Episode 1 - Lead like a learner: Helen Tupper on “squiggly careers” and the power of vulnerability
This week on The Lift, Ben is joined by Helen Tupper, the CEO and co-founder of Amazing If and the author of Squiggly Careers and Learn Like a Lobster.
Key takeaways:
Learning is a core leadership skill, not a side project
Vulnerability accelerates learning and leadership growth
Personalized, “squiggly” career paths drive engagement and adaptability
Turning off autopilot improves learning at work – small changes like reflection loops and varied routines increase learning agility without adding time
“Mistake moments” – openly reviewing errors – are powerful learning tools
Diversifying how and where you learn leads to longer-lasting growth
In this premiere episode of The Lift, Helen Tupper makes a bold case for modern leadership: learning isn’t a nice-to-have anymore. Learning is the job.
In a world where roles, tools, and expectations evolve faster than most org charts, the leaders who thrive aren’t the ones who “already know.” They’re the ones who stay curious, adaptable, and willing to be a beginner, even (especially) when it feels uncomfortable. Helen opens with a line that frames the entire conversation: Vulnerability is a normal part of the learning process – it’s not something to fight against; it’s something to grow through.
Her work challenges the idea that career progress should look like a straight climb upward. The “career ladder” model is limiting for individuals (because “up” isn’t everyone’s goal) and limiting for organizations (because it stalls talent mobility, cross-pollination, and resilience). Instead, Helen advocates for squiggly careers: development that can move sideways, diagonally, in loops, or into brand-new lanes. This is a career driven by learning, not just promotion.
Senior leaders often feel anchored by responsibilities to teams, reputation, family, and the pressure to appear “certain.” But Helen says it’s more about age than career stage. People often become open to pivots during moments of change: restructures, new mandates, burnout, or opportunity windows. The question shouldn’t be, “What if I lose?” but rather, “What if I learn?”
Helen introduces the earned dogmatism effect: When someone sees themselves as an expert, curiosity can quietly shut down. They begin to protect the identity of “knowing,” which makes learning feel like a threat. For senior leaders, this can be especially sticky because executive culture often rewards confidence and punishes uncertainty.
But when leaders act like they don’t need to learn, teams learn less, too. The cutlure becomes one where success is aligned with certainty. That undermines psychological safety and makes it harder for anyone to ask for help, admit mistakes, or experiment.
A major myth Helen dismantles is that learning must be time-consuming. Leaders often push learning to the bottom of the list because they picture courses, certifications, or big formal programs. Instead, Helen argues for “learning in the flow of work” by engaging in small practices with outsized payoff.
One of her simplest tools is asking a series of questions that serves as a quick reflection loop after a meeting, conversation, or decision: “What? So what? Now what?”
What happened / what did I notice?
So what does it mean (patterns, feelings, implications)?
Now what will I do differently?
This kind of micro-reflection turns everyday work into a learning engine without adding hours to the week.
Ben and Helen explore curiosity as “collecting and connecting dots.” Your brain will connect the dots naturally, but you have to collect them by varying inputs and breaking routine. Helen shares the “backwards bike” idea (a simple left/right reversal that forces your brain out of autopilot) as a metaphor for leadership learning: small rewires like shorter meetings, walk-and-talks, and different question prompts create conscious attention, which creates learning.
And when the emotions show up – frustration, fear, failure – Helen normalizes them as part of the process, not proof you’re doing it wrong.
Helen’s upcoming book Learn Like a Lobster uses the lobster as a powerful metaphor: To grow, a lobster must shed its shell, a process that takes energy and leaves it temporarily vulnerable before it grows back stronger. That’s the leadership invitation: If you want to keep growing, you can’t cling to the shell of “competence at all costs.”
For perfectionists and high-achievers, Helen shares two practices that make learning safer and more consistent:
“Mistake Moments”: Instead of rushing past errors, Helen’s team shares and unpacks them (what happened, why it happened, and what they’ll do differently). It releases shame, banks learning, and role models healthy vulnerability.
Ask for feedback first: Feedback is less threatening when leaders initiate it. Helen uses “What worked well? Even better if…” because it keeps you in the driver’s seat and builds a habit of continuous improvement.
Helen shares her own current “shell-shedding” experiment: evolving her podcast format in public by learning openly rather than staying comfortable on autopilot.
If you’re a senior leader feeling pressure to have the answers, this episode offers a liberating alternative: lead like a learner, because your adaptability is now your advantage.
