Tom Critchlow on Personal Branding, Freelance Consulting & The Future of Work

[01:00] Paul: Welcome to The Boundless Podcast. I'm Paul Millerd, and I created this podcast because I'm passionate about making sense of the future of work and having conversations with the innovators, creators, and thought leaders who are carving their path in today's fast-changing world. You can check out the podcast and more on boundlesspod.com. Today I talk with Tom Critchlow, who I think is really representative of a lot of the people I'm meeting out here in the freelance world. He has a diverse array of interests. He's a writer, he's a creator, he's passionate about art, he's co-founded an art collective in Brooklyn, and also is just figuring out his path and journey in the consulting world and shares a lot of his learnings and insights with you.

He's written a lot of interesting pieces on what it takes to be a freelance consultant and how to think about culture and consulting to a company. I'll link up to some of those articles and we'll dive into them in the podcast. I also, again, just want to thank people for continuing to support me. I'm having so much fun telling the stories of people like Tom and doing the podcast. It's been a learning experience for me and I'd love if you could share the podcast, retweet, share it on Facebook, add a review on iTunes, like it. And if you want to continue to support this and the work I'm doing, feel free to check out Why I'm Here on Patreon, which you can check out in the show notes.

Tom, welcome to the podcast today.

[02:43] Tom Critchlow: Thanks for having me.

[02:44] Paul: Awesome. So first off, I just want to thank you. I think you do an incredible job of telling your own story. I've stumbled upon a couple of things you've written, which we'll dig into later, but I also just resonate with your story as somebody that has many diverse curiosities. So you describe yourself in your bio and you, you have the personal mantra of move, think, create. I'd love to start there and just ask you, What does that mean to you?

[03:13] Tom Critchlow: That's a good question. Until you asked the question, you sent me an email kind of notes with that question outlined. And actually, I hadn't thought about that mantra for a little while. I've had it for a couple of years now just as a personal mantra. It's on my website. But I think for me, it really sums up the balancing of like an intellectual curiosity about the world.

Like, I always want to just be passionate about stuff. I always want to ask questions. I always want to try and think differently than other people about things and really question my own insights. I want to have creativity in the things that I do. So, I always want to challenge myself to be putting things out there in the world. And the move piece in particular is specifically I think around— it's kind of a personal reminder to both have work-life balance and also to just physically move.

You know, I think like many of us, we sit in front of a computer 17 hours a day and wiggle our fingers. And it's a good reminder that getting the blood pumping and getting out for a walk, playing basketball, going swimming, just being active is an incredible thing for the mind and the soul. So, yeah, it's been a personal mantra for a little while now. I think there's a fourth piece which I need to add in there somewhere around compassion or family. It comes across right now a little bit as too personal. And actually, there is a fourth kind of component to my own life, which is just kind of I want to make sure that I have time I want to make sure that I have time for friends and for others in there.

So, it's a little bit self-serving right now, but I found it useful over the years just to guide. When I get stuck in a rut, it's just kind of remind myself to move, think, create, put something out there in the world, challenge an assumption, or just get the blood pumping.

[04:52] Paul: Awesome. So, it's move, think, create, compassion now. Yeah.

[04:56] Tom Critchlow: I think maybe it's not quite as catchy that way. I need to think of a catchy way to do a 4-step, but that's the one.

[05:01] Paul: Yeah. Awesome. And thinking differently, have you always been wired that way?

[05:07] Tom Critchlow: I think so. And I'm not quite sure where it comes from. I think I've always enjoyed both looking up to people who are contrarian and somehow have always gravitated to people who've been on the fringes a little bit. Growing up in high school, I played a lot of role-playing games. So I was definitely one of the kind of geeks at the fringe of high school culture. And I think I've always— that's kind of stuck with me, I think, as a way to live outside slightly of the norms.

I'm sure there's more I could do to challenge some of my own assumptions as well. But I think, yeah, I've always been drawn to that, to people that try to think differently. I'm a big fan of Venkatesh Rao's blog, Ribbonfarm, and the way he kind of organizes everything around refactored perception. I think there's something really gratifying and rewarding about having one of your assumptions challenged or having one of your mental models kind of upended. There's something super powerful about that.

[06:00] Paul: Yeah, definitely resonate with that. I've really enjoyed his writing as well. It's, it's the kind of writing that just makes you think in a way you wouldn't even think of it, right? I've definitely read some of his stuff and it's kind of blown my brain open and forced me to look at things in new ways. I'll link up to that in the show notes. Would love to dive in.

So you have a lot of things you're passionate about. You You're consulting. You're the co-founder of a Brooklyn art collective. How do you manage so many different curiosities and how do you describe yourself when you're introducing yourself these days?

[06:43] Tom Critchlow: That's a great question. Introducing myself and describing what I do is usually a meandering, long conversation of things. The easiest way to describe what I do is I do digital strategy consulting. That's kind of certainly from a revenue-generating standpoint, the main thing. As far as the curiosities I have and interests, you know, art is definitely high up there. You know, I run an art business with my partner Aaron.

