Jason Snell is his own HR person

[01:46] Describing what Jason Snell does really can’t be done with one word. He’s been covering Apple and other technology companies for more than 20 years, ten of those as a lead editor at Macworld. But personally, I first came to know Jason from The Incomparable, a podcast that turned into a whole network of shows on Pop Culture.

He’s still doing that show, and if I’m counting right, he’s on at least five podcasts a week. On top of that, he’s the editor-in-chief of Six Colors, a site he started a little over four years ago.

All in all, one thing is for sure - a typical day in Jason’s life doesn’t really exist.

One of the nice things about what I do is that I don’t have a typical day, I think, so much. I tend to go in cycles, and every day of the week is a little bit different. If I would boil it down to a typical day, it would be that I come into the office, which is my garage inside my house; I walk in here at somewhere between 8 and 9 in the morning, and turn on the computer and start working.

Obviously, I’ll go out and I might walk the dog or go for a run or a bike ride in the middle of the day, make myself some lunch… The kids get home from school at some point in the afternoon, and I probably knock off somewhere between five and six-thirty; it sort of depends on the average day. I’d say somewhere between five and six I will turn off the computer.

Beyond that, the details of what I’m doing during a regular day - you know, I have two podcasts I record at 9 AM, so on Monday and Thursday I’m in here prepping, and then I’ve got other podcasts sort of strewn throughout the week - Tuesday it’s sort of midday, Friday it’s in the late afternoon.

I’ve got freelance stuff, so I’ve got that marked… Sometimes I’m writing freelance stories, and I’ve got those blocked off, because I’ve got weekly and every other weekly gigs that I’m doing; so I’ve got those blocked off. And if I’m not writing those, then maybe I’m writing something for my own site, or I might be working on something else. I might be working on editing a podcast, or making a video or something. So there’s not a super typical day, other than to say I’m probably in here 8 or 9 to 5 or 6, and I am probably doing a podcast and editing a podcast somewhere in there, and also doing some writing.

[04:08] And at some point during the day I may wanna take a break from writing at my desk and I’ll go write on my iPad on the counter in the kitchen, or I’ll go to the Starbucks that’s down the street and I can walk to in less than five minutes. That’s if I really need a change of venue in order to get the words flowing.

You do a lot in one day…

Well, that’s the thing, is that it’s not – it varies from day to day. If I had like the super-average day, it’s probably record a podcast and write something. But some days I definitely record a podcast, and other days I don’t. Some days I write more than one thing, and other days I don’t. And I don’t edit a podcast every day, because some of the podcasts I do I don’t have to edit, which is great. So it varies from day to day… And I do work a little bit on the weekend, too; that’s like my Saturday morning - I actually am doing some podcast editing on Saturday morning.

I do a lot, it’s true… It’s just varied. I don’t do everything I do every day; it varies, especially throughout the week.

Which I think is nice, because then you’re not doing a ton of context-switching in one day.

Yeah, I’d like a little bit of it. It can be really good. But there is a point where you start to lose momentum if you have to do 8-9 different things in a day that are all little. But I also like the break. That’s one of the reasons why I will sometimes write at some place that isn’t my desk. There is something to be said for context switching, because it makes you feel like you’re starting something new, instead of just moving on to the next piece of the puzzle… And starting something new is refreshing, in a way that just going to step two is not.

So you’ve been doing this for four years now… What would you say has been the most difficult thing about being self-employed?

I don’t know, I think for me – this is a hard question to answer. I think I would say deciding when I don’t have specific obligations, when I’m thinking of either projects that are long-term, or I’ve got a whole menu of items to choose from, I find that difficult. It’s way easier if I know I need to do three things in a day.

