Chris Krycho / An Unintentional Journey

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Disclaimer: This transcript is provided as a courtesy for accompanying the associated episode it represents. The content of the transcript may provide errors or incorrect statements from the recorded episode. Portions of the episode such as opening or closing comments may be excluded for brevity.


Jonathan So, this episode, we have Chris, who is with us today. And Chris, welcome to the show.

Chris Thanks.

Jonathan Why don’t you give us a few sentences about where you’re from, the work you do, and what your interests are?

Chris Oh, you asked me what my interests are. That’s going to be hard to keep it to just a few sentences.

Jonathan [Laughs]

Chris I’ll go in your preferred order and try to keep it brief, though. I grew up in Colorado Springs, Colorado. I did my undergraduate work at the University of Oklahoma, and for the last five years, my wife and I have lived just outside of Raleigh, North Carolina. I’m getting a Master of Divinity degree from Southeastern Baptist Seminary, and I have worked as a software engineer since I graduated college. I got a degree in physics and then switched over to writing software. And I’ve been working for a company called Olo for the last year. We do online ordering—thus Olo—for restaurants. So, if you order from lots of different restaurants, Chili’s and Applebee’s and Wingstop and all sorts of places. It runs through our front ends and our back ends. And I, on top of that, am interested in far, far too many things to list here, but I’ll briefly say that those include things like podcasting. I have a couple podcasts of my own. And nerdy things like reading the Lord of the Rings more times than I’m going to admit on air and general theology and writing. And the big thing I do that isn’t on a computer is running. I run a half marathon every year. This year I’m turning 30, so I’m going to try to run a full marathon. And I am going to try to do a sprint length triathlon in the summer, just for fun, because I like doing things like that to myself.

Jonathan My goodness. I was going to say, I’m not a runner. I love being outdoors, and especially in the winter, in the summer, year-round here in Wisconsin. But running is not at the top list of things that I do.

Chris It wasn’t for me. I got mono and I had to figure out some way to get back in shape for playing Ultimate, and so I started running, and while these days I mostly don’t play ultimate, but I just kept running.

Jonathan That stuck around.

Chris Yeah.

Jonathan That’s great.

Ari Sounds like you have a lot on your plate, there. A lot of different things you do. You know, a lot of people get into remote work for various reasons – it works good, for being able to move about location to location, for family, things like that. What’s your “why”? Why do you work remote?

Chris The biggest reason was that I was moving to North Carolina and I had a job, my second job out of college, working with a very small company in Oklahoma. And I figured I could find a job out here, or possibly find another job remote, but I liked the company I was working with overall at that point, and I was very willing and interested to continue working with them, and I pitched them when I moved out here and said, “Hey, I already know your domain pretty well.” They were in the energy industry and they had a software product that they used for both their internal things and sell to clients for dealing with risk analysis and hazard mitigation concerns. And coming out of a physics degree, and then having spent the better part of a year working for them at that point, I knew their domain fairly well, I knew the software and the code base pretty well, and I pitched them, “Hey. If you’re interested, I will be a contractor and work 20 hours a week and work remote, because that would be a pretty easy ramping on point.” And at that point, I had already been doing consulting from a coffee shop on most weekends, trying to save money for seminary. So, it wasn’t my first time working remotely, so to speak, but I think a lot of people do that kind of thing without thinking of it as remote work. It wasn’t the same as it was after I made that transition where I didn’t go to an office anymore.

So, I had used that time building up experience of working that kind of consulting, doing some web development gigs, to figure out how the remote working world worked, to some extent. You can log into whatever services and get stuff done. But I really considered my remote working time to have started when we moved here and I went to that fully remote, fully distributed kind of workflow with that company. And I did that for another couple years with them and then started working with Olo here, and all along the way, the concern has been I’m living in Raleigh and I have a lot of time allocated to school, and there are a lot of places I could work in Raleigh, but adding a commute in on top of working to get a master’s degree done, and I have two little kids, just didn’t seem like a great plan. And then, once I had started it, I discovered that I love working remotely, and when I started, I had a seven-month-old. I have two little girls. One was seven months old then. They’re now four and a half and two and a half. Our second little girl was born since we moved here. And so, what started as simply a matter of convenience of being able to keep the same job and not have to try to do onboarding and not try to find some place that would let me do 20 hours a week when the company I was at was willing to take me as a 20-hour-a-week consultant, that has changed over time into a pretty deep commitment to being at home, so that I can be around my family, to be able to help my wife, to be able to be a support for my girls as they grow, and to help discipline when they need it – which, you know, four and a half and two and a half, there’s some times when mom could use some backup with the discipline. And just being there for things like their first steps and when they started talking and all of that has been extraordinary, and I wouldn’t trade it, and I don’t really ever want to give it up.