We started that about 4 years ago now. And then I also just, you know, I like to be widely read and I try and be curious about all kinds of things. So there's lots of interests come and go. One of the downsides, I think, of having lots of interests is that there's many interests I've had over the years that I haven't pursued so deeply, right? You kind of— I think you have to come to terms with being okay at going into lots of things in a kind of shallow surface level function. And then, you know, thinking about or stumbling upon the things that you do care more deeply about that stick with you for many years.

So I think You know, it's interesting when you read a lot of like, um, productivity writing or the kind of shallow startup advice, there's a lot of talk about, you know, focus and hustle and these other things where, um, sometimes I like to think that I'm okay with just kind of swimming through a diverse set of interests and some of them will stick and some of them won't. I'll pick some things up and then abandon them, um, and that's okay, you know. I think, you know, not to say that I don't also have deep interest in certain sectors, but I think there's kind of a willingness and, you know, a kind of being comfortable with letting these interests kind of wash over you. And it's also, you know, you read those kind of books about creativity, and creativity is in essence is nothing more than just diverse connections between different fields and different people.

And so I think that's one of the things that I love about, you know, getting interested in architecture for a couple months, like read a book about architecture and follow up on that a little bit and then move on to something else. And I love that because then one day that will come back around and I'll pick something up from learning about architecture that I'll be like, oh, you know what, that's an analogy to this field or that person who was a famous architect. I read a little bit about them and now there's a thing over here that I can apply that to. So, I kind of enjoy that diverse connection making.

[09:04] Paul: Yeah, I love that. I have a similar reaction to those pieces. It says focus on one thing and do it. For a really long time, and it just doesn't seem to align with how life is actually lived, right? You're gonna be— people are naturally curious about what's around them, right?

[09:23] Tom Critchlow: Yeah. And I think also, uh, Venkatesh again has a great piece about this, but many startup founders, um, are in the very classical sense of the word psychopaths, right?

[09:33] Paul: Right. They get obsessed with that one idea.

[09:36] Tom Critchlow: Yeah, like in an unhealthy way. In many ways, obviously we're stereotyping, but I think a lot of the quote-unquote advice is not aimed at most people. But it's still perfectly possible to build a business or do something you love or whatever without relentlessly focusing on something 19 hours a day for 10 years.

[09:57] Paul: Right.

[09:58] Tom Critchlow: Yeah.

[09:58] Paul: So, I've been really interested about that idea of pursuing a bunch of different things but being almost strategic around quitting. How have you thought about, and has that evolved as you've gotten older, thinking about, okay, explore this, but like, if it's not working or energizing me, doing, moving on to that next thing?

[10:19] Tom Critchlow: Yeah, it's a good question. There's certainly a kind of a large archive of both failed and abandoned projects that I've done in my personal life and in my professional life, I guess. One of the things that has been really useful for me, so when I was younger, I think I used to want everything to be a business. All of my side projects had to be revenue generating or at least have some path to revenue generating. And one of the things that was really freeing for me was thinking of side projects as discrete projects rather than ongoing time investments. So rather than saying, I'm going to build a community for book lovers, which is one of the projects I had many years ago, that's a big time commitment over a long period of time to build a community around book lovers.

You need to build it and then you need to create a community and then you need to keep investing in the community on an ongoing basis. Now that might be a good thing and it might be something I want to do, but is there something I can do which is more of a one-off project to still scratch the same itch? And that's a better place to start, I think, right? So could I create a resource for book lovers? Which would be more of a standalone thing, would not require an ongoing investment for 5 years. And it still scratches the itch of shipping something out in the world, having a project, et cetera, et cetera.

And the thing that really, I think one of the breakthroughs I had was that even if it is a project or a standalone thing rather than ongoing venture, creating a naming and kind of creating an edge to the thing, like creating a container for it, is still really powerful in getting it launched and getting the idea out there. And so, I think it's not about necessarily all projects have to be revenue-generating, and it's about almost being wary of future time commitments to yourself, right? It's easy when you get carried away with a new idea to imagine launching it and it being successful. But is there a way to do a side project which scratches the same itch, has a good position in the world, whether that's a name, identity, or domain name or whatever?

And then can you use that to— if it takes off and if you are still excited about it and if you think that it's a long-term thing that you want to invest in, you can keep going. But it is not by design a big kind of investment of your own time over a long period of time.

[12:38] Paul: Yeah, it has that optionality. Yeah, I've personally found I've done several things that have gone nowhere or failed, but then you have this almost magical alignment of those skills you learned on that project that you get to apply on projects that might actually go some, somewhere further.

[12:57] Tom Critchlow: Yeah, for sure.

[12:58] Paul: So I'd love to shift to how you're thinking about positioning yourself in as a consultant. I read an article you wrote where you had rethought how you're positioning yourself. So I think you started out and you had positioned yourself as a brand and then shifted it back to as a personal brand. What made you make that transition and how are you thinking about it today?

