CEO Shell-Shedding Moments: Purpose, Perspective and Learning from Mistakes with Nick Bent

0:00Nick Bent:Hi everyone, it's Sarah here from the Squiggly Careers podcast. This week it is the launch of our new book, Learn Like a Lobster. So we've got some very special podcast episodes for you. Each day you will hear me talk to a CEO about one of their shell shedding moments. Something hard that has happened, what's helped them and how they have found their way to growing even bigger, better and stronger. just like our new friend and role model, The Lobster. And I really hope you enjoy hearing from the range of CEOs that you'll get the opportunity to learn from this week. CEOs who run massive creative companies, who run fast-growing scale-ups, charities, volunteer organisations, and even our very own Helen, who's our CEO, will also be talking about her shell-shedding moments.

0:48Nick Bent:So I hope you enjoy each of the conversations, and if you've got any feedback or reflections, we always love to hear from you. We're Helen and Sarah at squigglycareers.com. Nick, thank you so much for joining us on the Squiggly Careers podcast today. Hi, Sarah. I'm absolutely delighted to be here. Thank you for having me. So this is part of our special CEO Shell Shedding Moments series. I'd say that I have to practice that a few times to make sure I say that right. And I wonder if we could start with you just introducing your role, who you are and what you do, so that everybody's kind of up to speed before we dive straight into that shell-shedding moment.

1:26With pleasure, yes. So I'm Nick Bent. I'm the CEO of Upreach. I'm celebrating my third anniversary in the job at the start of 2026. I joined in January 2023. I absolutely love it at Upreach. We do some incredible work on social mobility. I've got an amazing staff team. And Upreach is one of the leading social mobility charities in the UK. And our specific mission at Utreach is to support undergraduate students from very disadvantaged backgrounds, working class backgrounds, low income 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.

2:06Nick Bent:Okay, great. So I think every CEO job is challenging, but I think being a CEO in the charity sector at the moment is probably particularly challenging. We know there's lots of challenges around funding and uncertainty and ambiguity, though those are words that we hear all across the world. so reflecting on you and the kind of the job that you do what's a shell shedding moment that you have had in your role as a ceo where things felt really hard where you perhaps felt vulnerable we often describe how when the lobster does lose its hard shell it honestly looks jelly like it almost you know you can almost see that it's like oh it's just got this moment of feeling really uncomfortable it's energy zapping but ultimately it's better because of it it grows back bigger and stronger but that that shell shedding moment is really tough and it's easy for us from the outside in for me to look at you and I was obviously I was doing my research beforehand and you just think wow Nick's so impressive he must be brilliant and everything must go swimmingly all of the time um so I mean if that is true this is going to be very short but hopefully you have got a shell shedding moment to share with us i i do there's there's plenty actually so some of the shell shedding moments for me and my senior leadership team have been around you know things like you know resetting the culture at upreach so there was um uh just a more supportive and inclusive culture for our team doing some major overhauls and investment in in our technology i mean a particular shell shedding moment for for for me usually involves technology because i'm not very good at technology i had one just before christmas in fact my final zoom call of 2025 was quite an important call it was with senior person at one of our key partners he was doing a handover uh to a new colleague so the new person who's going to lead on the relationship with upreach and for some reason this my laptop was glitching they couldn't hear what i was saying properly uh it was it was just disastrous and it was really embarrassing and i just felt like an idiots and I mean they were very nice about it but um it was pretty embarrassing for me and I hate messing up like that because I feel like I'm letting the team down letting the organization down um anyway I was able to rescue it eventually and send nice follow-up emails and and so on but yeah something that felt out of my control um at a crucial moment uh was was really unpleasant We sometimes talk about, you know, everybody has mistake moments.

4:46Nick Bent:That's like a, you know, a mistake moment. Sometimes those mistake moments are just your own mistake. You know, we are all human. And sometimes something out of your control just comes your way and you're having to deal with, you know, typically unanticipated stress and kind of pressure in that moment. and as you sort of described it like that I think we all can viscerally feel what it's you know what it's like when technology goes wrong because it's it sort of happened happened to all of us but in general as a CEO when you're in those moments you know where you you feel like this is this is not going well whether it's something in your control or out of your control what helps you what helps you in that next 24 hours what helps you to learn rather than repeat those mistakes or hold on to those mistakes i guess yeah i think for me there's there's two key things so one is a sense of purpose and the other is a sense of perspective nice and the purpose really matters because you know you should bring everything back to the why anyway and i tried to do that with the team at upreach you know we have this you know this big ambitious mission on social mobility that's why everyone who works at upreach is is there and is so dedicated to that cause but it's sometimes it's good to explicitly remind yourself that, you know, you're in this for the right reasons and you're trying to achieve a really worthwhile purpose.

