Focused - 20: Jason's Origin Story

Episode Date: May 3, 2017

David asks Jason to explain where he came from, the background of his career, and what the circumstances were that led him to become an independent worker, and then asks him to reflect on his two-plus years no longer being employed by a big corporation.

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 Snow. Hi, David. What's our topic today? I'm really excited. Our topic, Jason, is you. Oh, no!

It's all about you. No! Yes, every free agent's story makes sense in hindsight, but today we're going deep with you to hear about your origin story and how you got from there to here. So, we should specify that when we started this show 40 weeks ago, I suppose, we, it's not quite a year, we said we weren't going to talk about our own stories directly right at the beginning, but that we would eventually circle back to it. And that's what's going to happen over the next couple of months. You'll hear my story, you'll hear David's story. And we'll get those down, we'll get those on the record so that it's not just sort of our

oblique anecdotes and other episodes. We'll talk about it in a little more detail for those who don't know the history of how we got where we are. Yeah. And I think it is interesting because we've all gone on this strange path. And frankly, I don't know all these answers to your story, Jason, so I'm curious as well. Ah. The, you know, I thought when I started thinking about this, what was, I don't know much about you growing up.

I mean, I think the idea of being an entrepreneur is sometimes it's born into you, you're raised in a family that has a lot of entrepreneurial spirit. What was your situation? So, my dad was an orthodontist. And so, yes, braces, braces, braces, braces. So, he owned his own business though. College education. Well, this is the thing. So, on one level, I remember very much that He owned his own business, though. where I am now, I wouldn't call it entrepreneurial in one sense, which is, especially in that era, if you were a medical professional, you were self-employed, basically, unless you worked at a hospital or something like that. Doctors and dentists, they had their own practices. Not all

of them did. Some of them had a practice with somebody else. But in large part, you had your own practice. So, my dad had his own practice. And what was entrepreneurial about him, I guess, was he wanted to make a change in where he was living. He was living in the Bay Area. And so he started a practice up in the foothills in Northern California because he wanted to move out into the country, basically. And there was an area that basically didn't have an orthodontist. There was nobody up there doing that. And in the early 70s, you would have to go, if you wanted braces, you'd have to go, you know, drive an hour down into the Central Valley in order to see your orthodontist. And so, he was entrepreneurial in the sense that

he started a new practice up in the foothills. And then after a couple of years, he sold off his old practice in Walnut Creek. And then we, you know, and that was, um, just as I was being born. So I, uh, lived in the Bay area for the first like five weeks of my life. And then I, and then, then they moved up into the, up into the foothills. So, um, so yes, in a way he was, he was entrepreneurial and was a self-employed person. He had employees. He had, you know, like a lab tech assistant and a receptionist in the office. So he would have two or three employees at a time. And yeah, that was how I grew up.

And my mom was a nurse, so she worked in a hospital until she had me. My mom was a nurse, so she worked in a hospital until she had me. And then after about 10 years, when I was a baby and a young child, when I was about 10, she went back to work. I was talking to her about this the other week. She got trained up on being the receptionist in my dad's office. And the idea there was he had lost two of them in quick succession. And it was really difficult to train somebody new when the old person was gone and so the idea was to train her up so that she could always be the backup if somebody left and of course you can you can guess what happened which

is she just became a receptionist and that was it and that was her new job was to be the essentially the office manager and then talk about a mom and pop operation at that point for the rest of the time that my dad was practicing the the whole business was basically my mom my dad and this one woman who was the lab tech and assistant and that was it now uh where'd you go to school i mean i went to public school up there in the in the foothills so i went to i went to you know elementary school and then high school in the small town that I grew up in where, you know, basically if you had braces, you were probably a patient of my dad. So, everybody knew who my father was and all of that there. But that was it. And I don't know. It's funny. I look back now and I don't think about it as being that my parents had their own business, but they absolutely did. They absolutely

did. In fact, for a couple of years, they turned our house into a bed and breakfast. It's a long story, but that was yet another business they started that was their own business. So, I guess it was there all along. I didn't grow up in a house where there was a boss. Yeah, I was just thinking that. You didn have to see your dad like put up with stuff. No, I never saw either of my parents talk about how the boss was causing trouble, or we don't really know what's going to happen with the boss. They could sweat the books, they could sweat the, you know, the money, you know, and they and they had to do that about like buying new equipment. And, and they had to have their own pension plan and their own profit sharing system and, and all of these accounting

things that they had to do that because they were on their own, instead of having a big company. But in fact, it was the other way when I started when I got my first job out of school, I felt like from my parents, it was a very foreign experience to them, the idea that I was working for other people in a big company, that they didn't quite understand it, that it was respectable and all. But at the same time, I think they had ideas about like, oh, what are they going to do? And what, you know, what's your boss like and things like that. And I got the sense that it was the, they only had secondhand and cultural ideas of how that worked because they didn't experience that my you know neither of them had had an employer at that point for you know since i before i was born

