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Welcome to Jimmy's Jobs of the Future. Today I'm joined by Helen Tupper. She, along with her co founder Sarah Ellis, came up with the concept of Squiggly Careers over a decade ago. Many of you will know that we've done work with them in the past, various live shows and so on. They really are an inspiration. Although I almost didn't start the Jimmy's Jobs to the Future podcast because they have their own amazing one, which is all about learning at work and how you can develop careers and so on. But they've been great supporters of Jimmy's Jobs of the Future over the years as well, so it's brilliant to get Helen on. This was actually only the third time that I'd met her in person, though, so it was wonderful just to have a bit of a chat about how everything works and the way that they approach business. They came up with the concept of Squiggly Careers and wouldn't it be amazing if was the sort of tagline that they've called their company, and they have built a really thriving business off the back of it. So it was great to get Helen and chat to her all about their new book, How To Learn Like a Lobster, which is out now. Make sure you subscribe so we can continue to get bigger and bigger guests. All right, Helen, welcome to Jimmy's Jobs of the feature. Thank you for having me so excited to do this. You've just written the new third installment of the Squiggly Careers book, Learn Like a Lobster.
A
Indeed.
B
So much to talk to you about. Do you want to explain the premise of the book?
A
Sure. Maybe before the premise. The problem is that.
B
All right, yeah, go on.
A
So the problem is that it's never been more important to learn at work because of the pace of change, everything that's happening outside of often the jobs that we're doing, the world that we work in, but it's also never felt harder for lots of people. So there's this big tension with we need to learn. So we stay relevant and our careers are resilient. We, but people are finding it too hard to do. And I think if we do not solve the problem of learning at work, then a lot of people are going to get left behind. And so that's the problem really that we've seen in all of our work. We've seen this tension, we've seen this problem people often talk about. Haven't got time. I'm overwhelmed by how much there is to learn. There aren't any role models I can see. Like we don't really celebrate learners at work. So here are these brilliant learning role models. And we decided to take what we've learned about squiggly careers, which is, you know, give people a sticky concept, make complex, simple, make it easy for people to take action. And we wanted to take that and apply it to this need for learning to look like, look better, look different at work. And we found our answer in the lobster because it has three traits which we are very fascinated by, but more importantly we think are very useful when we're thinking about learning. Shall I talk about these traits?
B
Yeah, I can show off. And so I've read the book.
A
Okay, so what do you want to show off? Trait number one, what do you think?
B
Trait number one is that they never stop growing.
A
This is true indeterminate growth. So they never ever stop growing till the day they die. Yes, I'll whisper that bit.
B
Till the day they die. And they eat their own shells.
A
Well, that's trait number three. We've missed one in the middle, the first one, the first one is they never stop growing. The second trait is that this growth is enabled because they she their shell. So shell is a constraint to their growth. They recognize that constraint and then they put themselves in a position of vulnerability. So they break out their shell, crawl away from it, leave the shell behind. They're like a jelly lobster, I suppose, really, really vulnerable. But then that means the shell can grow back. And when it does, it's bigger and stronger than it was before. And they do it over and over again. They're sort of experts at recognizing their constrained, putting themselves in a position of vulnerability and growing bigger and better because of it. And then the reason to your point, the reason that most people don't know this, all these fascinating facts about lobsters, is because we don't see these discarded shells. Because our very resourceful lobster eats the shell to fuel its growth. And so it's sort of a self sustaining system for growth. And we think if you take those traits and apply them to learning. You would never stop learning. Like the lobster never stops growing. You, you would learn in your hardest moments when you're vulnerable. That would be the moment that you learn the most. You really look for the learning there. And then you would lead your own learning rather than making your development dependent on your manager or a department like our resourceful little lobsters or not so little. You would be a resourceful learner. Use what you've got in order to keep growing.
B
And I did your lobster profiling test as well.
A
What's your lobster skill?
B
Well, I was, I was a lobster that learned hard times.
A
Well, you're rare. You're rare. That is the least, like the least popular lobster. So these, this lobsters with the ability to learn in hard moments, which typically means good at feedback. Like, don't fear feedback. Good at asking for it, good at giving it. Okay, receiving it. You look for the learning. Also you're, you don't fear failure. So you, you know, failure is part of the learning process. And in those moments, you, you will look for the learning. That is the least skill that we have in workplaces. Most people are not learning hard moments. Lobsters.
B
That is interesting. So the, the example I give with this myself. Well, what. So I agree with your premise of that people aren't learning as much. And I think there's a few factors at play with that. I think one of the things is general social media kind of perfection of it looks bad to look rubbish at something. And the problem is whenever you're learning something new, you're going to be rubbish at the start. So people don't like that. And also I think generally the costs on business to make a slightly political point have got so high lately that it is very hard for businesses to carve out the time for people to learn because they aren't getting the kind of like, maximization from it. And I think it's a classic. We're both a big fan of him, Rory Sutherland. But like, businesses have become so driven by efficiency that they haven't actually sort of done some of that stuff. So I completely agree with that. And I think it's a real challenge actually, of like, how do you sort of put yourself in a position where you're willing to learn? Because actually that starts with admitting that you don't know something.
A
Yeah, I think it's, I think what we're trying to tap into is both like a learning mindset because if you have that, then you're going to look for learning, like, proactively. But then there are Almost. There's sort of the mindset and the moments. So can we prime people to look for learning? That's the mindset. And then can we help people spot more moments for learning that are already in their day?
B
Yeah.
A
So to your point, it's not let's take an away day and all learn together because that's more time, that's more cost. It's. We're already in 12 meetings this week. How do we add more moments of learning in those meetings? We could improve the questions. We could experiment with doing it differently. We could have an agenda item. We could do our agendas differently. So they're designed for learning. And that's what we're trying to do. Relook at where learning can happen in the moments we are already in at work.
B
Yeah. And I thought going through your calendar at the start of the week and being like where are the moments to kind of learn on it was really interesting. Also the other great stat that was in there. Well, I mean there were many, but one that really jumps out at me seeing as you mentioned meetings. 70% of people believe if they had less meetings that their job satisfaction would increase.
A
I know. Imagine that. You know how much we spend on increasing people's job satisfaction. And it's like just cancel a few meetings. I think people might be happier if they don't have to be meetings all the time.
B
Well, it's so interesting. Yeah. In that though, like I think it partly becomes such a kind of. Well, with meetings, I partly think they're a bit of a status play. Maybe that's a bit of my sort of Downing street overhang years in terms of like being invited to certain meetings. But I think it's true in commercial world as well. Right. It's like real, you know, are you in the room type thing. Like it's.
A
We've, it's a bit controversial. We've banned one to ones in my company.
B
Oh really?
