Focused - 48: Lousy With the Stink of Freedom, with Merlin Mann

Episode Date: May 29, 2018

Podcaster Merlin Mann joins us to discuss his long journey as an independent worker, during which he's pivoted from tech guy to productivity expert to a specializer in cult hits.

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 am Jason Stell, and I'm joined as always by my fellow host, Mr. David Sparks. Hi, David. Hi, Jason. Wow, you know, last episode you said we had a great guest coming up, and unfortunately

they couldn't be here today, but, no, it's true, no, this is the great guest. What are you on to? It's Merlin Mann from all the great shows. Hi, Merlin. Hey, guys. Thanks for having me on. This is such a delight. This is right in my wheelhouse.

This is exciting. Now, Merlin, people may know you from such educational films as Lead Paint, Delicious but Deadly. Here comes the metric system. Or from your many podcasts like Back to Work, Dubai Friday. Let's Save Tony Orlando's House. Reconcilable Differences, Roderick on the line. There might be others out there

that we don't even know about yet that are yet to be discovered. I first knew of you as a productivity expert. Actually, you're the guy who got me to use Dropbox. That was the first, that was like, you got me to use Dropbox. It's your fault. I funnel those people 100 bucks a year now.

So thanks. You're welcome. Thank you for having me. Yeah, I've always admired both of you guys. Jason, I admired you from afar forever. I mean, you were in my mailbox for many, many years, so it was a real thrill. That's true. It was cramped in there.

I'm glad you finally let me out. Then I met one guy at the OmniFocus booth, the OmniGroup booth one time at Macworld or similar, and that's how David and I got to be buds. Yeah. Well, you were on the phone with me when I was at the old firm, I remember. I think it was after one of my books came out or something. And we were just chatting and you said, you know, you're not going to be at that for much longer. You said that to me. You were the first person to ever even like put that in my brain. I think I probably was thinking about it. Oh, come on. You were lousy with the stink of freedom. You had it all over you. You were the first person to ever even put that in my brain. I think I probably was thinking about it. Oh, come on.

You were lousy with the stink of freedom. You had it all over you. You were so your butt was already out the door and you could smell it. Yeah, but nobody had ever said it out loud. And that was nice. I'll always be thankful for you helping me get that seed planted and going. I'm happy to take any credit I can. I'm really glad you guys do what you do.

So you've been a free agent much longer than Jason and I, but maybe we should talk just a little bit about how you got there. Yeah, sure. I mean, you know, how did I come to this? Well, you know, basically, I think I got the first awkward flavor of it when I got fired from a job in the mid-90s. And I'd been, not least because a huge amount of my time was wasted on AOL, burning my company's AOL hours or copy serve hours during the day. And I really loved the young web. And I'd started making circa 94, 95. I'd started making websites for stuff that I do, eventually made one for my band. And then I basically, I didn't have that, and I had to figure out something to do. I'm trying to remember what else I did besides web stuff, but mostly it was web stuff.

At first, very difficult. As I've said before, one of the difficulties of making websites, even into maybe even 97-ish, was your first job was to explain to people what a website was and why they might need it. So there was a lot of that kind of stuff. And, um, you know, the, the people who were doing it very much treated it. It was places like the newspaper would make you a website for $5, you know, kind of things that was your competition. So I was looking up to get hooked up with a guy who was involved with trade shows. And so what basically he would do a lot of the media and the multimedia for trade shows for at the time was called Blenheim. And so I ended up

doing a lot of the websites for things like PC Expo, and the horse show Equitana, and you name it, and it became pretty steady. And that's what I did pretty much up until I got a.com job that started in Florida in 1999. And what did you do there? I mean, I've heard you refer to that job, but I've never really heard. What was your response? Were you doing web development for them? I would say initially I was brought in for what I today might call, it was design, but

it was really production. So it was this cold fusion house for this real estate website that happened to have a really really really good tld that was basically the reason the site was successful because remember back in the day you type in the word that you wanted to search for an internet explorer would take you to the dot com of that well we had that so it's like homes homes.com or houses it was it was homes it was oh wow see it worked that's why that was our that's how we got 35 000 35 million dollars in vc money yeah yeah that's that's noun.com is a license to print money or at least it was in 1998 it sure was somebody was real smart to buy that so essentially uh a friend of a friend of mine

was like hey you know you should uh you should come here and check this out meet this guy who has this uh you know this wonderful island of misfit toys who made ColdFusion code. And it was really all about just pumping out ColdFusion code. ColdFusion, ColdFusion, ColdFusion. But nobody, it was like blah, blah, blah, something, something web design. And so, like, we need these buttons. And then that turned into a little bit, it was doing contract stuff with them to basically make their buttons and go live. But no, I was able to, you know, somewhat quietly introduce some improvements to the way they were doing stuff. But the best part of that job for me was kind of getting my ass kicked by this guy that I worked for, who I came to really love and admire, who taught me not to just come in and be the creative, fast and loose guy, that you had to learn what other people were doing.

And you had to always show your work it was one nice thing about working with you know programmers engineers whatever you want to call it was that you know there is a kind meritocracy such a meritocracy such a loaded word now but really a good good environment for saying like look if you have a good idea you need to actually show that it's a good idea how you would do it and then you're going to need to do most of the work yourself and that's what i ended up doing for for i guess a couple years for that company and its uh subsidiary And that's how you got out to California. Yeah, that's right. Yeah, so the startup was down in Menlo Park. And my wife at the time, or my girlfriend at the time, now my wife, worked at Stanford.