yeah and where did you go to college at went to uh san diego uc san diego um undergrad and spent four years there worked on the college, did a bunch of internet stuff while I was there, too. And then the economy was so bad, actually, when I graduated in 1992, that friends of mine who had worked at the college paper were getting these terrible journalism jobs, like at local weekly newspapers and small daily newspapers. If you could get a job you know, they were, if you could get a job at all, they were bad jobs. And I didn't want to do that. So I wanted to kind of hold out for the economy to be better and maybe make some connections. So I went to graduate school. I went to journalism school at UC Berkeley. And I got to say, my best journalism school was the three years I worked on my college newspaper, and that

those skills gave me all the skills I needed to succeed as a professional. The graduate school of journalism at UC Berkeley was great, but in reality, I went into that already being a capable reporter and writer and editor. And what I really learned in grad school was I had thoughts about doing broadcast, about doing television news. And so, I did the TV program the first year I was there. And what I learned is I didn't like it. I didn't like that medium. I didn't like the, it seems weird now, but if you think about it, as a writer, you need to be present and talk to people and write things down. And as a broadcast journalist, you need to haul heavy equipment, spend a lot of time setting it up, and you can only really do a story about whatever visuals

are in front of you. And I found the journalism in that under those constraints was actually really poor because you can have a great knowledgeable source who you could talk to on the phone and write a great newspaper story. But with TV, if the knowledgeable source wasn't somebody you could take your van over to their office and set up a shot and get video of them, but there was some terrible source who you could, the terrible source got on because you couldn't just have them on the phone. You had to get a picture of them.

And I got frustrated very quickly with the fact that the compromises that are required to do TV because it's a visual medium and today they try to get around it sometimes with Skype and things like that. But I didn't like it. And I thought I could probably do it, but I didn't like it. Um, and I thought I was a better writer anyway, than I was a video shooter and editor and on camera interviewer. So that's what I ended up doing was meeting, meeting my, um, there was a desktop publishing class at the J school that was run by an editor at one of the Mac magazines. And I talked her into giving me an internship.

And that was it. That was how I started on my way. So it worked. But, you know, it's interesting. This is in the early to mid-90s, I guess. Yeah. Was anybody in J school talking about, boy, I really can't wait to work for myself when I get out of here? Was that even a thing then? Well, no, right? Because that was that when you when when I was going to school, the media control was absolute. It was in the hands of huge,

huge companies, I would say the only well, there are a couple a couple examples of people who did think that way. But I wasn't really seriously considering those as career paths at that point. And one was, if you write books, but you kind of have to establish yourself before you do that. But a lot of the faculty were like this. They wrote books and then also taught. And that was how they made their living. And like, so they were employed, they were employed by UC Berkeley. But on the other side of it, the journalism side, they had a boss sort of in the sense that they had a book contract. But on the other side of it, the journalism side, they had a boss, sort of, in the sense that they had a book contract. But a book author, even nonfiction

or fiction, they're self-employed, essentially. If that's what they do, they're on their own. So, that's an example. And then the other example was people who make documentaries, who are filmmakers. They are independent filmmakers, essentially. If you're working for the local TV station or 60 Minutes or something like that, then it's not the case. But if you're a documentary filmmaker, you'll have producers and you'll have funding, but it's not quite the same. You are more independent in that way too. So, those two extremes, I would say, there was some thought of that kind of entrepreneurial aspect of it. And that was definitely something that they did try to train people for.

But in reality, it was all like, you're going to go work for a newspaper or a magazine or a TV station. And in your head at that point, you were not thinking about being an independent worker. Well, I, so, you know, I started a magazine when I, an internet magazine when I was in college, short story magazine called Intertext. And I, you know, I just made that happen on the internet. And that was, it turns out a model for my future career. But it was just too soon. Like the internet was not a legitimate publishing medium. I tell people who have come up since about like, why did I work for a magazine in, you know, did I want to be a magazine editor? And the answer is no, I didn't want to be a magazine editor. I wanted to write about technology, computers, the Mac in particular. I was excited about that. I wanted to write about

that stuff. The reality was the only way you could get a paying job anywhere was to work for a big publishing company because that was the scale that the only way you could do that. So I would say I had a lot of the same spirit. I keep thinking, um, when I was a junior in high school, um, we went to San Francisco, which is a three hour drive. And one of the few times that I remember being just down the city streets in San Francisco, we would go to the East Bay, go to Berkeley a lot. My dad went to Berkeley as well. But we had to drive. We were on Sacramento Street in downtown San Francisco at a consultant. It was a college consultant because you know this. You've been through it. I'm about to go through it. You get in that like, what do I do to make my child get into college and succeed and get the right college and all of those, the college mania. And this was our bit of that. And I swear this story has a point.

