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Boundless Podcast - Stephen Warley on the biggest shift since the industrial revolution (Episode 19)

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“Work as you know it is currently changing in fundamental ways that we have not seen since the industrial revolution”

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Stephen has been self-employed for more than 18 years.  At first, it was by accident.  He referred to himself as a “reluctant freelancer.”  We talk about how that mindset evolved into one where he now sees self-employment as THE option for today’s world.  He is the founder of Life Skills That Matter, a platform, and community to help people to build the real skills they need to build a life they are proud of.

There are many future of work “thought leaders” but that title would sell Stephen too short. He has been in the weeds experimenting in his own life and has helped hundreds of people carve their own paths in the world I would instead call him the wise elder statesman of the freelance economy. If you have ever thought about working for yourself, I recommend Stephen’s work over my own.

Stephen puts the emerging trends bluntly: “The only work left is managing yourself.  If you’re going to manage yourself, you might as well work for yourself.”

To get started, he pushes people to “work on creating…you’re not just going to get paid right off the bat, just enjoy the freedom of creation of whatever it is that you want to do, whatever form that is, however, you want to do it without judgment…just start doing that.”  Because that’s what really gets people interested when you can share your creations and there’s nothing more human than that.

Transcript

Stephen has been self-employed for more than 18 years. At first, it was by accident. He referred to himself as a “reluctant freelancer.” We talk about how that mindset evolved into one where he now sees self-employment as THE option for today’s world.

Speakers: Paul, Stephen Warley · 146 transcript lines

Read the full transcript

[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 Stephen Warley, who's one of my favorite people and the founder of Life Skills That Matter. He is passionate and devoted to helping people figure out how to create work for themselves and work on their own. He's been self-employed for 18 years about, and was at first self-employed reluctantly.

Reluctantly, he was ahead of the game, figured it out, and decided he didn't want to go back to working a full-time job. We'll talk about that journey and more about what he's working on. He is working on a book talking about the only work left, which he says is going to be self-employment. That's what our future looks like. I think you'll enjoy the discussion today. It was pretty lively and energetic.

Thanks again for listening and enjoy the pod. Stephen, welcome to the podcast. Looking forward to talking to you today.

[02:22] Stephen Warley: Thanks for having me. I know you and I are never at a loss for words when it comes to talking about the future of work.

[02:27] Paul: So the first time I talked to you, I think you were one of the first people I connected with after taking the leap to freelancing. I felt like I found someone that was very similarly wired and driven to help people do work that matters to them, help people figure out paths that make sense to who they are. Where does that drive come from?

[02:52] Stephen Warley: I also love— I'm so excited. I'm one of the first people. This is so exciting. And I'm glad you found me. I'm glad I found you. I talk to people all the time.

I just want to pay a huge compliment because you really understand it in this really deep nuanced way about what is happening with work in a way that I don't have the freedom to always talk to. And that's why I'm glad we've talked quite a few times and we get to share a conversation like this now. I think a lot of times people are just afraid about automation and that sort of thing. And that is just one small part of what is happening to work and how it's going to change in the roles of our lives. So, I'm glad we connected on that and it's fun to really expand our minds in that conversation.

[03:33] Paul: Yeah, that's great. So, I want to put a pin in that. Let's talk about how everyone's talking about automation and I want to bring that up. But first, where does the drive come from? For you? Like, you've helped so many people take the leap to self-employment.

Why, why are you doing this?

[03:53] Stephen Warley: Well, I had a good friend of mine, William Moore, who really pressed me on this a few years ago. He's like, why are you doing this? And I would give him these answers like, no, why? Like the deep-seated emotional response, you know, why are you doing this? Uh, because I'm probably doing this because I know how lonely it felt when I got laid off on Election Day, 2000. And that, that, uh, we are going to go through a big transition, like in life, the last thing you want to do is go through that alone.

And I've really learned that it's so important to surround yourself with like-minded people or people like you and I, just having that genuine understanding, or at least a tacit understanding, uh, because a lot of times back then for me, people didn't understand. So, uh, I really, but I still felt like that drive to say, you know what, For some reason, I feel like work is changing even way back then. I felt like I'm a highly motivated person. I'm a smart guy. I like working. I just don't like how I was taught to work or the way I'm supposed to work.

I think I'm a bit of a contrarian and a rebel, so that's what also drives me.

[05:03] Paul: So it never felt right, but I mean, that's actually pretty impressive.

[05:07] Stephen Warley: But I played ball. I played ball though. I was a good employee.

[05:11] Paul: But in 2000, thinking that the environment of work is going to change is pretty radical. People must have thought you were a bit crazy if you were telling people about that.

