B (2:42)

So I think career change is something that happens to all of us. If we're going to have four or five different types of career during our working life, which is probably quite a conservative estimate, this is something that we'll all experience. And actually, it doesn't matter what report you look at, quite a high percentage of people are always thinking or considering a career change. So the LinkedIn 2023 workplace report said 61% of people are considering doing something different. There was another report where it says at least 50% of people have already pivoted at least once. So this is probably something you either have experience of or are thinking about making happen. And I think what is tricky about career change is, is the unknown. You're moving from something that you've probably got some expertise in and which always gives you confidence into something new. Being a beginner in any area always feels hard, but when it is your job, which is where you spend a lot of your time, it can feel like a really big risk. So I think if people could wave a magic wand and just be like, well, I'd love to go and try out that different career for a while. I think loads of people would do that. But it's never quite as easy as that. And I think often the barriers to career change are some of those really practical ones. It's not a lack of motivation or that people don't want to do it. It's more the, well, how do I actually make this happen? Especially if it's quite far away from where you are today.

A (4:13)

The change times, uncertainty is probably where it kind of feels much harder. So if I think about sort of come career changes that I have made. So some that felt more manageable were when I was in, let's say Microsoft and I moved from evangelism, which, yes, that was my job, into a particular marketing role. And so that was a change. It was quite a different job that I was doing, but it was in the same organization and it was literally on the same floor.

B (4:37)

So there were lots of things down the corridor.

A (4:39)

Yeah, I knew some of the people in the team. So it was a change. It was a different function, it was a very different role, but there was a lot of kind of known in there. Whereas, if I think about bigger changes, probably like leaving Microsoft, going do what Sarah and I do now full time with what we do with squiggly careers and the work that we do in companies, that's a really big change. Like, that's not about working for a big organization. And I work for a small organization that, you know is growing fast. And I'm now a CEO and I'd never done that before. And so there was a lot more uncertainty in that change. And I don't think it's that any changes are better than another. I think it is just some are more uncertain and that potentially leads to more risk. And that risk just means that people might need a bit of extra support because changes can bring so many new potential and possibility for your career. And I guess we don't want to let the uncertainty or the fear hold you back from something that you might want to do. So let's learn a bit from Jenny Blake, the author of Pivot. And what I really enjoyed in my conversation with Jenny is she's just naturally practical. I think sometimes when things feel hard and difficult, sometimes you need a process and you need someone who talks common sense and someone who's got some very specific bits of advice for you. So that is what you are about to hear from my conversation with Jenny. Jenny, welcome to the Squidly Queers podcast.

C (6:04)

Thank you so much for having me. Longtime listener, first time caller, and I'm just thrilled to be here.

A (6:10)

Well, we're longtime fans, big fans of your work. And when we were thinking about career change and who is an expert who is going to give some very specific advice to people who are in just this moment, it was only you. So thank you for doing this.

C (6:24)

I'm so honored.

A (6:25)

So I've got three potential reflections that somebody might have who might be just in this moment when they're thinking about a change. And I wanted to run them by you and see what your advice would be for that person and maybe what actions they could take.

C (6:40)

Sounds great.

A (6:41)

So scenario number one, I can see what I want to do. It's very different to the job that I'm doing today. I'm a bit worried that it's maybe a too big a move to make, but I don't want to rule it out. So where do I start if this is my situation?

C (6:58)

Well, the first thing I'll say is that we're coming up at the time of this recording on five years since the pandemic hit and we went into global lockdown, every single person listening has gotten a black belt in pivoting the last five years. Nobody is walking away not having the skills under your belt. So in a way, if you've handled all the squiggles of the last five years, I know that you're well equipped for whatever comes next. One thing I would say is that a lot of pivoters and changers put too much pressure on themselves to solve the whole thing up front. And so in the case where there's more uncertainty or a little more risk or it's a little stretchier and edgier than something that seems obvious, I would go straight to piloting. So, based on your strengths and what gives you the most energy, identify a few small, safe to try experiments that can give you information. And specifically, you're looking to design these small experiments that can help you assess three E's. Do you enjoy this area? Can you become an expert at it? And is there room to expand, whether in your current role in your current company, or let's say you are pivoting or you're starting your own thing, Is there a market for what you're trying to do? And you might need to break it down into interesting projects because, again, it's not always going to be the big move and the big leap. Exactly. Embedded in the question is, how do I gather data? So to give you a metaphor, it's like lining up resources at the Kentucky Derby. That would be stateside. You don't know which horse is going to win. You need to lift the starting gates, say, go. And your pilots will show you which ones take on a natural energy and momentum so that you can double down.