And so we would drive all the way down the peninsula in traffic every morning. But it was an interesting job. I knew at the time that it was a crazy time. And in retrospect, I now realize how crazy that time was. But it was a good experience. And then eventually you went out on your own. Yeah, then I kind of had to go out. What was that moment when you no longer had a paycheck?

Well, like a lot of companies that were falling apart at the seams, they said, because 9-11. And a lot of things had to change. I ended up working from home for a while at that gig. And eventually it was like, this isn't going to go go on this is not tenable and i really scrambled scrambled big time i ended up doing um some freelance project management work for different people um because i had some kind of affinity in that and it went okay it was uh freelance i think it's important something you guys i'm sure is a keystone here, is there's a difference between being independent, being freelance. It's kind of almost a difference between a boss, a manager, and a leader.

Like having to keep finding new freelance work is such a separate job. I found it very challenging. To cut to the chase, in the ample free time that I had, I started that site, 43 Folders. And at that time, when blogs were kind of on the ascent, and that kind of became my thing for a few years. So I was doing that, you know, pretty much on my own. That's all. Eventually, that's what I was doing. Now, you're not doing it now, which I think is there's, there's some really ripe discussion in that that since you've gone out on your own, you're not doing what you were doing when you went out on your own, which suggests to me that you've done a lot of kind

of iteration of bringing things in as things go out. Has it been, as your job has changed, has that been driven by opportunity? Has it been driven by things going away uh has it been driven by your just your interest in doing different things because one thing that we don't talk as much about on this podcast is the idea that you go out on your own to do a and then five years later you're doing j and not doing a anymore but that happens to to a lot of people and it certainly seems like happened to you on the amount and the amount of time that you're getting up to speed on F, maybe a goes away. That's part of the crazy part is that you're really,

you know, you're shooting at a, at a moving target. I feel like, um, it's a very, very long story, but you know,

there was a point I used to do this show called you look nice today, a podcast starting in, I think 2008 that, you know, the three guys did that. We all really liked it. And we'd even had like conversations about like, wow, I wonder if we could ever do this as a thing. Oh, that's hilarious. How could

we do that as a thing? How would we ever make that a thing that not to say you get rich off of it, but how would we even get a sponsor for a show that talks about the stuff that we talk about? I mean, and that was around the time that I was, I guess, even a couple years before that, I was a regular on MacBreak Weekly with Leo Laporte. So I mean, and that was around the time that I was, I guess, even, I guess,

a couple years before that, I was a regular on Mac Break Weekly with Leo Laporte. So I was doing that every week. I mean, just as a side note, that was terrific training for me because of the two things I learned from doing stuff with Leo was something I wish everybody today learned, which is that, you know, you need to do this over and over. You need to treat this like it's live. And basically, I feel like a lot of my chops came from acting like no matter what I'm doing right now and how good this is, I need to pretend that there's not even the opportunity to edit this. And I think that was a really good lesson.

So I did that and eventually did a podcast for 43 Folders. One thing led to another. I did Back to Work with Dan. And that's kind of when I started realizing maybe this could be kind of a thing. Yeah, you really have changed your profession a lot since you've been out on your own. I do think that's an important point for people that want to do this. I mean, whatever it is you're doing when you first go out, I think it's highly unlikely you're going to be doing that in 20 years.

I mean, things are going to change. And if you want to stay out on your own, you're going to be doing that in 20 years. I mean, things are going to change. And if you want to stay out on your own, you've got to be willing to look into that. How do you know when it's time to pivot? That's a good question. Can I just double down on your point, though? Because I think you're right. Something back when I was somebody who talked about the productivity part of this, I feel like one lesson that was difficult for me to learn that became valuable was to not, how do you say this without sounding like a douche, but to not minimize the things that you know or have learned or have experience in that may be more important than you realize. You get

so caught up in trying to chase that A that you forget there's a B, C, D, and E. Like, oh, you had this summer job and you were kind of a manager at that job. Like, you know, I think it's important when you're getting started in any kind of employment, whether that's independent or working for a company, to not minimize the things that aren't the main thing you're trying to do, to your point. So for me, the huge thing that set me in this direction to begin with in 1986 or 7 was learning to use a Mac and using PageMaker. So basically laying out a literary, literary, I mean it was this very silly zine, but like learning to do that. Like that became what I started

doing right after college. And that led to doing graphics work. The graphics work and line editing stuff led to the job I had in the 90s, etc. etc. etc. So in retrospect, it's easy to look back and go, oh yes, all these pieces fit together and this is my story. But that's, if there's any kind of like dumb piece of advice I give there, a small piece of advice is to, yes, keep your eyes open to what's out

there, but to not minimize what you're maybe not giving yourself credit for, that you're actually already kind of good at. And oftentimes that's a soft skill that is not the thing you think you're chasing. So there are so many people out there that are chasing a hard skill, which may be good, like a, you know, a tech skill, but not realizing that they're actually really, they're a persuasive person. As we say in D&D, they're a wiser, charismatic person. Like don't minimize that because that is incredibly valuable to anybody who wants to hire someone. I can't imagine how many of the things that I did that I picked up with side projects or hobbies or whatever you want to call them that were things that I did because I wanted to explore. I wanted to try things out that ultimately became incredibly valuable to my actual profession over time. But at the time,

I wasn't investing in a future profit-making skill. I was doing something because I thought it was new and interesting and cool, and I wanted to try it. And some of that stuff probably went away very quickly when I discovered that it didn't interest me or I didn't have the skills that were really required. But the ones that stuck around, obviously, were the ones that did interest me and where I was building up some skill. And so doing a short story magazine on the internet in, you know, starting my junior year in college, like, I gave it away for free. The stories were free. Everything was free. It had nothing to do with anything.