I also found that, by comparison, I hate offices. So, kind of a combination of all of those things. I get more work done at home and I get to be around my family, so whoever I’m working for gets a better deal out of it. I don’t have a commute, and I hate commutes even more than I hate offices. It’s just a win in every possible category for everybody, including whoever’s hiring me at any given time.

Jonathan So, going back, when did you graduate school?

Chris I graduated in 2009, and I started doing remote work-type things at the beginning of 2011, when I first started doing that consulting-type work on the side. And then I went fully remote in 2013.

Jonathan So, when you were in school and doing your undergrad, did you have this idea that, “Hey, some day I’m going to work remote”? Or was it just kind of something that happened? Was this a strategy?

Chris No. When I was in my undergrad program, I honestly didn’t even know what I was going to be doing for a job when I graduated. I seriously considered getting a PhD. in physics. I also pursued some education in music composition and I thought about pursuing that as a career. I ended up moving toward software mostly my senior year of college, because I was using software for my physics projects and found that I enjoyed it and decided I didn’t want a PhD. in physics and thought I can go get a job in software. And my first three years, other than that consulting on the side, I was driving to and working in an office building. And that particular office building is probably a big part of why I ended up hating offices, because it was a Department of Defense contract, and the building I was in had a lot of classified material in it. There was literally one window in the building, and that was for some very specific equipment testing and was in a room that I didn’t have clearance to go into. So, I sat in a gray box with no windows for three years and I hated it. So, it was more a strategy that developed self-preservation in response, I think, of “I must have sunlight”.

Jonathan I can relate to that, for sure.

Chris You can see on the video here, I have a window. It’s good. [Laughs]

Jonathan I contracted for nine months in the basement of a building, and I think my response was the same. I was in Omaha, Nebraska at the time. And I would...I would get there about 8:15 in the morning and, you know, you go in and it’s still dark out, and I’d come out about five o’clock or shortly thereafter and it would still be dark, and I had no idea if the sun had been out at all. So, it kind of sucks your soul a little bit.

Chris Yeah, it really does.

Ari I mean, I’ve been the same way. I’ve worked as a SysAdmin. I’ve worked in a knock, which is completely no windows, in the middle of a building somewhere, no windows. And my current job is also of a security nature. It requires it to be not accessible directly from the outside. So, luckily I have other people around, but still, not accessible directly.

Jonathan That knock that you worked in, does it look like on the TV shows with the huge screens and the flashing lights and the servers behind you?

Chris Part of it did.

Ari Excellent!

Jonathan Well, that’s at least some bonus. So, it sounds to me like this progression into remote work kind of followed a series of different types of engagement. So, you were kind of doing some freelance, self-employed side work, and then some contracting for 20 hours a week, and then now kind of into a full-time arrangement. So, you really kind of eased into it. It wasn’t like a massive jump with both feet at once.

