Portfolio Conversations with Mike & Zed: With Guest Charlie Rogers, Author of "Undefinable Life Design"

Episode 14 -
===

Another episode of the Peering podcast. If you wanna see the future, the best way is to peer into it together. Back with my good friend, Zarir, or rather Zed Vakil. Welcome, Zed.

Zarir "Zed" Vakil: Thank you, Mike

Mike Richardson: Yeah, it's good to have you here, man. And a big, big, big, warm welcome to Charlie, Charlie Rogers. Really excited to have him with us, uh, and, uh, have a rich conversation about what he calls undefinable life design.

And he knows what he's talking about because he's published a book by the same name, "Undefinable Life Design: How to Design a Unique Life That Sustains Your Energy and Income," and has a whole website devoted to that, and indeed is building the Undefinable Life Design community, and we're about to find out a little bit about all of that.

It's great to have you here, Charlie. Welcome.

Charlie Rogers: Appreciate it, mate. Excited to talk more about it

Mike Richardson: Yeah, excellent. And, uh, before we do that, um, Zed and I have been working together now for what? I don't know, three, four, five years, Zed, something like that. And we had never met until, uh, about a month ago when I was in the UK on my way to Europe for a cruise, and we managed to spend a day together.

It was great to meet you, Zed, at long last.

Zarir "Zed" Vakil: I- indeed, in, in the flesh, only to make me feel considerably shorter than everybody else in your company, Mike, given that I'm a lowly 5'10" and he's a h- highly

6'4".

Never mind.

Mike Richardson: uh, but it's, it was, it was one of those post-COVID things, you know, where, or despite having never met, it felt like we'd met years ago, of course, and there was no, there was no sort of strangeness about it whatsoever. Uh, it was, it was remarkable. So hey, Charlie, it's great to have you here. Um, perhaps, uh, Z, you can get us rolling here 'cause I suspect you met Charlie a long time before I did.

Uh, how and when did you and Charlie first meet?

Zarir "Zed" Vakil: you know my background goes right back with, uh, what, uh, was the Portfolio Collective and I hope will still be in the future. They're going through some restructuring. But, um, Charlie and I met, I, I believe when he was first, and he can correct me on this, uh, chief of staff for Ben Legg, who was then CEO of, uh, the Portfolio Collective.

And I'd been with the Po- Portfolio Collective right from the beginning and I think, um, Charlie maybe midway through or something like that. Can't quite remember. And, uh, I was part of that community having been a portfolio professional myself for maybe 20 years up till that point. Uh, didn't even know it had a name actually.

Um, and, uh, that's where, where we met,

uh, Mike

Mike Richardson: Yeah. What's your side of that story, uh, Charlie? How do you remember first meeting Zed and coming across,

Zarir "Zed" Vakil: be kind, Charlie. Be kind

Charlie Rogers: So I remember, yeah, joining TBC, The Portfolio Collective, in April '23 as more closely the founders associate to Ben and Fiona of The Portfolio Collective, and they were going through the list of founding members, people who had invested a lot of time and energy into the community. And yeah, both your names came up very much from the beginning around being, "Oh, he's a guy to keep an eye on."

And, um, yeah, often talked about the long emails you'd like, like to send and all the detail you send across when you're kind of proposing something, but also communicating and talking through other community members as well. So it might have been on a, a kind of community networking event we met or it might be a specific session, but

I think it's, uh, always heard of you before I saw you

Zarir "Zed" Vakil: Hey, look, I've always been part, I've always been part of the awkward squad, so

n- no worries

Mike Richardson: Awesome. Well, hey, Charlie, uh, perhaps tell us a little bit about your portfolio career. You've been hanging around this world now for quite some time, and sort of what's the makeup of your portfolio and, of course, beginning to lean into, and how did you arrive at putting this concept of the undefinable life design at the heart of your portfolio?

Charlie Rogers: So like for me, I've never had the corporate job and then become a portfolio careerist. I've sort of stepped into it Without realizing it first. So the big kind of decision matrix for me was in my second year of university, I had to decide how I was gonna spend my third year. Most of my peers were going to London to do a corporate role, and about 1% of us in the business school, perhaps even less than that, had the opportunity to go and do a year in enterprise where we'd start our business, and I decided that was the path for me.

But I also worked part-time two and a half days a week as well with a, a graduate business owner helping them with their marketing. And so at the time I had two and a half days a week paying my bills, and then I had the rest of the time to build my first business that I called The Time Postie, where you could attach a parcel box to your house to receive a sorry we missed you slip.

So very much was the entrepreneurial entrance point of like, I need to pay the bills while also building something. Um, and then I closed that business in March 2020 because COVID came along and then we were very much all at home, so receiving deliveries was very easy. And then the following month I co-founded, um, House Hack, which then became the second business.

At the time it was a lockdown project. We brought together some students who just lost their graduate jobs with these businesses who were adapting to COVID and then brought them together into a hackathon that we hosted online, and then built it over the next year and a half, two years into a talent assessment day for startups to engage with Gen Z talent.

