Zach Holman is a software developer and founder of the recently launched company Signed. He is also a startup advisor to companies like GitLab and StackShare.

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1) To kick things off, could you tell us a little about your career background and current role?

I’m primarily a software developer. Previously I worked at GitHub from 2010-2015, seeing it grow from 9 people to almost 300. After that, I started a calendar startup called During. It did great and did everything you’d want a new startup to do except, you know, be successful. I’ve also done a bunch of startup advising to companies like GitLab and StackShare the last few years.

Currently I’m starting a new company called Signed; we started it a few months ago, so it’s still in the “very new and everything is exciting but it’s very possible we have no idea what we’re doing” stage of a company.

2) What does a day in the life look like for you? Can you take us through a recent workday?

Most of my day is just dealing with early startup development work. Lots of code, not a lot of things other than that. Time is flexible, of course, so I spend a lot of time with my Hopper, my 11 month old golden retriever, and my fiancée, in between building things.

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

Yup, Signed is entirely a remote-first company: it’s just two of us at the moment, but I’m in San Francisco, and Justin, my cofounder, is in Portland. That we’re both in quarantine right now doesn’t really change a lot of our day-to-day work, in any case.

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4) What does work-life balance mean to you and how do you work to achieve that goal?

To put it simply, I think it’s just a mixture between your happiness and your productivity.

Definitely blew this earlier in my career. And I can totally see why, in hindsight: I was having a blast. Working with great people, building really fun stuff, getting all the side effects of working at a hugely successful company. And yeah, at that point, shit, I’ll work 22 hours a day, who cares, I’m having so much fun.

At some point, though, the house lights come up and things started changing. But I still operated in a similar fashion. I still would hang in the chat room, answer emails late into the night. Would work long nights because I felt like, well, that’s just what I’ve been doing, so let’s keep doing it.

As a company grows, you necessarily add more employees to the mix too, which has the side effect of making your own work less impactful. More people can help out, the organization gets more complex, you spend less time on impactful work and more time talking about work.

I didn’t catch the changeover. So I kept working and burned myself out. It was just unhealthy, it so many ways from productivity, to being a empathetic teammate, to my own mental health. It sucked. What’s more is that the debt you incur doing that for a long time takes way, way longer to fix than the amount of time you sunk into doing it wrong.

Code in particular is a immensely creative activity. There’s just a lot of creative problem solving that you need to do, and a lot of that depends on being in the right mindset to be productive.

5) What do you think are some of the best habits or routines that you’ve developed over the years to help you achieve success in your life?

I find myself cutting loose earlier.

Code in particular is a immensely creative activity. There’s just a lot of creative problem solving that you need to do, and a lot of that depends on being in the right mindset to be productive.

The Flow, among other phrases people come up for it.

I try nowadays to identify when shit sucks so I can eject for awhile. Work on something else, do something else, physically be somewhere else. Seems to help in terms of keeping my longevity present on project.

6) Are there any books that have helped you improve over the years?

Nah, not really. Only books I’ve been impressed with lately is the Three Body Problem series, which is sci-fi but changed my thought process on the universe.

7) What is the number one thing you do to make sure you get the most out of your day?

I’ve been more focused on todo lists. Break down complicated tasks into smaller tasks, so you can feel momentum, and better predict future momentum. It also has the side benefit of being able to look back on your week and remind yourself that hey, you actually were productive when you might not have felt like it.

8) If you could read an interview about work-life balance by anyone, who would that be?

Maybe someone in a completely different field, like a musician. I want to know more about how people get into their particular flow, where they become ultimately the most productive. That’s a really tricky thing to slot yourself into sometimes.

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

I’m kinda continually realizing how much my thoughts on work-life balance change every couple of years. The 20-year old me would probably be pretty confused about my viewpoints nowadays. And I’m sure a 45 year old me would be just as amused as I am now, at 35.

I think those changes are good to see happen, and more importantly, take note of it every now and then. Things move fast these days, and taking stock of how you fit into things, and more importantly, seeing how you’ve changed and adjusted. I’ve just come to appreciate that a lot more.

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