Chris That’s right. And I think, in a lot of ways, it would have been a lot harder to make the transition jumping in with both feet. I was able to build up a lot of the important habits that you need to be a successful remote worker, because I had a limited amount of time and projects I was trying to get done for that consulting stuff. And basically, I had all day Saturday, and what I got done in all day Saturday is what I got done. The hours I put in were the hours I got paid for, and the guy I was consulting for was great, but he wasn’t going to keep paying me if I wasn’t giving him good value. And so, I had that for a couple years there and was able to start building up sort of the mental calluses or stamina or however you want to think about or describe that, so that when I did make the transition to working fully remotely, whether in that consulting role or now as a full-time employee role, I already had all the habits and the mental furniture, so to speak, that I needed to be able to do it successfully. I think, had I jumped into that straight out of college, I would have floundered. The first job I was in, in particular, I didn’t get great mentoring on the job in that job, anyway, but I...I would have just fallen over. I would have had no idea what I was doing or how to learn what to be doing in that job, had I been working it remotely. Now, I don’t think that’s true of all remote jobs. I have heard people on podcasts and talked to occasional people where they have good cultures of mentoring and onboarding in a remote context, but I think that’s pretty rare. I think it’s even rarer than good onboarding in a non-remote context, which I think is pretty rare itself.

Ari Well, I guess you came into remote in a bit of a different way than some, because you came into remote by saying, “Hey, I know I’m... I know our company has an office, but I’m going to work remotely,” as opposed to working for a company that was fully remote. So, I guess that did cause a bit of a learning curve both for you and for the company you worked for.

Chris Yeah. I would actually say, I don’t think they would do remote again, and that’s mostly a culture thing. I did a lot of good work for them, but they’re a small company, and I was the only person working remotely. Though they would be out of office a lot, traveling to meet with clients, etcetera, and they would do what I would describe as remote work at that point, the idea of having an employee who was just dedicated out of the office all of the time didn’t mesh well with their culture, and so, there was a lot of learning curve for them, much more, I think, than for me, because again, I had already had a lot of the relevant experience. I could get my job done just fine, but we never really got the hang, culturally, in that job of using the tools effectively, whether it was Hangouts or something like that for communication, of getting really good, clear write-ups on what a given bug fix or feature required. We would often have to go back and forth if I would implement something and they would say, “Oh, this wasn’t quite what we wanted,” etcetera. There were a lot of those kinds of mismatches. And, you know, no skin off their backs. They were, in a lot of ways, also learning just how to have full-time software employees, much less adding in a full-time remote software employee. There are just a lot of skills there that somebody who’s not a software person doesn’t necessarily have, and they take a lot of time. That was very different. There was a huge learning curve. And there have actually been learning curves in my current role, as well, for the company, but those look very different.

Jonathan So, who are the people or the pets that you’re co-working with?

Chris So, I mentioned I have two little girls and a wonderful wife. We also have a cat, who we’ve had for about three months, now. My wife decided she really, really wanted a cat and I humored her because I love her, and he’s a good cat. But I am around my wife, who is a stay-at-home mom and does an incredible job with our little girls. She’s also an artist and a writer, and so she does those things during nap times and whatnot. But she’s around most of the day. She’ll be out a little bit and she’ll take our girls with her for things like going grocery shopping or taking a trip to the YMCA to get her workout in three times a week, etcetera. But for the most part, they’re around all day, every day. And so, I do have to figure out ways to avoid those interruptions. Gladly, the cat has been trained not to get on my desk, lest he be unceremoniously dumped right back off the desk. And a couple of times of dumping him forcefully off the desk and he stopped doing that. But I do have the cat around. Usually, he’s sleeping on the bed behind me here in our bedroom, which passes from my office.

Ari Apparently, I’ve heard cats seem to think they know how to write code.

Chris They love keyboards. It took a couple weeks of frequent unceremonious dumping off the desk before he got the memo.

Jonathan [Laughs] I’ve got three dogs, so thankfully, they have not jumped on the keyboard yet.

Chris I’m really a dog person, overall. I’d much prefer to have a Golden Retriever than a cat, but my wife wanted a cat, so cat it was.

Jonathan I can give an amen to that.

Ari Well, I can tell you, a dog jumping on your desk, like a Golden Retriever like yours, Jonathan...

Jonathan That would not go well.

Ari Yeah, might break the desk.

Jonathan It would. Not to mention the shedding and the dog hair that would be everywhere.

Chris There is that.

Ari So, Chris, given your situation with having your wife around the house, having your kids around the house, and the cat, how have you set up your work office environment? It seems you’re in your bedroom there, you’ve mentioned. How have you worked that work environment as some kind of office space inside of your home?