And so we kind of engaged 500 plus students, placed like 50 of them into tech roles, and went on quite an entrepreneurial journey there. But even as I was doing that in the first few months, while it's not paying us, I was still working like two, three freelancing roles across different startups, doing some product management, doing some video editing, like just testing my hand at anything that would pay me.

And then as we got enough traction with the business, I was then like, okay, I can drop those side projects and focus on this business. And then I guess I took a more formal leap into a portfolio career when I closed House Hack at the end of 2022, and then took on a kind of three-day a week project management role.

Did some work with LinkedIn on how to hybrid, uh, and then did-- start my newsletter about, at the time, what I called Mastering Your Twenties, how to master your twenties and develop the different skills you need to do that. And then over time, that then evolved into, I just kept writing every week, kept showing up, and it became kind of Undefinable Life Design as I then rebranded it.

And that became the genesis of some of the ideas in the book that then flowed out from the newsletter, but also then some of the initial concepts around what it means to be undefinable. And I brought together a lot of the readers of that newsletter into a community that's now called Undefinable Community, which is a separate nonprofit, uh, element of what I do as well.

So there's different threads here overlapping. And then April 23 is when I joined the Portfolio Collective four days a week. So even as I decided that was the right move for me to get a lot of experience and learn about the future of work and future careers, I was still in my head like, "It's four days a week, not five.

It can't be five." And they advertised it as five, but I was like, "No, it has to be four." And so I remember negotiating with Ben and Fiona and saying, "Look, it's gotta be four for me." Um, so yeah, I've always had this- different approach to work, and I always think that things are w- are way more negotiable if you merely ask the question,

and that's definitely been a big attitude of mine

Zarir "Zed" Vakil: I, I often joke when we, uh, hear guest bios, uh, like you've just done very eloquently, um, uh, and say something crass like, "Well, uh, what do you do in your spare time?" As a joke, right? But I'm afraid to ask you that 'cause I know you do a lot in your spare time.

So what... Tell the folks what you have been doing, 'cause some of it is really amazing, uh, particularly your, your, um, your, your GB involvement. But that, that, that would put an icing on the cake,

Charlie Rogers: Yeah. I guess like my, my premise on this is that I don't necessarily see

it as spare time. I see it all as the same time. So 160

Zarir "Zed" Vakil: very good point

Charlie Rogers: we design it, um, there's no like separation in my mind, uh, for better or for worse. But I guess how else I spend my time separate from the main role, um, is that I've competed for GB at triathlon level as well.

So age group end of 2024 went out to France and represented them. I've also done an Ironman, uh, that same year as well, and I've also done a ultra-marathon the following year as well. So I've been pretty into my running throughout my life since I was 14. I joined as one of the worst ones there and then went to Loughborough University, which is a big sporting university, and become again, one of the worst ones there.

And then they normalize training 100 mile weeks and so you get pretty good by the time you leave. And so I've got some pretty decent times, like a 14:49 5K and a 1:09:55 half marathon and the

like. So yeah, I can, I can move pretty quick.

Zarir "Zed" Vakil: I told you it'd be scary, right?

Mike Richardson: Yeah. G- GB being Great Britain, everybody, in case you didn't catch that for our, for our global, for our global listeners. Um, boy, there's some rich stuff in there to come back to, but one thing that caught my attention as we went through that was mastering your 20s.

Charlie Rogers: Hmm.

Mike Richardson: it too late for me to master my 20s?

Has that ship sailed already? Um, I like the idea though. I

Zarir "Zed" Vakil: Way too late, Mike. Way

too late.

Charlie Rogers: about it.

Mike Richardson: um, because Charlie, I've

always thought, and I've heard Ben Legg of TPC say the same, I've always thought about, you know, my 20s being my 2.0, my 30s my 3.0, so now I'm on my 6.0. I'm in my 60s now, as you can tell from all the gray hair.

At least I've got hair, as they say.

Zarir "Zed" Vakil: Hey, hey, hey.

That's not fair.

Mike Richardson: and,

uh, and hairstyle

yeah, and, um, you know, how do you master, you know, how do you master each of those phases and sort of not end up in a dead-end street? You know, how do you future-proof yourself? And I'm sure that's part of what we're about to talk about. So Charlie, let me ask a little bit more.

The word undefinable, um, how did you arrive at that? Because I think that sort of opens a door here to a very rich conversation. How did you arrive at that word?

Charlie Rogers: Hmm. So as you've seen, I guess, from my story, there are different parts of myself showing up here. There's a athlete that loves to compete and to train hard. Uh, there's also someone who likes to write and will share weekly thoughts about future of work, how it's changing. There's like a community builder who likes to hold space for other people.

So there are lots of sides of myself, and there's many more other labels that I can introduce here. But as I was growing up in particular, but also as I kinda came through university, I always found myself like part of many groups at once. Like, I would go to the, the running meetups and be like, "Yeah, okay, this is part of me, but like it's not the whole of me.