[05:23] Stephen Warley: Yeah. I mean, it is. Well, even today, which it bums me out. Today, if you're listening and you're like in college and you are struggling to, because you want to work in the way that Paul's been advising you to, the way that I'm advising you to do, and your parents are like, "I don't know." I mean, Paul, it bums me out. Like there's still people in college today right now who are struggling to explain this to their parents about why they want to work in these new and different ways. And that's why I do what I do.

It's a big education because we have to provide people with the language to help this, to explain to other people, like, I'm going to be okay. It's all legal. It's what I want to do. It's how I'm wired. But a lot of times, we really need to take the time to explain that to our loved ones, our family, our social circle. Otherwise, you're going to get trapped doing the work you think you're supposed to do just to make other people happy, but you are miserable on the inside.

And that is like something I will not tolerate from anyone.

[06:19] Paul: All right, well, talk to me how this is possible. A lot of pushback I get is that, oh, you work for good companies, you can do what you're doing. And I, I will often counter to them and say like, everything I'm doing, the clients that hire me, I need to put my reputation on the line every time. I need to actually be good at what I'm doing because in contract work you can get fired at any second. So like maybe to those college students or early career professionals, I mean, you've talked to a lot of people that have taken these leaps, but how would you think about even taking a first step to carving that different path, even if you are employed or thinking about taking a job?

[07:00] Stephen Warley: Well, the first step is a little bit different for somebody who is still in the early, early stages of their career of being in college versus somebody who's been 5+. Let's start with 5+. I'm going to assume a lot of your listeners are probably knowledge workers in some capacity, which is actually the easiest genre of employment to convert into self-employment. And I talk to lots and lots of people within a 2-year period, even less, they will end up making the same amount of money per year as they did in their last job. Difference is they can do it in a lot less time because their hourly rate, that means, dramatically increases. So, the first step is, it's really a simple one.

Actually, somebody recently asked me this. I like to really break things down and not overthink this. You got to make time. Right? You are in this river of energy of being an employee and all that, that, that comes with all that lifestyle, the thoughts, the everything that you're supposed to be. So the first step is in order to kind of like start pushing back at that raging river is you have to leave work on time and don't go in any earlier than you have to.

And the people I work with on average, they work an hour extra a day from what they were originally hired to do. So I'm saying, take that hour back. That's yours. And then, when you have that hour, you have to schedule time. If you're serious about doing this, you have to schedule time on your calendar just— and I always tell people, "You are now your most important client." And for a lot of people, that's kind of a radical concept to say, "Whoa, I never thought of myself. I'm a client." And when you really put yourself a client meeting on your calendar, I always tell people next is then write a very short list of like 2, no more than 3 things that will prevent you from having that meeting.

Obviously, if there's like a family emergency, a healthcare crisis, please, if you're having a heart attack, Cancel that meeting.

[08:49] Paul: So it's almost like you're— I love that step because it's almost acknowledging the excuses before you're about to make them.

[08:57] Stephen Warley: Yeah, you know, you know me too well, Paul. Like, let's bat those excuses right out of the way. And that's what the two things people tell me why it's most challenging to do this. I don't— I can't find the time and I have all these fears and it's like, great. I've heard that so often. I know how to dismantle all of that.

Because really, when you're making the shift from employment to self-employment, you're starting to change your identity. So, all of a sudden, that step to saying, "I'm going to leave work on time," you're starting to change your identity. You feel weird because it seems like you're leaving work early, but the rest of your— and you're going to start feeling judged, but it's like, you know what? You got to push back at that. That's this idea we want to be accepted. You have to really start pushing back and say, "No, this is what I want." And the benefit of not only using that hour to start working on your day is it's going to force you to start thinking about how to make your existing workday more efficient and more productive because we're all wasting time with office politics, water cooler talk.

[09:55] Paul: Yeah. So, in one of my previous jobs, I stopped accepting meetings. I like you. I mean, there's this—

[10:04] Stephen Warley: Why were you not in my life sooner?

[10:06] Paul: So, I will acknowledge I think there's a certain recklessness to— like I tell people, you need to be a little comfortable with dropping the ball at work. Work because you're creating space for potential future opportunity. But so I did this. I would like try these things while I was working. I always thought if I'm going to give people this advice, I got to try it on myself. But I started rejecting this one meeting, which was really just like a catch-up call and talking about people's meetings.

And the side effect was that people would follow up with me and say, oh, you must be swamped. Like, are you doing okay? It was like, really? No, it was just creating more space.

[10:44] Stephen Warley: But to add to that, I remember when I would— my last business, I was a sales trainer. I did consulting and a lot of different aspects of that business, but I would have client calls and I would always limit them to 30 minutes every single time. And when I started the call off, especially if it was a group, I would say, listen, I got to go in half an hour because I have something to do, whatever it is. And people would just never. But it kept people on track. And I'd be like, 20 after, we still haven't gotten to what we need to get to.