A
Yeah. Because like we. My background's corporate, my business partner's background's corporate and our business is not the scale or size of a corporate. We're a small agile organization. But we found a bit of corporate carryover was creeping in. So, you know, one to ones bit of meeting culture going on over. Over process for things that don't need to be that complicated. And all these one to ones were filling my diaries with no agendas. I mean it was nice to talk to my team but it just didn't feel like a great use of time. So there's an idea that's in in the book that started in our business with how can we make more of our meetings? How can we learn more from them? So we don't call them one to ones anymore because it just, it just felt like a nice chat. And, you know, there are other ways to do that, but not, not at that moment. And so every meeting now has to have a decision and discussion agenda and you can, you can have as many of those with us. It's not that we are saying you can't meet, it's not that. It's just we want the meetings to add value. We want the meetings to be more primed for learning and it has been so helpful. So I go in. We. It's really clear people, both people feel better at the end of it because the time has been well spent and they've got what they wanted from it. It's. It's been a bit of a game changer. But we had to get rid of one to ones for that to be possible.
B
What was it again?
A
Decision is a decision discussion agenda. So I had, I had one today with someone in my team actually, about podcast stuff. It was, these are decisions we need to make today. These are some things I need to discuss. And you look at it and we kind of work our way through. It's even better if the agenda items and the things you want to discuss are framed as questions. So rather than just bullet discuss Helen and Jimmy meeting, it would be. The question might be, how can Helen and Jimmy record the best podcast ever? And because your brain loves a question like it ponders it, it thinks about it, you get more out of it than just a dry bullet point with a statement on which is what if meetings even have agendas? That's what most of them look like.
B
Right. Well, it's Jimmy's job's away day tomorrow, so re ordering the agenda slightly in terms of questions. No, but I think that's like, it's, it's good. Right, because we're coming out tomorrow partly to have a bit of like, think strategy, like, where's everything going? But also, you know, Sunny's big thing is like, well, we need some decisions that come out of it and some actions and. Which is totally right. So, yeah, it's interesting. Where can you remember where you got the first idea from? For the lobster.
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Yes.
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For the book.
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Yeah, I do remember it. And the evidence of it is on Instagram, but you have to scroll a really, really long way back to 2020. So this is pandemic times. And I, I actually can't remember where I saw it, but I do. The bit that I found out about was about the lobster shedding its shell and the. When it is vulnerable, that is the moment that it grows the most. And at the time it made me think lots of us have shed our shelves in the pandemic where we're a bit vulnerable. And I used it as a way to share with our community that, like, if you're vulnerable, it's actually an opportunity to grow. Like, if you treat like the lobster, it's opportunity to grow. And we've got this like, picture of a lobster that sort of. It's all an. And that we posted and it connected with lots of people, lots of lovely comments at the time. It sort of served its purpose of hopefully empathizing with our community. Then it just got, you know, shelved. It was just one of many ideas that. I mean, we never thought it'd be a book. It was just. It was just an insight. And it wasn't until about two years ago we were writing a book on confidence gremlins that we kind of came back to this. The lobster just came back. And the more that we started to look into lobsters, the more we. We realized there was to. To learn from them and to use it to help other people learn. But, yeah, it was just. It was sort of just hidden in the back of our brains for a little while. I think that's interesting, an idea in
B
waiting maybe how those things can come to the fall though, right? Like reading about them and so on. I think it's. I think for everyone, you do, you have to through your career, right, Shed various sort of skins like that. That happens and so on. And yeah, most growth comes from after it largely because you've been perhaps constrained for a little while.
A
Yeah. I don't know. We could dive into your career, Jimmy, but I would imagine there have been like, pivotal moments in your career where you've obviously made big changes and it's a change of identity, it's a potential change of income, it's a change of your network. Like those pivot moments in careers are really exposing, but then the growth that can come from it. Like, you know, just take the podcast like this. What's been possible because of a hard decision, learning in a hard moment leads to lots, lots more growth.
B
I do occasionally listen back to the first episode. I don't do that, but yeah, exactly. I mean, you've done like 500 podcast episodes. But it's just so. It's so funny to kind of do that and listen back to Them just because it's a reminder of that you're just rubbish at anything. And the thing was, I knew. I knew I'd got the sort of skill set of asking decent questions and getting to the number of a point. That was a lot of what I was doing at number 10. But it's obviously doing it for a different broadcast audience was a different skill and required it. But I think that sort of. And I think that's quite hard in terms of. And it gets talked about a lot, right. Like transferable skills. But actually knowing what your transferable skills are, I think is quite difficult because it's difficult to see across an industry that you don't really know. You've got an idea of how you think it works. But often it comes more from popular culture than any kind of realism.
A
I think feedback can help you with that. So we often use this question of what three words would you use to describe me at my best? And you could make that even more specific. You could say, what three skills do I use when you see me at my best? Like, you could. You could kind of really focus it. If you're looking for, like, what is it? Is it presenting? Is it that I'm really good at data? Is. I'm really good at questions. But sometimes when we haven't got that answer for ourselves, which can both be a lack of awareness but also a lack of confidence, like, we don't sometimes own the abilities. If you go and ask five people you've worked with for a while, what three words would you use to describe me at my best? Or what three skills am I using when you see me at my best? That's data for your development, which is something we talk about in the book. And there is a lot of data for our development around. We just often don't have the questions to access it. It's quite useful. It's quite. You ask. Ask five people that question, 15 bits of data for your development, and then there's a decision because you get all those answers back, like, what do you see me? What words you use, describe it and best. And then the decision is, but is that what I want to be known for? Which is. Which is really where I think the time should be spent from us. We're not. We know what am I good at? Go ask other people that. You decide whether what they think you're good at is actually what you want to be known by.
B
Yeah, because it's one of the things that I say to young people a lot is go and ask people what you think you're good at because I think it's particularly hard when you're, I mean, literally posted about this on LinkedIn this morning. But it can be particularly hard when you're sort of starting out to know what you're good at because you just assume that everyone is good at those things and so on. But then equally as you get further on your career and you're supposed to look like you know everything and you're supposed to have some, you know, that can be hard then as well. And also the skills change and what you need to kind of like grow a business is different to starting one, etc. Right.
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Yeah.
B
You will appreciate that.
A
I wonder whether sometimes like a bit of a confidence curve, you know, like you have low confidence at the start because like you don't know what you're doing and then you get to like, oh, I think I'm competent. And then you get to like, everyone thinks I should know what I'm doing, but I don't know, I've never really thought about. But I do wonder in a career where there's like a confidence, it's not, it's not this kind of very linear trajectory confidence, like the longer your career, the more confident you are. I think there are, you know, there's probably moments where we lose confidence because we've reached a different stage or we lose confidence because everyone thinks that we're supposed to know what we're doing, but we still don't feel like we do know what we're doing.
B
Yeah, absolutely. Well, it's a squiggle.
A
Yeah.