We go to this consultant and one of the things they do is they take an interest inventory and you take some tests and they're trying to find out things like what kind of careers do people who think like you go in and what subjects are you interested in? And they came back with a whole report, which is actually, they suggested UC San Diego as one of my options, and I did go there. So, I think it was worth it in that way. But the thing that sticks with me is, and I was a straight A student, I finished second in my class. You know, I think my parents were a little disturbed with the result of the interest inventory exam, which was, what is the mindset that you are most like? And it said, musician. And my parents are like, okay, I'm like, you know,

it's fine. I'm a straight A student. I'm going to go to a serious university. It's all fine. But I think about that all the time because in the sense of being a creative professional who is not, who ideally is working on their own, working on stuff and making stuff and putting it in the world, I think they nailed it. Like, that is me. That is who I am. And I'm not a musician and I don't do musical things.

But if you abstract it a little bit, yeah, that's kind of how I ended up. And even though I spent a lot of time working in a big company and managing people, I think at my core, the thing that motivates me the most and that I like the most about me professionally is that independent creation streak, which that, that in my junior year in high school, that, that test that I took in Sacramento street in San Francisco nailed it. Pete Did you, did you accept that? I mean, I guess my question is when you were going through school and going to Berkeley, were you thinking, man, I got to get out on my own or were you thinking about going the

traditional route? The way it manifested was always as side projects. I always had a side project, right? So, I started Intertext when I was a junior in college and also the news editor of the college newspaper, right? So, and then I was the editor-in-chief my senior year. So, full load of classes. I graduated a quarter early. I'm the editor of the school paper. And somewhere, somehow, in the middle of all of that, I said, you know what I'm going to do? I'm going to create an internet magazine to publish fiction on the internet via Usenet and FTP. And I'm going to learn how to do that. And I'm going to lay it out and I'm going to get submissions and I'm going to edit the submissions and I'm going to post the

stories. It's like a whole other thing. But the fact is when I was working in the nineties at the computer magazine, I started a blog about television called TV. Um, and it was an early blog before they were even called blogs. And, um, and I did that and that was a side project. And then when I was a little more, um, uh, advanced in my career, I started the incomparable and that was a side project. And then when I was a little more advanced in my career, I started The Incomparable. And that was a side project. So I think that's how it manifested is I knew I wanted an outlet where I could make something and I could control the whole thing and get it out in the world. And at that point in my life, I didn't see a career path that would let me do that for a living. So I did it on the side. And it was only when I was

miserable in my job. And I looked out and I saw people like Jim Dalrymple and Federico Vatici and John Gruber on their own, making a living, doing these things with skills that I felt that I also had, that those two things came together. And I said, I got to do this, I got to try this, or I'm never going to forgive myself. But it took a while. So it was always bubbling in the background. It just hadn't come to the foreground. You know what I'm thinking? When you had the full-time job and you were doing all these side projects, it must have been really hard to get a good night's sleep. Oh, no, I would say I slept well. I mean, you could argue that the side projects were the therapy for the full time job. And there were times like, it's not like I wouldn't work hard on the full

time job. But it was another part of my, my brain, another, another need I had creatively, was the thing on the side. And it also became, and this is one of those things that people ask, have always asked me, like, what are your hobbies? And my answer is always essentially the same thing as what my, what my job is, which is on one level, that's really good. Or what are your, what are your outlets and who are your friends? And the answer is always my side projects tended to be projects that I did with my friends to help us stay in touch. And we all wanted to work on cool, creative projects together that were fulfilling something that our jobs didn't fulfill. That was true with TV, especially, and The Incomparable was like that too. And so, I would say it was all just kind

of part of the whole. It made me a more well-rounded person. And I know there's some employers who, I never really felt this, but I'm sure some employers felt like, you know, why aren't you devoting yourself body and soul to us? But, you know, in my case, there was stuff that my employer was never going to let me do that I needed an outlet for, and that's why I created these other things. And it helped being in tech and writing about tech stuff, that I could use the side projects as experiments to inform my professional work. So like posting the blog, I learned a lot about running a web server on a Mac, in fact, for a long time and about like early days of HTML. And then I wrote about HTML and domain names and all these things as we were learning how to make a website, I was making

a website. So the side project influenced my job. And likewise with podcasting the same way. Like my side project of doing that podcast gave me knowledge of an aspect of technology that I could use to write articles about and still do to this day. Yeah. Well, I agree. But I bet you could have got even better sleep if you had a really good mattress. Interesting. Interesting. Interesting. That is one of the most clever segues I have ever heard.

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Thank you, Casper, for supporting free agents. All right. So you were doing all these side projects and you were also an editor of a major magazine publication and other things as well. At what point did the idea start germinating that you may just need to start out on your own? Well, like I said earlier, I think some of it was seeing other people do it. So, John Gruber was a good example. And John wanted to go out on his own and he was brave enough, right? He was brave enough to do it. He started Daring Fireball as a side project. One of the advantages that he had was that he wasn't being paid to write about technology for a living. I couldn't do that as a side project if I had wanted to. did and and and he's a very talented writer and it picked up steam and he was able to to stop doing other work and focus on daring fireball and that was the first thought i had of like oh independent writer making it um i i you know most of who we work with were freelance writers and i always