But that was publishing on the internet before it existed. And by the time, you know, people wanted to publish on the internet, I could say, yeah, I know all about that. I can help with that. I know how to navigate that. And that was never part of the plan. you know people wanted to publish on the internet i could say yeah i know all about that i can i can help with that i know how to navigate that and that was never part of the plan you could put an even finer point on it though where if you had said i'm going to go into journalism but i don't really like computers right i mean that would have been that's that's a weirdly pyrrhic approach to approaching you know i mean so what do you become a journalist about? Like, you had some focus to that because you'd had that background in that, right? I mean,

isn't that some part of it? Yeah, I was driven, at least in part, I'm asking the questions here, wait a second, what's going on? Sorry, counselor. It was driven by that in part, but I think that there is a broader point here, too, about I don't know if there are people who, like, totally close themselves off and say, who are we kidding? Of course there are. I don't know if there are people who like totally close themselves off and say who are we kidding? Of course there are I don't know if any of them are listening to this but the idea of like well I've known people like this over the years where it's like well if it's not If there's not a direct line between here and my job or money or you know, whatever it is I'm gonna cut all that stuff, right if I can't make money off this soon Even it's not a thing that would be worth pursuing.

Right. And at a certain level, if you're a certain kind of person, maybe that is true. But I kept thinking when I would see things like that, like, don't cut yourself off from possibilities because, one, you're cutting yourself off from being a well-rounded person, which is a problem on a larger scale. But two, you don't know what the future holds. And if you are continuing the art of self-discovery, then when things change in the future, you may have a whole bunch of things in your back pocket that you could pull out that'll be like,

aha, I do know how to do that because of this other thing. And that really goes to David's original question about the knowing when to pivot. You know, what's Rumsfeld say about, you know, going to war with the army you'd like to have? Well, there's a lot of times where, you know, if you can pick up these little threads and these little bits of stuff, you may find, I mean, I think it's important to not just say, oh, this is about some kind of like entertainment gig or social media gig. Because I think it can be true for anything. There are aspects of every job, whatever that job is. There's the topic. There's job is. There's the topic, there's the field, there's the medium, there's the kind of people that you like to work with or find

yourself working well with. So I think it's actually, it requires a huge amount of openness to think about all of those things because they are all related. You know, David, you and I have talked about how many times the number of people who think they want to be, they want to go into law until they spend a lot of time with other people who are they want to be, they want to go into law until they spend a lot of time with other people who are also going into law. And they sometimes realize they don't really like being around certain types of people. They don't like certain kinds of environments. Like it's amazing that you could be so highly educated and not realize that until you're at a point where you're actually about to go into the career you don't want to have. So looking at all those little

bits and pieces and those little bits of thread and buttons, you can find yourself fashioning ideas for different things if you're open to the different ways you can pivot. And then as the market and the audience changes, you may find things where you follow your nose and realize, well, I've already been kind of doing that a little bit. The interesting piece of this is so often on the show, we talk about the importance of saying no and how you have to have a filter and you have to be able to give yourself space. And it may be easy listening to this to say, well, if I'm saying no, how am I going to try out this stuff?

And I think what we would all agree on is you say no, so you've got time for the whimsy. So you have time to try and pull out some of these things that you're passionate about that can turn into something for your future. I agree, but I think it's also more practical than a lot of people give it credit for. It feels like you're being fancy when you say no to things, but what's the potential corollary? Well, do you want to take every bit of work that comes along,

even if there's 100 red flags on those projects? Because in some ways, there's not a, I mean, you're underwater at that point. If you're working with a lot of people who, where neither of you really respect what you do, or can pay the wage that's reasonable for is like, what do you want a lot more of in your life? Because be careful what you ask for. So it's, I feel like in some ways there's two kinds of people working independently, people who get comfortable with saying no and people who will eventually get comfortable with saying no. Yeah. You don't want to be, you don't want to be the dog that catches the car sometimes. Totally true. This episode of the free agents is brought to you by Squarespace. Make your next move with Squarespace. Squarespace lets you easily create a website for your next idea with a unique domain name, award-winning templates, and more. Maybe you want to create an online store or a portfolio or a blog. It doesn't matter. Squarespace has got you covered with their all-in-one platform

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Thank you, Squarespace, for all your support of the free agents and Rel spaces to get 10% off your first purchase. Thank you, Squarespace, for all your support of the free agents and RelayFM. Make your next move, make your next website with Squarespace. So what about this idea of the little voices? You were talking about that earlier. I think that's an interesting point. Yeah, I mean, it's kind of related to that idea of, I mean, it's almost like the way I put it is you want to listen to the right little voices because there are the little voices that are always, that could be sort of a negative tape loop. fact that there's sometimes a sub rosa monologue or dialogue going on in your head. Sometimes you can find your own sources of both inspiration and direction by looking at those kinds of things. And I don't really have a better or clearer way to put it. You could think of it as an itch or a nudge. But you know, sometimes think about like when you met people as a kid or as a teenager,

where you met people where you're like, oh man, all I know is I want to be like that person. Well, what is it about that person that really moved you? It could be that they're confident. It could be that they're relaxed. You know, there's all kinds of, like I say, there's all kinds of angles that you can pivot to. But like in my case with the podcast stuff, I mean, there were years and years where I just thought a podcast as a loss leader is too strong a word.

