Squiggly Careers Podcast: CEO Shell-Shedding Moments—Purpose, Perspective and Learning from Mistakes with Nick Bent
Date: February 5, 2026
Host: Sarah Ellis
Guest: Nick Bent, CEO of UpReach
Episode Theme: Navigating Vulnerability and Growth Through Leadership Setbacks
Overview
This episode, part of the “CEO Shell Shedding Moments” series, features Nick Bent, CEO of the UK charity UpReach, which champions social mobility for undergraduates from less advantaged backgrounds. Sarah Ellis leads a candid and insightful conversation with Nick about those critical 'shell shedding' experiences—moments when leaders are forced to confront their vulnerabilities, learn from missteps, and emerge stronger. Drawing inspiration from their newly released book, Learn Like a Lobster, the discussion explores the emotional reality of leadership, the importance of organizational culture, and the vital role of support networks.
Key Discussion Points & Insights
Introduction to Nick Bent and UpReach
[02:24]
- Nick Bent introduces himself as CEO of UpReach, celebrating his third work anniversary in 2026.
- UpReach’s Mission:
"Our specific mission at UpReach is to support undergraduate students from very disadvantaged backgrounds...and help them on their career journey while they’re at university so they can get amazing graduate jobs when they finish their degree." —Nick Bent [02:31]
Shell Shedding Moments—Owning Mistakes and Vulnerability
[04:15]
- Nick discloses that his toughest 'shell shedding' moments often revolve around technology mishaps.
- Notable Anecdote:
He recalls a particularly embarrassing Zoom call with a partner where his audio failed:
"My final Zoom call of 2025 was quite an important call...my laptop was glitching. They couldn’t hear what I was saying properly. It was just disastrous and I just felt like an idiot...It was really unpleasant." —Nick Bent [04:22] - Nick emphasizes the personal embarrassment and the feeling of letting his team down, while also highlighting the importance of recovering and following up.
Recovering and Learning from Setbacks
[06:30]
- Nick's Two Pillars: Purpose and Perspective
- "There’s two key things. One is a sense of purpose and the other is a sense of perspective." —Nick Bent [06:30]
- Purpose:
Anchoring oneself and the team to the core mission of making a difference—even when circumstances are tough.
"Remind yourself that you’re in this for the right reasons...the hard times, the moments where you mess up, are still worth it, and that’s just part of normal working life." —Nick Bent [06:45] - Perspective:
Actively seeking the opinions of others to gain a balanced view of mistakes. Often, what feels catastrophic internally isn’t as dramatic to others:
"Generally what may seem like a horrendous thing to you, it’s probably not that bad. Talk to someone about it...they’ll be able to offer you a bit of personal support." —Nick Bent [07:27]
Building Support Networks and Social Capital
[09:18]
- Social Capital:
Nick stresses the value of having a diverse network to rely on in challenging times—peers, mentors, and even connections from previous jobs or training programs. "A big part of being able to handle those setbacks...is down to your social capital...how strong is your network of people you can draw on for advice and support?" —Nick Bent [09:22] - Deliberate Network Building:
Actively seeks leadership courses and peer communities, especially with other CEOs, to continually expand his support system. - Host’s Commentary:
Sarah highlights the concept of “support speed dial” and relates a recent example from the Squiggly Careers community, showing the power of peer-led learning and support:
"Anytime someone is getting stuck...they’re all sharing it in a WhatsApp group. We’re doing nothing, I’m not being useful, but they are being so useful for each other." —Sarah Ellis [11:37]
The Human Side of Leadership—Relationships and Serendipity
[12:42]
- Relationships Endure:
Nick reiterates the significance of human relationships in work, especially as careers become less linear. "So much of this is about the quality of your relationships with other people. It’s always been important, it’s still important now." —Nick Bent [12:45] - Power of Kindness and Professional Courtesy:
Practical reminders that how you treat colleagues will always matter—including possible future role reversals: "You never know when you’re going to bump into people again...the power dynamics could be very different next time around." —Nick Bent [13:32] - Memorable Example:
A former business colleague from 25 years prior recently became a trustee at UpReach (Nick’s new boss), demonstrating the long-term impact of past relationships.
Resetting Organizational Culture—Company Shell Shedding
[16:16]
- Collaborative Culture Change:
Nick’s approach as CEO involved launching UpReach’s first-ever anonymous staff survey, giving employees a safe space to share difficult feedback: "That first staff survey gave people on the team an opportunity to vent anonymously. Some had some very challenging things to say...some people were feeling battered and bruised and wanted dramatic change." —Nick Bent [16:35] - Intentional Listening:
Set clear intentions to listen and learn before making changes. Nick’s ongoing mantra for the organization:
"High performance and high well-being. Keeping those two things in tandem, in creative tension, is really important." —Nick Bent [17:54] - Sarah’s Reflection:
She points out that culture isn’t a one-time fix, but a continuous commitment:
"There’s no point where you tick the culture box...if that’s how you see it, you’ve probably got it wrong." —Sarah Ellis [18:19]
Advice for Listeners—Surviving and Thriving Through Growth Moments
[19:25]
- Embrace Challenges, But Don’t Go It Alone:
Nick’s guidance is practical and reassuring: "Embrace the challenges and see them as opportunities to learn and grow. But don’t do it alone...talk to people you trust...working life is not like The Thick of It or House of Cards...in real life, a problem shared is generally a problem halved." —Nick Bent [19:26] - Sarah Summarizes:
Key takeaways:
"When something goes wrong, remember your purpose and get some perspective. I think that is really going to stick with me." —Sarah Ellis [20:51]
Notable Quotes & Memorable Moments
-
On Human Error and Recovery:
"I hate messing up like that because I feel like I’m letting the team down...but yeah, something that felt out of my control at a crucial moment was really unpleasant." —Nick Bent [04:44] -
On Perspective:
"What may seem like a horrendous thing to you is probably not that bad." —Nick Bent [07:33] -
On Culture and Leadership:
"The big mantra that I always use to sum up the culture at UpReach is high performance and high well-being." —Nick Bent [17:54] -
On Support:
"Asking for help is always a sign of strength and never a weakness." —Sarah Ellis [12:26] -
On Professional Serendipity:
"Somebody I used to work with in business 25 years ago has just become a trustee of UpReach. So she’s now one of my bosses." —Nick Bent [13:41] -
On Opening Up:
"People are generally more charitable and more nice and more supportive than you think they’re going to be." —Nick Bent [20:07]
Timestamps for Key Segments
- [02:24] — Nick Bent’s introduction & UpReach’s mission
- [04:15] — Nick’s shell shedding moment: Zoom tech failure
- [06:30] — Anchoring in purpose and perspective
- [09:18] — The value of network and support
- [12:42] — The enduring power of relationships
- [16:16] — Resetting UpReach’s culture and staff survey
- [19:25] — Final advice: Embrace growth opportunities, don’t go it alone
Conclusion
The episode delivers a relatable, inspiring dialogue on what it truly means to lead—warts, wobbles, and all. Nick Bent offers actionable wisdom on purpose, perspective, culture, and community, making a compelling case that being vulnerable and open—personally and organizationally—is both necessary and powerful for growth. Listeners are encouraged to not only accept but embrace their 'shell shedding' moments, always leaning on purpose, perspective, and, crucially, each other.