But if I have a day - let’s say I have a Wednesday, and I have no writing obligations specifically, especially freelance (I don’t have any podcasts that day), what do I do on Wednesday? That is difficult for me, because yes, I can write another story on my site, I could work on a video… Do I wanna do a video? Well, a video is gonna take probably more than a day, but I could start it; but do I have time to finish it? Do I have a long-term project? Is there a book project that I need to work on, that I should start planning? Or do I say to myself “You know what, you work really hard and you work six days a week, so maybe Wednesday morning you should go see a movie, or something like that.”

That for me is the most difficult thing - I’m having that moment of paralysis, because I don’t have just the next task in front of me, and I have to do long-term planning and I have to create that structure around me… And those moments when I don’t have that structure and I’m not sure what the best path forward is - those are hard.

I could say not having a regular paycheck and not knowing where the next amount of money is coming from, but I’ve been doing this now for almost four years, and I’ve got a bunch of different projects going, and fortunately, they’re all fairly consistent. I don’t have that kind of wake up at two in the morning and think “Oh my god, where is the next paycheck coming from?” and I’m very glad that I’m not in that situation.

Instead, it has a lot more to do with kind of getting out of my short-term – it’s so easy to get in the short-term… It’s almost like a rut, or you can say you’re in a groove; that’s the positive kind of rut, I guess. That’s great, but you do have to think about the long-term and the big picture and give yourself new assignments to do, and think a little more strategically. That can lead you to a moment where you’re sitting there on a Wednesday at 10 AM and thinking “I don’t even know what I should be doing right now.” That’s when it’s actually really good to take a walk with the dog and sort of clear your head and think about what you’re gonna do, or go for a run or a bike ride, or whatever.

[08:07] One of the things that I heard you say a few different times is the fact that you go for a walk somewhere… How important has that been for you, doing what you do? Because I think sometimes as creative people we don’t give enough credit to how important it can be to take a break…

I have to remind myself to do it… So it is important, but it is something that I have to remind myself, and it’s very easy for me to get out of the habit. I am always surprised - and I shouldn’t be - when my wife comes home from work and I say “Oh, I didn’t do any of that. I didn’t take the dog out…” I mean, I worked, but I didn’t take the dog out. I didn’t get out of the house today.

The problem is that I don’t mind working in the house all day. I know it’s not good for me, but I don’t mind it, and so I have to remind myself; I was getting stir crazy, I would feel differently. And some people say “How do you deal with being on your own and not having co-workers?” and things like that… It’s like, I like in a house with three other people.

My kids - they aren’t here when it’s school time; in the afternoon they’re here, so I actually have a fairly small window where it’s just me and the dog and the cat in the house. I don’t feel lonely, and I do need to remind myself to get out and move, and it feels good and it’s the good thing to do, but you always have to fight against the fact that every hour I spend out of the house, taking a walk or whatever is an hour I’m not working. You have to get in that mindset; it’s essentially part of the cost of doing business, or in this case, the cost of being a healthy mentally and physically kind of person and worker. You can’t just sit there and grind all day and then go lay down. You have to kind of break it up.

I will often do that where I will come in and work in the morning… I haven’t taken a shower or anything, I just kind of roll out of bed and I come in here and I start working, and then midday I have that where I’m like “Okay, now that I’ve sort of completed some task…”, or I’m at the point where I’m now ready to context-switching, what I’m gonna do is I’m going to walk the dog, take a shower, maybe make myself an early lunch and then come back and keep working.

You try to - at least that’s what I’m trying to do - break it up into little blocks of work, and I have much more flexibility to do that being an independent person and being in my house. It’s a lot easier for me to say “Work, shower, work some more, lunch, work some more, walk the dog, work some more.” I can do that if I want to, the work that I’m doing, in blocks like that.

I think it’s interesting that you say that it is so much easier for you to do that since you work at home… When I find that a lot of the people that I talk to that work from home - that’s what makes it so hard for them.

Well, it’s both, right? I mean, you have to do it. When I was working in downtown San Francisco and I was riding a bus for almost an hour to get in and out every day, I couldn’t exactly roll out of bed and work for a little while and then take a shower. I can’t do that. I had to wake up, take a shower, walk to the bus, ride on the bus. All that stuff was inflexible.