thought about the fact that i could probably be a freelance writer for whatever reason i think my career was going so well that I just never really considered it. I loved what I was doing and I kept advancing. And so I never really thought about the fact that at any point, I mean, once I was the features editor at Macworld, I could totally have quit and said, I would like to write features for you instead. I was writing them on staff, right? And just being paid as part of my salary. I could have done that. I could have quit in, you know, 1999 or 2000 and said, I'm going to write computer books and magazine features for

a living. And I probably could have been successful doing that. But I was at that point, like the editor of the magazine, and then I was the editor in chief. And we were just starting to have kids and I kept getting promotions. And I love my job and I love my co workers. And it was great. So I just kept doing it. I mean, being the editor in chief was my dream job. That was the job I was shooting for. And I got there at whatever 31 32. And it was great so i didn't think of it seriously i think there's a certain amount of courage involved with going independent no matter what your circumstances are but when you have a family and you've got a job that has insurance and you know and you know at least that perceived permanence uh right giving something up like that to go independent is takes

it's like a whole new level. And it didn't feel like it would have been an improvement. I think that's the big thing, is that at that point, I didn't feel like giving up being editor-in-chief to being a freelancer, even if I could make the same amount of money, which I probably couldn't have, but let's just say that I could. I don't think it would have been an improvement. It certainly wouldn't have seemed to be an improvement because at that point, I was pretty happy with what I was doing. It was only later that these two things continued to happen where there was somebody we laid off, Jim Dalrymple

from Macworld, and he went out and started his own website and he made it. It was hard for a while, but he was successful doing that on his own. And, you know, I look at somebody like Federico Vatici, who never had a traditional job to speak of in the media, and built his own business that supports him doing Mac stories. And so I would see these examples and think, this is interesting. is uh this is interesting and this this was coinciding with the fact that i took another promotion to a job that was not editor of mac world but was the editorial director for all of idg consumer and that was a much harder harder job with a much less uh supervision of editorial content and more of editors who were doing the content and there were more layoffs and the media business was getting harder and harder and idg's business was rocky. And so there were budget cuts and layoffs and more layoffs. And that was the moment where I did not enjoy that job. And in fact, I would say if I had to

do it all over again, I wouldn't have taken the job. I wouldn't have tried. I would have let my colleague who also wanted the job and didn't get it and left the organization, I would have let him take it. It was a difficult situation because I felt like we were basically pitted against each other and one of us was going to be made the boss of the other one. And I wanted that to be me. In hindsight, I don't think I would have been happy. In fact, if he had gotten the job, I probably would have considered leaving anyway. So it was a difficult position to be in. But also in hindsight, that was a terrible job that I shouldn't have had.

Right. So I took it for career advancement reasons and I got a big promotion. Great. And I was unhappy in the job. And then all of a sudden, the prospect of going out on my own was much more appealing because now the balance shifted, the scales had tilted and being an independent worker, um, because the things that had fueled me were no longer part of my job and just getting the paycheck and dealing with the crap of my job. Um, I didn't have anything

left that fueled me and my colleagues on the outside who were independent, they were doing the thing that fueled me that I wasn't getting anymore. And that was the moment when I started to seriously consider leaving. And it took me some time even still, but that was the moment. And just in hindsight, I mean, the market was evolving to a point where you could very practically open something like six colors and make income off of it. Yeah, the example, that's the perfect example. And I could have probably done that earlier, right? When I was editor-in-chief of Macworld, I could probably have said,

I'm out of here, knowing what was coming, and started a site then, and established it even longer and been even more successful with it. But at that point point i didn't want to go so but yes the the change in that time span made it possible you know jim dalrymple didn't go didn't leave macworld and go well i guess i'll just apply for a job at some other website he could have done that but he started mac central or not mac central he started loop instead and the first version of the loop was basically mac central and then he changed it and made it more like daring fireball and i think it was much more successful as in its second iteration and jim would say that too um he had

to work all that out but the the the world had changed an independent person could go out there and and make content and not just be like a freelancer but but start a start a blog and and make a living at it and that was something being an independent worker on the internet was not something that was a thing before, you know, a decade ago, really. sponsors and a loyal audience. And so it's not a huge percentage of my income. I have to say I did the math, but it was, it was something. And it was, it was an additional part of the plan. It was part of the part of the plan all along was I'm not just going to quit my job and write articles. I'm going to quit my job and do podcasts and write articles and do these other podcasts. And that's what I'm going to do. And that's how I'm going to make it work. And that is how I've made it work. All that being said, how did you feel when you finally told them, hey, guys, I'm out of here? It's a long and complicated story. It was a very painful time.

There were lots of layoffs. I've referenced this on previous episodes of Free Agents. I actually, there were a series of layoffs and I was very unhappy with my job. And I actually, there were a series of layoffs and I was very unhappy with my job and I actually gave notice. I said, I'm going to leave. And they talked me into staying and said, once we get through this round of layoffs, we've got new management that's just come in. Let us, it's not going to be like it was. We're going to fix this. We're not going to, you know, we're not going to have more of these rounds of layoffs.