Chris I had a desk for a long time, which was awful, but it fit this little cranny in the corner of our bedroom, and I’ll come back to the desk issue in a moment, because about a year ago, I upgraded, and it has been the best thing ever. But there’s sort of two kinds of dynamics I think about in terms of the home office space, and one of them is the equipment of it—computer and desk and everything that goes with that, the fancy microphone I record my podcasts on—and the other side of it is just the space being somewhere I can get work done without constant interruptions. And there are some interruptions, because I have small children, and if one of them is screaming because she, you know, ran into something, I’m going to go help. But for the most part, we’ve tried to establish that, when Daddy is working, if he closes the door, you don’t go in and bother him. You could run in and give him a hug, but not all the time. If you’re about to go down for your nap or you’re about to go to the Y or you just got up from your nap, you can go say hi to Daddy and give him a hug and whatnot. But for the most part, if I close the door, we’ve kind of established Daddy’s working now, don’t do that. And similarly, my wife and I, though this took a while, especially when I first went remote, established some ground rules and expectations that she asks for my help if something is urgent; if something isn’t urgent, she’ll let me know, she’ll send me a text message, or she’ll poke her head in and say, “Hey, when you’ve got some time...” or whatever else. Sometimes, she’ll even send me an email. But let me know she could use input on something or help with something. And, as I said before, it’s nice that I’m at home. So, if there’s an actually urgent need, I can help. But if there’s not, she can just let me know, “Hey, I could use your help with this in a minute,” and when I take my next break, I’ll go help her with it.

Office space-wise, I’m in a corner of our bedroom, and I look forward to having an actual dedicated office sometime, because I don’t love that part of it. But it works. We’ve got a two-bedroom apartment and four people live here right now, so that’s the only space we’ve got. I last year upgraded this office substantially from the hand-me-down desk that was free to me and was a great choice when we first got it, but was not good, and the $50 Walmart chair that I bought when I was a freshman in college, which was a good choice when I bought it but was not good; to an Ergo Depot—they’re now called Fully—standing, sitting, adjustable height desk, and I try to stand about half the day to three quarters of the day, most days. I get pretty bad back aches if I sit all day. I also bought a good chair, which helps for the times when I’m sitting. I got whatever the Wirecutter’s recommendation is. It’s the Steelcase Gesture, and it is a fantastic chair. Literally the most comfortable chair I’ve ever sat in, and hilariously, yesterday, my wife sat down in it after months of not having done so because she just doesn’t normally sit down at my desk for any reason, and she went, “Oh. I forgot how nice this chair is. This is so comfy!” So, I did that. I upgraded my home-work machine to a shiny, new, 27-inch iMac and got it on an arm so that it’s adjustable and it’s at the correct height, and when I stand up, I can adjust the height of it so that it’s still at the correct height, and so on. And then, of course, I have my fancy microphone that I’m recording this with and that I record my two podcasts with. And other than that, I try to have nothing but a water bottle and some headphones on my desk, because I need a clean working environment.

Jonathan So, tell us about the structure of the team that you collaborate with.

Chris So, Olo is increasingly remote and trying to move toward a remote-first culture. The team I work with is about 50-50 remote, and our engineering base is about 50-50 remote. Last time I checked with our director of operations, we were 43% remote as a company. The company’s based in New York City and started out everybody on-premise in New York City, and starting just about two years ago, they started actively hiring and giving people freedom to move remote. And since they’ve done that, more and more people have moved remote, whether for just interest in living somewhere else, or active interest in getting out of New York City, which has a lot of upsides for being there, but also a lot of downsides, just in terms of commute. People often have two or three hours of commuting a day, and I have about three feet of commuting every day. So, people see that and it’s appealing, and people can live wherever they want and work wherever they want. We have people all over the country, and we also have a couple teams in Ukraine who work for us and work with us. So, we’ve very distributed, and like I said, my specific team is about 50-50 onsite in New York City and all over the country. We have people in Seattle area and the middle of...I want to say Idaho. We’ve got people in Colorado. We’ve got people all over. I’m here in Raleigh, but I expect to move to Colorado next year. Pretty well distributed, at this point.