I'm like, listen, I only got 10 minutes left. I'm like, okay, yeah, yeah. So what it is, it's just constantly remind people will fill up and waste time at every turn and every opportunity. So you have to set—

[11:20] Paul: it's called Parkinson's Law, right?

[11:23] Stephen Warley: I don't know, you got to get me on that.

[11:24] Paul: Yeah, Parkinson's Law, I believe that's it. It's, uh, it's basically the work is going to expand to fill the time.

[11:32] Stephen Warley: Yeah, I've heard the concept. I know.

[11:33] Paul: Yeah. But it's pretty fascinating anyway because people will—

[11:38] Stephen Warley: and but also I then I kind of got a reputation among my clients like Stephen the Taskmaster, you know, he gets things done. And it's just because I don't like wasting my time and I like getting things done because I'd rather go do other things. And that's the other thing that you really realize when you start working for yourself. You have all that time back in your life. You can actually get what you need to get done in a lot less time. The whole 8-hour workday or the myth of the entrepreneur constantly working 60, 80, 100-hour weeks.

That was never me. It's about knowing what needs to get done, what do you want to accomplish. Obviously, in the learning curve phase of that, it's going to take a little bit longer, but then you have a really good idea how long things take and just get it done. Yeah.

[12:21] Paul: Well, I'm interested to hear what you think about that too because I think almost the misconception that if you're going to be self-employed, you need to be this entrepreneurial type person that is just absolutely hustling and crushing it.

[12:36] Stephen Warley: I think it might— what does that mean, right?

[12:38] Paul: I don't know what the hell those words mean. But recently, this is—

[12:41] Stephen Warley: I'm glad you bring this because it's kind of bugged me. I feel like the universe is saying something to me right now because I've come up against this a couple of times. Even somebody wrote on a LinkedIn post recently about what it means to be a real entrepreneur, and I took great offense because what I— when I, when I hear that out there is There's a couple of ways to look at this. Number one, I, we, I think there's a lot of people feel like the definition of entrepreneurship is the Silicon Valley definition of entrepreneurship, right? That you do scale up, grow super fast, and then exit and make a lot of money. Then you're, then you're allowed to call yourself an entrepreneur.

But what about the person who's created a job out of nothing? They pitch themselves to a company. I mean, to me, that's an entrepreneur too. And I know there's a lot of people throwing that entrepreneur label around a lot and they're not doing any actions to back it up. I do have a problem with that. You know, I don't like people who are just calling themselves a writer and they're not writing anything or they're calling an entrepreneur and they're not doing anything to really build a business.

So, the happy medium here is to— I actually wrote a whole blog post about this. You get to define yourself in the way that you feel comfortable. And that's really one of the biggest shifts in work. It's about deciding what makes you productive, how you like to work, who you want to work with, what you want to work on, what your work style is. For me, I don't have aspirations of being a millionaire or billionaire. That does not make me feel successful.

What makes me feel successful is that I get control. Control over my time. And when I want to spend time with my family or have another life thing that happens, I can adjust my work in such a way that I can do that, right?

[14:12] Paul: Yeah, it's a privilege.

[14:13] Stephen Warley: I recognize it, but it's hard to, to give myself that privilege.

[14:16] Paul: Yeah, I try to reject the term entrepreneurial or entrepreneur for myself. I think there is the act of being entrepreneurial, which is basically putting ideas into the world and being terrified of— being terrified in that moment of, uh, what it feels like because you're creating something new. You're testing new ideas, new perspectives, or creating work on your own that's really your own responsibility.

[14:41] Stephen Warley: And I think that's really what's happening to work to me, I think. Even if you're going to be traditionally an official traditional employee with a W-2 form, corporations even right now are requiring you more and more to make more of your own decisions, manage more of your own time, and to think for yourself because everything is happening so fast. Everything is accelerating so quickly now that it doesn't have enough time to go up through the chain of command anymore to go, ask somebody, like, should I do this or this? Sometimes you just got to make a decision on the spot. That's what you're being hired to do, right?

[15:12] Paul: And that's, uh, that's Seth Godin's Lynchpin, which I read because of you. It was, uh, amazing.

[15:17] Stephen Warley: One of my favorite books. A lot of times people— I guess everybody else likes all of his other books, but I think that's one of his better ones. I think that's the call to arms book.

[15:25] Paul: Yeah. And I listened to a podcast with him. He actually listed his own book Lynchpin as his top 3 favorite books.

[15:34] Stephen Warley: He's a great guy.

