Focused - 25: Breadcrumb of My Life, with Stephen Hackett

Episode Date: July 11, 2017

Relay FM co-founder Stephen Hackett discusses his origin story, including an abortive attempt at being an Apple blogger, a fateful meeting over tea with Jason and David, how he left his job to become a full-time podcast entrepreneur, and the personal challenges he first encountered when he went independent.

David Sparks and Jason Snell spent their careers working for the establishment. Then one day, they'd had enough. Now, they are independent workers learning what it takes to succeed in the 21st century. They are free agents. Welcome back to Free Agents, a podcast about being an independent worker in a digital age. I'm David Sparks, and I'm joined by my fellow host, Mr. Jason Snell. Hi, David. How's it going? Good, Jason. We have one of our special interview episodes now, don't we?

Yes, we do. We do. And this is a friend and someone who listens to Relay may know this gentleman. He shows up on it once in a while. Welcome to the show, Stephen Hackett. Hey, you know, I was a little misled. I thought Matt Alexander would be here reading the intro live, but he's just a file. They are free agents. Yeah, we don't want to rely on Matt for anything after the one time, so we just play that file back and he's our excellent, most excellent of announcers. I'm not supposed to have favorites, right, amongst the podcast.

But I think y'all's intro is probably the best intro. It is. It's pretty good. After Matt read that, he got into a car that turned into a submarine and he disappeared. That's true. There was a smoke screen. It was just an amazing kind of assemblage. So we talked to Mike a while ago, Mike Hurley, for those who don't know or remember,

Mike and Steven are the co-founders of this podcast network that we're on. And both of them, at a similar time to when David and I left our jobs, they left their world of employment and went out on their own. In fact, it's funny, not half an hour ago, Steven and I were recording a different podcast. And completely while I was making my lunch in between podcasts, because that's my life now, I was thinking about Stephen and about like how his era of fun employment, as we call it, was going. And then I thought to myself, oh, you know, I'm going to be talking to him in half an hour about just that so I can ask him about that.

So, but before we get to that, we should probably maybe Steven, have you explain a little bit about what you do today and all your projects and stuff that you're working on now. So people can get a sense of where you are now. And then we'll talk about how you got here. Sure. Yeah. So, so primarily I am the co-founder of RelayFM. Mike and I started the business, I'm sure we'll get into this, back in 2014. And I oversee about half the company. He oversees about the other half. And that is my job. I do some other stuff, too.

I've had a blog since 2008 called 512 Pixels. I write about Apple and tech and journalism and design. That blog has since spawned a YouTube channel, as these things go. And I do just the tiniest bit of freelance writing and consulting and stuff on the side. But my primary thing, the thing that puts most of the bread on my table, is this very podcast network. All right. Very nice. I feel like we – this is one of the original free agents episodes took place in the tea house in San Francisco right after we quit. And, uh,

Steven was there with us contemplating it. And that was one of, you know, that was one of the formative experiences for making the show happen. So yeah, Steven's been a part since the beginning. We may be jumping ahead a little bit, but the four of us, so the two of you and then Mike and I were having tea at WBC, I guess, two years ago. And I was on the fence of quitting my job and we had a really meaningful conversation. And that was one of the factors that led me to go ahead and do it. And I ended up quitting my job not too long thereafter, but I'm sure we'll get to that. There was some peer pressure involved. And I ended up quitting my job not too long thereafter, but I'm sure we'll get to that. There was some peer pressure involved. And I don't just mean that we were all sitting there

going, do it, do it, drink some more tea, do it, do it. But you did have, and we will get into it, but you did end up sort of leaving your job and going full-time independent worker a little later than the rest of us. So you got to kind of watch us take the take the dive into the into the pool and make sure that there weren't like sharks or piranhas or something yeah before you yeah big bankruptcy sharks looking at the bottom of the pool what i'm saying is you're smart you've waited waited on us to see just just how it was gonna go katie floyd told me once i was definitely her canary in a coal mine before she went solo. She wanted to see, you know, if I crash and burned. Yeah. I like that. All right. Well, let's go, let's go back a little bit. Um, uh, you didn't just start out as an independent

worker. At one point you worked for the man. I did. I've worked for a lot of mans, uh, men's men worked for a lot of mans over the years. yeah yeah yeah so uh like jason i have a journalism degree i went to school for journalism uh i studied newspaper design and layout so you know not really using cork express very much anymore booming industry yeah yeah it's like learning it's like you know i was like the last generation of j school students i think to really learn some of those skills that have really faded away. But I, you know, the student newspaper in high school and then in college, some of my most formative years, some of the most formative times in my life took place in those two rooms where I learned how to write. I met the Mac for the first time in my high school newspaper.