I'm not gonna give my entire soul to this one part of my life." And then I'd go to like a writer meetup and be like, "Yeah, I love writing, but like I don't know if I love it as much as you do. Like, I think this is your entire thing, but it's part of my thing." And so a lot of the spaces I entered, I often found myself fragmented in that it was only a part of me that I could show them, not my whole self.

And I think that that was a big part because I knew I could be a few different labels and I can hold them all at the same time. I love meeting different people from different parts of my life and bringing them together. And so my own journey then kind of led me to reflect and think, "Okay, what is it about that?

Well, how do I give a word to this ability to cross domains and to intentionally do it?" And I was like, "Okay, it's living beyond labels. What does it mean? It means the opposite of being definable. Okay, it's undefinable." And

Mike Richardson: Uh

Charlie Rogers: the kind of origin of that word was very much at my, my birthday party in 2023 in, in June.

I actually gathered around like 50 people for a bit of a, uh,

Clapham Common meetup. We actually got our next one a couple weeks' time

Zarir "Zed" Vakil: Joe, for God's sake, don't tells, tell us it was a run or something, please, uh

Charlie Rogers: No, I wasn't alone. I wasn't alone. It was, um, a bunch of friends who I started to gather together under what I called Mastery, a 20s community at the beginning. I was like, "We need a new name for this. Like, I think it's something like this from my experiences." I've got a list of different names, and we just kept brainstorming.

So it was a very collective de- final decision that was made, but it was one of the list of various names. But it was trying to give a word to that feeling of being across many different spaces and not

feeling that you can be your entire self in all of them

Zarir "Zed" Vakil: just as a, a segue there, I think it's very resonant to, um, our giving birth to PXO as it happens, given the un- undefinable nature of portfolio professionals. And I wonder whether we wanna just, just broaden that out now or a bit later. Um, but I think Charlie, just, just coming back to you, this undefinable, you know, w- we've-- people have tried to put monikers on this, uh, type of career for years in different ways, and, uh, often with terms that people can't even spell.

Um, and the, the, the, the truth of it is, I think you've landed on something where there is a word undefinable, which everybody can understand. Everybody can a- anticipate that that means that I'm not gonna put myself in one or other pigeonhole, which is much of what we're trying to do with PXO Exchange, where the X is what are you as a portfolio professional?

A bit like we've got accustomed to using, uh, CXO or CEO, CMO, et cetera. I think PXO does m- m- much of the same thing as undefinable in trying to make sure that people know there's a home for those who are not following a traditional, if we can call it that anymore, uh, career, uh, path, but following something which is much more, um, made up of

components.

Mike?

Mike Richardson: No, I think that's exactly it. Uh, we actually posted a LinkedIn thing, Charlie, where we, we brainstormed all of the X's, right, that, that could fit into the sort of what, what we loosely call the PXO. Sometimes we call ourselves self-employed, sometimes we call ourselves gig workers, freelancers, consultants, coaches, trainers, speakers.

And I think for me, where it goes off track a little bit is sometimes we talk about entrepreneurs, right? And it's like, well, kinda, but there's-- that takes you into a whole different bucket, doesn't it, right? Where, yeah, entrepreneurs could be a one-person solopreneur, but could easily become a five-person, 10-person, 50-person, you know, 200-person, you know, startup/scale-up, which is-- that's not what we're talking about with the, with the X, right?

And perhaps with the undefinable. What, what are your thoughts in the mix of all of that, Charlie?

Charlie Rogers: So I think what I was trying to capture with the word undefinable was the identity, so the way you see yourself versus the mode of work that you operate in. And I also wanted to normalize the fact that, like, you might still be an undefinable person, but you might take a full-time job at the beginning just because it makes the most sense to do.

But you might also then side hustle, you might also then do things around the side with the intention to change your-- where you are along the spectrum of work later on. Like, there's no, in my mind, um, constraint of how you have to do work, and I think that that's the beauty is you can design it however you'd like, and you can take a more traditional path.

And they're not always the worst paths to take. Some of them can be the right ones depending on your industry and space. And so for me, capturing the identity of the undefinable felt more powerful and resonant than simply labeling it a mode of work that I feel people could

enter and leave at different-

Mike Richardson: Yeah. Yeah. Beautiful. I like that a lot. I, I... J- Zed has heard this story before, but when I took the leap from the corporate world in the spring of 2002, um, uh, a, a headhunter guy that we had used in the corporation, he said to me, "Mike, are you retiring?" And I, I said, "Actually, no." His name was Charlie. I said, "Actually, no, Charlie, I'm not retiring.

In fact, I expect to work harder than I've ever worked. I'm just going independent." But he couldn't compute, because in his world, you had a corporate career or you didn't. You had retired from a corporate career and, and just didn't have this sort of concept, which is pervasive now, but back then less so, that no, I can go independent and I can follow my own path, and I can define my own future, my own portfolio, my own identity.

And I-- for me, it was a fabulous discovery journey, Charlie, of sort of following the scent of that, right? I wasn't exactly sure what I was chasing. It got a little clearer and clearer and clearer over time. I'm not sure I've ever really caught up with it and fully understand what I've been chasing all of these years, and I'd like to come back to that.