[13:24] Tom Critchlow: It's a great question. So there was a, I think it was a number of emotional things kind of wrapped up together for me in, you know, I'd been out on my own for maybe 2 years and had been doing my consulting work and it's just me. So I don't have any employees and I felt like I was missing upside by doing it under my own name, right? By being tomcritchlow.com as the website I had. And when somebody, when I send an invoice, it comes from Tom Critchlow, that felt like I was being a little bit amateur somehow and that I was leaving money on the table by not presenting myself as like a bigger, more grown-up agency or organization kind of entity. I had friends that do very similar things to me and they would have a name for their kind of agency or consulting practice, like a brand name, and that seems to be working well for them.

And I thought, you know what, Maybe I should do the same. And so, I went into the well and I did a bunch of kind of thinking and experimenting. And I came up with this positioning and brand and name called YesAnd, which was kind of a riff on improv kind of stand-up playing where there's this kind of game where somebody says something and you can only build upon it. You can't shoot it down with a no. You have to say yes and then you have to say and and you have to extend the idea. And I think there's a a wonderful analogy to that improv nature and also kind of business consulting.

And, you know, I'm also, frankly, I'm usually quite a positive individual. So I felt like I also brought a positive spin to business and positive spin to strategy that reflected on the name. I really liked it. I came up with a visual identity, a website, etc. And I got very close to launching and kind of going all in on it. And it was a couple of kind of crucial conversations with some close friends of mine that ultimately persuaded me that it wasn't quite rights and that I should be better served continuing under Tom Critchlow.

I think the core reasons were that actually the thing that people are hiring is not an agency or NC, it's me. And I'm the one who does all the work. I don't have any employees. I don't have any staff. When you work with me, you're working with me directly and that that's a strength, not a weakness. The alternative of working with an agency or working with a bigger organization is that you don't get that experience, right?

And so, I should lean into the fact that it is just me and it's kind of, you get all of me, including the weird interests and passions and side projects and so on. But I bring all of that to bear when I work on a consulting project. So, I decided to kind of scrap the brand, scrap the name. It's definitely something that I still think about. We talked about Venkatesh, for example, he has his website, Ribbonfarm. Would that be the same brand if it was just VenkateshRao.com?

Maybe, maybe not. There is definitely a power and there is a strength to an idea that has a name, right? And I mean, for example, you've got a name that you're doing your consulting and podcast and so on under. How do you think about it?

[16:32] Paul: Yeah. So, turning the tables to me, I like it. Uh, so my, my evolution was, uh, so I started a consulting brand and I realized it didn't really mean anything. Uh, it was just kind of a brand that, uh, and I did that on purpose because I did— I don't think I really knew what it was going to be at the start. And then recently actually shifted to a word, Boundless, and have been positioning things around that because I've also been shifting some of the work I'm doing around telling stories like this on the podcast and trying to embrace an idea. I think it's very similar to the yes and, right?

It's, it's an idea I want people to embrace in the world of thinking we're capable of more than we believe. And I also was just doing so many different things under different names, and that seemed to be an idea or name that made the most sense, but Probably like you, this will evolve and be a very different answer 12 months from now. I think that's just the nature of freelancing.

[17:40] Tom Critchlow: Yeah. I mean, we have such flexibility to reposition or change the moves that we're making. I think that's a great name, by the way. I think it's funny, when I wrote that article, I was really just kind of— in some senses, it was just kind of— therapy for me because I just put all this work into a new website and a new brand and then abandoned it last minute. And so I kind of wanted to write about it. But a lot of people did treat it as me saying that you should not have a personal brand, right, if you're an individual kind of freelancer or consultant.

And that's absolutely not my point at all. My point was that me at that moment, the brand that I was about to choose was not right. But I think Boundless is a great name and I think it really does reflect well with what you're doing. I think everyone's got to make their own choice there.

[18:25] Paul: Well, thank you.

[18:26] Tom Critchlow: Do you have designs to have employees, do you think, at some point? Do you think the name gives you the flexibility to scale more?

[18:35] Paul: Yeah, good question. I'm not thinking of it in terms of employees. I'm thinking much more in terms of how can I bring together more people around this idea, less so in terms of building a business or making money and much more around bringing people together and hopefully just creating more positive feedback loops, right? I brought all my content under that platform more because I wanted to create more connections with people rather than send them to Medium and help Medium with their business.

[19:07] Tom Critchlow: Um, yeah, I feel like there's more and more access for Medium these days, but maybe that's a conversation for another podcast. Yeah.

[19:14] Paul: So I'd love to, uh, dig into your writing. So you write a lot. I've found for me, writing has been such a great tool to make sense of what I believe and just share my story to the world. So, what role has writing played in your journey?