A (8:39)

I really like the idea when you talk about pilots. I think it takes the pressure off pivoting because, you know, I say I need. I need to pivot. There's quite a lot of pressure there and you knowing the right thing and it working out. But to the idea of, you know, letting the horses go see who wins the race and having a few pilots, I think it makes it. Well, I think it makes more. More about learning, that the process is about learning about what you can do rather than committing before you know what the right thing is to do.

C (9:04)

Yes. And in fact it's not even just nice to have it's requirement now. Like we just don't know. There isn't actually a way. Even if you wanted to have all the answers up front, it's almost impossible without these baby steps. So when you are feeling that sense of pressure or feeling super stuck or very anxious, those are all signals that it's time to make the next moves even smaller.

A (9:28)

Scenario number two, if people are going to look at my CV or my resume and think, maybe I don't look like the right candidate for this move that I want to make, but I really think I can add a lot of value. How could I convince someone to take a chance on me?

C (9:44)

A year ago I would have told you, okay, look at the impacts that you've made in your roles and maybe look at, we talked about interesting projects as a really crucial unit of measurement and enjoyment and satisfaction and purpose. So just looking at impactful projects and how those might connect. But today we have such an incredible tool at our fingertips, which is generative AI. I know you've recently just done an episode on that. Now here's what I would tell you. Upload your resume to ChatGPT or whichever one that you use. Upload your strengths assessment results. So whether you do CliftonStrengths, Gallup Strengths Finder, Strength Scope, there's so many, your astrology, your numerology, like upload them all, train the AI on you. And you can even use NotebookLM is Google's tool where you upload. It's all your own resources and you essentially create this notebook that you can query against. So for someone who's feeling kind of stuck on this now, I would say partner with AI, upload everything that you have about you, what you've done, your extended cv, and then ask this exact question. So can you map my resume to this role and copy paste the job description. I've even had coaching clients upload all of that information. Then ask AI, what types of job roles do you think are a good fit for me? What's out there? Or these are the top 10 companies that I'm really interested in. How would you make the case for me as an ideal candidate for them? So I know that I'm giving you maybe a cheat answer a little bit because I'm having AI do the work, but that's exactly what it's good at, which is taking in all this information and I'm sure you've said it many times on the show, it's hard to read the label from inside the jar. Well, now here you have this, like, uber intelligent thought partner to help you read the label from the outside.

A (11:36)

So I think the third question I have for you is really important, given the advice that you've just shared. So AI can help you map your experience to a position. It can help you spot possibilities. Brilliant. What it might not be able to help you to do is to feel confident about the move that you want to make. So it might look, make you look competent on paper because you're like, look at all the things I'm good at. Look at how it maps the role, but in terms of confidence. So my third question is, I'm a bit concerned that I might make the big move, maybe the one that AI has told me I'm good at. But then what if I feel like a bit of a failure? So. And I know that I've got a learning curve. I know that I've. I've not done this before, but, you know, what if I'm not good at it? What if this isn't the right move for me? What, what do I do then?

C (12:22)

Three things on this. Number one, don't even expect to feel confident. In this environment that we're in, with so much volatility and uncertainty and complexity and ambiguity, you're really not going to feel confident. Like, if you do, you're rare. And that's amazing. And you should also be a guest on this show. My mantra for myself, I have a few of them. One of them is 51, 49. I can be 49%, insecure, worried, anxious, afraid. And then I just need to tip toward action. 51%. Or if I'm nervous to publish a post, I can be 49% nervous. And then 51 is schedule it anyway. The second thing I remind myself, and that's in Pivot the book, decisions are data. You really cannot know. That's, in a way, what makes them exciting. That's what makes the squiggles of our careers and our lives fulfilling. And then the third thing is, nobody that I interviewed for the book about their pivots expressed regret no matter how they turned out. Sometimes a pivot was an interim move that I call it a leapfrog pivot, because there actually was a very strong, compelling vision, but it was two moves out and they needed to make an interim move or an interim squiggle just to get a new vantage point or even get unstuck from the old thing before moving to the real and true next thing. So sometimes there is this kind of wobbly, I'M calling it a step or a lily pad in the middle where you're not that stable. Maybe it isn't the end all be all, but if you don't judge yourself for it, it's still getting you moving. So to build on this piece, Daniel Pink wrote a book on regret. And in fact, people regretted the bold moves they didn't make much more than the ones they did that quote unquote, failed.