B
Almost original kind of idea. I think it's interesting. I mean, I lost quite a bit of confidence I think in the pandemic, trying to work out one of I was going to do next. But then also there was a sort of fun kind of element of, well, nobody's doing anything for the first few months of it. But I'd already been out of a job for six months at that stage, so it was just sort of like. But it was an interesting time. But also that was one of the key things when I was reading the book that I saw in myself was about like how to become a better thinker and are you an out loud thinker? And obviously I know your business partner reasonably well as well, Sarah. But I was thinking you and I are so like out loud, really annoying
A
to be
B
like, you can send people voice notes, etc. And I thought, yep, that is, that is me. But it was, yeah, fall back to the pandemic. Yeah, no wonder, sitting in a Box room on my own was so blooming difficult, like trying to work it all out and whatever. But yeah, explain to us that has be a better thinker and out loud thinkers.
A
Well, so you kind of have defaults just because of your, your kind of natural style. So kind of my default is that I will be an outline loud thinker. So if I've got a problem, I need to talk it through, I need to talk it through with somebody. Like I kind of bounce off and in, in articulating the problem, I create almost, I create the solution. Like I kind of create some sort of clarity and that's how I think. Or you can be someone who's more of a quiet thinker, like my business partner Sarah. And she will, you know, she will kind of process and sit and, and reflect and think through herself and ponder and she's considering all the scenarios and all that kind of stuff. And it's not that one is bad and one is good. It's just that what we really want to do is, is, is be a bit of both, like not always default. Because actually my, my style is very dependent on someone being able to listen to me. Right. So what do I not think? If you're not available, that doesn't really work. So we want people to experiment with. You know, for me for example, being someone who does quiet thinking like my business partner, I can't do it as long as her, but I could do five minutes, I could blow and think. Do I get to better answers? Maybe do quiet thinking before I do out loud thinking? Maybe the quality of my out loud thinking would be better if I'd actually done a little bit of that before. And a lot of like the looking for learning that we want people to do is to sort of recognize their patterns. What do you default to in a hard moment? What would you default to when you need to think and say well here's a different approach. Experiment with it and see what you might learn.
B
Yeah.
A
And you might learn that it's not right for you. You might think, well no, I'm better at being an out loud thinker. But that's okay. That's okay. But not trying means that we are missing the opportunity to learn how we could do it differently. And, and that's what we're trying to encourage people to do.
B
Yeah, yeah. I could certainly do a bit more thing because mind mapping is one things that you kind of come up with.
A
Yeah, right. Yeah, yeah. Mind mapping. Or even again just kind of think or do a tendencies here which I have a do I'm very action orientated. Even just forcing yourself to just sit and think with. No, no mind mapping, no doodling, like just to, just to ponder. Just to let your brain connect the dots. Not you connecting them on a piece of paper, which is what we do in mind mapping, but just to let your brain connect the dots and see. And it's quite uncomfortable, I find that's what I learn. I, I struggle with that. A pen and paper to create clarity or a conversation to make it connect. But the quality of your thinking can be better if you do that. And it's, it's just, it's like a bit of brain training. Would I do it for half an hour? No, I would find that too hard. Could I sit and think for five minutes and force yourself not to. What a lot of people who are doers that create mind maps tend to do is they might turn their mind maps into a sort of to do list.
B
Yeah.
A
So you start doing it. So you know you're doing this, it just comes through and you're like, oh, that's a great idea. I'll just email Jimmy, I'll do that afterwards. And you kind of get distracted by the great idea that you've put down on paper and it basically becomes an idea to action. Our brain is magnetized towards that. Whereas just sitting with the thinking is what we're really trained to do. Only you or I know if we're cop. It's like a cop out. But that's the point. And how hard I always think, gosh, how hard do I find it to sit and think without any, without pen and paper, without looking for the answers on my phone.
B
But I think one of the things is we've almost eliminated boredom.
A
Yes.
B
Right. And so it's actually just really like you just don't have it. Occasionally not as good as I would like. But I'll try and run without music. Right.
A
Okay.
B
Just like let, let the brain kind of go because it's, it's interesting where it goes. But again it probably shows something about my kind of like general fidgety. I need to be running at the same time. But it is just really difficult just to sort of sit and think. But this is why people say, yeah, they get good ideas in the shower, on the loo or whatever. Right.
A
My, my answer to my son at the moment. He's 11. I read some research about basically that we're not allowing children to be bored. But actually in that, in that moment of boredom is actually where kind of creativity happens because you have to Find a way through it. And so every time he's like, goes to me, I'm bored, I go, brilliant.
B
I see. I think my kids, they don't say they're bored at the moment, they just say they're hungry.
A
Are you feeding them? Jimmy literally just had lunch.
B
Like, you know, I was just like, I want a snack. Yeah, no, it's. I think it's how it's all sort of changing the wiring of our brain. Right. And the. And the learning side of it, because it's become one of the most important things I think, is as the world is going to change and it's going to get quicker and quicker over the next few years as well, is that the ability to learn is going to be absolutely paramount. And it's the skill that when we're recruiting that we look for more than anything is can you learn quickly? That's basically going to be the biggest predictor of whether you'll be a success.
A
But I kind of feel like learning is a bit like, like the word trust. If I say, oh, you know, trust me, like, trust is a small way, but it's huge. There's so much that contributes towards trust. Same with learning. Like, if you say, oh, you know, we need to lear. We need to be better learners, actually, people might be like, yeah, we, we do, but it's that.
B
But who's going to disagree?
A
Yeah, like, like, but how? And so what we're trying to do is. So if you break down the book, there's basically those 12 different ways to be a better learner. That's except effectively what we're doing, particularly at work. Like, we're very anchored around at work. How do we be better learners? And so whether it's, you know, talked about beginning, for example, how uncomfortable that is, being a better beginner, finding feedback easier, looking at failure and mistakes, adapting, playing, connecting, sharing, like, these are all practical ways that are proven to help you learn. And none of them look like going on a course. None of them. It's not about going to course, it's not about that. It is about these practical things that we can do every day so that we can learn better. And I'd really like to demystify, like, what learning can look like. It's not very sexy, but I think it's quite useful.
B
That is so interesting. Right, so let's take two things that I've done in my career. Two courses that I've done.
A
Yeah.
B
Because I think I really reach for that as a sort of like shorthand type thing. So leaving number 10 wanted to kind of learn about entrepreneurship, etc, went out and studied at Stanford for a couple months on their Exec EDS Ignite course. And it was amazing. But the biggest thing was probably changing my environment actually.
A
Okay.
B
Rather than. And also because the course was evenings and weekends, it gave me time to think and meet people in the day. So that was really important. But then I also did a stand up comedy course as well because that was one of the other things I wanted to do post number 10. And it was partly ridiculous doing a stand up comedy course because you just for that instance, you need to learn by doing. Yeah, that is the only kind of like way. And I thought actually, you know, the whole course is about 30 hours and it was good and it gave me a bit of confidence. And there was a gig at the end and you met some people through it as well, which was also useful. But actually if I just done 30 hours kind of on my own, like I would have. Yeah, I'd have got to the same place, probably would have done it quicker.
A
So I was just thinking like, if I think about what we know, like in their stand up, for example, you're experimenting.