[19:29] Tom Critchlow: So, I just wrote a piece actually with the title, "In a Land of Hierarchy, the Networked Individual is King." And I think that phrase sums up a lot of my experiences in my own career, which is that writing, blogging, podcasting, even conference speaking, which I think of in a way, it's kind of a cute term, but I think of it as network speaking, right? I think the idea that you create something not as kind of a standalone thing, but you create it within and for the network has been a really powerful idea and one that I've been involved in for many years, but only more recently have really come to fully appreciate the power of. You know, back when I was early on in my career, I was working at my brother's agency called Distilled, a small SEO content strategy agency in the UK. And we blogged under the company name. We would put all kinds of crazy stuff out there.

And through the process of doing that, through the process of learning how to write for an audience and how to just write full stop in an engaging way, I gained such incredible opportunities, both career opportunities, serendipitous kind of interesting introductions, friends that have been lifelong friends. It really kind of helped put the company on the map as well as me personally and professionally. And so, it's something that I've really continued and kept up with over over the many years. And now that I have my own consulting practice, it is kind of the best outlet that I have for sharing my thinking, for connecting different people to different ideas, and for also just kind of scratching that itch of creating something, right? It's the easiest way, putting words down on the internet, that is kind of low cost and there's no barrier to entry and I can write whatever I want.

It's my own platform, it's my own site, and I really enjoy that.

[21:21] Paul: So you touched on how you started your career. You helped co-found a consultancy with your brother early in your career, and then you ended up going to Google for a period before you became a freelancer. So getting a taste of not really following that default path early in your career and then going to a big company like Google, how did that feel and how did that shape when you decided to finally take the leap to go on your own?

[21:47] Tom Critchlow: So I really enjoyed my time at Google. I would say that the biggest mistake I made, if I made a mistake going to Google, was not going in at a more senior or strategic level. Now, obviously, that's easier said than done. But my point there is that Google, for all of it being a great place to work and, you know, having a strong culture and so on and so forth, is still a big organization. And big organizations by default are resistant to kind of bottom-up ideas, right? They must necessarily be so, otherwise they would be changing, you know, 10 times a day.

And so I saw that other people that came in, for example, via acquisitions or who came in at a more senior strategic level, had more weight, buy-in, access, etc. And so I learned a lot while I was there. I also bounced around a little bit internally between a few different teams. My background before I came to Google was kind of in consulting, digital strategy, SEO, and I went to work for what was essentially an internal ad agency, which was a very big kind of change of pace, deliberately so from my perspective, I wanted a change of pace. But it meant that I didn't look much like the other people that I was surrounded with every day. And I think that caused some friction on both sides.

I don't think I did I did a great job on some of the projects that I worked on, but I also think that I tried to take an approach which I thought was right in certain situations and kind of butted heads or clashed cultures with some of the management that I was surrounded by. So, I bounced around between some different projects and ultimately felt like I wasn't working on anything that I was fully invested in. And so, I felt like, you know what, I'm too young to retire and just kind of walk the halls of Google aimlessly eating the free lunch. So, I thought, you know what, I should leave. So, I kind of set out on my own to do my own consulting thing.

[23:44] Paul: Yeah, when was that first moment you thought about going out on your own?

[23:50] Tom Critchlow: Well, when I got my green card. That was kind of a technical limitation that was stopping me just walking out the door. No, but I think, you know, so there was a moment when I was working on the Google Cardboard team for a period of time, which is that kind of early virtual reality prototype. It was a very small team. And it quickly went from a small team to Google building a real dedicated virtual reality team inside Google, which is actually a super fun, rewarding project that I was working on. And I love the people that worked on that project.

And they actually wanted me to come work with them. But it involved moving out to San Francisco, or more accurately to Palo Alto. And I was like, I think I want to stay in New York. And so that was kind of the straw that broke the camel's back right at the end when I was— when I couldn't continue working on that team. And I thought, you know what, now's the time to head out.

[24:44] Paul: That's great. So I'd love to shift to some of your writing. I think two of the pieces I mentioned at the beginning really stuck out. One was talking about becoming an independent freelancer and how people should think about that. We'll dig into that one, but I'd love to start with the going with the grain of a company. I'd love if you could share a little about what that idea means and how you think about it in terms of consulting and your freelance work.

[25:15] Tom Critchlow: Yeah. So the title of the piece was The Consultant's Grain, and there's kind of two big concepts wrapped up in that post. So let me back up for a sec. When I do my consulting work, and one of the things that I think is a huge benefit to hiring an individual or freelance consultant versus an agency or a more traditional relationship is that I'm gonna embed myself in my client's organization much more heavily, much more deeply than a traditional agency would be able to or might want to. And, you know, for example, I usually get access to Basecamp, to Slack, I get like a company email address. You know, I really want to feel like I'm really under the skin of the company.

And the reason for that is that I want to actually affect change at the organization. I don't just want to create a bunch of PowerPoints and reports and have them sit on someone's desk. And so, if you're going to actually change an organization, you have to understand their culture. You have to understand why have they not changed these things already. How do they think about changing? Who is responsible for changing?