6:08And, you know, and that means that, you know, the hard times, the difficult times, the moments where you mess up are still absolutely worth it. And that's just part of normal working life. You know, you just have to acknowledge that sometimes things will go wrong and you have uncomfortable, uncomfortable sometimes painful moments so that sense of purpose is always i think quite restorative and the sense of perspective also matters because generally what may seem like a horrendous thing to you it's probably not that bad so talk to someone about it you know get their perspective on it and they'll probably be thinking you know why is he stressing about this it's not that that bigger deal they'll be able to offer you a bit of personal support maybe some ideas some insights that will help you fix whatever it is that's gone wrong or that you've messed up so I think that yeah that sense of purpose that sense of perspective are really important for getting

7:07Nick Bent:you through those tricky moments yeah I often reflect on how distance gives you a different kinds of data you know when you're in it it's like when you just described you could really remember and describe that moment I was with this person and that this didn't work on we we're so good at remembering all the details of when things go wrong um and often not quite so good at remembering all the details of the things that go right because you know we move we all move on right you move on to the next thing and you think oh well how do we grow and how do we get better and I think that's often just just human nature do you have uh kind of go-to people you know sometimes CEOs might talk about the importance of things like mentoring or a personal board or perhaps leaders they've worked for before how do you approach getting the right people around you so that they're there for the hard moments because I guess you never know when the shell-shedding moments are going to come but what you probably can guess is that they will happen you know like in every job they're inevitable because of the uncertainty and the ambiguity yeah and having the right people around us kind of feels important so I was just interested to know like how intentionally you about that like how how do you make sure you've got those people?

8:20Yeah absolutely I mean I do think that a big part of being able to handle those those sort of shocks those setbacks whether you're a CEO or anyone else in the professional world is is down to your your social capital sort of how much social capital have you got professionally how strong as your your network of people that you can draw on for for advice and support um we all have sort of concentric circles of people around us whether it's you know family and friends people that work that we work with particularly closely uh you know who you've got a trusted relationship with but sometimes you need to tap into a broader network of people maybe you know somebody who's he's more experienced and he's been through similar challenges before that you happen to you know you might have their number from 10 years ago sitting on your phone or you connect with them on LinkedIn and you just want to pick their brains or even have a coffee with them I do you know I do seek out opportunities to to build my network particularly of other CEO peers um both within the charity sector and more broadly so when i've had the chance to do you know sort of leadership courses training sessions that involve my peers i i've always

9:42Nick Bent:i've always gone for that i think for anyone listening maybe considering you know who is in your career community and also do you have a range of people because actually listening to you you talked about some things then that were probably a bit more structured so you'd asked to yourself almost like what do I want to learn where do I want to learn and then you've sort of found those kind of peer peer-to-peer relationships through those things but then some of it is more informal from jobs you've done or people you've perhaps worked with and I think when you have a shell-shedding moment it can feel really lonely and you can feel really isolated and we also know that loneliness at work is increasing and actually that's not connected to working at home or working in the office which is everyone's initial assumption it's actually much more about how connected we feel at work yeah so do do i feel back to your word about kind of purposeful do i feel connected to my work do i feel like i've got people around me who care and who i could i mean no one uses speed dial anymore but we used to call it your support speed dial you know like who's on when you're having a shell shedding moment who is on your support speed dial and if you're at the moment thinking oh i'm not sure then that that's okay too but then that might be a bit of a prompt to start to think about just how do i find some like-minded learners i see it in the squiggly careers community um we're running something this week a big open sprint across the world and anytime someone is getting stuck or has a good idea they're all sharing it in a whatsapp group we're doing nothing i'm you know i'm i'm not i'm not being useful but they are being so useful for each other and just the amount of learning and connection just happening in that group is is incredible sometimes they're fixing fast sometimes to your point they're doing they're doing a bit of TLC sometimes someone's saying oh I'm doing this by myself because my organization isn't very into learning and they're getting a load of love of like well don't worry you can learn you can learn with us um and so people are kind of getting getting the things that they need and I always think as remember that asking for help is always a sign of strength and never a weakness I completely agree with that.

11:46So much of this is about the quality of your relationships with other people. That really matters. It's always been important. It's still important now. I think it's going to be important as long as human beings are around on this planet. And look, there are some amazing and exciting and sometimes a bit scary things happening in the world of technology, particularly around AI. But if anything, the advance of AI into our lives, whether that's working lives, personal lives um makes the human relationships even more important and i think for young people starting off in their careers or middle leaders or experienced leaders just remembering that the human relationships are so important is is is vital you know those human-centric skills being a good people person being a good team player good communicator even just you know common courtesy good british manners whatever you'd be nice to people whatever you want to call it it really really matters um and just makes everything that the easier to to deal with in a professional in a professional context i think it's also important to remember that precisely because careers are going to become more and more squiggly over time you never know when you're going to bump into people again yeah that you might work with in the same office or they might be a customer or a supplier or in a partner organization whatever it may be your paths could cross multiple times and actually the power dynamics could be very different next time around so i mean just one example from for me and upreach so somebody i used to work with in business 25

