Remotely Interesting

Work Style Profile: Daniel Vassallo

published9 months ago
4 min read

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Welcome to the next profile in our Work Styles series! In each profile, we highlight one person's untraditional workday. You'll get an inside look at alternatives to the traditional 9-5, Monday-Friday schedule (and maybe pick up something new to try).

Today, we're featuring Daniel Vassallo! In February 2019, he left a $500,000 job at Amazon to work for himself. Since then he's built a variety of "small bet" projects like his Twitter course, being a quarter-time Head of Product at Gumroad, and jumping into woodworking (he built the table below!).

In this profile, we get an inside look at his approach to optimizing his workday for randomness, what embracing procrastination helps with, and how discovering your personal preferences can change the way you work for the better. Let's dive in!

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Daniel with a wooden table he built himself

What does a day in your work life look like?

"I would say, I don't have a typical day. Beyond a few minutes of daily housekeeping (checking and replying emails, some customer support, etc), my work days are very random.

And that's exactly the way I like it. I only discovered this preference recently — I used to think I prefer having a concrete plan and focus on something very specific for as long as possible. But almost by accident I stumbled into a different arrangement that now I realize suits me more.

Basically, I let my mood determine what to do. Whenever there's something urgent, I'd be anxious to do it and so I do it. But urgent things are rare, so usually I do what I feel mostly motivated to do. Sometimes, I just wander about, looking for inspiration, and I consider that an essential part of my work day as well. Probably nothing comes out of those days for 360 days out of 365. But almost all consequential things come out from those random 5 days where inspiration strikes.

I also let procrastination shape my work day. If I feel reluctant to do something, I almost always consider whether I should reduce scope, wrap things up immediately, or abandon what I'm doing altogether."

What approach did you take to optimize your work schedule for you?

"I would say, I'm anti-optimization. If I optimize for anything, it's to leave a lot of slack in the system. Lots of idle, uncommitted time, to let my mood and inspiration direct me to things that I can do with my own intrinsic motivation. My approach is to try to interfere with that as little as possible."

Why did you choose to go against the standard 9-5 schedule?

"I didn't go against the 9-5 schedule intentionally. I chose to work for myself because I disliked working on somebody else's terms. But originally, I thought I'd still stick to a 9-5, 40hr/wk, stable schedule, even when working for myself. But once I gained more flexibility with my time, I started to unconsciously try different arrangements, and I stumbled into my random approach — and it stuck."

What's one area you're still looking to improve?

"There are some necessary things that are not very compatible with my approach to do whatever I feel like doing. Tax prep, dealing with payment disputes, and things like that. Those tend to linger until the last minute, but I'm not sure if that's the best approach for these things.

On one hand, leaving them to the last minute spares me from having to thing about them for most of the days. On the other hand, sometimes that last minute ends up being extremely inconvenient.

I don't know yet what's the best solution, but still trying to improve handling these "necessary but important" annoying things."

What is your top tip for someone wanting to transition away from the standard work schedule?

"I have a very general answer. It's to discover your true preferences.

We're all slightly different, but somehow we're conditioned to work and expend energy the same way. I believe you get a huge advantage in work (and life) if you know what you like and dislike. And the way you work, the frequency and intensity of how you spend your energy, what to focus on, and things like that, tend to be very different across individuals."

Big thank you to Daniel Vassallo for giving us an inside look at his workday schedule!

Highly recommend checking out his Portfolio of Small Bets course if you're interested in taking the small bets approach yourself. Also, follow him on Twitter where he regularly shares on this topic.

I'd love to hear from you! What did you find interesting about Daniel's workday? What could you potentially try out yourself?

Feel free to reply to this message or DM me on Twitter @mar15sa.

I truly appreciate you taking the time to read this. Hope you have a lovely day!


P.S. Who's workday should we feature next? If you're interested in being featured, fill out this form.

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