What are the strategic priorities? What have they tried before? You know, what are the biases that the founders of the company have? There's all kinds of these kind of nuanced questions which are not reflected in what you might think of as kind of a traditional strategy roadmap, right? You know, it's very well kind of crunching the numbers or doing the technical analysis, but you have to understand the actual culture of the company. And so when I talk about the consultant's grain, there is a whole set of things that you can try and change a company for, which I say go with the grain of the company.

And what I mean by that is these are kind of things that they are already primed to change, things they want to do, things they're already, you know, pretty closely able to do, or things that they're already investing in. And changing a company with the grain It can still be challenging, but is relatively speaking much easier than going against the grain. So when you're going with the grain, what I typically recommend is abandon the polish on your deliverables, move as fast as you can, and actually get to the output as fast as you can. So really it's about running with the team. It's about saying, how can we just make this project or this idea that you're already invested in or already primed for move as fast as possible, get as good as possible as quickly as we can, scale as fast as we can. And all of those things basically involve kind of a high degree of collaboration with the team.

That's kind of, I guess, like 101 consulting theory or management theory. But then the deeper level that I've become much more fascinated with is when you're trying to go against the grain of an organization. And what I mean by that is these are things that the organization are not willing to accept. Basically, things that they either explicitly or implicitly are not good at doing, don't want to do, don't feel like work, or are just structurally unable to execute on. And examples of this might be, let's say for example, I was working with a company last year that produces an extremely large amount of content online. And all of their workflows, everything they're designed, set up to do is to produce a large amount of content.

Now, when I started working with them, I said, you know what guys, we should create some more deeply thought out, researched, kind of more interesting content as well as the kind of volume content we create. And there was a lot of lip service buy-in, right? Like people were like, hey, Yes, it sounds like a great idea. How do we do it? And yet the culture of the organization and all of the incentive structures, the motivations, team structure, right? And so I talk about that as like going against the grain.

And when you're trying to go against the grain, I think that you need to be— you think the best analogy I have is thinking like a politician. You have to campaign for change. You have to continually repeat the same message. You have to bring it up in lots of different environments. You have to create compelling moments when it makes sense for the organization to make a big leap, you have to think about either a top-down and/or a bottom-up approach to kind of getting buy-in and support, right? So getting individuals on the front lines invested in your idea, getting executives invested in your idea, trying to kind of, you know, convince people slowly over time that this is a thing they should do and show them examples of what it looks like, etc., etc.

I even go as far as talking about internal blogging, as in releasing content essentially that is designed to win hearts and minds inside the company, whether that's kind of the old-fashioned memo you can think of it as, or whether it's kind of posts on their internal Basecamp or whatever knowledge management tool they have. So that's kind of the gist is when you're a consultant and you're trying to help a company change, it's really useful I find to kind of stop and ask yourself, Am I trying to get them to change with the grain or against the grain? And then, if you really want to start peeling back the onion, at the end of that article, actually, the very premise of that blog post, The Consultant's Grain, is you have to also recognize that you have a particular bias and a particular culture.

When I start working with a company, I'm going to have a set of ideas that I have about how business should work, about what is "the right answer" for them, what they should be doing. And I have to recognize that not all of those things are right. And I'm going to come with a kind of a preconceived set of ideas and notions, some of which will be right and some of which will probably be misguided, right? You know, there are certain things that I can draw on from my experience, but I certainly don't know everything there is to know. And companies come in all kinds of weird shapes and sizes. So you also have to recognize when you're trying to champion something which is a genuine good idea for the business, or whether it's just something that you think is a good idea.

For the business and kind of, you know, really deep question those, those—

[31:13] Paul: yeah. And that, that's almost good advice for anyone working at any company. I think I talk to people sometimes at different stages in their career, and they may be incredibly talented, but they're not actually in the context that's going to take advantage of those talents. So, uh, and I think as a freelancer, you have to continually think about that because you're, you're not only managing, uh, your business or the work, you're, you're managing your time and trying to maximize your energy.

[31:39] Tom Critchlow: Right. I'm curious, with the consultant's grain, you actually spent some time at kind of a big strategy consulting firm before going out on your own. Did you guys ever talk about any of the concepts like this, like the culture of an organization and how to work with it or against it?

[31:54] Paul: So I think at the big strategy firms, you do get the advantage of what you said. You're deeply embedded in person on the floor for months. A lot of what you talk about is building partnerships, and those happen— you might be a junior analyst and you're building a partnership with the manager you're working with on the other team. And those things happen very one-on-one. I think what part of my reflection in thinking about organizations and organizational change as well has just been that we still think of it in terms of something that can be designed and done, right? We don't think of organizations as living systems that are dynamic and complex.

So I almost think there's a fundamental flaw in how strategy consulting firms conceive change. It's seen as— and it would be the rational thing for them to say, right? They're not going to go into an organization and say, well, change is chaotic and we can't really plan or control it, right? They're getting paid to say and think and create frameworks that say change can be planned. Here's what it looks like and here's how it is conceptually. So you might have a process or a plan where that's easily laid out and everyone can understand it.