But it's been a wonderful journey of discovery and exploration and, and realization, Charlie. I mean, it's just been fantastic. What are your thoughts on, on that whole thing for our listeners?

Charlie Rogers: Yeah, I think that's the beauty is that, and one of the sort of chapters in the book that I talk about is like the lack of milestones when you take this path is something that can be very overwhelming because it can be a very different question that you ask yourself. It's no longer stay another couple years, hit some KPIs, and you'll get a promotion.

It's, ooh, okay, I could do this and get a certain revenue goal. That's maybe the easy answer, but perhaps also I want to have this level of flexibility so I can show up for my family in that way. Ooh, okay. Or maybe I wanna travel and blend that into my work in this way. Or maybe I wanna just do that artistic project that I've always been putting off, but it's really important for me to create.

So the lack of milestones that you get when you take this path, I think is something that's really interesting and that's often at the heart of some of my work is like, how do I give your, your life design meaning when you don't have any sort of general direction given to you about what this life could look like?

And so this whole undefinable ascent that I've introduced is very much towards a difference in here's where this portfolio career can go and here's tangible things to aim at at each stage, and it's giving that shape and that morph and that ability to, to direct oneself when they have their whole life in their

hands.

Zarir "Zed" Vakil: Yeah.

Mike Richardson: Yeah. Z, what's been your experience of that sort of

Zarir "Zed" Vakil: Well

Mike Richardson: as you go?

Zarir "Zed" Vakil: Yeah. Uh, wow. Uh, where should I start? First of all, I'm gonna say this, Mike, if you and I reach our 40 years as portfolio professionals, we'll buy each other a gold watch, which is what would happen if we'd stayed in corporate, right? Uh, um, look, I wanna go back to something that, uh, listeners of this podcast we- may have heard me talk about before, or may have heard you talk about before, which was a, a, a, a, a, a phrase, another phrase that we stumbled on for this, this, uh, this kind of surprise that people still have that you're gonna go off and do something unconventional and different and think you're retiring because you're a certain age.

And we came across this, Mike, if you remember, this, this phrase rewirement, and I really have, have leant into that quite a bit, um, in terms of my reflections of my career and, and where it has taken me, and I couldn't agree with you more. It has been a blast since I became... I, I said it at, at the top that I was in the awkward squad.

I remember a, a placement, uh, consultant that had been hired by a firm that was laying me off once said to me, he says, "I think you might be unemployable." And at the time I took that as a bit of an insult, but what he meant was, "You've just got too many jagged edges. You've got too much ambition to do this, that, and the other.

That's what you should be doing." And of course, at the time, no one was expert enough to guide you along that path and say, "Actually, do you know what? You're a portfolio professional. You have centered on your, your why. What I can help you with is designing that undefinable, um, uh, route forward and help you understand what is going on that is making you so awkward, making you unemployable," et cetera, et cetera.

And you know what? I get that now because when I look back, I think to myself, "Thank God I didn't sit in a chair for 40 years waiting

for a gold watch."

Charlie Rogers: Mm-hmm.

Mike Richardson: you-- how does that resonate with you, Charlie?

Charlie Rogers: It immediately makes me think of my dad, who

has literally done 40 years at the same company, um,

Mike Richardson: Bless him. Bless him.

Charlie Rogers: contrast. Um, but like for him it was very much like bricklayer up to construction director, and in something that he loves, shows up to every day, and is like a huge part of him and his whole identity.

And I talk about this recently about it being a bundle of work that he enters into of he met my mom, they're not together anymore, but he met my mom through work. It's where his friends have come from. It's if I walk into town with him back in where I'm from in Shrewsbury, every like 10th person we interact with knows his name.

It's like, "Hey, look. Hey, hey." It's crazy. Um, so he's very much built his reputation and his whole identity around it. While I think for particularly Gen Z, which is my generation, the reality that we've often been faced with, and particularly I kind of lived through some of the changes and the shifts, is that I actually was the youngest person to have vote, um, a- on Brexit.

It was on my 18th birthday. Um, and then I was also graduated into COVID. So I've had some of the milestones that have like shaped Gen Z, and I feel that this kind of bundle of work isn't offered anymore. It's very much up to you, the individual, to choose your community, learn while you can on the side to progress your own career and know where it's going.

And so there's a huge gap between sort of my parents' experience of work and my own, and it's very much on the individual to shape it with collaboration and different means of, of working rather than it just being one

company and progressing

up

a ladder like it used to

Mike Richardson: Yeah,

Zarir "Zed" Vakil: Love that.

Mike Richardson: Yeah, and,

Zarir "Zed" Vakil: and by the way, there's nothing wrong, there's nothing wrong with that, um, career

model. That worked and has worked for millions.

So we're just talking about the future,

right?

Mike Richardson: So one of our members offered to another who was thinking about the next phase of his career and his life and debating, debating if he should retire or not. He's in his 60s. And one of the other members offered the alternative mental model of, well, maybe don't think about it as retirement, which is a sort of binary thing, right?