I discovered that I could use a computer to take an idea in my brain and publish it into the world where people could see it and enjoy it. And that drug that I was introduced to in high school is what, like, I still love it today. Like, I can just have an idea, whether it be an article or a video or a podcast, and I can work on it. I can use technology to help shape that idea and form it into something real and then put it into the world for people to hopefully enjoy. And that act of publishing,

I just love. And like a lot of people who do it, I'm sort of addicted to it. And I just, I love that the idea, the idea of creation and then sharing them. That's really been something that's been with me since those early days, you know, as a high school and college newspaper student. And I, I quickly learned, uh, watching friends graduate college before me that going into print journalism, at least, um, you know, uh, in, you know, 2008, 2009 was probably a bad idea. And newspapers were folding and the economy was a mess. So I ended up working in tech. Most of my career before now has been in IT. And I learned those skills at the college newspaper in particular and decided that I've kind of got these two routes. I've got the technical side and have the creative side, and maybe the technical stuff

can pay the bills and it would allow me to be creative on the side. And that's really where I was for, you know, almost a decade of being an IT person, but then having a blog and podcasts and stuff I did in the evenings and on weekends and during my lunch break. You know, I'd like to talk about that for a minute because I know, Stephen, that RelayFM wasn't really your first push to go independent, was it? It wasn't. In, you know, 2010, 2011 sometime, I really put my foot down on the gas with the blog and tried for a while to see if I could grow it aggressively enough to go full-time on that. And along with some freelance writing, I was doing some freelance at the time. And it didn't work for a bunch of reasons.

One, I think if you have a website, it's going to be a full-time job. Most people need it to be more than one person. And I just couldn't keep up with the demands of that, just being a single person working on it part-time. And the money just wasn't in it. As little money as there is in now in web publishing, you know, articles and blog posts, there was more money then, but it still wasn't enough to support a growing family. And that was a really hard time because I really wanted to make it work. And I really put a lot of energy and focus into it and it just didn't pan out. And so I kind of backed off and decided to really focus.

I started what would be my longest job around that time and really decided to focus on that and once again put the website sort of on the hobbyist level. But I do like that story because I think there's a lot of folks out there that are getting ready to try and make a push towards some kind of free agency. And I think the way you did it is very wise going out and starting a side thing on the side. You're not necessarily quitting your job with no stream of income. You were trying to build it up from underneath. So then eventually you made enough money off of it that you could quit the day job without, you job without turning your life upside down. Right. But the interesting part of your story is you eventually realized that we're drilling an empty well.

We're not going to get enough out of this. Yeah. And it was a hard lesson. But what I walked away with it from is I think it would have been easy to turn my back on the writing and turn my back on that website. But really what it did was make me fall in love with it all the more, like no matter what happens with Relay or my independent career, you know, if it, something happened and ended tomorrow, I would still be blogging at 512 pixels. Like that's just, A, it's become a breadcrumb of my life over the last decade, but it is something I will always have. It's something that will always

be a part of me. And it was only after that experience of really trying to make it a full-time thing and, you know, it not happening, it not happening, not happening, where I was finally able to appreciate it for what it was, a creative output that, you know, it makes money and it helps pay the bills, but a place where I could experiment and do weird things and, you know, write long form stuff. things and, and, and, you know, write long form stuff. Uh, I once reviewed, uh, I've reviewed a couple of smartphones as, as like haiku poems, uh, much to the dismay of the PR people hooking up with those phones. Um, but it allows me a place to be creative without any strings attached. How long did it take you to realize that, that that plan wasn't working? I mean,

cause you were, I remember at the time you were writing a lot at 512 pixels. Yeah, it was probably a year. And, and in that year I was doing some writing for some magazines, some, you know, e-magazines and some other stuff. It was probably 12 months, I think of, of really, you know, really hammering on it. And I think in hindsight, I should have seen it sooner, but I was just like heads down. I wanted to give it time. Um, but at some point I realized that I was putting all this effort into it and it was too much effort for the reward coming out of it and that I needed to rebalance those things. So what was going on in your, um, in your work, work career at this point, were you, were you moving to different jobs? Did you have a single steady job that you worked at for years while this was going on?

Yeah. So out of school or towards the end of school, my timeline is confusing because I took seven and a half years to finish an undergraduate degree. Kids, don't do that. So there's a lot of overlap. But when I went from being a full-time to a part-time student, I worked at my local Apple store as a genius. I worked there for two years. When I quit that job, I went to go work for a consulting agency, and I managed an Apple service provider within that company.

That first day of that job is when I launched the website. Oh, I see. Okay. Because I couldn't blog about Apple when I worked at Apple. That's a great way to get fired. But when I left Apple, I thought, Hey, I have all this insight from being a full time employee for two years and a manager and like leading this genius team and eventually helping lead two genius teams. Like, uh, I can blog and use that as a filter for my, you know, my thoughts and opinions. And that's faded a lot over the years, but that was really sort of the hook at first. That business, unfortunately, did not survive that economic downturn we spoke

about. And I landed at the Salvation Army. I spent five years there planning, building, and opening 100,000 square foot community center. So I was in charge of all the IT, all the audio video, all the infrastructure, everything from like the emergency phone line. Like if you're in the elevator, you pick up the phone, like that phone line all the way up through, you know, hundreds of thousands of dollars of sound equipment that was all under my department. And it was really the beginning, like kind of that overlap between those two jobs or my, it was hammered down on the website. And I sort of realized like this job I had taken in the South East Army was really big. And I think there's a whole interesting conversation of like taking a job you're

not prepared for. And I had to really learn a lot as I was on the go, right? Like, okay, I've got to figure out all this networking. I need to learn a lot about networking. I need to hire people who are better than I am in these different fields. And I really just needed to focus on that job. But I spent five years there. And it really showed me that IT long term probably wasn't for me. Like the next level up in IT wasn't anything that was super interesting to me. But it was also in this time where I started podcasting for the first time, you know, super on the side with Mike Hurley. We met in 2010,

and started doing a couple little things together. And so, so, you know, school was winding down, I was at Apple, I left Apple podcasting started spinning up, it's sort of muddy there in the middle. But there was definitely a gradient where, you know, I was, you know, leaving school and turning into I, you know, an IT guy, but then adding journalistic endeavors again as a side project that is kind of always there in the background. So when you decided 512 Pixels wasn't going to support you and you were going to make that like a little side thing with no intention of turning it into a career, then for a while, you were just a company man. But at some point, the seed got planted again to go out on your own.