But in reality, when the change happens, it's never planned or like that. There's always unexpected things. So yeah, definitely resonates. I think we still— there's still big ways to go in thinking or shifting our thinking and how organizations actually operate. We see them as organisms that can be controlled from the top, and that's just fundamentally not true, but we pretend otherwise.

[33:45] Tom Critchlow: Yeah, I'm really, really interested about how people like you and I as kind of individuals and freelancers and kind of the new way of thinking about consulting can really take that head-on and kind of stop pretending that change can or does happen top-down. Um, and I'm really curious how you could kind of structure a client relationship or a consulting engagement around the idea of kind of organic, messy change, right? Like, it's a hard sell. There's a reason that the consulting firms are that way, because it's easy for everyone to get their head around. And it's also, by the way, it's unpalatable to an executive at a company to hire a consultant with the very premise that they have limited power to actually change the organization in the ways they want. So, I'm super curious about how we can kind of manage those things.

I don't know. There's a guy called Matt Webb, who I don't know if you've come across. He used to run a kind of an Internet of Things consultancy called Berg. In London a few years back, and he wrote this incredible blog post that really resonates with me about consulting in small groups and about how maybe the ultimate power of a consultant is just the idea of bringing the right people into the room and making the right connections, you know, explicitly kind of flipping it on its head from having the ideas and driving the change instead to almost playing like a facilitator role to have the right people in the room documenting the culture that you see and being a tool for much more organic growth. It's kind of a really interesting concept. I'll send you the link to the blog post so you can put it in the show notes because it really resonated with me.

[35:31] Paul: Yeah, it's an exciting time. I think part of people's shift to more freelancing almost changes— it forces the organization to think in new ways. Is they're not just going to hire you to show up and run a report every week, right? Uh, employees within an organization, there's all this extra stuff you have to do just to kind of exist as a citizen of that organization. And bringing someone like a consultant or freelancers, you actually have to start with a problem to be solved, right? So it almost shifts the organizational thinking.

And I'm wondering if, uh, organizations that do end up using more and different types of workers are going to be forced to say, "What are our problems we're solving?" rather than, "How do we maintain the organization?" Right, right.

[36:19] Tom Critchlow: There's another interesting point to the consultant's brain that I found in my own work, and this is advice that I give to a lot of other freelancers and independent consultants, is it's been really useful for me to have a mixture of what I call soft and hard skills. And what I mean by that is, you know, I have a background in SEO, digital marketing, content strategy, and when clients hire me, it's really, really useful for me to have something that they can pay for that I can work on every single month, which I call like hard skills, right? Like the SEO, the marketing, content strategy, where I can be— have a much more of a tangible output or a tangible input into those projects. Which allows me to stick around inside the client's organization long enough that I can do the things that are kind of much more messy and organic and slow and what I call soft skills.

That's kind of the wrong word, but, you know, I can campaign for change, right? But the only reason they're going to let me stick around long enough to do the campaigning for change is because I have those harder skills which allow me to kind of, you know, be in project in the organization for a sustained period of time, which I find is a really interesting balance. And I find that some of the folks that I've, some of the kind of peers that I know and I've worked with, had conversations with, they struggle a little bit with client engagements being too short to really get anything, to get anywhere, because they focus too directly on the soft skills and the bigger against-the-grain change, right? Having something to kind of pair it with that they can be paid for and stick around for every month Right.

[37:55] Paul: So it's, uh, you might go in and say, I'm going to help you with SEO. But once you get in there, you might have a couple ideas here. You've started to learn the culture and suddenly you're building a relationship and helping do things more impactful rather than starting with saying, let's, let's transform your organization. And then what I've found as a freelancer that will often turn into a back and forth over 6 months around a proposal because nobody really knows what they're solving for, right? And you don't ever really get started.

[38:25] Tom Critchlow: Yeah, those messy, undefined projects are really hard to— they're really hard to sell, they're really hard to get buy-in for, they're really hard to price.

[38:32] Paul: And also, yeah, there's infinite of them, right?

[38:35] Tom Critchlow: Right. So yeah, so I find it really useful to have them have something which is kind of a, like I said, like a harder skill or a more defined skill which people can kind of use as an excuse to get me inside the walls of the organization. And, you know, that— I think that could be any— you could Equally, you could think about in all kinds of other ways, right? You could have training as your hard skill, or you could have copywriting or web development. Like there's all kinds of other things I think that could replace that kind of SEO digital marketing piece as something more tangible. But I found it really useful to have that mix.

And I don't know how easy it is to, how useful that is as advice for somebody else who kind of, you know, might not have those skills readily available to kind of magic them out of thin air. But I find a lot of this is much more about just how you position yourself. And so, I think that could be useful.