A (14:11)

We had Dan Ariely on the podcast in January and he, he also talked about sort of, you know, decision making and not letting that fear get in the way. Because to your point, in the short term we regret the things that we might have done, but in the long term we regret the things that we didn't. And careers are long. Careers are really long. So you don't want to have long term regrets for your career. And then I've also been recently reading a book called the Broken Rung that talks about the moves that you make in your career and the impact it has on your enumeration. And it's not that everybody motivated by earning more money, but, you know, it is a factor of why we work, right? We work partly because it gives us money. And there are many other motivations. But they talked about it's the people that make the bolder moves in their career.

B (14:52)

They have this idea of skill distance.

A (14:53)

I don't know if you've come across it, but they said that in the average move is sort of 25 skill difference. So different to what I do today with my skills, the bold moves are sort of 40 plus. And it's people who make the bold moves, which I would translate to kind of this idea of pivots that actually over the long term earn more. And so whether you want to learn more or whether you want to earn more, I would argue it's the pivots and the bold moves that are more likely to make it happen.

C (15:20)

I come back to another mantra that I have is just may this unfold for the highest good for all involved. And I don't know what that is. So I actually wrote another post for like, I stopped making wishes. You know, even I don't know if you have this in the UK where you catch a little dandelion. If you catch it, you make a wish and you blow it up. I'm like, there's only one wish and it's whatever the situation, may the next steps unfold for the highest good, for all involved. And may I be able to tune into my intuition and just follow the one next step and the one after that, but with no attachment to the outcome other than highest good for all involved. And who am I to say what that is?

A (16:02)

I will take that away. I would take that away from this conversation. You know, sometimes you kind of go through life and work and you try maybe to control too many outcomes based on what you think is the best thing, but actually if you kind of let go of controlling and assuming what you think is the good thing, then may, may there may be more good things come. I love it.

C (16:23)

Sure.

A (16:23)

Yeah.

C (16:24)

There's a term I learned as well, future tripping, where like you're just. You're tripping on the future in so many ways. I mean, it doesn't have to be a drug reference. It could just be it's like getting in the way. Like, future tripping is that you're too many steps ahead, you're too far out from where you are now. It takes you out of the present. And that's usually when we find ourselves more full of that anxiety. So it's like, what's here today? What can I do today? Sure, I'll vision and I'll dream. And not overly future trip, like, oh, but what if I fail? Okay, that's a really far away from now. It's good to have some backup plans, but who knows what's going to happen?

B (17:08)

So we hope you found that conversation with Helen and Jenny useful. And you're now going to hear kind of some real world examples from Ollie and John, who are both brilliant. Just talking about what it has felt like to make really quite a significant career change and sort of leave behind something that they knew really well and go into the unknown. And they're very honest and open about that experience. I think you'll find it really interesting. John, Ollie, thank you so much for joining us on the Squiggly Careers podcast today.

A (17:42)

Pleasure.

B (17:43)

So I'm really looking forward to diving into your squiggly career stories. And you are both properly squiggly. I mean, we're all squiggly, but you have both done a really quite significant squiggle and changed careers. And I wondered whether, and perhaps John will start with you. Was there a particular moment or trigger that made you think, I need to do something different?

D (18:07)

So I ran a little independent music venue with my wife for about eight years. And I don't want to get political with this, but the sort of grassroots music venue ecosystem has been under threat for a while just because it's a hard business in general. And, you know, I think we both Just had enough of really, like, struggling through and working crazy hours to not really get a great deal of return. I didn't really want to step sideways. So, yeah, I just really wanted a complete change.

B (18:41)

I'm imagining you're really passionate about music and it's something that you love, and you. On paper, those things might seem like a dream job until the reality kind of kicks in and then it just gets to the point you're like, this is the kind of fun and reward and satisfaction can disappear quite quickly, I think.

D (18:56)

Very much so, yeah.

B (18:57)

And how about for you, Ollie? Was there a kind of conversation or a moment that you can really remember, or was it more of a sort of gradual thing?

E (19:04)

I'd say maybe slightly more gradual than John shared, but there was definitely a moment where it kicked up a gear. So, trained in tech. I was a tech recruiter, so I worked in a bunch of tech companies and spoke to a huge number of engineers while I was working there. And so I knew a little bit about the kinds of projects they did, sort of impact they had. And so I was interested in that for a long time. I always had an interest in tech that went beyond what I needed for my recruiting job. I worked at Meta for a while, and Meta at that time was going through a period of flux. They just announced the Metaverse and most of the recruiting team had been caught completely unawares as to what that was. And so I went and I did some research about what that. What that meant, and it led to kind of creating some training material for other recruiters. So I think I always was a bit of a technical nerd and I just wanted to understand how things worked. But I think what held me back from taking a leap of faith was just a fear that it wasn't for me. Like, it just felt too out of reach. I've got a humanities degree. I don't. I wouldn't have described myself as particularly technical a couple of years ago, but when I got to know people that had actually been through career changes and been through boot camp experiences, suddenly it felt more within reach. And I guess that was sort of the light bulb moment that this could work, if only the. If only I knew how to code sort of thing, and then it was that inspired me to go off and do those first simple Python challenges. And it was then, really, that I realized that I could apply quite a lot of the knowledge I already had, like problem solving and identifying patterns and learning languages, to, like, this new path, albeit one that's very different from the background I'd come from.