Do you know when that was? Yeah, absolutely. So I left the Salvation Army after we got the building open and went to work for an agency here in town. We did custom web work for clients, all client work. And I ran their project management team. About that time is when Mike and I started really talking about going out on our own with our podcasting. So we had been on the 5x5 network with a bunch of our shows and experienced a lot of growth there. It was a huge opportunity for us. We were kind of talking about what the next

thing was for this podcast thing we were doing together. At the beginning, I'm not sure I was thinking about it in terms of this could be my job one day. I think surely that was in the back of our minds. I think it was more in the foreground of Mike's mind than it was in my own head. But it was more about, you know, we want to control the entire thing for our podcast. And if it becomes a job one day, my line of thinking was that'd be great, but I just took this job at this agency. I really like it. I'm making really good money. Like I don't want to rock this boat. You know, I kind of thought, I think that if Relay is like five, 12 pixels, right, I can put time into it. I can, you know, have a place to be creative and it makes some money. Uh, the, Hey, that's great. I got play money. I can put it in savings.

I can save for my college, you know, fund for my kids. Um, but still that's great. I got play money. I can put it in savings. I can save for my college, you know, fund for my kids. But still have a job with insurance and, you know, salary and stuff. But that, that quickly changed. I think once we get into the conversation about Relay, where it went from an idea of, this would be a fun thing to do and a fun place to have and a fun thing to build to, Oh, this could be a job for Mike and, oh, this could be a job for me. You know, I didn't have an idea going into it, a real clear idea going into it, where it would end up, but I thought there was potential there at the very least. brought to you by Casper. Get $50 toward any mattress purchase by visiting casper.com slash free agents and using the code free agents at checkout. Now you may be listening and thinking why you should buy a mattress over the internet and have it delivered to your house. And let me

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casper.com slash free agents and using the codeagents at checkout. Terms and conditions apply. Thank you so much to Casper for all of their support of the show. So I guess we've reached the point where you decide to take the plunge. Yeah. So I think the timing of Relay is important. So we launched in August of 2014. So we're coming up on almost three years. We made it about a quarter in and Mike quit his job. That was earlier than I certainly anticipated. I remember him texting me and said, hey, you know, can you call me? And Mike and I don't speak on the

phone very much. We do more now. But at the time time we didn't speak very often on the phone. And I figured this is, this is an emergency of some sort, right? Like something's happened with his family or like, you know, so, you know, I stepped out of my office and called and, you know, he was like, you know, I think it's time I do this full time. And I was like, whoa, like between the two of us, Mike is the heart and I'm the head. I was like, Mike, like between the two of us, uh, Mike is the heart and I'm the head. I was like, Mike, buddy, like we got to think about this. So basically his shoelace broke. And then he said, I got to call Steven right now. Was that the next step after his shoelace broke? Yeah. So we'll dig it up. If you haven't heard that story, there's an episode of analog about it. I'm sure he spoke about it on free agents. Uh, we could put those in the show notes, but,

um, you know, we had had spent our basically our life savings starting relay he and i both put a ton of our own money into it to get it get the website built and the cms done and the artwork done and and uh we we've never taken outside funding we we own all of our company but you know we we had just made to the point where we had paid ourselves back. We had paid our loans off to ourselves. And we had enough runway, we thought, in ad sales that Mike wouldn't be homeless, right? Which is like a really good bar to cross.

Like, are you going to lose your place where you live? No? Okay, let's keep moving forward. And so, yeah, so we were not real far into it and Mike quit his job. And as you may imagine, and what is super obvious in hindsight is that Relay's first big segment of growth happened after Mike quit, because all of a sudden we went from the two of us working on evenings and weekends. And if you never heard Mike and I speak, we're not from the same part of the world. Mike lives in London. I'm in Memphis, six time zones between us. And so we,

we always were like, you know, I was working late at night and sometimes we'd cross each other in the night where he'd be waking up and I'd still be up. And, and at the very least we'd hand things off. That's one idea where the name Relay comes from, like handing things off between the two of us. But all of a sudden Mike was in it full full-time as opposed to just stealing time here and there. And we saw a big increase in productivity. We saw a big increase in the efficiency of what we were doing. Ad sales got better. And we operated that way for a long time where Mike was in it full time and I was still just part time because I still had a nine to five at the agency. And, you know, I was working nights and weekends. I was stealing time from my employer, which I think is a fascinating topic. And you guys have touched

on in the past of like, you're supposed to be on the clock for somebody else, but you're working on your own thing. And like, I was guilty of that, like just hands down, I did it. And for all the stress that, you know, was created in that, like really wore on me. And I think I really struggled there for a while of, you know, look, my partner's in this full time and I'm not. And, you know, maybe it will never get big enough where I can do it too. Or, you know, is he going to grow to resent me because he's working 40, 50, 60 hour weeks on this and I'm putting in 10 or 20 hours? It was a real stressful time for me. And just trying to do everything I could for my business partner while also like keeping a job down. Like, you know, like I didn't need my boss to come in and fire me because I was doing this other thing.