[39:20] Paul: Yeah. No, I'm thinking of it for myself. I'm trying to think, okay, what are my hard skills and soft skills? And I think that's super useful. So, speaking about advice for freelancers, you also wrote about what independent freelancers should think about and what are some things they can do for success. I think 3 things you mentioned were network, build credibility through content.

And do the work. So we've talked about those a little, but I thought one thing that jumped out that definitely resonated with me and people I've talked to that are considering becoming freelancers is that you should really commit to taking at least 12 to 18 months and saying, I am all in with this. I think sometimes I've talked with freelancers and they're like, I'm going to try this for 3 months, but if it doesn't work out, I'm going to 'Hey, take a full-time job.' And there's not really that 100% all-in buy-in. So how do you think about that piece of advice and what would you say to people who are thinking about taking that leap?

[40:27] Tom Critchlow: Well, I think I might reframe it slightly differently than you. I don't know if it's crucial to take the all-in leap on being a freelancer. I would take the all-in leap on building a network, right? So I think that the crucial thing for me is that You literally cannot be a freelance or independent agent without some kind of network, at least in my opinion. Like, it's just, you're going to have such a harder time if you don't have people that know about you, connections you can reach out to, a kind of trusted circle of advisors. Like, you know, that whole network of individuals doing interesting things in the sphere that you want to get involved in is just crucial for generating income, for getting sales, for having the trust, etc., etc.

But you can build that independently of being a freelancer, right? You know, there are many people who successfully have personal profiles and blogs and so on who have full-time jobs. And that is the thing that I would commit to. And I think that, you know, if somebody's just starting out freelancing and saying, maybe I'll give it 3 months, maybe I'll take a full-time job, etc., I would say commit to building a network, right? And I mean by that, like, you know, getting a public profile, getting a blog out there, putting putting things out there that resonate with people and make connections, and commit to doing that both before, during, and after freelancing, right? So that you're building that sustainable thing, because even when you take a full-time job, that's going to be useful for you.

And I think that it gives you the freedom and security to jump in and out of freelancing. You know, I've been lucky enough to have a kind of a wide variety of jobs, but you know, the other thing is when you go out on your own as a freelancer, It's really tempting to take a close to full-time job, right? I have a lot of kind of friends and people that I know that they go out freelancing and within the first 6 months, they'll end up with one client, which is like 4 days a week or, you know, 5 days a week for 2 weeks a month. Like they find these like close to full-time gigs, which, you know, pay well enough and they give them some security of revenue and all these kinds of things. And there's nothing about that which is wrong. Long, right?

That's great. If you can find that and land on your feet and enjoy it, then great. What I would say is just because your kind of free time is squeezed a little bit and because you have this kind of one stable thing, don't forget that you can keep building your network and you can keep getting the compound benefits of, you know, creating a personal brand, putting yourself out there. And I think that's the thing that I would commit to, to try and make sure that you're building sustainability for the future, especially because I grew up in the UK, but existing in the US is the kind of hire and fire at will and kind of the fragility of the modern employee, especially as a freelancer. You might get a 4-day-a-week thing, but if you're on 1099, then you're as fragile as a leaf in the wind in the scheme of things.

And so, you want to build some kind of resiliency and some kind of backup plan, which is, in my opinion, the network, right? Build that network and then you can always tap into it and leverage it and use it. Um, further down the line.

[43:28] Paul: Yeah, we definitely have some issues to, uh, figure out in terms of the future work here.

[43:33] Tom Critchlow: Yeah.

[43:33] Paul: So I would love to shift to some quicker hit questions.

[43:37] Tom Critchlow: Sure.

[43:38] Paul: What advice would you give to someone graduating college today?

[43:42] Tom Critchlow: Uh, all the same advice. Build a network. Um, uh, go work somewhere interesting. That's probably a good piece of advice is, um, yeah, we talk a lot about building a network and putting yourself out there, building a blog, but You can actually drift on the coattails of being at the right place at the right time. Now, you obviously can't know ahead of time where the right place and the right time is going to be, but I think earlier in your career, it is— I would encourage people to sacrifice pure revenue or stability in favor of interestingness. Like, go work at a startup, go work at the company in the blockchain space, or go work at the company in the virtual reality space.

The artificial intelligence space, like trying to do something less traditional will set you up better for the future. Obviously easier said than done, but right.

[44:30] Paul: So someone's sitting in their cubicle right now listening to this and thinking about potentially taking a leap years down the road and isn't really sure what to do. What is one small thing they could do today that's going to help them take that leap?

[44:45] Tom Critchlow: I think it would— so there's two things I'm going to say. One is build a network, because I'm going to sound like a broken record and it's super important. So start blogging, put out content.

[44:54] Paul: So let's dive into that. You say build a network. What, what's like the smallest possible thing they could do either today, tonight, or this weekend, uh, that helps them do that?