Jonathan What’s the spread of time zones?

Chris So, my team specifically has three time zones, because we have Pacific, Central, Mountain, and Eastern, and I said those out of order, so if anybody’s listening, they can snort at me for getting them out of order.

Jonathan [Laughs] I was going to say, that’s an exercise left to the student.

Chris Yeah. Did I say three? Counting. I don’t know how it works. We have all four continental U.S. time zones.

Ari I was just making sure I heard you right when you listed them.

Chris I think I said three, but then, I counted off four, so... [Laughs] I’ve been going since 5:30, so I make no pretense about being totally mentally coherent at this point in the day as we’re recording at 4:30 p.m.

Jonathan It’s okay. It just proves you’re a human.

Chris [Laughs] I am not a robot. I passed the test, Google.

Jonathan You did.

Ari So, a lot of companies have kind of a remote DNA, that they’re really built to be a remote company, so people can be really distributed... That’s the way the whole company’s philosophy is. Do you feel that the company you work for has kind of built that kind of a culture around it? Or is there something that really has to have changed, as you say, that people have become more recently?

Chris I would say we are in the process of building it. So, we’re figuring out how to do it well, and that’s been a process even over the course of the year I’ve been there. Certainly, it’s been a very much ongoing process since they started going more remote a couple years ago from talking to people who’d been there a little longer than me. And that’s had its share of growing pains – things like figuring out how you run meetings, especially the whole company meetings. You know, we have 85 people or so, and as I said, a little over half of those are still in New York City. So, you find that people whose teams are more remote handle that better. The engineering team, in particular, has been more remote for longer, and so the engineering managers tend to speak into the microphone and recognize that the rest of the room can hear them. There have been a couple of meetings where we had remote people had to keep telling other local to New York City people, “Hey, speak into the microphone,” because they were just habitually turning to address the other 45 people who were there in the room with them, and no one remote could hear them at all, because they were speaking away from whatever microphone they had hooked up to the Zoom call or whatever else.

So, there have been those growing pains, figuring out things like what perks do you try to share with remote people versus what perks do you kind of say, “This is the perk for dealing with a two- or three-hour commute.” So, I don’t really begrudge the New York City team, their cereal bar or their kegs of beer or their coffee maker, because for one thing, I make a lot better coffee than they do in my pour over setup downstairs, and for another, I have a 30-second commute, and that’s mostly the time it takes me to actually make myself get out of bed in the morning, versus being on the subway for two hours or whatever. I just... You know. So, we’re figuring those things out. Sending food to the remote employees sometimes for some meetings, like on the hack day we had back in December, they had pizza in the office and they gave everybody the ability to order lunch so that there was a sense of mutual participation. But you’re not necessarily going to do that for every remote meeting, and you know, just figuring out those dynamics, it has been a... There have been growing pains, but they’re actively seeking to do it well. One of the big goals for engineering, especially in 2017, is becoming a remote-first company and doing those dynamics well, doing meetings even better that way, doing hiring even more that way, and so on.

Ari All right. So, you say that there’s a lot of people still that are based locally at the main office while there’s a fair group of remotes across the company. Is this really something that you find across the whole company in every department, you have people that are working remote? Or is it really more concentrated in certain specific parts of the company.

Chris I would say it started concentrated. It started with mostly being an engineering-focused, software engineers being the remote people. But increasingly, we have more people who are not engineers who are remote. So, our director of operations lives in Seattle, and we have one of our... I guess she was a product manager. She’s now a VP of product who lives in the Pacific Northwest, as well. So, people are fanning out, and that is increasingly becoming the case for product and account managers and so on, as opposed to when we started, when it was mostly engineering. So, it’s becoming more whole company remote-first, rather than just those weird software engineer people who can work remotely.

Jonathan So, one of the things that is a hot topic about remote work is staying engaged in kind of performance feedback, and that you have to be very explicit with it. What is the performance or feedback process that you experience in your current remote gig?