And so trying to balance all that was really stressful for there for a while. And honestly, I think that that could go the other direction too. You could be envious of him that he gets to put all his time into this passion project and you have to go back to the man every day. Oh, definitely. And you start to feel angry or, you know, maltreated. Yeah. And that was, you know, thankfully that was only, I don't know, like nine months or so. I don't even think it was a year that we were in that arrangement.

And Mike and I, I'll speak for him too, our relationship is very good and it's very open. And if one of us feels like that, right, if one of us is upset with the other one or we feel hurt or there's something on our mind, we have always had a policy of just being straightforward with each other in that. Like we don't, we don't play games with each other and that sort of stuff. We don't try to hide stuff from each other. And part of that is that we're, we're, we're close friends. And part of that is too, is for this thing to work, then we need to be able to deal with things in a straightforward fashion as they come up. And so, you know, he and I had those conversations and he was very encouraging and understood, you know, my feelings on that.

I think I understood his. But, you know, eventually we got to a point where I was able to join him in, you know, full-time work. Now, one of the things that I think we definitely want to hear from you is the calculation you made to make that decision to leave. But before I get there, I'm going to postulate something here, and you can tell me if I'm right or I'm wrong. And I don't mean to—we all love Mike, but I will say Mike's situation when he decided to go off on his own while stressful, and he's talked about it with us, and he talked about it on Analog. while stressful and he's talked about it with us and he talked about it on analog mike was in a situation where he was leaving a good job that he didn't particularly love but he is not is not

married at that time still isn't but will be hopefully pretty soon um no kids and is his housing is fairly stable in that he is he is i believe at that point living with a family member and i don't know the details of if if the the pay and the paying the rent or paying the mortgage was partially dependent on him but let's contrast that with you married three young children and and uh and and a house you know presumably a mortgage um and sometimes i think that that these decisions to go out on your own like that is a calculation that we don't always hear about which is there's this modifier you have to multiply in the formula by how responsible you are for the livelihood of

your you know of the people around you and of your family and your cow you you have way more uh people relying on you at this moment in time when you're thinking of of quitting your job than than mike did so it's kind of understandable that it was not something that you were going to just jump into because it's different if you're a young you know a young single person who's living you know who's living at home and has like the money that you make is just yours to put in the bank, that's very different than if you're, I'm not saying that was my situation, but that's like one extreme. And the other extreme is your entire family counts on you for every dollar that takes care of the three kids and pays the mortgage. And that's a lot of a burden. That's a big burden

when you're thinking of leaving the regular paycheck, right? Yeah. I remember when my first daughter was born holding her. I mean, it's a big burden when you're thinking of leaving the regular paycheck right yeah i remember my first daughter was born holding her i mean it's a wonderful day but also at some point that day i realized if i screw up this person doesn't eat you know and yeah that that changes the i know that's one of the reasons why i was were at the firm as long as i was because of that i I get it. Yeah. Our youngest son was born like six weeks after we launched Relay. And so, but you know, I ended up quitting my job about a year into Relay. And so, you know, he was, you know, still, you know, a little one-year-old and we had two older kids and my wife works very part-time like two, you know, half days a week. And so, yeah, I was definitely in a situation

where I had a lot more, a lot more risk than, than most, and most people do, or most people talk about. And that was definitely a factor in my timing and waiting so long. And, you know, you got insurance to deal with, which is different in the United Kingdom. And it was just a lot of, which is different in the United Kingdom. And it was just a lot of, a lot of fear on my part that, hey, I'm going to do this and, you know, I'm going to, I'm going to fall on my face or, you know, this thing we're going to get three months into and it's not going to work and, you know, I'm going to have to go find something. And yeah, that was definitely something that weighed on me and definitely one reason it took as long as it did. Uh, you know, just based on the spreadsheet, you know, I could have left my job about six months before I did. I was making it relay what,

um, I needed to, you know, what I was making it my day job basically. And, um, but I just, every month that would be the case. And I would just wait a little, you know, I was like, give it a couple more months. I give it a couple more months. We were able to put, you know, most of that in savings, which is really nice to have a safety net. But it was definitely something that weighed on me of like, you know, am I being selfish? Am I risking, you know, my family's future to like go out and do my dream? And even after it was making sense on paper, I still had that like that thought in the back of my head. I was like, is this super selfish of me? You know, as selfish as it was like go to my, my

spouse and say, Hey, I want to spend our life savings on this company and, you know, hopefully we'll make it back, but maybe we won't. And her saying yes was incredible. She's a much better person than I am in every way. But, you know, then, you know, having that conversation again of, Hey, you know, I think, I think it's time for me to do this full time. And I think like most people, that's the most important conversation you have with a significant other in this process. But it was one that I, like I said, I put off because I had all these responsibilities. But you did eventually decide to make the move. I did.