I thought of it as a thing that I did because I like doing it. And we should come back to that because I do think that is very important. It does help so much. Whatever it is that you're going to, to paraphrase John Syracuse, if you're going to put wood behind the arrow in any endeavor, it helps to really, really love the medium or the platform for what you're going to be doing. And sometimes that little voice is saying like, hey, you know, maybe you should, maybe you should do more podcasts or maybe you should do more, I don't know, posts on medium depends on, on what it is. Maybe, you know, if you're in a profession, maybe you should be writing for the newsletter for your bar. Like, I don't know what it is,

but there, there's something out there that could be an itch and it does not take a hundred percent commitment to get a flavor for that. It's a, it's a Buddhist gift for you to go in and have a medium quality experience of something. Cause now a Buddhist gift for you to go in and have a medium quality experience of something because now you have more experience. You're learning more things. You're trying more things. So the important little voice to listen to or to ignore, I think, is the one that says, you know, don't try different things. Don't be different. It's scary and the world wants to destroy you. It's learning to differentiate though and to have, I guess, a certain amount of courage or stupidity to try stuff that you feel unqualified to do.

Yeah, I feel like so much of talking to people about this stuff is just giving them affirmation because it is hard. I think inside it is easy for, in my experience, to tear yourself apart over stuff like this. That's why it took me 22 years to get out. Yeah, 100%. So, Marlon, I want to ask a question. to tear yourself apart over stuff like this. That's why it took me 22 years to get out. Yeah. A hundred percent. So Marla, I want to ask a question. David and I both work out of our houses and, and have been doing that since we,

uh, since we started this. So you though you have an office, right? That is separate from your, from your home. How did that, you know,

how has your workspace changed since you've been out on your own? And how did you end up where you are now? Well, I mean, the truth is, like, I think you guys, I suspect both you guys, I think I know that you guys both, like, own houses. Like, you own a house. We've rented the same flat for something like 19 years now. And it's not, it's really nice in size

for a San Francisco place, but it's not huge. It's a two- nice in size for a san francisco place but it's not huge it's a two-bedroom house and so when our daughter came along by the time she was about one year old we realized that you know you know not realized but we accepted that like she needed to have her own space and i was my footprint in the house was becoming outsized and the amount of influence i needed to exercise in terms of everybody be quiet for two hours was you know a little bit onerous but mostly it was that she needed a bedroom. I don't really need, need, need this office. life versus office life, as I might put it, I feel like you really need to arrive at some pretty clear ideas about where those barriers are for yourself. And that can be easier if you have your own outside office or shed or whatever it is. But I feel like everybody struggles with that no matter how that setup works.

And there's ups and downs to both sides of that at different times in your life. But I think it's mainly been a really good thing. I wish I picked a place that didn't have a streetcar going by quite so often. You probably can't hear it. But that's mainly how it works. It worked fine for a real long time, especially when I was mostly writing and where my wife was going to her office job and I'd have the place to myself all day. But by the time my daughter came along, I had to,

um, I don't know. I always thought of as being like ice cube walls that could melt very easily. I had to develop some mental, um, bulwarks and all kinds of little tricks. Like you'd, once you get in sight of the house,

you take off your headphones and put your phone away and you don't open your laptop at the time laptop before ipads you don't open your laptop or your phone until the kid's gone to bed dumb things like that where you just make a rule for yourself um where you can basically be able to there's a funny difficult trick of like can you have the tolerance to set aside the stuff you know is going on at home to go do work? And then can you conversely have the tolerance to break off from work in a way that you have home life and rejuvenation that will bring you back to

work feeling refreshed. And I feel like that can be a challenge for your entire career, but it's something everybody faces, everybody struggles with, but it is a fight worth having. Do you go to your, space sort of on a set or roughly set schedule and are there and then come home? Or do you only go there when you have like a specific, like, I'm going to record a podcast, so I'm going to go over there and then I'll come right back home? How long are you over

there? Yeah, that's a good question. I mean, obviously, I'm here when I'm recording stuff. There's a lot of stuff that I can do. And again, this is the completely unsympathetic world of somebody who makes podcasts. But there is, Jason, I hope you would agree, a surprising amount of work that goes into somewhere between somebody talks into a microphone, and then you talk about it on the internet. There's a lot in between. So there's a lot of invisible work to what I do that's not particularly interesting, but writing show notes, gathering links, preparing for a show, doing stuff after a show, you know, a couple nights a week for me are spent collaborating closely with people in the preparation for putting up a show, usually that night. So like my Wednesday, my Thursday nights are due by Friday nights where there's a lot of

collaboration, a lot of listening, a lot of checking for edits, a lot of just dumb stuff like gathering all the titles, uh, getting all the notes and links. It's not difficult work, but that kind of stuff I can and do enjoy doing at home because I can kind

of be at least partially in the scene. But if it's something where I've got to really break off, I can just say to my family, Hey, I just need to go to work for 90 minutes. Is that cool? And that usually works out could be on a weekend, but, um, it's nice to have, it is really nice, nice privilege to have a place where you can go that you're away from it. And, uh, you can, you know, check out in a guilt-free way. And do you like go to coffee shops and,

you know, all the other places that a lot of free agents do or is it just the office for you no no um i don't um i it's so performative i see why people do it but there's so much performance going on it just makes me so sleepy um i will go and take a walk that's what i will do i will go and like my shrink used to say go out somewhere where there's lots of greenery where there's lots of leaves and grass and the kinds of things that will break up your weird dopamine and make it accessible to your brain. Go get outside, make it okay to be somewhere for 60 minutes. I will do that. I used to do that when I was doing more writing, but even then I would realize there was so much overhead. You know, it's like that episode of the Honeymooners

where Ed can't play anything on the piano without first playing like the beginning of camptown ladies like he can't do anything until he's played that song it started to feel like that so that can be good and i i feel like you guys have talked about this i think there is value to breaking up where you do work and jason i in fact emulated your ipad setup i'm embarrassed to uh, I love that setup with that stand and that clicky keyboard, but that's, I can take that and put it anywhere. So when my daughter and I are listening to a podcast in the afternoon, she could be making something with the glue gun while I'm doing some show notes across from her. So I'm still kind of in the scene. It's not disruptive.