B
Yeah, because.
A
And you're. You're experimenting, you're being a beginner. You are probably failing quite a lot. I don't know. I don't. I didn't see it. I didn't see it, Jimmy. But I'm sure some jokes did last.
B
Exactly. You haven't seen it since, so you know it hasn't. Not on that place.
A
I'm just making an assumption and then also connecting. So there's four elements, I would imagine, in what you did as part of that experience that actually lock in learning. And so yes, you could have read a book on how to do stand up comedy and you might have learned by reading the book. But actually what you will have taken from experimenting, failing, connecting those, those elements of. Are in like really, really important for making learning last.
B
Yeah, no, that, that's true. But I just think, I sometimes think I run towards the sort of shorthand of doing a course and I think it will navigate me through it quicker. So it was when you were like, learning does not have to look like a course. Like, I was just like, oh, feel seen there. You may have noticed we've been doing something different recently from our budget livestream to the episode where I sat down with the producers. We've been experimenting with new formats that you've been asking for. We want to do much more of that in 2026. But truthfully, those Episodes don't quite perform like some of our blockbuster ones with prime ministers or business titans, even though amongst our core fans, they're often your favourite. So in early 2026, we're giving you the opportunity to be even more involved with the show and we are launching Jimmy's Jobs backstage. The waitlist is now open and if you pledge your annual support, we'll etch your name into our brand new studio. We'll be able to bring you more into the show by listening to your guest suggestions and your questions that you have for them. And there'll also be more live shows next year, which you'll get early access to. If you or someone you know are a fan of this new way of doing media, check out the show notes to see how to join us backstage or give it as a Christmas gift. And hey, you might even be able to put it through your learning and development budget. See you backstage. Now, back to the episode. But what, what does learning look like then? Right? And what, what's it going to look like, do you think, in the next five to ten years as well? Right. As the world changes.
A
I guess the thing that I am, the two things that I'm really excited about that I don't see today, but I would love to see when you're like, what does learning look like? What I would like it to look like. I would really like to see more teams learning together. So we've talked at the moment very much about me learning or you learning. And I think there is a really big opportunity to find more moments for teams to learn together because that's where we're spending most of our time and in the meetings and moments we're already in, if we can be doing team experiments, if we, with this really great thing we call them, like helpful how to. So there's a, you know, a proven way that we can learn more is by sharing. So the, the kind of insight here is if I'm going to share something with you that I know, first of all I have to recall, like, what do I know about whatever this thing is? Then I have to think, how can I articulate that in a way that is useful? So that's kind of like another like mental loop that, that I need to go through and then I have to share it with you in a format that's going to be relevant. Those processes clarify that knowledge in my mind. So it's much clearer now. I'm like, oh, yeah, you start to think I've got a gap there. Maybe, I don't know that very much so. Sharing is a really powerful way that we improve our learning as well as moving it to someone else that we're passing that on to. And we have these things called helpful how to's. It's a really fun team experiment to do. We didn't constrain it to work. You could, you could say everyone in the team, you're in a meeting that you're already in. You go, everyone on the team has got five minutes. Here's a post it note. Everyone on the team has got five minutes to write down a helpful how to about something they know that they think would be useful for other people in this room to know. Now you could constrain it to work and people talk about, I don't know, copilot prompts and how to, I don't know, manage their meetings or create useful agendas that people can actually feel good about at the end. So you could constrain it to work. We didn't and we had everything from how to make a cold press coffee or something. So on my team knows a lot of languages, how to learn a language. I did how to create a custom GPT because I'm that geeky.
B
Someone else bringing it back to work.
A
Yeah, I've got nothing else to do me to me. But it was the, the it's a really fun way of learning in teams and so that's just like one element I think there is. We do these sprints. So we have. Yesterday someone messaged me over 120 people in Kerry company that we work Kerry dairy are sprinting this week and these are team moments for learning and it's 10 minutes a day that teams are doing. I think we. It is a lot easier to create learning cultures in companies if it's not just about every individual needs to do it for themselves or every leader needs to espouse it. If we make it easier for teams to learn together I get really excited about the potential there. And then the second one is I'd love to see learners celebrated. You know how, you know, we celebrate people getting promoted. Well done. You reached the next level. I would love to say like well done, look at what you've learned. I'd love us to put learners on a bit of a pedestal and because at the moment I'm having to put a lobster on the pedestal so I've got a role model and what I want to do. You know, I don't really want to replace lobsters but I would like lobster learners. I'd like the real people to be there to be role models in companies.
B
I think that's true. The individual side is interesting because I often think of the school system is generally quite weighted towards individualistic endeavors. And actually most of life isn't. Even though we put somebody on that pedestal sometimes, I think it's. It's one of the things that actually where the school system is, is most misplaced in terms of preparing people for the outside world. It's also the fact that schools massively over index on academic ability for first 18 years. Very few jobs actually require that kind of like academic ability. But I also think the school system gets a lot of stick. I don't think many people have come up with better ways for, like, how to change it. And I see my own kids at the moment, like for the first sort of few years of school, really, actually what they're being taught is, you know, how to write, how to count, how to do maps. And they are the basic building blocks of what you're going to need across the board as well. What's the most interesting thing you've learned lately?