So we alluded to this conversation earlier in the tea shop. So that would have been June, 2015. And at this point, you know, it was making sense for several months. I was, I was seriously considering it. I was really, you know, Mike and I were talking through it a little bit of what it would mean for the business, what I would take on. I, I knew that I didn't want to just do Relay. So Mike just does Relay. He's on more shows than I am. The trade-off I make is I'm on fewer shows, but I do the website and some freelance work and some other outside work than just Relay. And we came to an agreement on that. And so it was on my mind and we had our conversation and, and talked through,

you know, what it would mean. And I came back to Memphis and, you know, it was one of those things where I think I had made up my mind, but not consciously yet. Right. So I go back to work and I'm like, it's really hard for me to engage. Right. I'm kind of checked out already, even though I haven't quit. Right. It's just like, it's on my mind. I kind of made up my mind subconsciously. Well, I even thinking back to that day we had tea together i mean we liked it jason i like to brag right we had some role in this but i don't think we did i think you had already made up your mind then you were just looking for us to tell you that it was a bad idea yeah yeah i was like maybe you guys talk me out of this uh which you didn't i don't like to brag about that stuff

too because it's actually kind of as we've said on previous episodes i know david you're joking but it's like it's actually kind of terrifying to have somebody say i made a major life decision because of something you said it's like oh my god what did i do i still get nervous when people and listeners send me those emails but when we were having tea steven i mean it was very much like we had all made we had all made the move and we're not saying that it was horrifying and that you should run away. That certainly was the case that we're like, look, you know, this is working for all of us. Yeah. And, you know, what was so unique about the conversation is that the three of you understood the type of work I was going to go into, right? I've had these conversations, you know, I've got

other friends who work in different fields who are independent, and talking about independent content creation is a very different type of thing than, hey, I'm a – I don't know, like friends who are accountants on a freelance basis or independent attorneys like you are David like content creation I think is like its own special brand of crazy and the three of you were doing it and and of course Mike knew better than anybody because he was the other half of the company right he knows better than anyone what this is going to be like and so I you know I get back to Memphis I struggle for you know several weeks and then this picture was in the blog post on five, 12 pixels when I announced that I was going independent, but I was like late for a client meeting and I cut through town and I saw this church sign that said, if not now, when, and this is where I give the fine print. I did not quit my job because of a church sign. That's a crazy thing to do when you live in the South, but, uh, cause they're everywhere, but it was

just like, okay, like this sums up what I'm feeling and what I'm thinking that I'm making enough money at relay. It's stable. We have a really good runway in front of us of sales that are already booked in. I think it's time. And, and the conversation quickly became not, is this the time, but, um But it is the time. How do I do it? How do I actually go about doing this in a responsible way? And so, you know, I came home that evening and I told Mary, my wife, I was like, you know, I think we've been talking about this for months. You know, I think it's time.

I think that, you know, it all makes sense. I've spoken to these guys in California. I saw this church sign. Just kidding. I really am playing that up. But I was like, I think if I don't do it now, when am I going to do it? That was the point. and there's as little risk as possible in this because it has been proving itself for months, I just need to step off the silly pad onto the next one. And I know that next silly pad is going to be there. I can see it. Part of my weight's on it already. I wasn't stepping into an abyss, I wasn't stepping into the unknown. Relay was very much an unquant quantity at this point. It was stepping into just a different job, not, not one that I had to create on day one. It was already there waiting for me. Yeah. I mean, going back to the T place, I, the one thing I took from you that day is I could tell your responsibilities to your family was really weighing on you and that I think you wanted to

do this really badly, but we're scared. Yeah. And, you know, any parent, I think, would feel that way. And, or, you know, or if you care for, you know, an aging parent or, you know, if there's anyone that you're responsible for financially, you know, it is a big weight. And, you know, we had, you know, we had some savings. I knew that I could go find a job again, but it was still just like, it's like, get right up to that line. And then, you know, do I cross it today or do I put it off another day? How big of a role did that play in your decision, the fact that you knew you could get another job if you needed it? I think it definitely played a role.

I mean, you know, I figured, look, I've got these IT skills. Even though I've been in the agency life now for a couple years doing project management. I figured that, you know, I still think that, you know, if something, you know, goes sideways with Relay, then I feel comfortable that I could find something. You know, I think I'm marketable. And that once I really thought through that, that really put my mind at ease. You know, I hadn't really had that like conscious, like conversation with myself or with my spouse about that. But once we had the conversation, I sort of realized like, you know what, like, that's going to be fine. Like we have to do that. It's not the end of the world. You know, we'll be okay. And once I sort of settled

into knowing that it really helped ease that burden. That was huge for me too. Did you think about that, Jason, as you were making your decision? Sure. Of course. I think I tell myself that regularly, actually, to this day. And when you're in the media business, especially where, as Stephen knows, like things change so quickly that you just sort of really never know what it's going to look like in six months or a year, or certainly like five years, who knows what the landscape is going to be i do occasionally tell myself well if this all goes to hell um i have skills i'm pretty sure i can get a job using those skills and that is that's actually not what i felt when i was in macworld because i felt like um i had the job that was like one of it one of its kind in many ways where i was it was like exactly what I wanted and it was exactly

what I wanted to be when I was the editor-in-chief of Macworld and I knew that like I was if I left that job I was never going to have a job like that again probably because that that job doesn't exist kind of or there are very very few of those um and that would that made that decision harder my decision actually to take a promotion and leave that job and do something else at IDG. But these days I think about it and it's a much more positive thing of like, I am not an, I'm not an unhirable person. I have skills and it's a good reminder that like, it's not, you don't want, you don't want your foray into independence to fail, but it's also a lot less of a,

of a terrifying prospect to think that this isn't your only shot and that beyond this, you're, you know, you're, you're unemployable because that's not true. This episode of free agents is brought to you by timing, the automatic time tracking app for Mac OS between now and the end of July