They're giving us time to put in our plan. Give us a chance. You haven't given us a chance because there was new management that had just come in. And I let them talk me into staying, but I also said, I'm not going through this again. And they said, no, no, no, no, no, it's not going to happen. There's not going to be another layoff. It's, you know, we got it on the right track. And the reality is eight months later, the owner of the company died. A new management came in. They decided to fire the new management who had convinced me to stay and lay off a huge number of people, the biggest one yet.

And fortunately, the people I had told I'm not interested in staying through another layoff were the people making those decisions. And so I got to go. Like, they gave me severance, which is great because at that point I would have quit. And instead they gave me money to leave because I'd made it clear that I wasn't interested in staying. In hindsight, I probably should have offered to be in the layoff in the previous year when I had quit, because then I would have gotten the money and been out of there eight months sooner and not had to go through that next wave of layoffs that were terrible. But that's not how it happened. So, you know, it's a big ugly story where I got to the point where I didn't want to be there anymore. And I was kind

of talked into staying and said, you know, I'll give you guys a chance, but it was very clear that I was still not happy. And so it was a blessing when finally, you know, the, it was unfortunate that it was such a disaster eight months later that the guy who they told would be given a few years to work it out, um, was just, it was just like, they, they basically doubled back. The, the, the. The sordid story is that the owner of the company belayed their orders for massive layoffs, and then he died. And then they did the massive layoffs once he was out of the way. It happens. It happens. Oh, well.

You know, it's funny because I'm thinking back to Free Agents episodes, you know, zero, where we used to have our lunches together and pop each other up. And you used to get this like dead look on your face when you talked about the job, you know, it was before you left. And I hadn't really thought about it. But looking back, I've never seen that look on your face since. It was like, that was a special part of you that was very difficult to handle, I can tell. I was always somebody who took those management jobs because I figured somebody's got to do it, and it might as well be me. Because you need editorial management, right? Editors need to be editorial management, not suits. Nobody would accept an editor-in-chief or an editorial director who is a suit. It's got to be somebody who's got editorial credibility. in chief or an editorial director who is a suit. It's got to be somebody who's got editorial credibility. And I would say, well, I could do that job. Let's do it. And I would step up to

the next challenge. And, you know, my intent was, you know, not to build an empire. It was really just like, okay, somebody needs to do this. It might as well be me. But that got me to the point where I had given away all the stuff that I like to do. So that's why you got the dead look from me, is that it was a bad situation. And it's very hard, you know, the social contract is, somebody says, how's this going? You say, it's good, it's fine. They don't say, well, I actually hate my job.

And I'm thinking of leaving. You don't say that. But I have a hard time, like, faking it. So, yeah. So how long after you got started were you feeling comfortable that this was going to work out for you um i'd say well we we originally gave me like six or nine months of runway and it was very clear after like three months that it was going okay. And the runway stopped being a calculation. So I would say, you know, my wife and I talked about

six months or nine months and we reevaluate maybe a year. We'd watch the numbers, but we had some time to be patient. And it turns out we didn't need to be patient because after three months, it was clear this was working. And then after the first year, it was clear this is working. So at this point, we're just in the ongoing phase. So I would say in the first three to six months, we looked at the numbers of the money coming in from all the different sources and said, we can make this work. And in fact, that it was, we had like a level of like, well, this is the minimum amount that I need to bring in, or we have to say, you need to find a job, basically. And it became clear that we were going to be more than that number.

And there was always a question of like, how much less is it going to be than when I was working at the very end? Because I had this senior vice president title and was making a lot of money in that job. And how, you know, how can you compare it to that? But we got over that hump of like, we can make it if I make this number. And after three months, six months, we were like, we're can make it if I make this number. And after three months, six months, we were like, we're going to be able to make that number. So that was the, that was the moment where it became an ongoing concern instead of a, let's try this kind of thing. Yeah. Yeah. And we've talked on the show about, you know, how you got support and getting

things started, but, but what was the biggest surprise for you in those first three months as you got started? It's hard to say now. I think my biggest surprise is that it was working. Honestly, my biggest surprise was I was able to take money for advertising. I was able to make money, launch a podcast and put advertising in it and make money. I was able to get money rolling in for my business that was previously money that people paid to my employer and that then i got paid by my employer that was the thing because the incomparable had been making money for a little while a little bit but to have my tech stuff be there to have to launch the site to have a name to have people interested in reading and all of those things to have it really

happen and not be because you never know right it could just be you know a flop and it wasn't and i didn't want to take that for granted right i i talked to a lot of people are like of course it wasn't people want to read you everybody knows who you are they would tell me all these things and be like that's great but the fact is on day one i have no no readers and no traffic and no search presence, and nobody knows the name Six Colors. They only know my name. And that's where I have to start from is the nothing point and build it from there. And there's nothing, you can say, of course, it's going to be successful to me all you like, but that doesn't mean it's actually going to be successful. Did you ever in that first like six months or year start thinking, well, you know, should I keep my

options open? Should I be looking for outside jobs? I still have that reflex. And I certainly did in the first six months or year of hearing about jobs and thinking, should I apply for that? Is that a job I want? It's faded a little bit over time because there are a lot of those jobs now that I, before it was like, I'm qualified for that job and I don't have a job per se. So maybe I should think about that job. At this point, it's gotten to the level of, I don't want that job. Most of the time it's like, I'm qualified for that job, but I don't want that job. Has anybody tempted you and like said, hey, why don't you come work for us? No, not to make an admission.