Chris So, a couple things. One, we just use fairly standard software engineering practices. We have stand-ups three times a week. We have it only three times a week, because we have a couple days that we keep entirely clear of all meetings so that people can just be head down and get work done, which is really, really nice. Today was one of those days, and my productivity was just so much easier to keep flowing, because I didn’t have to stop at ten a.m. to have a meeting. But those other three days, we use normal, weekly...or daily check-in type things, where we say where we’re at, what blog codes we might have, plan out what the next sort of week will look like. We have a pretty high-performance set of engineers, and so, in my experience, the performance feedback side of that has mostly been making sure that we have the tools we need and the support that we need to get our job done. The closest I’ve come to having any kind of, “Hey, this isn’t going great”, was one I initiated, where I sent an email and said, “Hey everybody. I’ve been just having a hard time the last few weeks with a bunch of travel and class work and other things. Sorry I dropped the ball.” And then we have annual performance reviews, like a lot of places do. But again, it’s been much more “How can we help you?” rather than “Hey, get on top of it”. And I think a lot of that has had to do with our hiring. For the most part, we’ve just had really solid, competent people who are just getting their stuff done.

Jonathan So, it sounds like it’s a very ongoing, almost daily process, as opposed to, like, every three months or something. It’s being intentional about keeping that constant communication rolling.

Chris Right. And that’s very much a goal for a lot of modern software teams. It’s not sit down and plan out six months or three months worth of work. It’s just day in, day out, “Hey, what’s going well? What’s not? What can we do better? Let’s try to improve.” And the other thing I will say for our company culture, which isn’t specific to being remote, but has been enormously helpful regardless, is there’s no blame shifting or finger pointing. When something goes wrong, we all very much just say, “Hey, okay. That happened. Let’s fix it. Let’s learn from it.” And I think because of that, people are very quick and ready to take responsibility. People will say, “Oh, that was me. I screwed this up. Sorry, everybody.” And everybody just says, “No biggie,” and we learn from it and we move on, and that’s been, I think, a huge part of making remote work well, because even if you’re remote and you mess something up, or if you’re remote and you don’t know something, there’s no problem with just saying, “Hey, I don’t know what’s up. Can somebody help me figure this out?” And people do. So, there’s a lot of security in that, culturally, and I think that was probably equally important for being remote or being onsite, but I sure as heck wouldn’t want to be in a spot where that was different, being onsite versus being remote, where if you were remote and asking on Slack or whatever else for some help, and you were getting shot down, whereas if you ask somebody face-to-face that didn’ got the help you needed, well, that would stink. But it isn’t that. We have a very, very healthy culture that just handles those things across the board and is, as you said, Jonathan, very engaged, very just keeping it constant light but constant touch, to make sure everybody’s doing well and getting done what they need to and getting the help they need to to get done what they need to.

Ari Well, that sounds like a very good system overall, especially given the remote distribution that’s out there. So, given that you are remote, a lot of people have varying schedules working remote. A lot of them have flexibility. Some have to work a specific schedule, but a lot of people have a very flexible schedule. They’ll work a little in the morning, take some time off in the middle of the day, work at night, things like that. So, what’s a typical workday schedule like for you?

Chris So, my routine looks a little different from most people’s, even, because I am in school, as well. So, I’ll kind of talk through the whole shebang there. I normally get up at about 5:15. Got an alarm set that goes off at 5:10 and another one at 5:15, so I actually get out of bed. Then I go downstairs and make breakfast for me and my wife and make coffee for me and my wife, because coffee keeps me sane and it’s very important. I mention later in our shout-outs section what coffee I use, because it’s good. I’ll bring that back upstairs and give it to my wife and set it on my desk here, and then I’ll normally work through my devotions in the morning, read my Bible and pray a bit, and then I’ll usually start on school, try to get a couple hours of schoolwork done before I start on work for the day. And that aligns my workday schedule fairly well with everybody else. Our normal hours for the New York City office are nine to six, Eastern Time. So, if I do sort of 6:30 to 8:30 on school, and then I’m working by nine or so with my “job” job, and then I’ll work nine to five-ish, usually nine to six, somewhere in there, and I’ll stop sometime during the day and take a run, as I mentioned at the beginning. I run six days a week, usually, unless I’m doing triathlon training, in which case, I’ll run two days a week and cycle two days a week and get over to the Y for a swim two days a week. But basically, I’ll work that kind of nine to five, nine to six, get in my hours there, take a break for an hour somewhere in there for a run. You know, I’ll pause for a bit of lunch along the way, get a snack, get more coffee, because in the afternoons, that’s a thing. [Laughs] And then wrap up, like I said, five to six p.m., most days.