That's my version of that because I do a fair amount of the home stuff and the kid stuff. My wife and I kind of split that up. And that's been, again, it's a privilege, but it's a privilege I'm very happy to have. Yeah, I think there is something for a lot of people getting out and going to a different location. I get what you say about the performative element of trying to work in a coffee shop and just the whole scene. I mean, I'd go to a library. If that were me, I mean, if you want to get some work done, you could go to a library. It's just there's something about, and like I say, I get why people do that. I guess I get why WeWork exists. I feel like I do kind guys on Slack and on Twitter and you know, that's my pals. And when I get to record a podcast with somebody that I like,

that actually is, that's a form of human intercourse that's really valuable to me. So I think getting out of wherever you are, especially when you're starting out is not a bad idea at all. But also start to account for the overhead, like especially if you're spending $35 on coffee drinks,

like be aware of those kinds of things because that will kind of cut in to the bottom line. This episode of the free agents is brought to you by timing, the automatic time tracking app for Mac OS, head over to timing app.com slash free agents and save 10% when you purchase and get a 14 day free trial. As a free agent, I cannot understate the value of knowing where you're spending your time. There's really nothing more important. And with today's sponsor, Timing, that's easy. Distractions are always just around the corner, and this makes it harder and harder to stay on track of where you are with your projects and determine how much time you really worked. That's why you need an app to help you stay on top of your time. But manual time tracking interrupts your workflow and is easy to lose track of.

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the free 14-day trial and 10% off. What was the biggest surprise for you after going independent? Probably that I bought into a certain kind of mythology. I don't know if this was ever deliberately put onto me, but I definitely took this up that there are people who have arrived. There are people who will arrive and that there are people who probably will never arrive. And what I feel like I've discovered is that there's no arrival. I mean, sure, you can look at Ryan Reynolds and say, wow, you've really come a long way. You're Deadpool. But like, you know, as John Roderick likes to say, even Bono has a boss. Everybody has something else that they want. And the less that you've been exposed to what actual life and work is like, the more surprising it will be that nobody feels like they've arrived. Really, really.

So that was part of it. I kind of felt like if I hit some kind of a pinnacle in a given area, it's not like I was going to retire on it but it was a little bit surprising to me a that that was the case it was doubly surprising b that almost everybody i know feels the same way has the same fears and anxieties and the same sense that like i just hope i can keep what i've got today versus what i hope i have in 10 years i think people don't talk about that a lot because it's not fun but uh that's a big part of it i think was i i guess i thought there were people who arrived, and I'm not sure arrival exists, except in that wonderful movie.

Yeah, you're anxious to become a free agent. Then once you're a free agent, you're anxious to stay one. And it's the same struggle. Right. Imagine the rest of your life being some work, but mostly job interviews over and over and over, except you have to talk about money every time. Yeah. Fun. Yeah, right. That's great, love that. What's the best part about being independent for you? I don't know, it's so funny

because so much of the good and bad parts, it's like a yin and yang, they're so kind of involved with each other. But I think in practical terms, one of my favorite parts is, well, first of all, I don't have to have to have to do that much stuff that I think is stupid and damaging.

Like when you work in a company and you've got stuff and there's a schedule and there's a big Gantt chart, this is not a slam on a jobby job. But like I think one part that can really grind people down is the constant sense that what they're doing may not actually be contributing to something they think is really valuable. That can be frustrating. It's nice to be able to say no to things that aren't a good fit now. It's really nice to be able to say no to things that you know are BS. That's a really, David, I have to imagine that's a huge thing for you, is that you don't get saddled with some case just because it fell into your cage. That's one of the biggest benefits of me leaving. In fact, I have given up entirely sections of practice that I used to do regularly because I just don't believe in it anymore.

I used to be a big-time litigator. I don't do that anymore because I think it's just such a waste of time and so expensive. You could set up a shell corporation and sell access to the president or information about real estate. There's a whole variety of things lawyers can do. Yeah, apparently, apparently. But just on the litigation, I was sitting in a deposition after I had left. When I left, I had intended to continue to be a litigator and I was sitting in deposition and the deponent was lying, his attorney was lying. And there was a time in my life where that was celebratory you know you're like oh he just committed perjury i'm gonna crush this guy when we get to trial

and instead i just felt empty and i realized i don't want to be a part of this anymore isn't it also very disruptive potentially to your schedule like i feel like i used to work in a place that did litigation support and there were all kinds of fire drills that would come up or for one reason or another change of venue change a judge changes something there'd be all these changes and suddenly you just weren't gonna have a weekend for a while no i mean that's that's and that's a big reason why i also stopped doing that because i want to have time for the other half of my life but the um but even deeper it was like this doesn't bring me joy anymore so what am i going to do about that i also feel like i don't have a super strong opinion about this, but I feel like, you know, I mean, it cannot be overstated. It's really nice to be

able to have the dumb things you do be the dumb things that you did. That can be a really good thing. But you also have the opportunity to pivot. And that can be just little pivots. But I think that's more difficult to do when you're on the slow turning battleship of a very large organization where even if you're doing good work and being acknowledged for good work, you're still going to be serving the stuff that your bosses want you to do because that's how a job works. So, you know, looking just at the benefits, it is nice that you could decide to pivot to something slightly different