Going back to what I said about the thing that is most difficult - there is something to that, that you don’t have a map; you have to make your own map. You don’t have a boss telling you what to do, you have to choose what to do. That is hard, but flexibility – it’s the tyranny of choice, in some ways. Flexibility is great, but you have to build your ability to use that flexibility in ways that are positive.

Given how busy Jason is, one of the things that I was curious about was how he manages to strike a balance between work and being a husband and father. Unsurprisingly, the whole dynamic of that balance changed drastically when he started working from home.

My old job - I was out the door before eight, and often not home until after seven PM, and I still had other things that I was doing; I still had a podcast that I would do, so I would do some evening recordings, and I was editing podcasts on the weekends. So in some ways, being at home has allowed me – I’m home when my kids get home; I’m working, but I’m home and I can say hi to them and I can see what they’re doing, and then when I’m done, I’m at home.

That’s the other thing about being on a commute - when I was done, it was another hour before I was actually home after being done with work… Like “I can’t do anymore. I’ve hit the wall here. Great, well, now you’re gonna sit on a bus for an hour.” So all of that has gotten a lot of family time back. I do work a lot, I don’t love it, but when you start out, I think, you take on a lot of work because you do have that fear that you’re not gonna make it, that you don’t have a regular paycheck, so you wanna say yes to all the work… I’m gradually getting better at saying no and relinquishing jobs that I don’t really want.

I also probably work more than I need to, because I wanna keep a spread of things that I’m working on, because that way if one thing falls apart, I’ve got some other stuff I can do. If something goes down, maybe something else is coming up, or at least that thing is still steady… So I do probably work more than I need to in terms of supporting my family at this point because I want to have some diversity in what the income is that I’m doing.

If you could guarantee me that every single thing I work on right now would generate the amount of revenue that it generates right now for a decade, let’s say, I would probably quit doing a few things. It’s an ongoing thing.

I’m around most evenings, unless I’m recording a podcast. But that’s something that – I have some evening podcasts that I do, so that takes time.

We’re all home for dinner together, which is nice, and on the weekends I try to minimize that, but it also varies. We’re going away for two weeks this summer, and I’m already banking stuff for when we’re gone, because the work doesn’t stop even when you’re gone. This past weekend I record a bunch of podcasts.

The payoff is there are two weeks coming up when we’ll be on vacation and I won’t be doing any podcasts. My wife has been very flexible about this stuff, which I am appreciative of. If she put her foot down about something, I would make changes, but I think it’s working okay right now.

One of the things you said there was your diversity of income, and I think this kind of goes back to that question I asked you at the beginning - when I asked you the most difficult thing of being self-employed, your answer was not the “Where is the money coming from”, and I think that’s just a testament to how you’ve diversified where your money is coming from; that’s such a big lesson, I think, for a lot of people that want to be self-employed.

Yeah, it’s a great – not only there are legal issues… Like, if you have one revenue source, you’re kind of an employee, and the people who are paying you are not gonna like that. There are legal issues there. It’s always good to have multiple streams, if you can.

David Sparks and I talk about this on our Free Agents podcast, and we have talked about it a lot in the last three years… If you have one client, what happens when they go out of business or they drop you or they cut your work in half? You just lost half your income. If you have four clients and one of them goes out of business or drops you or cuts what they’re paying you in half - guess what? Your income went down by 12% or 25%, depending on the scenario. It didn’t go to zero, and that’s better.

[16:22] That also means that if you have four clients and one of them is a jerk, you can dump them and then go find another client, knowing you’ve got those three other clients to help see you through. So there’s so many reasons, if you can, to diversify. In my case, I’m diversifying not just in terms of clients, but in terms of industry. I’ve got a lot of podcast revenue and a lot of freelance writing revenue, which is good in either case of if the websites I write for go out of business, then I’ve still got the podcast stuff. And if the podcast ad industry falls apart, I’ve still got the writing. And then I’ve also got some direct audience support from my writing and my podcasting that’s in the mix there too, so it’s diversified in a bunch of ways.