Jonathan So, what are some productivity systems or strategies that you use while you’re working?

Chris A couple things. One, I have fairly aggressively embraced quote-unquote “Pomodoro Strategy” over the last few years. So, the Pomodoro Strategy basically tries to take into account that you only have limited ability to concentrate in a sustained way, effectively, for long periods of time. So, generally, you’ll get somewhere between 20 to 40 minutes at most of good, sustained concentration, and if you’re trying to concentrate for longer than that, your actual productivity and focus are going to drop off. And we see research that confirms that, in everything from people working office jobs to pedagogy and teaching strategy for students, if you try to keep students’ attention focused on just a stream lecture for 45 to 50 minutes without anything and sort of let people’s brains recharge, even if that’s just making a joke and kind of diffusing a bit in the middle of that lecture, you just won’t...people can’t keep it up and sustain it. And the same thing is true in software. Sometimes, you’ll feel like you’re in the flow for three hours, but the reality is your productivity peaked somewhere around 30 minutes into that, maybe, and two hours in, you’re just stymied. You’re not getting done nearly as much as you would have if you’d stopped an hour ago and taken a walk. And so, the Pomodoro Technique embraces that and says you just do cycles where you do 25 minutes on, five minutes off. And every 25 minutes, I get up and I take a walk, and normally, I’ll take a walk that’s about a fifth to a quarter of a mile long, all told. I’ll just pop out. If I need to grab a jacket, grab a jacket, and walk out my front door, walk down through our neighborhood to a point that I know takes me half of that walking time, turn around, and walk back. And, in doing that, I stay pretty active throughout the day, and that keeps my blood moving, keeps me from feeling sleepy. That’s especially important at that 12:30 to 1:30 period after I’ve had lunch, and I’m sitting there, and if I’m just sitting in a chair at that period, I will fall asleep. So, I do that. And then, every four of those, you get a slightly longer break. So, I’ll take ten to 15 minutes.

And if I’m going to check email during the day, if I’m going to look at social media, that’s when I do it, is on those breaks. I try to keep all of that shut down and closed anytime I’m actually in one of those working modes, with more or less success. Sometimes, I have Slack open for work, and then maybe one of the other Slack teams I’m in draws my attention with some vigorous debate about programming languages or theology, or programming languages and theology, or something silly like that. In general, I try to avoid that, though, because it does kill my productivity. And doing that helps a lot. I also am a very aggressive inbox zero adherent, so I keep my empty. I do use those walk times for triage. I’ll read things and delete them, or if these is an action that I need to take on it, I’ll throw that into my to-do app. I use Omnifocus. I mostly need something as thorough going and capable Omnifocus, because I am a student and a software develop and a podcaster. If I didn’t have all of those things going, I could very easily get away with a much simpler to-do app, but I just have a lot to juggle. And so, I push the basic level of Omnifocus pretty thoroughly. I get a lot of mileage out of it. And I’ll put due dates in there, for anything that has a due date. If it doesn’t have a meaningful due date, I’ll often just tag it with a “Defer this till a date when I think it’s meaningful”, and then it’ll show up in my “Things that are available to work on” after that, but if it doesn’t actually have a due date, I avoid putting a due date on it, because when I first started trying to use things this way, I would put due dates on things that didn’t have real due dates. And then I would kind of look at it and be like, oh, that doesn’t really need to be a thing. And then I would have things piling up as notifications from that that said this is due, and I’d be like, yeah, it’s not really. But then I would have things that really were due that were time-sensitive, and it only took missing one of those about twice before I said, okay, time to stop putting due dates on anything that the due date doesn’t actually matter.

Jonathan Because it was really diluting the due dates of the important things.