[15:37] Paul: He also has a blog post I've read which breaks down the dichotomy of freelancer versus entrepreneur. And he says too many freelancers think that like, "Oh, you have to build a business. You have to be big. You have to be—" And it really comes down to as a freelancer, you're thinking about creating things and getting better at creating those things, creating remarkable experiences. And that's really where you can build a sustainable path.

[16:02] Stephen Warley: And what really happens when a lot of, especially when you're going to be a first-time business owner, entrepreneur, freelancer, whatever, it's, you're going to end up trading your minutes for dollars. You're still going to kind of function like an employee. Like what I mean by that is you're going to create work in a specified period of time and get paid for that project or that time. And you have to keep doing that over and over to get really good at that, to see the nuances. So that way then you can have enough knowledge to say, ooh, I see an opportunity, a problem, a challenge that I can create an application. I can create a course.

I can create some other sort of digital product physical product. And that's when you can be creating what people would refer to as more of a passive income revenue stream. But it's rare that you can get out of the first phase of getting your hands dirty. Like I call it, it's the handmade phase of your business. And you need to go through that. And again, just working with your hands, as people can't see me right now, Paul can because I'm talking with my hands right now because it's so important.

I'm a gardener too. I just We overlook and we're erasing that tactile nature of actually using our hands and connecting that with work. And I think it's so important, especially when you're starting out, because I think it really reinforces the neurons and the wiring in your brain as you're learning something new.

[17:15] Paul: Well, let's talk about your path. You've been self-employed for 18 years. What did that journey look like? What was chapter 1 for you as you were getting started and creating your own path for the first time?

[17:28] Stephen Warley: Chapter, the first chapter was 5 years and it was called Deeply Stuck. So, it took me 5 years to even admit or accept that I was working for myself or I was going to be an entrepreneur. Throughout that 5 years, I always thought I was going to go back and get a "real job," which now when people say that, I laugh. I'm like, "What does that mean? Real job? Depending on somebody else for your livelihood?

Come on. You're better than that." So, my very first— because I applied for all kinds of jobs. I was part of the dot-com bust in New York City, was working in media, not a lot of jobs at that time. So, it was the first time in my career, like, I just could not get a job. And so, I refer to myself as a reluctant entrepreneur during that period because I had to accept other alternative work opportunities that I might not have normally accepted for because I thought they were taught to be too risky. Being a freelancer or something like that.

So anyway, I got a gig as a freelancer putting together an interactive CD-ROM for this healthcare communications company in Greenwich. CD-ROMs, I love it. Dating myself, right? And I had to do all these things that I had never had to do before. I'm like, "Sure, I can do this." I'm like, "I just want to work." Funny thing is even though it still freaked me out like, "Oh my God, I have to keep getting clients and I have to deal with my accounting. How do I pay my taxes?" But Paul, it was up until that point in my career, I was in my mid-20s, I was paid more per day than any job I had previously had.

I was making more money. That's crazy. So that— so I decided to get an MBA, which now, if you're listening, you want to work for yourself, I advise against getting an MBA because it takes too long. It's too much money. The best school for learning about how to start a business is to start a business. There's lots of stuff online that is free or low cost for you to like at least getting your overview or concepts, build a community of like-minded people, get some mentors, but save yourself the $100,000 in the 2 years.

That's what I would recommend. So, I ended up going to business school and I left business school still feeling like I got to get a job. I was up for a job. It was like $90,000 a year. And then, somebody came along and said, "Why don't you do some training?" Because I was actually writing this column about the future of work for this website. And about a year in, a company contacted me.

They said, "Hey, would you like to come speak at our executive conference?" And I said, "Sure." I didn't even think to ask to get paid. I was just so flattered. Somebody's like, hey, come and talk to us. And then— What year was this? That was in 2003. So this is really the beginning of that, of starting to accelerate and seeing like, oh wow.

And then there was somebody else as a result of writing that column that had this training business. He's like, all these broadcasters, I came out of the broadcast world, they're like all asking about how to make money from digital. I think you could put together a training to do that. So he started selling me. I started making money from that. And that's when I was like, huh, I can work for myself and I can make more money than getting that job at MTV for $90,000 a year.

Right. And that was the beginning. And then I ended up at the height of that business. I was doing traveling like 2 to 3 times a month, doing speaking, training, consulting gigs. I had an online business with 600 videos, 35 trainers. I targeted State Broadcast Association.

So I sold this membership to them. So I had 32 of 50 of them as clients. So I was making like $600,000 a year working at about 20 hours a week by 2012. That's incredible. And then I decided that I was making a lot of money because I was in such survival mode for so long of just having to make money doing something I was good at, which is a very common first step in all this. But then I wanted something more purpose-driven.

Making all this money was just not enough for me. So I sold off the online portion of the business to one of my original trainers and slowly got rid of my projects until they were all gone by 2016. So I could focus full-time on what I'm doing now is really educating people about the changing nature of work and how it's changing faster than people expect and it's going to be almost unrecognizable in 10 years.