A
That's a really good question. Probably we're doing a lot of work around saying the hard thing. Again, it's come. It's come from the book. And the point is that it's connected to feedback and actually that a lot of people struggle to say the hard thing. And so an awful lot gets unsaid at work. Margaret Heaven has talked about this with, you know, the amount of things that people do not raise that they want to at work is getting in the way of growth. And so we believe that giving people a tool and a framework to say the hard thing is, is a way to make this easier. But to your point, on what I've learned, so we've been experimenting this in our company with, Experimenting this with other companies. And what I have come at, the sort of surprising thing that I've learned is, is that the two skills. There is definitely the ability to say the hard thing. That is a skill. There's a skill and a framework, and, you know, that's a skill. But hearing the hard thing is equally important. And until I started doing this stuff, like putting into practice, I didn't realize that that is also a really, really important, important part of the learning process. Because if I don't, but I don't have the skill of hearing the hard thing, then what happens is you, you say it to me and you're, you're, you know, you've, you've nailed your framework. You're really good. You said the hard thing. Exactly right. But the learning doesn't land because I don't know how to hear the hard thing. So I respond in a very defensive way, like, oh, well, well, well, Jimmy. Or I get emotional or whatever. But hearing the hard thing, like holding or ignore it, do nothing with it, and being able to kind of hear the hard thing and hold it so that you can actually learn from it. One of my favorite things to. In hearing the hard thing is we have this sort of approach. It's called the multiplier effect. And this is, like, new. This is new to me. We've kind of worked on it, we've experimented with it, and it's really working for me. So let's say you say the hard thing to me. Something about today's conversation or some work that you've seen us do, and you're like, helen needs to hear this. And, you know, instead of me defending my work or being, you know, really upset by it, I would kind of acknowledge, like, I appreciate you sharing that with me, but I don't have to answer you then and there, okay, I need to acknowledge it, appreciate you sharing that with me. But the multiplier effect is where I go and take your feedback and I then go and talk about it with a couple of other people. Now, very quickly, very quickly could be same day, within the 40, 48 hours, I might talk to my business partner. I might say, oh, Jimmy's giving me this feedback on that's happened. I'd really appreciate your perspective. What would you do in this situation? And then I take that bit of insight and I go and talk to someone else, maybe my mentor. And I said, had this thing that's happened, I've had this feedback. I've had this advice. I'm really interested. Have you been in this situation? You know, what would you recommend to do? And these. What happens is each one of those conversations does two things. It puts me back in control because you saying the hard thing to me might have. I might not have been expecting it, but these conversations I'm in control of, control makes people more feel more comfortable and reduces the fear so that we can actually learn from it. And the second is I multiply the learning because I've got your insights. But instead of just responding to it and that being the end, I've then extended it by sharing it with a couple of other people. And the thing that is really important is that you then close the loop. So I then come back to you and I say, jimmy just wanted to, like, come back on the conversation that we had on Monday, I've taken it away. These are my reflections, these are some insights I've had and this is what I'm going to do. And, you know, I would probably say, just wanted to say thank you because I wouldn't have got to that learning without you starting that conversation. That is a much, much more powerful way to hear the hard thing and learn from it, rather than what most people do is they. They. You give it, I respond in the moment and it's, it's. It's the end of the conversation is the end of the conversation and I don't feel in control because you took me by surprise. And I've just. I've really been learning about the impact of it, personally. I've been practicing that. We've been working with companies. This idea of saying and hearing the hard thing is really landing in companies because people just aren't doing it enough. And I'm quite, quite excited about what we can. What more we can do with it.
B
Can you give a personal example of when that's happened in terms of the hard feedback and how you've done that multiplied thing?
A
Yeah.
B
What do you think you're. What are you not good at as well? I suppose.
A
Loads, loads, loads, loads. Well, I guess a more recent one, there was. Situation Sarah and I had recently. We were. She won't mind me saying this, she don't really say it. We were away, actually, at the National Lobster Hatchery in Padstow where we are now patrons, because we've. We've gone pretty deep in the world of lobsters. Pun entirely intended. We were there and we were having dinner and I decided this would be a great time to give Sarah some feedback. I mean, spoiler it wasn't. So we'll get to. We'll get to this in a minute. And the feedback that I was giving Sarah was that I thought she was trying to take control of too many things in the business and she was taking the lead away from other people in doing that. Like in a quest for control, she was limiting other people's autonomy effectively. And it was quite, it was quite, it was quite direct feedback to which Sarah quite rightly was quite defensive about, because I hadn't used. I. I hadn't delivered the feedback in a way that we have designed it to be done, which is like, start with an open question, acknowledge where someone is, say the statement quite quickly and then very quickly involve, like, that's what I should have done. I just said it and stopped, like, because I felt really awkward about it. Which is what, you know, which is what a lot of people do when they have a difficult message to deliver. And Sarah and I, you know, we've been friends for a really long time, so we kind of had a moment of discomfort and friction and then quickly flipped to curiosity because we're so. We're kind of wired to do this together now. But I took that moment because, I mean, I got sort of two things came from it. Like, one, I'd upset someone I really care about because of my inability to deliver feedback. And two, I hadn't kind of landed the message that I wanted for our business. It just. I was like, this is wrong. And kind of. Sarah sort of played that back to me. And then I talked about that with other people. I talked about it with some people in the team in terms of, you know, how are you finding how I give feedback? Am I too direct? Am I like, what's the best view? It's various different people that I talked to who would. Who would have experienced feedback with me.
B
Yeah.
A
And I took their insights, I talked to other people as well, who are more direct than me, and said, would you have done it like this? How would you have done it differently? Not doing it over dinner was a common. Was a common thread. Like, give someone the heads up, Helen. How's your dinner, by the way? Yeah, like, so it. But it allowed me to take a moment that I felt like I had failed in. And rather than the feeling of failure sitting with me of like, oh, gosh, how badly did I do that? And my, you know, my best friend didn't think it was great, I was then able to say, well, actually, you know what? Because I've taken that and I've talked about it with other people, I've learned more from their approach. I've learned more about my approach. And then. And then I closed the loop with Sarah, which actually resulted in us improving the model, Improving the model, improving the framework. And, you know, it's a bit meta in my world, because we give feedback, we write about feedback. It's a little bit meta, but it is the reality. I do, you know, I do have to say the hard thing. I am doing this in my own work as well as trying to help other people with theirs.
B
Yeah, yeah, no, I can. I can see that. And yeah, feedback, feedback, feedback loops, lots of them, constantly. I am very unfairly going to ask you at some point to use three words to describe me, actually, but I'm not. I'm not gonna do it. I'll let. I'll let You. I'll let work on background RAM for a bit. Maybe we can finish with it. Keep. Keep listeners engaged. Talk us through the business model of amazing if. Yeah, Squiggly Careers. Because I think it's very interesting because when I was starting out with Jimmy's jobs of the future, as I've talked about, I was looking for kind of like career podcasts and whatever. Came across this amazing one called Squiggly Careers and was like, huh, that's basically my entire ethos and so on and genuinely, for a while, for. Oh, well, maybe, you know, maybe there isn't something there. Now, obviously we actually have quite different sort of approaches, formats and so on. So there's definitely an interesting lesson there as well. But you have, over the kind of five years that we've known each other, you have really sort of built like, you know, quite a sustainable business. Now that's not just podcasting. Yeah, I don't think it's ever just
A
been podcasting, to be fair.
B
But yeah, there's. There's more there. So just, I guess, talk us through the kind of, like, Squiggly universe.