B (20:34)

Sometimes from a distance, you're just like, wow, it feels impossible. You're like, well, how could you go from that to. To that? And so, John, I guess your change was more dramatic in terms of what you'd done before. How did you figure out that you were like, well, going into kind of technology, into coding, into kind of where what you're doing now would feel like maybe a good fit, given I'm guessing you'd not really done any of it before.

D (20:57)

It was kind of my wife's idea because we were spitballing, like, what could we do? And I think she said sort of naively, what about web dev? We were just like, Googling things. I have lots of friends who work in the industry already, so I was like, that's not actually a terrible idea. And I'm not going to lie, it's been tough. The actual learning process, it's been pretty slow. Particularly when I was kind of doing it alongside running a business similar to Ollie, you know, actually diving into it and looking at sort of basics and Python. Hello, world and stuff. I was like, this is really cool, but I started the ball rolling.

B (21:33)

You did say there. It's been hard. What has been hardest for you?

D (21:37)

You know, you're building, like, tiny little functions and it's like, oh, my God, this makes sense. But then you're shown some massive program. It's like, I literally don't understand what any of this means. I suppose I could kind of compare it to learning an instrument. In a way. It is similar. You start off in, like, somebody shows you the real basics and it's like, okay, I think I can do that. But then there's just such a humongous scope that you can eventually cover. And it's just. It's just time, I guess. It's just the more you involve yourself in it, the more you start to sort of absorb it.

B (22:12)

Yeah. And, Ollie, do you feel like it's. You have to trust the process?

E (22:17)

I actually struggled with that quite a bit when I was early on in this sort of career change and bootcamp journey. Like, I. I think, coming from a recruiting background, I was used to being in work contexts where you kind of walk into a meeting and are expected to know all the answers. And so I got a little bit of whiplash almost from shifting context into, like, an engineering environment where, like, it's just not possible to have, firstly because I'm new, but also because in engineering, it's just too vast and it's changing too quickly for you to have a Real handle on everything. You need to get comfortable with the ambiguity and be able to trust in your cognitive abilities a little bit more, rather than just your ability to memorise a lot of stuff and hold it in your head. The way I picture it, this period of learning is like going into a pool where you've got the shallow end and then abruptly you've got the less shallow bit and then abruptly it just disappears and you're sort of like treading water. So yeah, like you said, trusting the process is key and it's something that I've had to learn to do. I think as I've gone through this bootcamp journey.

B (23:13)

If people listening are considering embarking on a career change, what could they get in place that might support them through what is clearly a daunting and difficult process at times?

E (23:25)

One of the things that's helped me the most is kind of finding a community of people who were in the same boat as me and making sure I kept in touch with those people. Job hunting and career changing can feel really lonely. I was lucky in that I went through boot camps and I had like a ready made group of people that were all going through it alongside me. But for people who are going through it more alone, I think it might take a little bit more effort, but it's so crucial to find the people that are going through it with you. So using meetups, community events of any sort, like meetup.com, if it's a technical thing, there's going to definitely be technical meetups that relate to the demographic that you're in or what it is you're looking for. The other thing I'd say, and it's also people related, is try and get yourself some sort of industry mentor. I was lucky because I was in a community of bootcampers and there was alumni and so it was easier for me to find somebody that had been through it and knew what it was like to be in my space. If you're going through it on your own, like, it might take a little bit more work, but definitely use LinkedIn. Try and find somebody that has gone through a similar career change to you. People are more open to helping and giving you their time than you might think, even if it's just for a one off chat, just to find out how someone did what you want to do. So yeah, definitely relying on people, but also relying on your ability to keep improving as well. Like, I've improved a huge amount through this job search. You've just like asking for feedback from interview processes and Putting myself out there and feeling uncomfortable quite a lot of the time, but still learning. Each time I, you know, submitted a project for someone to review or did a coding challenge or something in front.