Chris Yeah. That’s exactly right. And so, I try to throw anything that’s a real project in there, and then things that are just little, actual to-do type tasks, like, “Oh, I need to send this message to my wife later,” I’ll throw that in a much smaller and lighter... I use Do! app on my iPhone, and that’s just for simple time-like, one-off, do-this-one-thing type tasks. And so, I try to keep each tool focused on what it’s good at. I also use a notes app called Bear with the Pomodoro stuff to track goals and what I actually accomplish on each of those cycles, because I found the cycles are helpful, but actually writing down “Here’s what I want to accomplish in these 25 minutes”, and then also writing down what I actually accomplished in those 25 minutes, first of all, helps me focus and helps me say, okay, here’s what I’m getting done right now, and helps me stay honest, so that if, in that period of time, I actually spent 25 minutes chatting about programming languages, well, that may not be wasted time, but I clearly wasn’t focused and I need to focus more the next time.

And then, it’s also really helpful because I can look at that at the end of the day and see what I actually got done. And especially when you’re chipping away at a large issue, some big feature, or a bug that’s really stymieing you, seeing what you learned working on a bug or what pieces of a feature you accomplished, those things can be really helpful in actually feeling like you got something done at the end of a day, because otherwise, sometimes you’re sitting there feeling like, “Did I actually do anything meaningful here?” And the answer might be yes, but if you’re not finding some way to keep track of what that is, you may not feel it. And so, I found that to be very helpful as I’ve embraced that over the last six months.

Ari Okay. So, as we kind of start to wrap things up here a bit, how do you see remote work kind of fitting into your long-term career objectives? I mean, do you see this as something that you’re going to keep doing, or would you consider going back to commuting and working onsite somewhere in the future?

Chris I’ll just share the stock answer I’ve been giving to recruiters who email me lately, and that is, I’m not interested in commuter jobs anymore, and I am calling them commuter jobs. Among other things, I would like, actually, to see this become much more the default, in many cases. I would like it to be something that you have to think about, of, “Oh, you’re going to go into an office.” Because I do think there’s enormous value for families, and for my family, the value is so high that I do not see, unless there was some really surprising change of circumstances around what remote work looks like in the software industry, I don’t see ever taking a commuter job again. It is too important to me to be around my family. And again, as I said at the very outset, I do better work at home and I get more done at home, and I just don’t want to give up the two hours of commute time, either. I have too many other things that I care about too much to spend that time sitting in a car in traffic. So, I expect to work remote from here on out. And, I mean, I love my family, so if it were a “feed my family or take a commuter job”, I’d take the commuter job. But gladly, the economics of the software industry at this point are such that there are a lot of and an increasing number of remote jobs, and I expect just to keep tracking that way.

Jonathan So, what advice would you have for someone considering remote work?

Chris Think hard about why you want to do remote work. You want to make sure that it’s not because you want to slack off and not have someone looking over your shoulders. And look hard at your own personality. I have talked to people who just can’t do it. They need the physical presence of other people because they’re just really extraverted. I mean, I’m that, to some extent, and I get out to a coffee shop once a week to stay sane. But if you’re really extraverted, being home alone in a room is not going to be good for you. So, even if you want to go remote, figure out a way that that involves a co-working space or something else, a coffee shop, whatever it may be, so that you’re not going crazy. Be aware of the costs. There are costs. I mentioned I get interrupted by screaming four-year-olds sometimes. But also, look at the benefits and see if there’s a way you can make it work. But also, I think, evaluate it carefully in light of your company’s culture. Like I said, talking about that first company I went sort of fully remote with, it really wasn’t a good fit with their culture. And I don’t think it was a mistake to do that or try that, but it wasn’t a great fit there. And if the company isn’t willing to move thoughtfully toward doing it really well, it’s going to be a rough, rough experience for everybody involved.

But the other advice I would have is, if you’re a company thinking about it, go for it. And if you’re an individual whose company will allow it, try it. And step in. Get your toes wet, if you can. You know, work from home one day a week or something like that and start developing those muscles.

Jonathan So, this section of the podcast and the show is titled “What’s the Buzz?” So, Ari, why don’t you kick off this episode?

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