or experiment with something slightly different, something that maybe keeps you excited about the kind of stuff that you're doing. Maybe it's something that potentially becomes, God knows, lucrative for you. It's hard to know. But in any case, you know, that I think it's difficult to deny that the ability to control your medium term destiny can be a really gratifying and invigorating feeling. How do you keep up the enthusiasm for something over time? How do you keep the focus and keep your eye on the ball and not, you know, burn through something and be like, okay, I'm done with this thing now. This gets to another issue I mentioned to you guys where I feel like part of it is about

isn't, you know, I think there's a lot of mythology and happy talk about passion and inspiration and doing what you love and all that kind of stuff. And that's all well and good. You know, for a lot of people, that's never going to be a factor. I mean, for a lot of us, like to find not hating what we're doing most of the time or being forced to be around people we actively don't like, that's all a lot of people can hope for. And it's good to get in a situation that you kind of don't hate. But if you actually really, the way in which maybe above all, apart from being a white man that I feel privileged is that I make podcasts. I listen, I've, I've recorded, you're

my second podcast of the day. You're my sixth podcast of three days. And on top of that, just since I woke up today, I've listened to three podcasts. I really, I ain't front, like I super like podcasts. I get a lot of references because I'm probably listening to your show, right? There's just so much stuff that I can catch my own softballs. I genuinely love that medium. And I'm double super extra fortunate title to really like the people that I do this stuff with if and when it becomes a grind. Isn't it funny how on the one hand, something feels like

stability because you enjoy doing it and it's always Monday at 10. And then on the other hand, when something starts to feel like, wow, you know, we really need to bring in a cousin Oliver here because I'm not sure how we're going to proceed with this property. That's not as fun. So it helps to me. I've always said it's nice to have multiple projects you're working on. So for me, each podcast is kind of a different project. And each, I'm fortunate again, in that it brings out different parts of what I like to do, or, you know, because of my relationships with the other people, it brings on interesting things. So that part, it's you can keep enthusiasm about, but I don't know, you also just get burned out. Sometimes you just sometimes you just like I

said to you guys, sometimes I'm just so tired. You think you're tired of hearing my voice? Like I hear it all the time. And I think it can be difficult to keep that up. I think that is one of the challenges of being independent, in fact, is finding a way to stay open and curious about your options while also finding a way to be invested in what you're doing and to know the smart ways to change and improve what you're doing that aren't just gimmicks. Do you know what I mean?

Yeah, I mean, kind of turning it to the topic at the beginning, the good news is you can pivot and the bad news is you need to pivot. Oh, God, that's a good way to put it. It's depressing. It's true. Yeah, it's funny. You mentioned recording all those podcasts. That is something that by the time time this comes out it will have already

happened but you're doing a bunch of podcasts really quickly because then you're going away for a little while and that is something that we've talked about here that when you're independent one of the things you have to do is the work still needs to get done so you can go away but you've got to do all the work that you would have done during that period and get it ready to go. And that I had a period like this not too long ago, Merlin, where the same thing happened to me, where I recorded. I recorded like nine podcasts. Just when you went to Austin, I could hear it on every one of your shows. I heard it with Tim the week before.

And you're like, yeah, well, there's a huge amount of compression here. Many things have to happen. Many things have to. Yeah. And I had some I had some trip where where like I was recording two or three podcasts a day for five days straight. And again, podcasts ain't chopping wood or anything like that. But there is that kind of fatigue. But that's one of those funny things about this kind of work is that the job needs to get done.

And if you're the only one who can do it, then you got to do it. Even if you go away for a week, you got to do the work either while you're gone, which is one option, which sometimes happens. When I was in Austin, I did a podcast and I wrote a bunch of articles, even though I was on vacation because that was just how it had to be, or you front load it and then you're tired. But if you i will say this though um if you love it that certainly makes it a lot easier to do stuff like that if you are enthusiastic legitimately enthusiastic about what you're doing and it doesn't feel like a grind yes and i think about that that is top of mind for me as we approach summer which is like a clove of garlic a mirror

or a silver cross to podcasters. Cause summer is when everything gets complicated. The summer of fun, but you know what happens? Here's what happens is that everything touches up against everything else. And within all the great shows, many people do shows with each other and a horrible thing happens, which is that somebody's got to do a thing at a different time. So now you get to do this. This is so boring, but I think you know what I'm talking about. There's one change in schedule.

There's never one change in schedule. Because now once you do that one thing, John Syracuse is only available on these nights. But then John Roderick is available on these nights. But Marco and Casey are available then. Yes, but he has to be on this episode. And therefore, I'm pretty sure you have the craziest three-dimensional set of tile puzzles that you're trying to move around and then you end up having to as you say like like heavily front-loaded so you know some are fun that's what i'm saying yeah that's uh you just described scheduling an episode of the incomparable quite honestly

which you then get to edit you got to play nine-dimensional chess with that and that's just how it is but you know again if it was a grind, I wouldn't do it. That's the difference there, I think. I mean, that's the thing, right? Let's say you're going on vacation and you do need to record a bunch of extra podcasts in advance. I mean, in my experience, I enjoy making the podcast. It's exhausting, and I guess that's another conversation. It is tiring doing this stuff, And it is hard getting it out.

But the process is fun. And it's even stranger for me when I go on an extended vacation. I really miss it. There's part of me that wants to get back on the mic. I want to talk to Katie. I want to talk to Jason. I want to guess somewhere. I want to do something because it's a part of me.