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guessing how you spend your time and instead focus on doing what you're good at. Go to timingapp.com and get your copy of Timing Today. All right. So you did it. You quit. You went out. And how'd it go? It went really well. So even my interest in an independent life was slow. Because the way our agency was structured, I had like 50% of the company's work on my desk as a project. And it wasn't a job where I could give a two weeks notice and walk out and be responsible. hedging a little bit that if I need to go back somewhere that the agency world in Memphis is not very big. And if I burn bridges on my way out, that could come back to bite me later, right? If I need to go back and like, oh, well, you rage quit that job. Like, you know, it's a small community. And so I, I basically took like six weeks where I slowly transitioned out. And so for a while I was, you know, half and half, you know, between my old job and Relay and then eventually just working on one project

for my former employer and just very slowly, you know, sort of eased into it. And at first it was, I mean, obviously everyone has like the excitement of it. It's a lot of fun. You can do what you want to do. But because Relay was already up and running there was already there was a lot of stuff that i needed to to spend time on immediately so the biggest example was our our membership program so you can you know listeners can support a show directly uh through membership and you get extra content we want to do that since day one but we

hadn't had time and i took it on as a project and I took it on immediately. And what I should have done was acclimate to working full-time independently. And then, you know, then add something new to that list, you know, because really it was preexisting, the website was preexisting. I knew what those workloads were going to be. I should have just gotten used to that first. And even if that, you know, meant shorter weeks or something, instead, I jumped right into a massive project that took months to finish. And that was in hindsight, the wrong decision. I think I needed to pace myself a little bit better. And, you know, I just didn't have an understanding of what it was going to be like, I thought that I'm going to leave this nine to five. And all my side work, I'll

just slide into nine to five. And I'll have my evenings back. And in reality, that wasn't true at all. And it's like anybody you interview on this show ever will say, you end up working more, you end up working longer hours, because I didn't have any checks in place to say, it's okay, if you leave this tomorrow, it's okay if you leave this for tomorrow. It's okay if you push this project off. You need to pace yourself a little bit. And you bit off a lot, I remember, as your friend at the time seeing how busy you were. right? Or if I took any, any time away that I was being somehow like grossly irresponsible with my company or, you know, that, that I didn't, I needed to prove that I could do it like to

myself and to the people around me. And the way that I went about that was just, just trying to get it all done, you know, as get as much done as possible, as quickly as possible. And to, you know, just, just always have my head down, always be working. And that was, that was not ideal. Uh, it really created, um, a situation where I was pretty unhappy in my independent work. And even though I'd quit my job to like work on my company that I started, you know, uh, the dream job working for yourself with your friends, making stuff you love. It was, it was pretty rough sailing, getting, getting used to that. How did you work that out? How did you smooth it out so that you're in a, I assume you're, you're in a happier place now.

I'm in a much happier place now. Uh, yeah. So, you know, I made it my first, you know, three or four months into independent life, you know, so to the end of 2015, you know, early 2016. And I just realized I was really unhappy and not just like work was stressful, but like deeply unhappy. And, you know, spoke to my wife about it in depth over the course of a couple of weeks. And part of it was I needed to admit to myself that, hey, this is working on paper. Financially, we're fine. But this isn't working for the family. It's not working for your own health.

Things need to change. And I didn't want to face that because it felt like failure in a way. It felt like, oh, this isn't going well in all aspects. So let's just ignore that and work harder. I've had periods in my life of depression and just deep-seated anxiety, and all of a sudden I was back in that world. Even though on paper, we're fine, we're making money, we're paying the bills, I'm working my dream job, I felt really bad. And I just needed time to

sort of reconcile that and to understand why it was happening. For me, that meant visiting with a therapist, it meant really honest conversations with my wife and with my business partner, with a therapist. It meant really honest conversations with my wife and with my business partner and people around me of, this is what's going on. And even though I'm productive and on a paper and an omni-focus, everything looks great, things aren't great. And it just took time to sort of realize what was wrong and then starting to put together a list of things to change and to tweak in my work life, my personal life to help find that balance better. I was going to say, I'm curious how much of this, you know, finding a way into a better place was changing, you know, was internal changes, was changing how you set goals, changing how you think about your

productivity in your life. Um, because I, I've definitely experienced that. And also how much of it was you realizing you, you know, you needed to, to adjust the way you do your work. Yeah. That's, you know, that's a distinction that may seem small, but I think it's actually really important. As far as like how I went about work, you know, some changes were as simple as setting a schedule, you know, the end of my work day is going to be 530. And if I need to go past that, because I'm recording a podcast, or, you know, something happens, I need to communicate that with my family, right? That my wife doesn't need to be unsure when I'm going to quote, come home, even though I'm working from home, when I'm going to be done with work, right? Because it was five o'clock one day, then seven o'clock the next day,