13:27Nick Bent:years ago has just become a trustee of upreach so she's now one of my bosses and i think we got on fine you know 25 years ago but basically none of us can remember really but um it seems to that you know we had we had a great working relationship back back then um and that's just one example of how people that you work with in in your professional life could keep popping up again in very different contexts yeah and i that has definitely been true for me too um you know i work in a very different area now to some of the teams and organizations that i've worked in the past and yet sometimes someone will pop up on my LinkedIn and say oh we love squiggly careers we listen to your podcast um I remember working for you and I'll be there thinking right like I wonder I wonder I wonder what that experience was like and usually like you say you you could either you can't remember or hopefully it was okay but I do think just that note know that that squiggly serendipity is is definitely is definitely a thing yeah I wanted to ask you a bit about um you talked about kind of resetting culture um at reach which is always that's almost a shell-shedding moment for the organization rather than not just kind of you individually but almost for everyone and i'm kind of interested to know like what helped people through that because letting go of a kind of an old culture kind of figuring out what your new culture looks like it's always it's quite a hard task because it's all about what you do not really about what you say and it's kind of behavior change which we for anyone who's ever tried to give anything up is always we all know is hard um so that was almost like a company shell shedding moment so what do you think helped everybody because that will have felt different for everyone it probably would have felt uncomfortable there will have been some tensions probably some uncomfortable truths that have to be said out loud if i'm kind of guessing you know it's a collaborative effort the culture needs to be understood and owned by everyone in the organization regardless of their role or which team or office they work in.

15:28So it's collaborative. But, you know, as a CEO, you've got to be intentional in saying that the culture needs some work and we're going to kind of reset it together. You've got to make it clear that you value everyone's voice and input. One of the first things I did as a CEO was to launch a staff survey. There'd never been a staff survey at Upreach. An anonymous staff survey, you know, we've repeated it every year. And actually, that first staff survey gave people on the team an opportunity to vent anonymously. Some of them had some very challenging things to say about how they'd experienced working life at Upreach previously.

16:09Some people were feeling pretty kind of battered and bruised and wanted some pretty dramatic change. And it was important that people could say that anonymously knowing it would be heard and knowing that there'd be no um you know there'd be no sort negative consequences from them being so so so candid about about their opinions so that was a really important part of the process um and yeah me making a real effort to to listen i when i came in as the ceo i said look i haven't got any secret plan to sort of shake things up and make lots of changes in the first instance you know I want to listen and learn and just you know and build on what's good at upreach but I always say you know I want upreach to become one of the very best places in the UK charity sector for people to to work and to thrive professionally the big mantra that I always use to sum up the culture and upreach is high performance and high well-being and keeping those two things you know in tandem uh you know in creative tension is really important

17:18Nick Bent:that's really interesting and i think it's a good observation that there's no point where you tick the culture box and almost if that's how you see it you've probably got it wrong you know like oh we've done that now culture done um i think the fact that you see it as like a continual commitment and you've kind of got that mantra to keep coming back to which is a really nice i that's kind of got an andness about it i sometimes describe that as like and agility it's like you you two of those things can be true at the same time you can have high performance and high well-being and i think sometimes people see those as trade-offs whereas actually what you've just described is that actually no they're complementary and you know we'll all be better because of both of those things if you were to leave our listeners now um with one bit of advice if they want to learn more from the work they do, but in particular, if they want to find their way through these shell-shedding moments that we all have, the big ones, the small ones, the ones that maybe sometimes we create our own shell-shedding moments because, you know, maybe we're a beginner or we choose to do something for the first time in our squiggly careers, or sometimes they happen to us and we've got to find our way through.

18:25Nick Bent:What do you want to leave our listeners with today? Yeah. So I think embrace the challenges and see them as opportunities to learn and grow, but don't do it alone. You know, it's really important to talk to people, you know, talk to people in your workplace, maybe some of your, you know, some of your peers on a senior leadership team, your line manager, or just somebody who you really trust in the workplace who might be more of a friend than a direct colleague. so embrace the challenges but don't do it alone i think it's always useful to remember that what may seem like a really horrendous problem or really big deal to you is probably not quite as big a deal as you imagine and also remember that people are generally more charitable and more nice and more supportive than you think they're going to be so if you open up about a mistake that you've made or a dilemma or challenge that you're facing chances are people are going to be going to be helpful and that's going to make make it better rather than making it worse you know working life is is not like the thick of it or house of cards where people are looking for you to make a mistake so that they can exploit that and cynically use it against it in real life a problem shared is generally a problem halved well the thick of it is one of my favorite tv programs but I am very glad that that is not my day-to-day reality.

19:52Nick Bent:And I think your two points that you've sort of reinforced there on when something goes wrong, remember your purpose and get some perspective, I think that is really going to stick with me. So, Nick, thank you so much for our conversation today. I really appreciate you taking the time to share your insights and your ideas and your experiences with all our listeners. So thank you so much. My absolute pleasure. Thank you, Sarah. Hello, it's Sarah again. I just wanted to say thank you for listening to today's episode. I hope regardless of what role you're in or what stage of your squiggly career you're at, you're finding listening to these CEO interviews useful and relevant.

20:28Nick Bent:And there's something you've heard today that feels helpful for you in your career. And so that we can all learn a little bit more like a lobster. Thank you for listening. And we're back again tomorrow with another CEO interview.

20:47You