And it's way more than just something you do to make a few bucks. Yeah, I totally agree. I was listening to Clockwise this morning and when Steven was going through the listing of what he does in a week, I almost passed out. I was like, I'm never complaining about this again. Well, I think Steven's still early enough in his journey into free agency that he's probably saying yes to everything. That's my guess. I don't know how those guys do it. I really don't. What's the hardest part about independence for you? The hardest part about independence? I mean, you know, I think a big part of it is that, you know, I feel like sometimes I feel like it's whatever, whatever came out is what came out. And then you

live with it forever and move on with the next thing you know sometimes there's always been this this goes back to the blogging days i guess where there was that feeling of like oh to this day the one feeling that has been constant for me all along is it's so cathartic to hit post it feels so good to be done with it have all the notes done everything's formatted the line breaks are light right all the dumb things that nobody cares about and like you hit post and and that feels really good. But there's also this part of you that's like, oh, that could have been better. I could have done that better.

I try not to listen to that voice too much, but it's definitely there. There's definitely some part of me that's like, oh, you know, you could have edited that to make that better or you could have like not talked over that person and now the little voices are out. But like, you can't do that. You've got to, I mean, it's a rally, not a race.

You've got to just keep showing up every week and being a hundred percent engaged with the people that you're talking to. So, and like you say, that's not the worst thing in the world. If you're going to make a dent, you have to be willing to ship it at some point. And I do think that you look at the people who are most productive and it's okay if they have, I I'm always willing to give them a pass when there's a little something here

and there, so long as the overall quality is good. And I do feel like if you want to make it perfect, you will never get it out the door. Yep. I mean, one of the things I really admired about you, Merlin, was when, I mean, 43 folders, I don't know the details of the traffic, but it was a super popular website. And at one point, you just, I got the impression that you just didn't feel passionate about it, or you had new

things that you wanted to do. And you just moved on. And I don't think that's easy when you have something that is that successful. Well, it is and it isn't. I mean, I like to think that I specialize in cult hits. I feel happy and honored and i don't know happy when i find out that people i admire like what i do and i'm a small enough person for that to make a big deal to me you know in that case that was that was perhaps an example of what you guys are talking about where i feel like that racket had really moved on from what used to be a fairly wholesome thing to being a somewhat less wholesome thing um so that was not that difficult. But one nice thing about doing the show with Dan, I mean, as much as we talk about comics and bathrooms,

like the distinction that I like is instead of talking about getting all of the affordances and mental brace work and apparatus to try and like make your job easy, I think it's more fun to explore why jobs are hard and why creativity is hard. And that is kind of a through line with Back to Work

that's been really rewarding. So the feeling that I got of eventually feeling like I was just vending productivity porn, I do feel good about being able to take questions. Every week we take questions from listeners who are like, what do I do about this situation at work? And trying to be creative with helping them frame or reframe what they're doing, trying to zoom in on one detail of what they're saying they might not have caught.

That's incredibly satisfying to me in a way. I'm not to slag on 43 folders, but that makes me feel really good. We get a lot of really nice feedback from people who are able to think about something slightly differently, and that's so great to be able to do. So day in, day out, you say to yourself, I got this. I got this down. I know what I'm doing. I got it totally wired. Do I? Do I? Is that the Merlin Mann approach? You're like, it's supremely confident. And you got it all figured out now? I got nothing to worry about,

no anxieties. I don't think about anything. I'm all'm all good no it's um but you know that's that's one of the things that you know it's impossible to think about going back and giving yourself advice because you know you'd break the timeline but but the truth is that and uh there's one point on reconcilable differences where syracuse and i were talking about like going back in time and giving a message to yourself and of course john was completely obsessed with like how i would know it was me and it was a bad avenue to go down with that particular character but but you know i mean there's certain things you wish you could tell yourself a little bit when you were younger like okay you're not gonna until you die you're not gonna die right that's that's a good thing to know but the other thing that i mean i there's a message that would

be impossible to have to send or have been adequately received by pubescent me, because I did hear the message and it still didn't matter, was everybody's struggling. Everybody's having problems. And almost everybody at some point feels like they don't know what they're doing. Some of the people who act most confident about knowing what they're doing are actually the most clueless. And I know, I guess getting a little bit more comfortable with that slight uneasiness of not always being sure exactly what you're doing. And having that feeling does not mean you're unhealthy all the time. That means you're being somewhat honest with yourself.

And I guess I wish I'd learned earlier on to be somewhat okay. You don't want to become life controlling. But realizing that you're always a permanent amateur in some ways can be a really good thing. you're always a permanent amateur in some ways it can be a really good thing you know um only only there's some professions where you have to be professionally confident all the time but being a little bit broken in public can also be a nice gig the people who arrived are also the people who don't have any doubt and are fully masterful of everything they do those are the people yeah those same people who have arrived and i don't know who those people are lobbying they know real estate investments steven spielberg you know steven spielberg sure i think he maybe knows he he arrived right but uh you know there's not that

many of them out there i just pulled that one out of the hat but like most of us we didn't arrive we're still working on it and we aren't supremely confident and i would i would say this goes back one of my favorite news stories or uh i guess it's a science story but over the last like 20 years was that fuzzy puppy where he uh it's about space no and related subjects it's not uh was about the concept of being incompetent and well dunning dunning kruger exactly right that the the people who are truly incompetent don't know it because they're incompetent at gauging their competence at it but everybody else feels some degree of of of

incompetence and that means that you're on the scale that you are capable of measuring and then you struggle and that is i think about that a lot when i think about people who've made it or people who are like supremely confident versus the rest of us who are like, you know, always racked like, I could have done better at this. I could have done better at that. It's like, if you lose that, I mean, I think that you may not be incompetent, but at the very least you've lost your edge. You've lost a thing. Like sometimes with musicians or other artists, I'll have that moment where I'll think like what changed. And I wonder if what changed is that they got told that they were brilliant so often that they finally believed it.