You either do or you don't. Think about it as rewirement, right? How do you rewire yourself so that you might, um, be on a sort of progressive glide slope into retirement? And in fact, in, in my own case, I always talk about I have a never retirement plan, right? Why, why would I ever want to retire from my passionate purpose?

That doesn't end well statistically. So when I was listening to you earlier, uh, through that frame, Charlie, I heard you sort of, well, I, I sort of wired together an intersection of a bit of this and a bit of that and a bit of the other and a bit of this, no one of which I felt was my we- was my place, but an assemblage of those things that I wired together became almost like a new node that possibly puts you in a minority of one in the universe, right?

Nobody else is occupying precisely that same node, certainly not with your journey, and especially when you wire in all of these other activities like ultramarathons and that kind of thing. And I loved what you mentioned in there as a little passing comment. You said, "I don't think about time that way. I don't think about it as work time and play time.

I think about it as time." And I love that idea because I'm sure we're all the same here. I don't talk about work-life balance. I mean, what are you talking about? That's a zero-sum proposition, right? More of this means less of that. I think about work-life harmony, and how can I live in a harmonious integration of work and life because then, uh, I, I, I can live in this zone where I don't-- You know, being with you guys today, I don't know if this is work or life.

I don't know. It just is, and it's a

Zarir "Zed" Vakil: Oh, it's hard work with you,

Mike.

Mike Richardson: to bring a- I wanna shift gears, if I may, a little bit, Charlie, 'cause when you talked about The Portfolio Collective, you, you said that you started to get into the zone of thinking about the future of work, thinking about the future of careers, and so let's pivot to that a little bit.

And, and what's your sense of where the world is going, and therefore how it aligns with this concept of an undefinable life design and how that can be part of the solution to the new problem that, that young people in particular are facing these days, but also frankly older people, right, who can't afford to retire, right?

They're gonna have to find a way to elongate, um, their, their income stream. How do you, how do you see that landscape shaping up, Charlie, and how does it begin to align with, with your sense of this pathway of undefinable life design?

Zarir "Zed" Vakil: Mm-hmm.

Charlie Rogers: Hmm. So I think there's-- One of the biggest insights from my time at TPC was the survey we ran at the end of 2023, which was on the interview, I think it surveyed, like, 250 members. And what we found was that the focused expert, the person who's known for one thing, they deliver many ways, earns twice as much as the freelancer, the side hustler, and the multi-hyphenate, which seems logical.

But also to see, like, an average £800 day rate versus £400, £400, £300, it's like interesting. Okay. So they can get back twice their time. We're simplifying to day rate. You can also charge commission, you can charge set fees, you can do everything, yeah. But simplifying into day rates, I think that that insight of the focused expert is gonna have a lot more financial freedom on this portfolio path is super interesting.

So it's then flips back to this undefinable who wants to be everything, how are they gonna be an expert? That's then a really interesting part of this is what you mentioned before around how you can take different parts of your experience and combine them together into a category of one, and that's very much at the heart of this, is how do you brand yourself and how do you draw on your different unique experiences to create your own IP and way of thinking that you cannot be replaced and turned into a just another person that fits in this square box that can just replace you.

And I think that the- those who can do that, those that can leverage themselves as independent workers who have their own IP and are focused experts, they will win in this new economy, and they will win because they have the freedom to choose their gigs. They are the ones that are hired specifically because it's them, not because they're fulfilling a role or a job advert that's put out there.

But those on the other end, who perhaps we might call gig workers, who take just gigs that exist and they pitch themselves for gigs, that's a very different experience. You think about the Uber driver, think about the Deliveroo person, you think about those on Fiverr. It's a race to the bottom marketplace, and it's those who are trying to buy are spending less and less trying to get everyone else to compete for the opportunity there.

And so that can be a starting point to develop skills 100%, but as a long-term career solution for an individual, that is at risk, and I'd say is something which will inevitably lead you down a dead end. And so there's that path of, like, when you step into the portfolio space, how do you turn yourself into a kind of- solopreneur portfolio of one with IP versus ending up doing freelancing, repeated work on platforms that are gonna pay the lowest rate possible.

So I think there's that element, and then I think the other element, which is really interesting that I'm beginning now to explore and talk with more organizations about, is how we can move past the identity of it simply being an employer-employee relationship and into a lifetime advocacy model where they don't see them as simply you've done a year and a half, two years here, now you leave.

What? Why? That's unbelievable. I can't believe you're doing that. On the way out, the exit interviews are terrible because they just absolutely hate you for not staying long enough. But the reframe instead should be, "Oh, welcome to the wider ecosystem. Okay. And when you come and refer someone back to us who perhaps is a new young person, maybe it's a cousin of yours that then wants to go and do some work here, you're gonna say, 'Yeah, I had a great time.'

But also you're gonna come back as a supplier maybe to work part-time, maybe in a contract. Maybe you're gonna be a buyer from another company." And so seeing the play of ecosystems of organizations and the way in which people can interact with them being like a sliding scale of it not simply being employed or not employed, but being even from the element of being a buyer, like a, a customer into like a fan, into like a part-time worker into a full-time worker.