[21:30] Paul: I love that story. So, you moved on from that business and then did you found what you called Unstuckable?

[21:38] Stephen Warley: Yeah. So, in that transition moment because I'm also a big advocate of transitioning, I think there's the old myth of being an entrepreneur of like you got to like burn the bridges, max out your credit cards, get a second mortgage. I got to be all in. It's the only way you can do it. For some people, that works. For the majority of it doesn't and I was one of those folks because again, I was taught that you can't work for yourself.

You have to be an employee. So I was much more cautious about this path. So I did, as a research project, start this podcast called Unstuckable because I felt like more and more people are getting stuck. I'm like, what is that about? So I interviewed about 150 people for that podcast. And what was getting people stuck is that I discovered that people were working out of alignment with who they are, with who they are as humans.

But they'd never recognized this before or given the language. And I kept asking people, "What gets them unstuck? What's getting you unstuck?" And a lot of times, a very common one, you've done this for yourself, is travel, just getting away from your normal routines and journaling, doing a lot of writing so you can really start reflecting back at yourself over the patterns in your thoughts of what's important and not important to you, being around like-minded people. I always tell people, "If you want to work for yourself and your entire social circle is working for somebody else, 1,000 times harder to work for yourself. You got to be around people doing what you want to do. So those are some of those basic things that I learned about what got people unstuck.

That's pretty incredible.

[23:05] Paul: So what are some of the things that really helped people kind of have those aha moments and say like, okay, this is who I am? I mean, I think in a lot of ways, I mean, the way we're working in the jobs, I think most people would probably intellectually acknowledge that this isn't supernatural, right?

[23:26] Stephen Warley: It's unnatural, people. You heard it here first. The 9-to-5 lifestyle is actually an unnatural form of work, right? We have to— we have to— we design an entire education system to condition ourselves to think that this is normal.

[23:40] Paul: It's not, right? And but I think people probably acknowledge that. They say, okay, yes, that makes sense. But then how, how do you figure out how to understand what the major disconnects are for you?

[23:54] Stephen Warley: Well, let me back up a second first because this was the interesting question. As I interviewed these people, like who actually changed? Like who made this? I would generally say it was the result of a crisis in their life.

[24:09] Paul: Ah, interesting.

[24:10] Stephen Warley: The way it was either economic like it was for me, it could be a health crisis, whether themselves or another family member, or it could be a positive crisis like getting married or having a child. So, most people— and the other genre of person was they did have a natural tendency because that's the other thing I like to debunk. Everybody thinks like there's only a small group of people in the world who can really work for themselves. Yes, just like in anything else, there's a natural tendency for artists, for being a gardener, being a football player, whatever. But then, there's another larger group of people that can be taught this and through hard work and understanding the nuances of their nature, they can do it too.

So, I am just curious now is— so, then there's the natural tendency in the final group of people are people who had at least one influential person in their life, generally a parent or close relative who is an entrepreneur. Ah, okay. So, now I'm saying if I'm coming at this perspective and I think you are too, it's like we got to retrain the entire population. So, are we going to self-induce mass crisis? Are we going to have a mass existential crisis in America?

[25:16] Paul: Yeah. Well, can you manufacture a crisis or I mean, if you live long enough, the crises are going to come, right?

[25:23] Stephen Warley: Well, yeah. So, that actually does happen because we all have feelings. I know whether you believe this or not, you have this feeling inside of you, this thing you want to do, even if you're not quite sure how to articulate it right now. You feel it. That's why you're feeling a little off. You're feeling overwhelmed, stressed out when you come home from work every day or you get the Sunday night blues.

That is when they get stronger and it gets over time, those get stronger. And then especially when you add in a writing exercise, you start journaling about them or you start talking to other people. So what you're doing is starting to give some fertilizer to those feelings, starting to give them some recognition. And that is when they become really unavoidable. It's almost kind of another thing I've used and no disrespect to members of the LGBT community, but it's coming out of your career closet. You're like, this is what I always want to do.

You know what I mean? This is like my thing. I always wanted to bake cupcakes even though I'm on this. I interviewed a woman who was this very successful lawyer in Washington, DC. She gave it all up to run, to lead mountain expeditions all over the world. I love it.

Because that's what she discovered. That's what she really wanted to do. That was her essence, her center of gravity that she was never allowed to previously cultivate, that she feels totally in alignment now. With herself. But again, society deems these certain professions as what is successful, not successful. So, I think a self-induced crisis is coming as people— generally, I see people like as early as like their late 20s.