If you’re a lawyer, probably the reality is you’re gonna have a bunch of different clients. If you’re an artist or a writer, you’re just gonna have a bunch of different clients in your field. I feel fortunate that I’ve ended up being able to diversify across these different media types too, because that gives me a little more confidence. I don’t think all the tech websites are gonna shut down AND all the podcast advertising is going to go away immediately. I think it’s unlikely that everything just goes bad immediately. You never know, but it seems a lot less likely.

Yeah. My last question for you is what has been your method for overcoming burnout or lack of motivation? Because most creative people deal with this.

So I was burned out at my job, and I left my job… [laughter] I healed slowly, and I got back to the stuff that I really wanted to do. My story of being independent - it really is that I’m back, doing the stuff that I always loved to do, which is creating things and writing and making podcasts and stuff like that, whereas my last job I was doing a lot of management and a lot of budgeting, and running a lot of meetings, and not making things. I was managing people who were managing people who were making things. And when I did make something, I felt like I was kind of playing hooky from my actual job; when I would write an article, it would be like “Well, that’s not really why we’re paying you”, and I would just do it to keep sane.

So some of it is focusing on the things that I love to do and I want to do and that I’m good at. I’m not a perfectionist, but I definitely am somebody who wants to keep making things and wants them to be good, and I feel like they can always be better. That’s not say I don’t believe in perfection, so I can’t be a perfectionist, but I want them to be better, I want them to be good. I’m always thinking about things that I’m doing that could be better and why, and trying to strive for that. That gives me a lot of motivation. Not having a paycheck gives me a lot of motivation.

[laughs] Right.

And that diversity of income also feels – you know, having a diversity of things that I’m doing so I can shift gears, that helps a lot. If somebody said “Oh, well you like to write. What if we pay you what you’re making now and all you’ll do is write about the stuff you write about now? You’ll just do it all day, every day. That’s all you’ll do.” I don’t think I wanna do that.

Right now, I get to make what I make and do what I do, and I am doing podcasts, and I am doing different podcasts. I do a tech podcast where I’m hosting a panel, and I do one where it’s two people chatting. I do a TV podcast, I do a space podcast.

[19:30] And then I’m writing - I’m writing for Macworld, I’m writing for Tom’s Guide, I’m writing for Six Colors, and I can write different aspects for all of those different places. That’s really rich and it allows me to do some of that context switching in a good way. I get to do a bunch of different stuff during the week, instead of it literally being you’re chained to your desk. I could do it and I have done it, but I would rather not if I don’t have to, and it helps. It helps to be able to shift.

Well, I ask you because I feel like even when you’re doing what you love, and even when you’re in an ideal - whatever ideal means, because is there an ideal…? But even in your situation, where you love what you’re doing, you have this diversity of things that you get to do, it’s a pretty ideal situation for you - even then, it doesn’t mean that every day is easy… You know what I mean? There’s still tiredness, and there’s still some lack of motivation, and that’s why I ask you about that.

For me, what I try to remember in those moments is that I am my own boss, I am also my own HR person, I am my own manager… I need to give myself permission to not overdo it. I need to give myself permission to take a break. If I know that the weather forecast is really good tomorrow and I don’t have to do a podcast tomorrow, and I could go to the beach, maybe I go to the beach. Maybe I do something that is not work.

The reality is that - for me anyway - a lot of this takes care of itself. For every super-busy week, like when there’s an Apple event, I find that I’m almost subconsciously like – I take it a little easy the week before, and I end up taking it a little bit easy a week or two after, when things subside a little bit. I don’t know if I’ve got one technique here… Just trying to give myself a break when I realize that I’m kind of pushing it into the red and I’ve been doing that a little too long… And recognizing that about yourself is hard, but I try to do that.