It would be great for my ego if I said, yes, I have been approached numerous times by people to go work for them. That hasn't happened. I suspect part of that is that I keep saying publicly on places like this that I would rather be an independent person than go back work in a corporate media job ever again. But so I may be putting them off or it may just be that they're not you know i'm not on their radar and that's fine because i'm not i am not interested in that um if i have to go back i'll go back um well that's not true i actually have a couple people ask me about some things and i've said you know thank you but it doesn't make sense and honestly i do the math and the way my businesses are going right now i have a hard time seeing what kind of job would give me the would give me a better thing than i've got going right now like what would you have to pay me that would be more than what i make on my own that we

and what would i be doing and what would my commute be? And either it's a, it's a, uh, a lower paying job and I might as well just stay where I am, or it's a higher paying job that is all management at some subject I'm not interested in that I wouldn't want. So it's hard. I'm not, I'm not saying to this day, I would say, I'm not, not saying I wouldn't I'm not saying to this day, I would say, I'm not saying I wouldn't consider some amazing job offer. It's just that I've gotten a more realistic view of it in the last year and a half than I had in the first year. In terms of just because I could do that job doesn't mean I should think about it a lot. Because it's not a job I want and it's not a job I need. So what's been the effect of this experience on your,

your own like happiness and satisfaction? Well, you could ask my wife who would tell you that I'm much happier now than I was, which is not to say that I'm not concerned about business, but my mindset has changed completely. And, um, that's, you know, I, I, I think about where the business is going now and, and less about like oh, geez, what about that one specific thing? And I know that I can do this. And all of us are at the mercy of the economy and the ad market if you have ads or you know they're always shifting things in media they're always going to be issues they have been since i started in this business 25 years ago but my mindset has changed and i don't i don't my work doesn't torment me in a way that it did

yeah um it's just it which is not to say that it isn't hard and it doesn't say that i don't struggle with the work but it's it's honest work it's good work and it's work that i like and that i i think i do a good job at and i'm always questioning myself and i'm always wondering where i take the business next but the context has changed where now it's very much like where do i take this business in the future as this this revenue source goes down, what do I need to be building for new revenue sources? And that's how I think of it. And I think the first year I would have been like, oh, geez, I don't have an advertiser next week. Maybe this is all a mistake. It's like, I don't think like that anymore. I'm trying to think bigger picture about it. How does your happiness rate now to the better times when you're in the magazine business before, you know, you got an upper management and things got a little weird? It's different. I think it's still good.

Not having a commute thing is great. The management, you know, I was never a natural manager. I was okay at it, I guess, but I never really thought it was a core skill. I never thought I was good at it. What I miss is there were a lot of great people I work with and I miss collaborating with them. I still do some of that. Like I collaborate with Dan on Six Colors a bit and Stephen Hackett writes a thing for the Six Colors newsletter. And I have the people that I collaborate with, like you, on podcasts. But I do miss that a little bit of more interaction with people and bigger projects. Like, I don't do big projects on Six Colors for the most part, because that's not how

the site works. The site is little stories here and there. And when I do a big project, it's usually me doing the project, not me working with five other people to execute a huge project. And I kind of missed that because that was a lot of fun and working with those people was great. But, you know, that's about it. Well, you know, before we go on, I was thinking you were talking about advertising revenue and getting paid and we got to get paid too. We do. Yeah. So let's take a minute to talk about our sponsor today fresh books um fresh books is the company that helps you get paid um let's say you're racing against the clock to wrap up a bunch of

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All right. You survived that opening phase. I think that when you start your independent business, that's in that first six months, that first year that you were saying, well, is this going to work for me? Now, what are the challenges you feel like you face now being in this a little over two years? I think it is sort of self-regulating and guarding against complacency and sort of like I was saying before, thinking about the big picture, thinking about where you want to go next, not, what's great about humans is that we get in a groove and the problem is that it can also be a rut. And the difference I feel like is being able to step back and look at the big picture. And so that for me, that's my challenge

constantly is sometimes a week goes by and it's smooth sailing. We're recording this on a Thursday. This has actually been a pretty good week. I was sick last week. It was not so great, but this week it's been pretty great. And yet I have this nagging feeling in the back of my head, which is if all you're doing every week is grinding out the things that you need to grind out, which not to, I mean, it's kind of gross when you think of it that way, but like, what did I do this week? Did the podcast I do on Mondays and the podcast I do on Wednesdays, the podcast I do on Fridays. Did the story I do on Tuesdays. I did the story I did here. I did this thing I do monthly. I'm done. Good week. Good week, everybody. The problem is, eventually, in the fullness of time, doing what I do every week won't work because things change. So, I need to have another part of me that's thinking,