A
Yeah, yeah, the Squiggly universe. I think they're probably the easiest way to talk about it is to. To share our flywheel. So we use Jim Collins, the kind of concept of a flywheel, to think about how we scale Squiggly, how we. How we keep growing squiggly. So I guess at the heart of it is an ambition to make squiggly careers better for everybody. So that's kind of like, what. And you start to kind of go, what does that mean? And how do we do that? And. But that's at the heart of it. But on the flywheel, there are four elements of our flywheel. So the first is create useful career content. Like, that's the very first bit. And I. I resource my team against these four elements, by the way. So I have people whose job it is to help get out what's in mind, and Sarah's head to create useful career content. So whether that's the books, whether that's the podcast, whether that's writing for Harvard Business Review, like, we try to create as much of that as possible. So that's kind of the first part that then leads into to create sponsors and supporters of Squiggly careers. And they are distinct things, and we manage this really carefully. So supporters are. They're our Squiggly career community. They're the people that sprint with us. They're the people that post pictures of themselves, of lobsters. Like, there are these. There is a community. They identify with Squiggly Careers. They want Squiggly to do well. They put the Squiggly emoji in their LinkedIn bio. You know, they see themselves as Squiggly. And we want loads of those people because it helps us get feedback, it helps us to grow. It makes. It makes Squiggly bigger. It makes it a movement, not just a company. So that's our supporters. And then we have our sponsors. And our sponsors are people that take us into organizations or they, they're people that say, do you know what? We, our company needs to be more Squiggly. I've seen what you do. I believe in what you do. I want you to come and do it here. And we do very, very little, if any direct outreach to companies. All of it comes in because of the sponsors and we make it easy for them to sponsor. So we've created the Squiggly Careers company toolkit because people were showing us the decks they've created with very funny squiggles and things that they've written. And we're like, oh, that's probably not how we describe it, but great. So we try to make it easy. Now we've got a toolkit so they can take it into their company and put it in whatever, whatever decks that they want. But we. That that leads to sponsors and supporters is something that we think very strategically about. The next part of the flywheel is that buy products and services. So we look at, well, you know, what are we selling? What are we selling to people? What are our workshops, what are our sessions, what is our pricing like? And there's definitely work for us to do there. I think there's lots more stuff that we could put into that area of our world. And then the final bit is that leads to data, insight and income, and that then that feeds our ability to create more useful career content. So obviously we, we are a company that is revenue generating. We do make profit. That is an important part of us. We're called purpose and profit as a business and we have targets around that, but also all of that insight and data that we get. So we, you know, the feedback from our sessions, the insights from our sprint, like, we're pretty obsessed with feedback, as you've probably got. You've probably got another feedback loop in our business. But all of that goes back into creating useful content. And that might be, oh, so that's going to mean we're going to do that podcast or that's going to mean our next sprint is going to be on that, or that's going to mean our next book is on learning. Because everything that we're talking to about companies keeps giving this problem and so we need to solve it with more useful content. And I have people in my business aligned to every element of that flywheel. And the harder I work on the content, so the more content I put out, the more advocacy we get. It just spins. So we, we just. That's how we manage the business.
B
I think that. And sort of taking the end point of the sprints and so on, and then what to kind of create content around is like your own sort of like Google Trends data 100, 100.
A
And it all sounds. I'm going to want to make it sound very boring and dull. It's not like we're all sat there going, like, where are we at the flywheel? Like, it's fun. I love it. I love the community, love the insights. It's, it's. You know, there is also, there is also a bit of randomness in it where we'll just randomly. I was talking to someone this week about someone in our. Here you go. Someone. We have lots of WhatsApp groups with these different communities. And Katie, who's in our community, sent me a picture because she's hacked her diary. She's turned her diary into a squiggly diary, and she's taken lots of our tools and prompts, printed them out and put them in her diary so she can fill them out each week. And I was talking to our team and I, I was like, we need to create a squiggly career development diary. So all these tools and models, people can. People have got it, make it really easy because we have a saying like, if it goes in the diary, it's more likely to get done. So if we create a squiggly career development diary, it's. It's all. It's already in. It's embedded in the diary. And you know that that's not on the flywheel. At no point have I strategically gone, we should do this. But we might have a bit of fun. We might create one for one year, do a short print run, put some digital ones out and we'll just see because we're small and we can do that. And if it doesn't work, we learn. And if it does work, we do it again. So it is, yes, we think about the flywheel and we think about it strategically, but also like experimenting and having
B
fun, because it's Fun.
A
Yeah, because it's fun. Because it feels right. Give it a go.
B
It's what. Actually, one of the big things that we're discussing tomorrow a bit is how to have more fun. Like, we had a very serious, like, 20, 25. Like, it was great in lots of ways, but, yeah, some of the more sort of irreverent fun stuff and so on is important. Right. Because it's. It's partly why people come to work.
A
Yeah.
B
Right. It's a big sort of driver of it, I think, and we don't often talk about it enough. What go.
A
I was going to say, in the book, there's a chapter on play. So play is part of learning some really interesting things about the NHS and people's performance increasing when they introduce moments to play in the workday. So I was just thinking of a quick one that you could steal, like the. The. I quite like. The Spotify playlists are fun as literally a fun way of playing. So everyone in the team has to pick a track that is either meaningful to them or they think represents them and they play the track. You don't have to play all of it, but, you know, you play like the first 30 seconds of the track, so you need, like an owner of the playlist. Someone's going to play it and then they explain, like, why. What the track says about them, why it's meaningful to them, but it's fun and it's a good way of learning about each other. And so, yeah, I. You could have a go at that as a fun. You could add that in tomorrow. Literally very easy.
B
Tomorrow. I say what we've done a few times, which is good. And actually, one of the things you quite like this probably as an idea, is that we always bring in a couple of, like, external people as well.
A
Yeah.
B
Sort of tangentially. And we've got somebody coming in tomorrow who's basically on some extended paternity leave and is just doing some kind of, like, job experimentation and so on, which I'm really looking forward to sort of coming in and whatever, because I think you're the same as well. Right. It's like a cool company. Right. And he just wants to kind of come in and just see what we do and what we're about. And I was like, we'll come to one of these sort of strategy days. It's always useful to get a bit of outside perspective as well, and it stops us sort of talking to kind of, like, internally, as it were. But one of the things that we've used and We've done a couple of times now is bring in an item that means a lot.
A
Yeah.
B
To you, like what you would save in a fire. And that's always really good. But, yeah, I think we'll.
A
Everyone loves music. Gives. It gives a bit of energy. Back to the fun. It's like everyone's. Oh, my gosh, Tina Turner, Jimmy. That's a strange choice. Like, it's just fun.
B
Yeah, definitely. How do you know? Okay, so that's. That's great. And do you. Do you have sort of ambitions? Like, you've done so well in kind of 10 years? Like, what are your kind of ambitions for the next 10? Like, where would you really like to take all of it?
A
We want Squiggly to be synonymous with careers globally. So I want it just to be common language. I quite like it to go into dictionary Squiggly careers. But I want. I want it to be common language. I want people. I just want it to be normalized and I really want it to be credible. So I don't want to just be a word. I want it to be this practical. Like, people know what they need to do to create a Squiggly career culture. People know what they need to do to own their Squiggly career. And we, Sarah and I, start our PhD this year. So part of a. Part of us being. Look at your face, both of you. Yeah, both of us. Yeah. We're going back to where we met. It's all very romantic, really. So we came back to where we met at university and we're doing it. We're doing it there because they've got an executive PhD that we can do alongside growing our business. But we're doing it on Squiggly. We're doing it on Squiggly. We're doing it on. How do we solve this problem with progression that we see in companies? What are the initiatives that make the biggest difference to how we manage progression in organizations? Whether it's the leadership, the language, the talent matching to projects, we are. That's what we're going to do on. So we're going to work with the companies that we already work with, but we're going to do research programs. And we will prove. We will prove that Squiggly progression is better for people and companies than just presenting promotions, which is what we've relied on for a long time.
