shape of our days, Helen argues that it’s time to throw the career ladder in the skip and embrace something much less linear.

Here are five wonderful lessons from Helen on how to navigate the future of work without losing your mind, your joy, or your humanity.

1. Throw Away the Ladder (Before Your Best People Wander Off)

A squiggly career is about having the freedom to grow in a direction that actually feels right for you, rather than climbing a ladder just because it happens to be leaning against the nearest wall.

If organisations force people to stay on a rigid, narrow track, those people will eventually pack their bags and look for an adventure elsewhere.

Helen points out that changing this culture doesn't require a massive corporate overhaul—it starts with the small, everyday words we choose:

Instead of asking, "What’s your next step?" ask, "What moves are you curious about making?"
Trade tired chatter about levels and grades for genuine conversations about learning and growth.
Swap rigid career plans for open possibilities.
Focus less on promotion and much more on progression.

"The more we address ladder-like language and swap to squiggly, the easier it is to create a foundation for the kind of careers that people want to have," Helen says.

2. Leave Room to Make a Mess

When new technology comes our way our instinct is often to freeze up, terrified we’re going to push the wrong button or look silly. But if you expect people to be perfect at something new on day one, nobody will ever dare to try anything at all.

Helen says leaders need to move from expectation to experimentation—and that means "learning loudly" in public, wobbles and all.

She remembers a manager from early in her career who tasked her with launching new products. He pulled her aside one day and gave her some great advice:

"If all of them succeed, then you're playing it too safe... You've got to do some stuff that doesn't work so we can learn."

When a boss tells you it’s okay for a few things to go sideways, the fear evaporates—and that’s usually when the real magic happens.

3. Forget the Job Title and Ask: "What Do You Want to Be Known For?"

We love labeling people. We put someone in a box marked "Senior Inventory Co-ordinator" and assume we know everything about what they can do, what they care about, and where they belong.

Trying to map out everyone’s technical skills can turn into a giant, dry, administrative nightmare. Helen suggests having a simple, human conversation instead. Ask your people two things:

What do you actually want to be known for?
Where in our organisation is that needed right now?

When you stop treating people like job descriptions and start treating them like human beings, you suddenly find the right people in the most surprising places.

4. Learn Like a Lobster

Lobsters are extraordinary because they never stop growing. But to grow, a lobster hits a snag: its hard outer shell becomes too tight. So, it breaks out of its shell and sheds it.

For a moment, it exists as a soft, vulnerable, jelly-like lobster, floating in the sea without armour. It's risky, but it’s the only way a bigger, stronger shell can form.

And then, just when you thought this analogy couldn’t get any stranger, the lobster eats its old shell to fuel its next stage of growth.

In a world that’s changing faster than ever, Helen says we all need to "learn like lobsters":

Notice when your current routines leave you feeling cramped.
Be brave enough to step into that uncomfortable, vulnerable space of not knowing everything yet.
Feed on your past mistakes, awkward feedback, and failed experiments, using them as fuel for whatever comes next.

5. Be the Knot in the Bow Tie and Cage the Gremlins

People managers occupy a special place in any company. They’re the knot in the bow tie, holding people’s individual aspirations and the company’s big strategic vision together.

But even when an employee has brilliant talents, there is almost always a voice inside their head holding them back. Helen calls these "confidence gremlins." The voices that whisper, "You’re not smart enough for this", or "Everyone thinks you’re a fraud".

Left in the dark, those gremlins run riot. But when a manager sits down, listens, and creates a safe place to talk about them out loud, the gremlins suddenly shrink down to size. A great manager doesn't just manage tasks; they help you cage your gremlins so you can see how capable you really are.

At its heart, the future of work, AI and all, isn't about turning ourselves into more efficient, productive machines, even if that’s where much of the conversation is currently.

It’s about leaning into the very things machines can’t do: being curious, being vulnerable, learning from our glorious mistakes, and helping each other to grow. So go ahead, celebrate squiggly, shed a shell or two, and leave the ladders behind.

About the Author

Patrick Evenden Head of Thought Leadership, EMEA Workday

Patrick is the head of thought leadership, EMEA, at Workday. It’s his job to find creative ways to tell stories that people love with an editorial focus on the UK and Ireland.

Before joining Workday, Patrick ran a creative studio, creating content and campaigns for a variety of clients, including world-leading technology brands Amazon, Microsoft, Nokia and Sony.

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