what do I need to do differently? What do I need to stop doing? What do I need to start doing or lay the groundwork for doing? And I actually have been doing some of that this week too, about thinking about making changes to things that I do for Six Colors and, you know, starting to toy with ideas of like, where do I take my business in different places, as well as being open to new opportunities. Last week, as we record this, I had an opportunity come to me where somebody said, I'm in a completely different kind of business from you. But I might be interested in hiring you to do this other thing that uses some of my skills, but not in a different way than I've been using

them. And instead of being like, now that's too far afield, I thought about it. And I actually was like, okay, what would it take for me to do that? And I put together a proposal and send it off. And I have no idea if anything will come of that or not. But I thought to myself, if I can structure this in a way that I'm happy with it, and they are happy with it, then I've got a new revenue stream. Maybe multiple times. Maybe it's not even a one-off. Maybe this is a future business direction for me.

So trying to be open, but also not trying to say yes to everything, but trying to be open and trying to make decisions. In that case, I made a proposal that was for a lot of money to do this thing, In that case, I made a proposal that was for a lot of money to do this thing because it was in an enterprise field doing a corporate gig. I'll be vague about it. Not trading on my name at all, just trading on my skill as an interviewer and a podcast host. And I thought, I'm interested in that, right? That could be a part of what I do. Or it could not be.

right? That could be a part of what I do, or it could not be. But the bid that I gave them was large enough because I wanted it to be like, if I wanted this to be part of what I do, this is what I would need to be paid. My goal was not to scratch out some money. My goal was to think what would be a sustainable number so that if I did this, and if I kept doing this, I would never regret that initial offer. And so that's what I did. And I'm thinking about stuff like that too. So, for me, that's the difference now is that when I get in a groove, it really feels good. I want to always be questioning that. Like, do I have a long-term project I want to work on? Maybe. I think about it, funny because it's the weather's warming up here um i think about um summer as a project time and i'm not quite sure that's really accurate but like because like

apple's developer conference will happen and there'll be betas and stuff like that but i start to think in spring and summer like what could i do now because the fall and the winter is pretty crazy early on with uh apple stuff that i that i write about but this time of year it's like i could do a long-term project now if i want to what would it be and and so that's bubbling in the background too so that's a lot of it is just like what do i do that is above the base level of the groove and if the groove fills all of my time that's bad because i need some time above the the level of the groove to think about what else. Yeah, I think there's a healthy fear of complacency is what I'm hearing from you.

Yeah. And I think that's probably a good idea. When I started, I shared the outline with you for today's show and some of the questions I wanted to ask. And at the end, I said, well, where do you see yourself in five years, 10 years, 20 years? And literally writing those questions down for you was making me nervous thinking about it because, you know, who knows? But to what extent have you given thought to like long-term future? I mean, I think about it all the time. The, I don't know. I mean, the problem is the media business is so bad that I don't think I can count on anything long-term. So my goal, my goal is to keep doing this long-term. That's, that's

basically it. My goal is to keep doing this long-term and finding ways to do it. And if that means changing it up, I fully anticipate that means changing it up as I go. And that my revenue mix five years from now will not be what it is now at all. But that's okay. But that also means that I'm not counting on it being there in five years or 10 years. And I'm also always open to the possibility that the media landscape will change to the point where I can't do this for a living. But I'm also, I mean, I'm open. I had this conversation with Mike Hurley all the time, like one of these years, and it may be 2017, my revenue as a podcaster is going to eclipse my revenue as a writer. And in five years, could I do podcasting as my primary job? And that writing is just an aside, if anything,

it's possible. Totally possible. It's also possible that I'll discover that in order to make ends meet as the bottom falls out of the web advertising business that I start doing, you know, I start doing product marketing for or something, because that's the only way to make ends meet. Anything is possible. So I think the goal is I would like to keep doing this long term as long as I'm happy with it and I can support my family. And if I can't, then I'll do something else. But that's the plan is just to keep adapting. Yeah. But I mean, you're in the right place. And like one of the things you've done that I think is very smart and probably not entirely intentional is you've got this brand around Jason Snell. I mean, as a Mac user,

I trust you and your, your thoughts and opinions are things I'm interested in. And I think a lot of other people are too. So, um, I feel like you've got a big advantage in that regard over someone just coming out of Berkeley that wants to be writing about this stuff. It's, it's so hard now for them to find a voice. Yeah, it is. It's tough time. Um Media business, I don't recommend people go in the media business. It's not great. So, yeah, it's not great. But that's where I am. And I love it. But it is completely unstable and changing all the time. And that's just how it is. And so, if you love it,

and you want to be in it, there's lots of opportunity, but there's never a dull moment. Well, either way, you have a success story of being an independent worker. And that's… So far. You know, that's all we can think about. And that's all we ever have. Everything is so far. Exactly right.