And then, and then they were no longer interesting. And I'm not saying that we, you know, that, that all of us are, are, are like artists,

like famous musicians are, but I am saying like, I think workers, especially in creative fields, but even in general, like if you're questioning your decisions and saying, how could I do that better? That is what keeps you alive and moving forward and doing good work, not necessarily creating great art, doing good work. And the moment that you stop, the moment that you're like, nope, I got it wired. I'm good to go. That's the moment that I think you stop doing good work

because you're not thinking about it anymore. you're not actually analyzing what you could do better or how things are changing and how you need to modify them and apologies for the rant but i mean like that's what i keep coming back to is like your self-doubt is what makes you good at what you do in a lot of ways yeah i i don't think that's a rant at all i think the the only thing that i would the only thing that I would, the only pepper that I would put onto that particular cereal is, you know, also curiosity. How do you remain, it's not that you should be unsure of yourself, but like knowing that there's always room for you to do something better or different, but also just staying curious, which is surprisingly difficult to do because part of life tells us that we must not be vulnerable

and wondering and searching. And it's not like you've got to go out and like walk with wolves, but the idea of finding new things to be curious about and to be an amateur at is also a huge part of not just being a good independent person, but just being an interesting adult. That goes, they go together too, I think. I mean, it's the idea that you get real comfortable and are like, I'm doing great. Everything's great. The world as it is, is all that I need to see. And that's when you stop questioning your, you know, your work and could this be better? But that's a worldview, right? Which is, I don't need to explore.

I don't need to be curious. That new thing, I always think about it in terms of, especially writing about technology, that new things coming down the pike. The moment that you're like, I'm not interested in that new thing. That's a bad, that's a bad moment i i get that not everything coming down the pike is good and some of it is confusing yeah you could always pivot to saying like uh now it's my job to understand why this is interesting to other people it's not a way of of casting some kind of spell on it that says you must go away because i don't like my space it's a way of like saying like okay well what is it about this that people like like i do that with instagram i

want to understand the love of instagram i don't want to do it but i i understand that it's important i blew it with video games and now like with any kind of technology that comes along there's some like voice control stuff that like oh my god i'm over the moon about this stuff i can't believe how excited i am about it but like you know you're right i mean anything that there was uh, anything that was, anything, well, I'm not going to go through the whole cliche, but you know the cliche about anything that happened before you were 30, after you were 30, etc. You're supposed to, you know, forget about that. Well, we're all past 30, right? So the goal there is you've got to try to keep some of that curiosity and interest.

You've got to fight. Steve Martin's girlfriend says, let's go camping. And he goes, sorry, we're closed. The sense of curiosity and getting older is one that's always been on my mind. Even when I was young, I was surrounded by older folk that were not curious. And I always wondered, if I get older, am I going to become like that? Is that something? I was aware of it. And I'm not old now, but I get older, am I going to become like that? Is that something I was aware of it?

And I'm not old now, but I'm older. And I feel like I'm more curious and interested in the world than I've ever been, partly because I feel like I have a little more control over my life than I ever had. But I haven't felt that, but I think I'm aware of it is probably why. It helps to, I mean, this is one of those great things of spending time with John Syracuse. You learn to be rife with self doubt. Um, cause he's really good at making you feel that way,

like kind of professionally, but, but you know, honestly, uh, I, I've learned to try and like listen for certain kind of easy catch phrases or easy answers to things.

And, and I do have to credit him in part for that. He would not agree that I'm improving, but I'm trying, but you know, sometimes you'll catch yourself thinking something or saying something. Every parent has had that phase in one of the first times they find themselves saying something very stupid that their parents said. And you go, oh, that's what that feels like. You can catch yourself sometimes if you, you know, you're writing something up before somebody is even done explaining what something is. You try to look for how it's bad, stupid and dangerous

instead of being curious. And curiosity is a kind of vulnerability. It's a kind of emotional and intellectual vulnerability to say, like, I don't understand this thing, and I'm certainly not an authority on it. You know, the quick route to that is just call it dumb and walk away. But it requires a bit of vulnerability, which I think is a good thing to rehearse until that muscle, it doesn't pain you to use the vulnerability muscle. And I'd add to it, I think curiosity is an important element if you want to try and make a go of it on your own. Yeah, I hear that. All right. Well, Merlin, it has been a pleasure to talk to you today. I know you've been through many podcasts. I'm glad you can choose many podcasts. I'm glad you chose this one. It's been a pleasure to be here. I'm

glad you guys are doing what you're doing, and thanks for the chance to talk about this stuff. I appreciate and enjoy both of you very much. Well, people should listen to Reconcilable Differences, which is on this very podcast network, which is why I'm going to mention it first, because it is you and John Syracusa, two of my favorite people,

and two of my favorite podcasters, and then you talk to each other, and I can never remember which one's the bad cop but uh it's enjoyable i'm always the bad cop and john always reminds me what i'm doing wrong um which is a nice thing for the listeners i think it's good if you want to learn how to be on time you know talk talking from your children learn about the privilege of punctuality anyway you're in the barrel this week so thank you for being in the barrel thank you for having me and uh we'll be back in a fortnight with more Free Agents, but until then, you can find us on the Twitter at FreeAgentsFM.

You can go to relay.fm slash freeagents and click the contact link to send us an email if you've got a question. And yeah, we'll be back in 14 short days, but until then, David, it's been a pleasure as always. See you in two weeks.