There's a whole spectrum there, and I think as long as we play along the spectrum, the organizations see the value of that, they can really start to blend how people engage with it beyond it being simply you're a worker or you're not. And so I think that excites me because that offers the opportunity to have both parties meet a more equilibrium

in what they both want from work

Zarir "Zed" Vakil: I love, love,

Mike Richardson: that. Ed, what are your

thoughts?

Zarir "Zed" Vakil: that encapsulates something that perhaps in my, in my head has always existed, some kind of virtuous ecosystem cycle that, uh, upcycles, recycles, whichever way you wanna look at it. Th- this whole body of people that have wonderful networks, wonderful relatives and friends that can be repurposed by this individual who's, who's either exiting or incoming, uh, et cetera.

I absolutely love that and buy into that, as, uh, brilliantly put, uh, uh, Charlie. And, and one of the things, Mike, that occurred to me that during our, um, uh, portfolio peer forums, um, something that Mike and I do a lot with our members is ask them to experience that, um, after they, they've come to the conclusion about what their purpose and their why is, to actually then not stop there, but proactively design what it is they want to look like and what activities they're gonna be involved with.

Because what I have found in my work and the work we do on peer forums is the real golden goose is quite often not the individual components of their activities and their interests, but what the overlaps reveal about the really special thing they could be doing, and I think that has a genuine power, and I've seen, um, new portfolio pr- pr- professionals' eyes light up when that revelation is, has been put before them.

And s- uh, and you often hear them say, "I never thought of

that."

Charlie Rogers: Yeah. Yeah, yeah

Mike Richardson: Yeah, no, I think that's it. I think that's what I'm loving about your work, Charlie, is, is you are reframing this into new paradigms, new mental models, new lenses with which to look at the, the, the topography of the landscape taking shape in front of us, and, and introducing new vocabulary and new sort of categories of thinking about it.

For younger people in particular, I think, to sort of make sense of this craziness, uh, this, this warp speed change, not least of all fueled by AI that's, you know, potentially, you know, turning everything on its head,

Charlie Rogers: Yeah

Mike Richardson: not feeling lost in the face of that craziness, actually feeling somewhat more cool, calm, and collected, courageous, that if I decide to be master of my own destiny, I can find a pathway through all of this with a progressive sense of prosperity. And one of the things that really catches my attention about your work, Charlie, that you talked about the other day, we had the blessing of having Charlie come and speak to our peer forum only a few days ago and give us a sort of flyover of, of the book in many ways. You talk about the golden thread, excuse me, the golden thread, Charlie, and I've always thought about that this way.

We live life forwards, and we understand it backwards. And now here in my 6.0, looking back through my 5.0, 4.0, all the way back to my 2.0, I can now begin to understand, oh, this has been the long thread of my career. Tell us more about the golden thread, Charlie.

Charlie Rogers: So the golden thread I see as being your evolutionary purpose, your direction that's worth following when you have a portfolio career. So as I said at the beginning, like this lack of milestones is really hard, so knowing what to say yes to is particularly difficult. There's an obvious answer, say yes to the most highest paying thing, but that often won't lead you to the thing that you actually wanna do.

So-- and it'll probably remind you, why did I leave that role before

Zarir "Zed" Vakil: Yeah.

Charlie Rogers: I was doing that anyway? So you need a better barometer of saying yes to opportunities, and what I see the role of the, the golden thread being is that it takes these raw ingredients of your interests, and if we were together in person, I would literally get out some, um, some Post-it notes and we'd t- like write on each Post-it note your many interests, and then we'd stack them together and find the categories of which they are part of.

So for me, if I like my hiking, my running, my cycling, why do I like them? Oh, I like them, I might have called it before because they're endurance sports, but now I might call them immersive adventures because I might also throw under that same list, uh, my love now of wild camping and sort of taking a van out and traveling around different parts of the UK and Europe.

Like there's different parts of that. Oh, it's immersive adventures. Okay, cool. So I now have a word for it. Once you get several categories, five to seven, then I'd ask you to use those categories to find the overlaps. And what I've done in my workshops is literally take pins, put them through these categories on these boards, and then take the golden thread and wrap it around all of the interests.

And that's a metaphor of course, but it then shows how you can start to take parts of yourself and put it into your direction worth following, your golden thread. And so from it you can use it and turn it into a formula, which is what I have and what I use to articulate it. But it's-- you don't have to follow that concretely, but it's just a way of giving language to yourself, which is I help who.

So is there someone that you feel really called to, or someone that you give advice to without realizing, or perhaps that you already help but don't get paid for, or maybe you already get paid for but really enjoy it compared to the other work. So who's the who? And when you think about that, thinking about it beyond the labels, 'cause it's really easy to just say, "I help entrepreneurs."

Great. There's so many of them. They're everywhere. But you-- speak to me deeply. I like what is it about them? You, you love the ones that are like super visionary about changing how humans think about the world and how they think about education particularly. Okay, cool. Bang. We have a much more clearer who because that gives us a much more tighter scope for you.