then 6.30, and there was no regularity to it. And so setting, hey, if I'm going to go past 5.30, I need to communicate that and communicate why that's the case. And I need to make it a rare thing. Another big thing was sort of where I was working. And, you know, you guys have spoken about workspaces in the past. And I think for me, like most people that was out of my control to a degree, it's like my desk is in the bedroom, like it is for you, David. But I was leaving the house to record podcasts on the other side of town with an office space that I shared with somebody. And that caused a lot of stress. I was perpetually in the wrong place. I was perpetually late. And we moved and now I have a studio space at home that's completely mine. I record in, I work in, I'm out here every day. that's completely mine. I record in, I work in, I'm out here every day. And just having that sort of physical boundary of if I'm out here, I'm working. And if I'm not out here, I'm not working. Not only is it good for me, but it's good for my kids. It's good for my marriage to have really those clear boundaries. And for me, at least it was hard to do that when I worked inside the house.

I should have done a better job of it. I should have thought of some way to signify when I was working and when to turn it off. But because it was there and it was so handy to be at my desk, I was just at my desk all the time. And I sort of lacked the self-control or awareness to see how that was affecting others in my life. And I think lastly, I started to think about the work calendar in terms of quarters. So we have always at Relay, we've always sold our ads basically in quarter slots. So we have four big pushes a year. And I decided to adopt that schedule for other stuff. And so something like WDC, which the three of us were all just at, we do events that week, you know, public events.

And something I do is I don't worry about those until March 1st. They're on the calendar, they're waiting for me. And what it allows me to do is not worry about that until that calendar date rolls around. And so instead of racing ahead in the calendar and worrying about all these things, I can worry about things and work on them when it's appropriate. So something like every month I close the month every day. So I reconcile a bunch of stuff, pay a bunch of people. I would start working on that days in advance in the past. And it wasn't any more or less time, but what it is, is it, it, it spread the stress out of closing the month. And now I've got it compressed to two days.

Part of that is I'm more efficient at it and I've changed some of the processes. But it is also worry about that when that day comes around. And until that day is here, you have plenty of other things to do with your time. And sort of sectioning things off and putting things in places on the calendar has been hugely helpful. I do some freelance writing. Most of that's on a monthly basis. So I know the same couple of days each month I'm going to be working on this article for this person or this column for somebody else. And that way it's not always on my mind.

I know, hey, when it comes up, I need to start on it and it has a due date. And then I can put it away and come back to it again in four weeks. And for me, that rhythm has proven invaluable as I've, you know, continued to get into this. Did you feel overwhelmed at some point, maybe when you got started? Cause it sounds to me like you've taken a lot of steps to, to manage that part of the business. Yeah. I mean, the workflow part of that is that we, when we started really, we were both part-time. So the processes and things we put in place were shared very evenly between the two of us. Now, when Mike went full-time, that shifted. And our two-person organizational chart, which is a sidebar, if you are independent,

even if you're not alone, if you're independent with a partner or somebody else, having an org chart, even if it's only two or three people, can be incredibly useful. So for us, we have a public email address. And depending on the type of email that comes to that, I know that I can archive it or I need to reply to it. And Mike knows what he needs to archive or he needs to reply to. And very rarely is there a message that I'm not sure whose it is. So we just communicate real quick. And one of us takes it. That has helped unbelievably in the in like the sort of chaos of like, what do I do? What is what does Mike do? But you know, I was definitely overwhelmed when I was in it full time for a couple months. And you know, we're getting membership going and all this stuff. And I just felt like there was never enough time in the day to get work done that I was, I was always behind, always trying to catch

up, always scrambling from one show to one column to one freelance thing back to the relay admin and just running in circles. And, uh, it wasn't that the workload was overwhelming. I think it was mostly that my approach to it was wrong, and I needed to really think about it in more clear ways, as opposed to running around from fire to fire to fire. If I took some time and planned, I could avoid a bunch of that worry on the back end. And it just took time to sort of change that approach. It's remarkable how many folks we've interviewed on the show who really found that the key to being independent is to have a lot of the same, you know, discipline and procedures that you may use in the Fortune 500 company. Yeah.

You know, it's, you know, Mike and I have titles, right? Like, so, you know, all these, they're not our real legal titles, but they are, if we were a 300 person company, you know, we would be in charge of these departments. And it's just been a nice way to, to think about those things. And, you know, we can have a conversation about that and it's not emotional. It's not about any individual task. It's about like area of responsibility. And with two of us, we can split those things up, where if he has a skill set, that's more in line with one type of task or one family of tasks, then he takes it. And if there's something that is more in line with my personality or my skills, you know, I do all the tech stuff really because I have that background, then those

things sort of fall into their natural buckets over time. And it is less stressful for everybody just kind of having those definitions. So what are the big lessons now that you've been out on your own for a little while? I think the biggest thing for me is when you're planning to go independent, of course, do all the work you need to do to make sure that it makes sense financially. If you're not doing that, you have no business doing it yet. But you got to make sure it makes sense financially. But you also have to make sure that it makes sense, you know, life-wise and really consider how this will affect, you know, life-wise and really consider how this will

affect, you know, if you have a significant other or kids or a parent or somebody you care for, how it affects them more than just financially, right? I was so worried about, can I put food on the table? I didn't really think about, am I ever going to actually eat at the table with my kids, right? And I had to retrofit all that stuff, in when I was just feeling beat up and feeling like a failure. Then I had to fix that stuff. And I wish I had spent time and conversations with my business partner, with my spouse early on before I did it. It's like, what does this look like? When should my workday end?