But you've done it. And congratulations, Jason, because like I said, the dead face is gone when I see you. Thank you, David. I think that's important. Yes. I'm doing the stuff that I love to do. And like I said, it's not that it's not hard work. It is hard work.

I'm working hard. But I'm working hard doing things that I like to do, and I have control over my destiny in a level that I didn't before. And that's all good. And healing from a few years of a bad job, that's the other part of it, is kind of reconnecting with the stuff you love. Pete What's the, do you, you've heard the term lifestyle business. Do you consider this a lifestyle business? Jared Yeah, I mean, I would say that's accurate.

My goal is not to build an empire. I mean, if I could find a way, and this goes back to about collaborating with other people, if I could find a way to build the business so that it was larger, so that I can employ people and collaborate with them and have it be bigger, I would do that. But even then, my goal would still be to build a business that allows me and the people who are working on the projects to have, to live their life and support their families. I'm not, um, I have, I have lots, well, not lots. I have had some ideas of things that could be a, you know, a big business or a venture funded business or things like that. Like this would be an interesting area. And, you know, it doesn't really interest me to do that, to take on other people's money and

then try to go for a big payday and all of that. It's just kind of like not, it's not really what I want to do. So, I'm happy. I would be happy to be an independent worker writing or podcasting or other things like that into my retirement years, in fact, because obviously it's true that I'm always going to have those side projects. So, am I ever truly going to want to retire and just sit on an island somewhere and do nothing? That's not going to happen. So, I'm okay with that. But I would like to keep doing this as long as I can. A couple years in now, what's the hardest part of being an independent worker? Giving yourself time to do that, making sure that you're not wasting time. You know, I'd say that's still hard.

I'm not, and the flip side is giving myself permission to be sick if I'm sick and not try to force myself to work. So it's a little bit of both. It's building up structures to make it so that I am focused. And then also being able to give myself permission on to not be focused all the time. If I'm trying to live my life, I mean, like, right, if you're your own boss, that's one of the things you've got to do is you've got to be a boss to yourself. But you've also got to be a compassionate boss. And that for me, that is something that's an ongoing challenge. It's not about like hitting deadlines or things like that. It's about seeing the big picture of the business

and making some smart decisions there. And it's about being a reasonable person in terms of work discipline and also the ability to shake off the discipline if I need to run an errand or I'm not feeling well, or I'm a little tired and I need to lay down for 20 minutes and being okay with that part of it too. What's the best part been out of two years? The commute alone and being able to stay at home is I'd say maybe number one. Like I would probably, if I had gone to Macworld and said, here's what I want to do. Like I would probably, if I had gone to Macworld and said, here's what I want to do. I want you to turn me into Chris Breen and just have me be on staff.

I'll write a lot for you. I'll do your podcast and I'll do it all from my house. If I'd gone to them and said that, would I be as happy as I am today? Probably not. But would I have gotten a huge boost? Yeah, I would have, right? Because I would have given away the management stuff and I would have gotten to get rid of the commute. And those would have been big wins. So I have to say the commute is first and then just being back making things again instead of doing management and budgets and fighting with corporate politics and things like that. Yeah. You know, it's funny because I think we're all in the same spot. We, a lot of us really want to be these independent workers. We really want to have this happen, but there is this underlying fear that you've got to keep it working. And, um, and I hear that from you,

but I also hear that it's working out for you and that makes me really happy. Yeah. It's great. Well, gang, there's Jason Snell's origin story. David Sparks' will be coming. At some point. Not right away, but soon-ish. I'll turn the tables on you, David, because I'm not going through this and not making you go through it.

Okay, well, we'll give him a little time. There's only so much of this somebody can take. But I'm really happy for you, Jason. As a consumer of what you make i uh am particularly happy because i feel like i get more of jason uh jason's thoughts on technology now than ever and everybody out there who appreciates jason stuff i encourage you to go subscribe to six colors and become a supporting member because there's a lot of great extra content there for you um uh in the meantime meantime uh thank you to our sponsors casper and fresh books today if you want to

learn more about the free agents go especially this show go to free agents at um relay.fm slash free agents slash 20 if you have feedback we've got a great facebook group that you can send comments into there's a very active community there. I'm very happy to see the way that's growing. So I like seeing all the free agents talking to each other. If you have feedback on this episode, let us know. We always are planning feedback episodes. We really like hearing from you.

And you can also send us an email at the website, at the relay.fm slash freeagents website, and find us on Twitter. We are at freeagentsfm. Gosh, I wish for us on Twitter. We are at free agents FM. Gosh, I wish I'm going to get there. Tricky. Yeah. Uh, I am at max Sparky on Twitter.

Jason, you are, is it Jason? No, Jason. No. On Twitter. Yes.

And, and definitely send in your feedback for our feedback show, which will be the next episode. Hopefully we want that. We want that information. Send us your comments and questions and anecdotes and all of that. And then that is a big fun show where we get to let the listeners speak, which I like. Until then, we'll see you all in a fortnight. Bye, everybody. Thank you.