B (24:47)

Of someone, we talked about what's hard, John, but what's the thing now in your week that you enjoy the most, that gives you the most energy from kind of what you do today?

D (24:55)

I think the maker's process put you in a huge group of similarly paced people. We're all going through this at the same time and you can sort of rely on each other. We've just started paired programming, which is a really, really interesting, nice way to tackle problems because, you know, one of you might have a bit of an idea how something works, the other one might have another slightly conflicting idea.

B (25:20)

Right.

D (25:20)

The two things join together and the problem usually gets solved a lot quicker when you're working together. So I guess the sort of the team working mindset, that is my favourite thing currently.

B (25:32)

What about you, Ollie?

E (25:33)

I second all of that. I think the peer groups are a real highlight of the day. Just knowing that even though sometimes it's hard and you're grappling with something that's really complex to you at that time, like, you're not alone in that. The favorite thing for me at the moment is just like the learning. I think one thing that meant I wanted to change careers in the first place was I just didn't feel like I was learning a huge amount in my previous roles. I wanted a career that was going to keep pushing me. And then obviously makers every week because of the pace of it, you are grappling with something completely new, diving into a completely new concept and getting a really broad understanding of technology in the process.

B (26:06)

And so, Ollie, if you were looking back over the last year, or it might be slightly longer than that, since you started this process, is there anything in hindsight that you think if I knew then what I know now, I would.

E (26:20)

To be honest, this might sound a bit ironic from a former recruiter, but I wasn't prepared for the job market that I entered to try and find that first role. The world of tech that I knew as a recruiter was one where typically engineers are in high demand. You would struggle to find a job even if you were a junior. Whereas when I came into it, just because of the wider context of what's going on in the world and the economy and everything, like, I met more and more alumni from makers or from other boot camps who were job hunting and I was just feeling an increasing sense of dread at how competitive it was going to be and how challenging it was going to be to land that role, just given the scarcity of opportunities out there. So something I wish I'd known was that the key really was relying on the people in my network more. I think I was nervous to shout about the fact that I was doing this just in kind of just in case it didn't work in a way I didn't want it in a position where I was like, oh, do you remember Oli? He was, you know, tried to be an engineer. That didn't go very well. So I was a bit nervous about it, just putting myself out there, reaching out to old colleagues, getting new tips and even old candidates. Like, I messaged people that I'd, like, put helped get jobs before in the end and was just like, oh, I'm actually looking to do this myself. Is there anything that you'd recommend or advise or here's my cv, if you got any feedback or whatever. So the more I put myself out there and, like, ask for feedback, the more I got actionable insights as to what wasn't working in the CV that I put together or the project I'd done or the interview that I'd gone and done. So relying on the people in my network or going out and seeking new people in my network. The more you can get people in your corner and giving you actionable advice, the better.

B (27:46)

And just to finish, if you were going to give people one piece of career advice, what advice would you leave us with today? Ollie, do you want to start?

E (27:54)

There are lots of things that you can do when you are trying to figure out how to do really well in an interview or how to send off a great application. There are loads of things you can optimize to heighten your chance of success. However, some of it is luck. And so what I think I made the mistake of doing quite often was if I got knocked back or if I got rejected from something, or if something didn't go anywhere, I would look for the reason why I wasn't the right fit, why I'd done something wrong, why my performance wasn't good enough. And to be honest, I'd start over correcting at times and I would fix things that didn't need fixing. Obviously, look for the gaps in what you're doing. There will always be gaps and there's always going to be things that you can optimize to heighten your chances. But I know from the recruiting background that there's also another 10 reasons why it didn't work out for you that time and then they're not to do with you. So having drive and determination, but also just having some patience with it as well. Patience with the process. But patience with yourself is a matter of time as much as it's a matter of ability and practice.

B (28:49)

What about you, John?

D (28:50)

I'd say try and be as prepared as possible. Trust yourself, trust your instincts and don't give up. I was kind of at a point where I thought, just don't think it's going to happen. Is there any point me like continuing this journey? I'm so glad that I didn't just completely quit because I wouldn't be here now.

A (29:12)

We hope that you have learned a lot today from listening to Jenny and from listening to Ollie and to John. We would love you to keep learning. And so that is what the guide is for. The questions that are in there, the tools that are in there, are designed to help you reflect on what a change might look like for you and also to take action so you can get a bit closer to what it is that you want to do. The link for that is in the show notes and it's also on our website, amazingif.com worth following amazingif on LinkedIn because we are posting everything there and you might be able to connect with some other people that are interested in making a career change too.

B (29:44)

But that's everything for this episode. We'll be back with you again soon. Bye for now. Bye, everyone.