It also might exist beyond labels. It might be a behavioral thing that they do. They all have a similar belief system. So when you define the who, and in my case it's those who live beyond labels, the undefinable, then we get to the how. So what's the transformation? What's the end result of how you help them?

So when you're done with them, how will they feel And for me, it's design their lives for uniqueness. Okay, so they're gonna have the ability to design their lives for uniqueness. Cool. Then you get to the what, and the what is where we draw on these interests that you stack together. So you take parts of who you are, and then you wonder which ones you could apply as a service or a product or a way of helping that individual the best way you can.

And so I often love threes, if you can't tell. So I will put three at the end, three different whats. So in my case, it might be intentional transitions, life design frameworks, and intimate spaces. They're not all of my interests, they're not all of my categories, but these are the ones that I want my career to be focused on right now.

Uh, and sometimes that can change, yeah. Like my words for my golden thread are always evolving. It's not something I choose once and I'm done with. It's something that I get greater clarity on as I move closer towards the purpose Acropolis that I've defined for myself and that I'm closer and further up the mountain towards it.

So yeah, I'd say it's an evolutionary piece of who you are that can guide you and allows you to say hell yes to one thing and hell

no to another thing

Mike Richardson: Yes. Beautiful. Well, hey, Zed, as we, as we begin to turn a corner here and, and land the plane in a, in five or 10 minutes' time, what else do you want to ask, uh, Charlie about, Zed?

Zarir "Zed" Vakil: Well, first, Charlie, I think it, th- this is a, you know, having sat there and listened to you, I cannot believe that I'm the only one who's saying, "Wow, that is so interesting. How do I get to know more?" And it might be just worth saying a few words. Shameless plug, uh, spot, Mike. Uh, say a few words about the book, what is in the book,

uh, how can that help people who are trying to self-help

Mike Richardson: everybody find you?

Charlie Rogers: Yeah,

Zarir "Zed" Vakil: cetera.

Yeah. Yeah

Charlie Rogers: yeah. So undefinablelifedesign.com if you're interested in, in workshops or interested in one-to-one guidance, but the best starting place is always with the book. So Undefinable Life Design is on Amazon, and you can find it on there. You'll search it in. It's got 38 five-star reviews, been featured in Forbes, Amazon bestseller, all that good stuff.

And yeah, I-- in this book is very much the answers to some of the challenges we've spoken about today. So I talk about the undefinable ascent being the model for how to direct your portfolio career, and within that, we've touched on a few elements of the purpose Acropolis. So gather your many interests, categorize them into different labels that define you, and then find your golden thread and give words to it.

Then create your signature expression, your design principles for how you'll show up with life, and then the roof-- And then put the pillars together of your value stream. So again, one of the elements here of not seeing work and life in separate is the value streams are how you spend your 160 hours a week.

So some might be paid as income streams, some might be unpaid, but still important to you as well. So the purpose Acropolis is like the end destination, and then in the book, what I also cover is the energy toolkit. So it's how do you pack yourself with the ability to sustain the climb? What gives you capacity?

How do you anchor yourself to your environments? What's your boots saying? What's your flask, your stopwatch, your ice axe, your field guide? How do you pack them all in together and to give you enough to sustain yourself? And then what is the income pathway that you use to navigate to the very top? And so there's metaphors there about planting base camp, saving enough financial runway to make your portfolio career possible, because at the beginning it can be hard to land those first few clients and to offset some of the risks.

And then plant your flag, find the first 100 advocates who care about your vision. Then get a foothold, experiment with offers until something resonates and you find something that works. Then build a beacon, so take those experiments and use them as social proof. Share your testimonials, get yourself in the right rooms, the right spaces, and then price your value many ways.

Construct a signpost, and then the final steps are build a stairway where you can productize your time, so you're no longer just selling per hours, but you're instead being able to build products that can deliver without you even in the room. So that's the journey of the book where I take you, and I use metaphor.

I use stories of people I've met along this portfolio journey. I use exercises that you can use in your own time as well, and there's nice illustrations throughout from who's actually Colin, my old running coach, who's now also an illustrator for this book as well, which is a great fitting narrative of him being the undefinable himself.

So it fits together all these

pieces into a very complete package.

Zarir "Zed" Vakil: Well, folks, go buy the book. Um, sounds fascinating. Mike, quick story if I may, which those of you sitting back listening to Charlie saying, "I don't need to buy the book, I can get Claude AI to do all of that for me." No, it can't, and I can tell you why it can't, because I recently was asked for a CV. I haven't been asked for a CV for I don't know how long, and I was rather embarrassed digging out my CV to find out it was eight years old.

That person isn't me anymore, right? And so I s- I, I tried to prompt Claude or any other AI platforms are available to say, "Can you write me a CV based on all the things you know about me?" And hey ho, guess what it said? It said, "No, I can't." And we had this conversation about how it was almost impossible for Claude to write my CV, but it offered then to write two CVs and two profiles instead to meet with the audience that I was speaking or presenting to.