I think it's coming earlier now for Generation Z, even in college, they're recognizing that the gig is up. Some people, they never give themselves permission to explore those feelings. And I think a lot of times the other crisis is that people are in work and they're getting more and more frustrated about by not being able to work in the way that they know how to work. So, they go outside and create their own work. I interviewed another woman who was a research scientist and she had a couple of different jobs starting off her career and she felt that it was a very male-dominated culture that she would never be able to thrive as a woman in what she wanted to do. So, she started her own business.

She created her own reality. She started a subscription box service for 9- to 12-year-old girls. So, she sends these science experiments once a month to their— to them. And so she really took her own, what she saw resistance in the world and wanted to change it for the next generation. So I think there's a way. I think the way you can do a safe self-induced crisis, and I think the way to begin that is by journaling, like to start being honest with yourself.

You don't have to tell anybody else, but stop lying to yourself.

[28:04] Paul: Stop telling yourself stories. Yeah. I mean, something that has been— I haven't really done journaling per se, but I've constantly written down what my principles are. First, it started out kind of like career principles, more leadership principles, but kind of evolved more to life principles. And I would print those out and have a calendar entry on my calendar every quarter and just review those. And I realized a few years ago, I got to the point where I was like, I am just way off.

Like I can't hit the mark in the system I'm part of in the corporate world and be proud of like the person I want to be. So now I'm trying to create new rules and, uh, a lot more uncertainty and unpredictability, but, uh, definitely with— what's one of yours?

[28:53] Stephen Warley: More fun. What's one of your principles?

[28:56] Paul: Um, let's see. I think, uh, one of 'em is just about like never take anything too seriously. And I was noticing I was working with a lot of people that took a lot of the work we were doing incredibly seriously. And I think part of it was just like, perhaps they should be with other people that take it as serious as them, but I didn't take it that serious, the work we were doing. I didn't find any life-changing value in it. So that was one of them.

I mean, a lot of this stuff for me is about family and relationships and balancing that. And just the idea of like work-life balance kind of like it started out as a good idea. And like I never really worked crazy hours. I always had good quote unquote balance. But for me, I kind of realized I was starting from the wrong principle of like starting with the work, right? And why not start with life?

First design that and then like try to find work to fit it in. And I think that's much more how I've experienced freelancing.

[30:05] Stephen Warley: That is a shared belief I have too, is this idea of why are we squeezing life in around work when we should be designing work that fits our life?

[30:13] Paul: Yeah, what could be, what could be a better phrase for work-life balance? It's like, I don't even think like that.

[30:20] Stephen Warley: Yeah, it's like, it's a maybe an overused term. I guess it gets It starts a conversation, but I hear as a criticism, I still think we look at it in too linear a fashion. And it's too compartmentalized where I look at— I love in my interviews now, this is kind of quite a few times where people talk about their work in terms of seasons, whether it's regular seasons or in the seasons of their life. And what they mean by that is they might work really intense for like 3 months and then it might be a little lower for 3 months. Or they might be just focused on helping a family member for 2 years and then they work hard for another 2 years. And I had to do that this past— last summer.

My wife's father unfortunately got very ill and unfortunately passed away. We spent 3 months in Boston helping them. And my wife is a professor, so she had the summer off and I have the flexibility of working from anywhere, but I was still able to even restructure my business. Because when you've got anybody who's gone through something like that, guess what? That's the only thing you can think about every day. You can't think about anything else.

And the thing that bugs me is how many times, how many people are in traditional employment settings who you're penalized. You're not allowed to do that. You have to make choices. You know what I mean? And you can't be there. Yeah.

There are some good companies that do allow that, but they're too rare or too few.

[31:42] Paul: I wonder if it's counterproductive that those companies have such good benefits that like we kind of expect it to come from an employer. Rather than just being something we should be doing. But I don't want to go down the rabbit hole of political discussion.

[31:58] Stephen Warley: It's just understanding about what are your values, what are your choices, and that you should be able to do that. And I think a big part of this, and I think you and I share this too, is in order to make a lot of this happen is you really have to do what you can to simplify your lifestyle and be very clear in your expectations because I think, again, as a society, we are constantly conditioned and marketed to always want more. And when you really start realizing— when I went through this process, especially getting laid off, I had to really start looking at my money differently. I had to really start paring down and saying, "What's important? Where do I want to spend my money and where do I want to really be totally frugal about it?" And I think a lot of times, we're not walked through that exercise.

I've talked to you quite a bit about this idea of identifying the cost of your lifestyle. I do a whole calculator with people about it. If you're interested in it, you can go to lifeskillsmatter.com/calculator. Because everybody's saying like, how much money do you need? Oh, I need to make $100,000. I need to make $200,000.

I need to make $1 million. And I'm like, where'd that number come from? You have no idea. It just sounds good. Like, actually do the calculations based on what you want. And you'll be surprised, you need a lot less money than you think.