[45:05] Tom Critchlow: When people think about blogging or writing online, I think one of the things that that people often overlook, especially when they're kind of getting started, is you don't have to write for everyone. And in fact, the internet is an incredible place for connecting, you know, people that have some specific interest or some specific overlap and getting them all to read the same thing. And I think that what I would encourage you to do is I think you should be having output online, whether that's writing or blogging or podcasting or vlogging, whatever it might be. But think about it as a way to create connection to people you're interested in. So think about people that you respect, you know, and when you create stuff online, literally send it to them. And I think this is a step that people overlook often is, you know, people are very approachable, right?

If somebody emailed me today and they said, hey Tom, I read your blog, I wrote this piece about why I'm not an independent consultant, why I have a 9-to-5 job, and I thought maybe it would resonate with you as a counterpoint. I'd love it if you could read it and share it with your followers. I would take the time to read the email, click on the link, and I probably share with my followers. And I think that, sure, I'm not Seth Godin, I'm not Tim Ferriss, I'm not like the most famous person in the world, but I have an audience and a network. And I think that people forget that they can just email people. And I don't mean like spamming people, I don't mean mass emailing.

I just mean like pick the 5 or 10 people that you really respect or you really like or you admire their output and create something that you think they'll be interested in and then write a personal email to them and say, hey, I did the thing. What do you think? Would love any feedback. Would love your advice. Would love your support in sharing it. And that's how you get started.

And so, I think that's kind of a good place to start. The second thing that comes to mind when you talk about, you know, how do you— someone who's got a glimmer in the eye of going out consulting is stop and ask yourself, like, look around you in your day-to-day work and really, really like self-interrogate on the things about work that turn you on? Like, which, which of the, which of the activities, or which of the moments in the day, or which are the types of work where you feel like you light up, right? And is that running a workshop? Is that creating a spreadsheet? Is it solving a big strategy problem?

Is it working with other team members? Is it project managing a project? Like, we're at whatever the, the format or type or piece of work is, and then literally just try and do more of that. Just lean into it more and more and try focus on those things that light you up. And when you can do that and when you start to get clarity around it, that's when I think people are starting to get ready to say, "You know what? I could go do this elsewhere." If you can't identify a passion like that, if you can't find it, I think you should keep searching for it before you make the leap.

Like making the leap to freelance or independent is not going to solve all your problems if you still don't know exactly what you want to do or you still haven't figured some of these things out. You can do a lot of that exploration within a company. You know, you like, most companies will have opportunities for you to go do education, for you to take a course, or for you to even listen in on other departments' activities. Like go exploring, right? Go adventuring inside the walls of the organization you're in, um, to try and discover the things that interest you. And if you can find those, then it becomes much easier to lean into them and to build a business around them.

[48:23] Paul: Yeah, I love that question. What lights you up? What is something recently you've read that's inspired you?

[48:31] Tom Critchlow: I'd say two things. One is there's a book that I'm in the middle of reading right now called Seeing Like a State, and it is exactly about what you mentioned earlier, Paul, about the idea that top-down change doesn't work. And it's all about how governments and cities and organizations try and impose top-down change and all of the ways in which it fails. And I just find it deeply fascinating. I think there's tons of analogies to consulting and organizational change that you can apply. I'm still in the middle of reading it, so I'm not going to pretend to know all the answers yet, but I think people on this podcast will get a kick out of that one.

The second thing that I read recently, which really had a profound impact on me, was a piece on Ribbonfarm. It wasn't by Venkatesh. I forget exactly who wrote it. I think it was Tyler. Called The Blockchain Man.

[49:21] Paul: Oh, I've read this. Yeah, I think it's Tyler Pearson. Yeah, Tyler Pearson.

[49:25] Tom Critchlow: That's it. Yeah. And despite the title, it's not actually about the blockchain for those who instantly get put off. I mean, it talks about the blockchain, but only as a backdrop or context for the future of work. And when you read the piece or when I read the piece, what struck me was we think about the freelance economy or the fluid nature of work as being a trend, trend for the future of work. And I think it's absolutely true, but the deep structural ways that will change society are as yet unexplored.

And when you read, he frames a whole piece around The Organizational Man or The Organization Man, which is this kind of piece of fiction from the '30s, I think, about showing up with a briefcase every day and being a member of a club and the structure in which the 9-to-5 member of a kind of company dictates and influences your life, and what the analogies for that might be in the future when we're all freelancers and fluidly working in, with, and around, and for different organizations. And so it really inspired me to think about what are the other ways in which culture and lifestyle and work and revenue and so on will change as we enter a more and more fluid society.

[50:43] Paul: Yeah, I'll link up to that article for sure. That, that is one that, uh, definitely has me thinking about, um, the future of work and what that means for how we build communities and work together, collaborate. And, uh, super helpful. I love those. Um, well, it was great talking with you today. We'll have to see if we can, uh, get Ribbonfarm to, uh, sponsor us.

[51:06] Tom Critchlow: We had enough shoutouts to them, but, uh, yeah, yeah, yeah, yeah, definitely come I was a bit of a fanboy today, but if you don't know about Ribbenfarm or Venkatesh, then you should.