B
Definitely. I also think, like, job titles and promotions are sort of a bit of a dying thing anyway, actually.
A
Yeah.
B
I mean, that's a whole nother topic. There's another bit in the book which is all about job crafting and that really struck a chord with me because for 10 years I've sort of crafted my job since basically being at the Institute of directors before, number 10 had very kind of, like, supportive bosses there who let me take on lots of extra things and it was just great. And I just wondered if you could just talk a bit about job crafting and how to go about it.
A
Yeah, yeah. It's. Again, we could do a whole episode on this. But I'll sum it up. So the idea of job crafting is evolving the role that you do so that you can both create the most value for who you're doing it for and be at your best. Because very often when we apply for a job, we're getting some outline of, like, the perfect job and what you should do every day, and the reality of that actually ends up being quite far away. So our jobs, our jobs kind of get crafted anyway by the company. But job crafting is something we want the individual to be in control of, but it's not, how do I get to do more of what I want? Because that's quite hard for people to say yes to. It's this, how do I create more value while at the same time being at my best? It's this kind of two things we've got to get right. So that's. That's what job crafting is. Loads of ways you can do it, but I think one of the easiest ways to do it. Again, I think it's quite a fun way. I'm clearly biased about all things careers, but go and look at some job descriptions of jobs that you are intrigued by now. Go on LinkedIn, go find five jobs. We'll call it job scanning. Go find five jobs that you're like, if I wasn't doing this, then I might do that. And this isn't because you're going to apply for those jobs. This is because you are going to go through the job descriptions of those jobs and you are going to highlight specifically what it is in those jobs that you find appealing. Maybe it's partnering with people across the business, maybe it's leading initiatives, maybe it's having a budget, responsibility. Whatever it is, you're going to highlight it. You can do it for five jobs and then you're going to spot the similarities. Actually, in, you know, four of those jobs, I highlighted leading a team. In four of those jobs, I highlighted collaboration, like, whatever it is, and those are the things that you want to think, well, how do I get to do more of that in the job that I'm in right now? Because clearly that's things that I want to spend time doing. So how can I design that into the job that I'm doing in a way that is valuable for who I'm doing it for? And then the last point I would say on that, that how valuable for the people I'm doing it for. The best thing to do is think about how what you want to do can solve a problem or an opportunity that that person cares about. That is, that's how you kind of pull it. Otherwise it's push, it's like, well Jimmy, I want to do some more collaboration. And you're like great, Helen. But actually we've got this problem of profit and so that's not that helpful. Whereas if I said I've really noticed that team over there, their performance is really good. I bet if we collaborate with them I can take some insights, bring it into our team so we can work on that profit problem. And then you're like, yeah, makes, makes sense Helen. Like give it a go. So those kind of areas I think are really important. You might job the job scanning activity is quite good because sometimes people don't know where to start and it's just quite a practical. It's quite a practical place to start, definitely.
B
And yeah, working out what your boss doesn't want to do as well, what your boss's problem is.
A
No, I like your framing what your boss doesn't want to do. Ye, that's a really good thing.
B
Yeah, it's like take that off. Like it's going to help you, help you develop and be seen for everybody. How has your hiring changed over the years?
A
So we, I don't think anybody we've hired has done the job before that they're doing for us. And so we hire people in and when we, when they come into our business, amazing. If they come in as a contractor, which is interesting because not everyone wants to start as a contractor, you know, that's more, you know, I'm not sure I would have done when I was in corporate life. It feels like a bit more of a risk. So it potentially limits the pool of people. But part of the reason that we do that is because it, it helps us to understand whether the person's the right fit. And I think in a small business that just really matters, like finding. I think it matters in any business, but it just, it just feels really important that we find the right fit. Someone who is exemplifies Our, the behaviors, we have these behaviors of kind of responsiveness, care, initiative and simplicity. And I kind of want to know like, does, do you like these behaviors? Is this how you, is this how you work at work? So it helps us to find the right fit and work out whether it's the best use of that person's strengths, but also it helps us to work out the role. So very often when we're, when we're hiring people. I've had this conversation today with someone who's come into our team where I was basically like, are you okay with the ambiguity of the next nine months? Because I'm not sure what the job is going to be like. The aim is go from contractor to a permanent employee on the payroll full time or part time, whatever that person wants. But at the moment I cannot tell you what that job is going to be in nine months time because what we do with people is we have a number of projects, we work out what that individual is really good at, we think about what the business needs and then we have this period that is very malleable. So for example, the individual I was talking about today is both working on research for our PhD, a really big purpose project that we've partnered with an organization on to create squiggly starters. She's also working on our, in our client team on improving our proposal process. It's broad, but the idea is that together we co create a role that is both valuable for the business and the best use of that person's strengths. And sometimes it doesn't work. Sometimes we go either the fit isn't right or, or the roles like we haven't, there isn't a role right now and that's, that has to be the end of it. And we then help that person with wherever they want to go next with our network and knowledge will help that person or what has happened several times is we end up with a brilliant role. Our head of delivery came in working as maternity cover for our team manager and then we saw her talents, we saw our gaps, evolved the role and now she is, now she's our full time head of delivery for amazing if. But that, that role didn't exist because we kind of didn't know what it, we didn't know what it was but we co create roles.
B
Well, it's a bit like job crafting.
A
Yes, it's very active Joe.
B
Job crafting. So yeah, that's, that is. Say it again as I knew this would be. And I can see Sonny's getting annoyed because I said we wouldn't record for this long. And we. We are doing. So I'm going to. I'm going to throw that final one to you.
A
Okay.
B
Well, actually, before I. The final one about three words.
A
Yeah.
B
How do you create a custom GPT and what have you used it for?
A
Oh, I use them all the time. I created one this week. I love it. I love it.
B
So what's the one you've created this week?
A
The one I've created this week is about how to introduce yourself. It's based on a TED Talk that I saw where the person had five formulas for how you create a powerful introduction in fewer than 20 words. And there's like, the breakthrough introduction, there's the strengths introduction. So I created a GPT for our Squiggly careers community where it will ask you five questions and then it will use your answers to create your five. Your five, like, powerful ways to introduce yourself. And obviously, you know, anyone can do it. It's an open, open one. How do I do it? I do. I do it on Chat GPT, because that's my preferred platform of the present time. I click the create button. Do you know what I actually did this time is I used ChatGPT. I said, I want to create one. Write all the documents I need, because you need to load them in for it to learn. I said, write all the documents I need. This is the TED Talk. This is my podcast script that I've done on the TED Talk. This is what I want. Write it so I can create it. And then I literally clicked Create. Upload the documents, had a bit of a practice, send it to some other people, got some feedback, improved it. And that's, that's, that's it. I could create a better how to, but that's basically. It took me about 10 minutes.
B
You know that clip will do well on LinkedIn, right? And finally, three words to describe.