Yeah.

[33:04] Paul: And well, so I think the money thing is like, that brings up so much pain and insecurity. It does for me.

[33:12] Stephen Warley: I admit it.

[33:16] Paul: I've thought a lot about— we think we need money because we think we have to be completely self-reliant, but we're part of communities and we have connections of people that would take care of us. How have you thought about that?

[33:30] Stephen Warley: I mean, you and your wife— It's these two— again, this linear thing. We talked about work-life balance. The other thing that was diametrically opposed to each other is the this human need to survive, which is kind of represented by money right now in our modern society, and then this need to just be myself, my center of gravity, my essence, my tendency of like this is just as a human, I just want to do this. I can't explain why, it's just what I gravitate toward. And, a lot of times we look at these things as either/or that we can't have both. And, I think that is, again, another huge myth we need to bust that this is life.

We can't integrate all of these different things. I I think money, I think it's one of those things that you have to explore in yourself where you could do a lot of journaling or talking it out. And also, by the way, just journaling, sometimes it's a loaded term, but anyway, in the way that Paula described too is like any way that you can just get things out of your head, draw, take pictures, whatever way you need to express yourself is fine. You don't have to do a formal journal. Sometimes I do prompts. I have a prompted journal that I share with people.

What's—

[34:39] Paul: so what are some of the— like, give us 1 or 2 questions you might have people journal on.

[34:45] Stephen Warley: I'll give you all 4. All 4. These are the 4 questions you should ask yourself every single day if you want to make this transition, if you want to grow every day. Number 1, what did I learn about myself today? You're going to learn something about yourself, right? And that gets you starting to hone in on your self-awareness practice.

Number 2, what did I learn today that is going to help me achieve whatever goal or how I want to shift my life? Is it a skill? Is that a concept, a piece of knowledge? Number 3, did I meet somebody today? Are you building out your community? Did you follow up with somebody?

Because, again, you have to build that community of like-minded people. You are human. You are going to do this with other people, not alone. And finally, did I create something today? So, this idea, did I write? Did I tinker?

Did I do a prototype? Did I do an experiment? Something. These are all the things that we avoid in traditional employment. We aren't regularly reaching out to meet new people. We aren't regularly learning new things.

We kind of wait for our managers to tell us if we need to learn something new or not. We aren't always asked to develop ourselves. We're just viewed as a resource, not as a partner. And especially in work with corporations want things to be perfect. They want sure things. And that's just not the world that we're moving into so that we really have to create and express ourselves.

That's what what humans did for thousands of years to get to where we are. They were constantly just trying stuff out to see if it worked or not. Right.

[36:11] Paul: That constant tinkering and experimenting. So, I mean, from the outside in, it might look like, "Oh, Stephen's got it figured out." But what are you tinkering with these days?

[36:22] Stephen Warley: I will tell you one thing. One thing I do have figured out is that you will never have it all figured out. I know it sounds comforting and maybe I'm being a little glib about that. But there's actually a certain comfort in that of knowing like it can never be all figured out. And it's— and also we're moving into an era of accelerated change that we have never seen in human history, and it's only going to get faster. So it's going to be impossible for us to like be perfect, know everything, right?

Have it all figured out. So then it's— then it kind of just forces you into this more present moment of just like, I want to experience the highest quality with the time I have, the energy I have of whatever it is that I'm doing. So tinkering now, is a book and is writing a book that I've always wanted to write. I've written 2 books in the past, but they were for other reasons and somebody else's agenda. This is the book that I want to write about. And so, that is one project.

We can get into that if you want. But the other thing I'm tinkering on is always learning new things. I'm always learning different outreach methods. One thing I really fell upon, I recently did an accelerator with some folks looking to work for themselves, just how much we are— even if you're an extrovert, we really don't have really strong habits with continually reaching out to people and really developing those relationships. And it's so critical for your growth and development. And there's no one way to do this.

You can be a writer and more of an extrovert. You want to create content, or if you like networking, you want to go to an event once a week. So, you just kind of commit to that. So, one thing I'm doing for myself is I'm doing different marketing experiments every 30 days. And I hate even to say marketing. It's not that loaded way that people do.

It's more of this outreach way. I just want to see how I feel, what I learn. So, the first one I'm actually doing is reaching out to other podcasters like yourself to say, "Hey, I have some story ideas. I've been listening to your show. What do you think?" And just to really understand what is it like because it's not even just teaching me about how to get on other podcasts, but it's actually just teaching me like, how can I add value to them? How can they add value to me?