And I think that in itself speaks volumes about how our careers have changed, where you can't be pigeonholed, and even AI cannot pigeonhole me anymore. So, um, let that be a, let, let that be a sort of a

juncture to,

um, move on

Mike Richardson: So everybody, it was, uh,

undefinablelifedesign.com and, uh, of the same name, you can find the book on Amazon, which I literally in the last 30 seconds just bought the soft cover version of for my son who's arriving home on Sunday. He's in his mid-30s and, uh, he's been very successful, and he's not sure that he's found his groove yet.

Charlie Rogers: Mm-hmm.

Mike Richardson: And he's been in sort of

corporate roles, and he's been with a couple of startups, and he's just not sure that he's found his groove, and so he's posing lots of questions to himself. And so Charlie, I'm gonna be, uh, writing something inside the cover of that book. It arrive-- The book arrives on Sunday, uh, to say to him, "Look, um, I've been in this portfolio world for 25 years now.

I've invested a lot of thought leadership in this myself. This book is the best that I've come across in recent times. This is the one you need to read, Craig." And so that's the gift that I will be giving him, uh, on Sunday. So thanks so much for blessing us with all of your work, uh, Charlie. Um, what else we, what

else-

Zarir "Zed" Vakil: until, our book comes out later on in the

Mike Richardson: yeah, that's Right.

That's right. Yes, yes. So, soon to be eclipsed, of course, by, by our book. But, uh, Zed, what else, uh, before we land this plane, what else do you wanna

Zarir "Zed" Vakil: Well, look, what, what a wonder-- you were right at the top, Mike, to say we'd have a wonderfully rich conversation. I really, really hope that listeners to this and viewers of this will get a lot out of it. I mean, it's genuinely a, a, you know, at the kind of foothills of designing and, and explaining and, and, um, visualizing for people how this works.

Uh, and, and I think more and more, uh, people are going to be taking on these tasks of finding out what really... And I, I always end up with this, what really makes you happy? Because that in itself is a driver towards looking at yourself, finding these things like the undefinable design, about por- portfolio careers, about PXO, and really, really leveraging, not forgetting, not throwing the baby out with the bathwater of all the things you've learned over your 2.0, 3.0, 4.0, et cetera.

But grasping the nettle now, if you've been playing and thinking about this for too long, a- and getting yourself organized so that you can... It's not easy. Uh, I think, uh, Charlie, you said that, that y- you can't drop out of, you know, Google and suddenly become a portfolio professional. It doesn't work like that and ends badly.

Where it works is when people take time out to redesign their lives, uh, and that's what

we've been talking about,

Mike Richardson: Beautiful. Yeah. And Charlie, I, I get on a plane in a couple of weeks to go spend, uh, a couple of days with a, a new client, and, uh, it's almost bizarre. I would never have imagined that I would be the right guy in the right place at the right time to be the number one person that they wanted to work with. I'm not gonna go into more details, but there's a sort of bizarre combination of things that I've done in my career that many people would never be able to guess, that have just come together as this intersection that, to a large degree, makes me the right guy in the right place at the right time. And, and I'm-- you know, I've been engaging with them progressively virtually over the last few weeks and months, and I'm having so much fun with it.

Um, you know, it's, it's, it's fairly prosperous for me financially, and I'm very excited about, you know, the footprints that I can leave in their journey, um, it, you know, because of the combination of experiences that I've had. So I'm, I'm just sitting here thinking, he's right. It's like, it's unpredictable, it's undefinable,

it's un-- it's some, in some ways it's unplannable, right? You, you sort of know it when you see it. What, uh, what final thoughts, Charlie, would you like to leave with our listeners before we land this plane?

Charlie Rogers: I would say even with that unpredictability, even with that changing landscape, and I see it the lens of the world is becoming exponentially faster, and it's hard to visualize what exponentially means in the sense it's not linear, it goes to the nth degree. And even in that world, I think there is opportunity, there is challenge, there is everything.

But if you are to tune in to yourself to find that golden thread, to listen and speak and commit to the hard decisions and the hard questions, you will find answers that in today's world you can actually have the tools to go out and pursue that life. And I think that that's a huge opportunity and beauty.

So I would say reflect, sit down, use my book if you'd like to, use other resources as well, and get to some of the answers about how you want to design your life, and then use them because there's no better time than right now

Mike Richardson: Beautiful, beautiful, beautiful. there we there we are everybody, another episode of the Peering Podcast. If you wanna see the future, the best way is to peer into it together. We've been peering here, blessed with, uh, Zed, of course, as usual, blessed with Charlie, and, uh, uh, go to the undefinablelifedesign.com.

Buy the book everybody, and you will not regret it. Zed, always a pleasure, my friend. Thanks for being here.

Charlie, you

blessed us. We're

so happy to have met you and to learn about your work, and we can't wait to stay in touch. have a great time everybody, and we'll s-

Zarir "Zed" Vakil: Thanks, Charlie

Mike Richardson: you next

time in the next podcast.

Take care.

Creators and Guests

Mike Richardson
Host
Mike Richardson
Agility, Peer Power & Collective Intelligence
Portfolio Conversations with Mike & Zed: With Guest Charlie Rogers, Author of "Undefinable Life Design"
Broadcast by