A
And remember, you have to decide whether these are the three words you want, which you could decide later. But here's my three words. Three words describe Jimmy at Jimmy's best. Curious. You're. You're super curious. You've always got a question and you've always got that look. You've got a curious look as well. Like, even when you're not asking the question, I can see, I can see the question forming. Connected. So connected. Like, before we started, we were just talking about people, and you're like, oh, yeah, you're so. You're so good at building and connecting with people, which I think is brilliant. That's Obviously. Now, part of what enables a podcast, and I would also say challenging. Quite a challenger like you don't. You don't take something at face value. You're. If you've got a different opinion, you're not afraid to. To have. I think you do it in a. I see it in a very agreeable way, but I do hear the challenge. I hear that you're, like, comfortable with challenge.
B
Yeah, no, I think that's fair. I think there's the three things. I mean, the interesting. You say curious at the beginning because I've always thought the mantra of stay humble, stay hungry is very kind of important and then. But I always had a third one to that, which is stay curious as well. So, yeah, I think I would. I would take those. And they're all literated. Such a wordsmith as well. Oh, brilliant. Oh, well, look, I'm so amazed at everything you do. It's brilliant. I'm so glad we've got to do a few podcasts and live shows together as well. I think what you're doing is brilliant. And, yeah, it's so great to get you on and support and people really should get the book Learn like a Lobster, because it's.
A
Hey, thank you so much, Jimmy.
Jimmy’s Jobs of the Future w/ Helen Tupper
Release Date: February 11, 2026
Host: Jimmy McLoughlin (Boxlight Creative Studio)
Guest: Helen Tupper, co-founder of Amazing If, co-author of "Learn Like a Lobster" & "The Squiggly Career"
This episode explores the future of learning at work, challenging the conventional wisdom of workplace courses and formal training. Host Jimmy McLoughlin chats with Helen Tupper—co-founder of Amazing If and champion of “Squiggly Careers”—about her latest book, "Learn Like a Lobster." They discuss why traditional courses are insufficient, introduce the "lobster" model for continuous learning, and share actionable strategies for embedding learning into everyday work life. The conversation is practical, insightful, and candid, moving from personal growth to business models, team culture, and even playful ways to boost learning.
[02:01–03:20]
“If we do not solve the problem of learning at work, then a lot of people are going to get left behind.” [02:06]
[03:20–05:50]
Lobsters embody traits that map powerfully onto personal and workplace learning:
Never Stop Growing:
Shedding the Shell (Vulnerability):
Resourcefulness (Eating the Shell):
“You would never stop learning, like the lobster never stops growing... In your hardest moments when you're vulnerable, that would be the moment that you learn the most.” – Helen [04:55]
[06:54–08:14]
“We're already in 12 meetings this week... How do we add more moments of learning in those meetings?” – Helen [07:16]
[08:36–10:40]
“It has been so helpful. Both people feel better at the end of it... It's been a bit of a game changer.” – Helen [09:42]
[14:19–16:11]
[16:12–17:27]
[17:49–21:55]
People have natural problem-solving preferences:
Challenge: Try out the opposite style occasionally to expand your mental toolkit and deepen your learning.
On Boredom & Creativity:
“We're not allowing children to be bored. But in that moment of boredom is actually where creativity happens.” – Helen [21:55]
[23:18–26:06]
“None of them look like going on a course. It is about these practical things that we can do every day.” – Helen [23:40]
[27:45–32:17]
“Sharing is a really powerful way that we improve our learning as well as moving it to someone else...” – Helen [29:15]
Teams in companies (like Kerry Dairy) already run daily "learning sprints" together—10 minutes a day as a team.
Celebrating Learners: Companies should recognize learning (not just promotions), celebrating those who model continuous improvement.
[32:17–40:10]
“Hearing the hard thing, like holding or ignoring it... being able to kind of hear the hard thing and hold it so that you can actually learn from it.” – Helen [33:41]
[41:19–47:13]
[47:14–49:31]
[49:56–51:23]
“We want Squiggly to be synonymous with careers globally... I want it to be normalized and I really want it to be credible.” – Helen [50:01]
[51:30–54:58]
[55:18–58:12]
"If we do not solve the problem of learning at work, then a lot of people are going to get left behind."
— Helen Tupper [02:06]
"You would never stop learning, like the lobster never stops growing. In your hardest moments when you're vulnerable, that would be the moment that you learn the most."
— Helen Tupper [04:55]
"None of [these methods] look like going on a course... it is about these practical things we can do every day."
— Helen Tupper [23:40]
"The ability to learn is going to be absolutely paramount... It's the skill we look for more than anything."
— Jimmy McLoughlin [22:26]
"I would love us to put learners on a bit of a pedestal... not just promotions."
— Helen Tupper [30:46]
"We co-create roles... together we co-create a role that is both valuable for the business and the best use of that person's strengths."
— Helen Tupper [57:16]
"Curious, connected, challenging."
— Helen Tupper describes Jimmy at his best [60:03]
| Segment | Time | |------------------------------------------|--------------| | The problem with learning at work | [02:01–03:20]| | The lobster model explained | [03:20–05:50]| | Embedding learning in meetings | [06:54–08:14]| | Banishing pointless meetings | [08:36–10:40]| | Using feedback for self-awareness | [14:19–16:11]| | Out-loud vs quiet thinkers | [17:49–21:55]| | Ditching the course mindset | [23:18–26:06]| | Future: Team-based learning | [27:45–32:17]| | Saying & hearing the hard thing | [32:17–40:10]| | Amazing If's flywheel business model | [41:19–47:13]| | Play & learning at work | [47:14–49:31]| | Ambitions for Squiggly | [49:56–51:23]| | Job crafting explained | [51:30–54:58]| | Co-creating roles & hiring | [55:18–58:12]| | Three words to describe Jimmy | [60:03–60:58]|
Helen banishing 1:1 meetings:
“It just felt like a nice chat... All these one-to-ones were filling my diaries with no agendas.” [08:41]
Reframing feedback with the multiplier effect:
“I acknowledge it... But the multiplier effect is where I take your feedback and I then go and talk about it with a couple of other people... you multiply the learning.” [34:55]
Helen’s playlist idea for team fun:
“Everyone in the team has to pick a track that is either meaningful to them or they think represents them... it’s fun and it's a good way of learning about each other.” [47:44]
Co-founding patrons of a lobster hatchery “because we've gone pretty deep in the world of lobsters. Pun entirely intended.” [36:51]
Helen and Jimmy present a compelling, down-to-earth vision for the workplace where learning is constant, visible, playful, and collaborative—not confined to cumbersome courses or formal training. The "lobster" is a sticky, practical metaphor: we must continually shed our shells, embrace new challenges, and consume our experiences for future growth. Their approach offers practical tools for individuals and organizations to rewire habits, boost team connectedness, and keep evolving in the world of squiggly careers.
Recommended Action:
Read "Learn Like a Lobster" and look for opportunities every week to "shed your shell"—find one real, vulnerable learning moment in your daily work and use feedback as fuel for growth.