Or, what else am I learning in my journey as I actually have a As I'm reaching out to podcasts every day, I have different notes of different things I'm learning because that's the other thing. When you are creating and you're interacting with other people, back to those questions, right? I'm asking people to think about every day. You start learning about yourself. You start learning about other people. And that's the kind of funny thing is you really have to take action.

You have to do. That is the number one way to learn anything. You can't just have Paul telling you stuff to do or me telling you to do stuff or reading a book. That's a good start. But until you do it for yourself, you haven't learned it. Yeah.

[38:55] Paul: I don't know if I'm the best either. I might be telling people to do less.

[39:00] Stephen Warley: I do believe that—

[39:01] Paul: Take a day off and do nothing.

[39:03] Stephen Warley: Well, you'll be part of my next longer-term project after helping people understand the future of work. A buddy of mine, William Moore, I think I just mentioned him earlier, we want to start the slow life movement. Oh, wow.

[39:16] Paul: I'm on board. I don't really know what it's about, but—

[39:20] Stephen Warley: And it doesn't mean like not doing anything and it doesn't mean that But it's just about having priorities. I think it's already infused in a lot of what I'm doing is to understand what it is that you really want and having the courage to not fall in and get sucked into all this other stuff that you really don't want but different parts of your brain wants to be accepted. So it's just kind of creating some guards against that.

[39:40] Paul: Well, I need some slow lifers to hang out with because part of my journey, I've kind of decided that I'm not trying to maximize earnings. I'm actually trying to work less to create more space just for being generous, volunteering, or just literally being a layabout, a term I stumbled upon. But I need other slow lifers to hang out with. Last week, it was like 80 out and I was just wandering around the city by myself. But I could use a community of slow lifers who want to take some days off during the week with Yes.

[40:17] Stephen Warley: And we're going to make some time to get up to the lake in Connecticut. Awesome. Chill out, talk about life, floating around on a raft.

[40:28] Paul: Exactly. So what message do you want people to take away? I think you went into this earlier. In the podcast, but like, what message would you leave people with?

[40:48] Stephen Warley: The title of my book, The Only Work Left. The only work left is going to be managing yourself in some capacity. And I have to say, if you're going to manage yourself, you might as well own yourself. So work for yourself. And the things that you're going to need to work on to figure that out is you're going to work on yourself and really get into understanding what makes you tick, your motivations, your energy levels, who you like to work with, what you like to work on, how you like to work in a way that you have not been given permission before. Number 2, you have to work on your relationships and really building up your community, your tribe, whatever you want to call it, your peeps, your crew of people who really understand what you do and what you want to do.

And they're going to challenge you, they're going to support you. They're not going to just be a bunch of yes people, but they're also not going to be a bunch of negative Nancys and telling you no. And finally, Work on creating. You know, you're not just going to get paid right off the bat. Like, just enjoy the freedom of creation of whatever it is that you want to do, whatever form that is, however you want to do it without judgment. Just start doing that because that's what really gets people interested.

We can share your creations and there's nothing more human than that. So, that's what I just want to let people know that my biggest kind of the alarm bell I want to raise to everybody is that work as you know it is is currently changing in fundamental ways that we have not seen since the Industrial Revolution. And I don't think the leadership of our society is raising the alarm bell loud enough. And I think it's the greatest policy crisis of our time. Well, I look to you as a leader.

[42:16] Paul: So I think there are some leaders doing some good work out there. But so people are definitely going to want to reach out to you after this and find out about your work. How do they work with you? How do they find out more about what you're doing?

[42:30] Stephen Warley: I think the best place to go is lifeskillsmatter.com/getstarted. I have a whole bunch of free resources to get you started, the first 5 steps to self-employment. You can also tweet me. That's my preferred social media platform, slowly getting off of Facebook. And drop me a line, Stephen Warley, S-T-E-P-H-E-N, @lifeskillsmatter.com.

[42:52] Paul: Awesome! Thank you so much, Stephen, and keep fighting the good fight.

[42:55] Stephen Warley: Great. And you too, my friend. Thank you.

[43:02] Paul: Thank you for listening to the podcast. This has been an incredibly fun experiment for me, and I'm loving talking to such incredible guests. I've received some awesome feedback, and I appreciate all the suggestions and just the praise. I'm kind of blown away. It's just so amazing to have such positive support. I hate asking for further support, but would love if you could share or recommend the podcast to one friend.

If you are inclined to support more, I've actually set up a Patreon page which I am experimenting with and potentially going to release some exclusive content. And with the goal of building a community of people who are passionate of making sense of the future of work and enabling people to do work that matters to them. To learn more, you can check that out at BoundlessPod.com. Again, thanks for the support. And if you have ideas, questions you want me to answer on a future Q&A podcast, or just suggestions, would love to hear them all. Please email me at paul@think-boundless.com.

[44:13] Stephen Warley: Com.

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