When is it okay to break away from dinner and go take care of something? What constitutes an emergency, and have those conversations. Not that I would have had it all solved, not that I would have known 100% what it was going to be like, but just that there was some sort of baseline, something in the books already to help define that stuff. And there are all these great reasons to go independent. You see your family more, you're less stressed, et cetera. But you can't actually achieve any of that without working for them. That stuff isn't – when you quit your job, you don't automatically see your family more.

That's not the case at all. You have to make that a goal and work toward it and put things in place to make it possible. And I think I just took all that stuff for granted thinking, hey, I'll do this and I'll be around more and I'll see my kids and go walk the dog every day and like I can do all that stuff but it takes planning and foresight and a willingness to step away from work when I need to and it was just that was a lesson that I I thought would be easy and it was not easy at all I mean you could make the argument that you know know, working for a company, I mean, assuming it's the right job and you're happy there, if you just want to spend time with your family, that's a lot easier way to do it than going independent. Oh yeah. I mean, if you work

nine to five and you walk out of the cubicle at five o'clock every day, you're home by six, you have every weekend off, you know, that there's that structure, right? Even in my jobs, I didn't have so much of that because it especially when you're management you're kind of always on call right like perpetually something breaking at work i have to go in after hours or whatever so i already had some of that kind of programmed in but when you are independent if you're on your own or if you have a partnership like i do stuff always comes up like i have this joke that the Relay web server only explodes right as I sit down at dinner. It's like it knows I'm having dinner and it's like, time to blow up.

And my phone goes off and I have to go deal with it. That stuff's always going to be there. But if the things I can control, if I can rein those in, then yeah, I can plan to go pick my kids up from school or, you know, have a lunch date with my wife or, you know, take my youngest to the pediatrician. I just need to be willing to make those decisions and, and have the foresight to say, Hey, you know what? Maybe I don't need to book out every hour of every day. If I want to see my family, maybe I, I need to program that, program that in and have that, you know, carved out to make sure that it takes place. Makes sense.

I don't mean to say that as being a downer. It's incredible. I'm incredibly lucky to do what I do. I'm thankful for it every day. And I truly do love it. I don't ever want to go back. I want to do Relay until I'm an old guy talking about how we used to have to touch our computers. You touched the first iPad.

It was crazy. Like, I want to be that guy. But whether or not it's the case, who knows? Hopefully it will be. But every job, independent or not, comes with trade-offs. And like I said, when someone else is providing that structure and like the rigidity of your workday, then in some ways it's easier.

When you're independent, you have to make those goals for yourself and work towards them yourself. And, and that can be hard and you don't get those things by default. You don't get to see your kids more or go on vacation more or, you know, have more freedom or, you know, work in flip-flops and jeans every day, unless you, you set about that as a goal and work towards it. That's not just granted, you don't get a golden ticket to see your family more when you quit your job. It's something that you have to really focus on if that's one of your goals. You know, whatever your goal is, to be less stressed, to make more money, whatever it is, that has to be a goal just like, I want my business to grow this much year over year, or I want to do, you know, these creative endeavors this year. Those life things

have to be thought about in the same way. I think if the transition to free agency works for a person, your worry goes from, can I do this and become independent to how do I keep it going and remain independent? I think that's the sign that you're in it and you're enjoying it. Yeah, absolutely. And that's definitely my mindset now. You know, Relay is healthier than ever and continues to grow.

And so I don't have the worry now of, am I going to wake up tomorrow and my business goes away? But now I'm thinking about two years down, three years down, five years down. You know, what does this look like? And at least with the kind of work we do, we would see anything catastrophic coming on the horizon, I think. work we do, we would see anything catastrophic coming on the horizon, I think. But, you know, just knowing, you know, that if the worst does happen, then it's not the end of the world either.

You know, I can't get a job. I continue to provide for my family. I continue to pay my mortgage, which I've been told by many adults is super important to do each month. Yeah. I can still do all that, even if this all goes away. And just being – for me, it's – I get to wake up and do something I love and with people I deeply respect, including the two of you. And that's awesome. And just being thankful for that and kind of living in that moment all the time is a great way to kind of stay focused on it. And even when the work is less than fun or frustrating or hard, remember why we're doing it, I think is key. You can take it all for granted really easily. Well, Stephen, thank you so much for telling your story here on Free Agents. You bet. Thanks for having me. And that brings us to the end of this episode of Free Agents.

You can check us out at relay.fm, the website that will be up unless Stephen is having dinner, us out at relay.fm the website that will be up unless steven is having dinner relay.fm free agents 25 you can get all of our show notes and links and things there you can tweet at us at free agents fm and visit us on our facebook group facebook.com slash groups slash free agents group we'll be back in two weeks with more but until then david it's been a pleasure as always i'll see you in two weeks with more. But until then, David, it's been a pleasure as always. And I'll see you in two weeks. Bye, everybody. Thank you.