How working weird hours can give you more freedom

I spent five months in Australia earlier this year and continued to work remotely for Bolster, a U.S. based company, the entire time. During this time, I was committed to staying as plugged in as possible and continuing to overlap for key meetings with my colleagues.

To make this work, I had to adjust my schedule in a pretty serious way. Here’s a look at a typical day from my time in Sydney.

  • 3:45 a.m. — Alarm goes off
  • 3:50 a.m. — Grab work “uniform” (aka my Bolster hoodie)
  • 3:55 a.m. — French press poured
  • 4 a.m. — First Zoom call starts (2 p.m. ET the day before for my New York counterparts)
  • 9 a.m. — Zoom calls end (5 p.m. MT for my Boulder counterparts)
  • 9:15 a.m. — Get second coffee and breakfast
  • 9:30 a.m. — noon — Get all of the things done I promised I’d do on all of my Zoom calls
  • 12 p.m. — Nap / lunch

When I told people about this schedule, I typically got a mixed back reaction of horror and downright confusion. Understandably so. Getting up before 4 a.m. daily. requires a special breed of…um, something.

But here’s the thing: In a weird way, I kind of loved it. Here’s why:

Every day felt like a weekend… or a redeye flight… or both

Back in the days when I used to travel for work, my favorite flight in the world was the 7 a.m. direct flight from JFK to SFO. I’d get up at around 4:30, be out the door by 5 and at the airport by 6. I’d get first breakfast at the airport, a big coffee, and work for five hours straight through on the flight. Then, I’d land around 11 a.m. PT, with still enough time to make it to a lunch meeting, an afternoon coffee, and even a dinner with a friend or colleague. That kind of “double day” is like getting to the extra bonus level on a video game. It almost feels like you’re cheating. And I felt like that every single day in Sydney. I was working so hard and in such a concentrated way. And I was living just as hard.

Yes, I was up at 4, but I was so damn motivated to get my shit done because I knew, come noon, I was not only free to explore a new city, but free from any possible obligation of getting a text, an email, or pulled into another meeting. Because every colleague in the world was already fast asleep. I have a lot of fond memories about my “double days” in Sydney. I’d grab a beer at 2 p.m. or go to an art gallery. I’d catch up on personal projects or take my baby out of daycare for the afternoon and take her to the Taronga Zoo. One one particularly ambitious day, after a fun series of IRL meetings with Australian VCs, I impulse bought a cheap ticket to see a ballet at the Sydney Opera House. Was it worth staying up past 10 p.m. for that experience even though I was up at 4 a.m. the next day? Absolutely. Would do it again.

Every day was chunked by nature

One of the hardest parts of working with a lot of stakeholders and also being in an external facing role is knowing how to block your calendar to find time to get work done. (I’m currently in pretty deep email debt here due to a week or two of back-to-back calls that have set me back.) And while it really requires a special kind of focus to be able to sit through 4–5 hours of Zoom meetings back to back without a break every day, it also meant I didn’t have any of those weird blocks of time wondering, “Well, what can I get done in this 30 minute window?” Every day, after 9 a.m. I knew I had as much time as I needed of real, deep work, to hunker down, grab that second cup of coffee, maybe change locations to a coworking space in the city, and just get stuff done.

In a remote era across multiple timezones, I find this chunking particularly hard to find from my U.S. vantage point. Noon on the East Coast is 10 a.m. in Colorado and more days than not, I’m in meetings clear through lunch. If I’m not careful, I can be working and responding to emails from the minute my first NYC colleague is online around 8 a.m. to then minute my last Colorado colleague is online at 9 p.m. I’m not saying this is impossible to manage, but it does require management, vs. what I had in Australia, which was as sort of “forced shutdown.” When I first got back from Australia, I briefly advocating for a period of “synchronous meeting hours” and still wonder about whether any businesses set blocks of time, regardless of timezone, during which all team meetings take place as one way around this. But there may be no easy replica for just being 10,000 miles away.

Every Monday was a catch-up day

This was a real treat — Mondays in Sydney were Sundays in New York City. So on those days, I could start my workday a little later (typically I “slept in” until around 5 or 6 a.m.) and then worked a relatively normal-ish day of 6 a.m. — 2 p.m. I’d get everything done from all of the Friday email traffic (that came in on Saturday my time) and got mentally prepped with schedules and projects for the week ahead. Just as having forced blocks of “deep work” time uninterrupted every afternoon was a dream, the Monday-without-meetings day really gave life back to my workweek and took me out of the grind I fall into far too often when I’m working the 9–5.

I had rare “me time” while the sun was still out

As a new mom who had a baby right at the start of the pandemic, this one really hit home for me. In a good way. Obviously the pandemic threw everyone for a loop. For me, it basically meant that I didn’t get the maternity leave I’d pictured in my fantasy-land imagination. Couldn’t go in stores, couldn’t go in museums, couldn’t have fancy brunch out with my baby in between naptimes, couldn’t meet up with friends in the middle of the day, couldn’t bring her to the office to show her off to my colleagues. Being in Sydney felt like a second chance at maternity leave to some extent. While we were there, the city was relatively COVID-free and operated as close to normal as possible.

But there’s another important reason why this mattered so much. When my workday ended around noon or 1 p.m., yes I’d take a nap and grab a bit to eat. But my baby was still in daycare until 5 p.m. which meant I rare coveted 3–4 hours each day of daytime hours without the baby. I could do things like, go grocery shopping, get new diapers, get her new clothes. Even things for me, like take a yoga class or get a haircut. And then pick her up from daycare and launch into the frenzied dinnertime-bathtime-bedtime routine. I maintain — having that pause during the day in between work and baby o’clock was a real gift as a mom. And unfortunately, that’s another thing that’s hard to replicate in the U.S. When your workday starts and ends at the exact same time as your daycare hours, it’s a lot trickier to carve out that special (but essential) “me time.”

One important note — None of this would have been possible without the support and flexibility of the entire Bolster team back in the U.S. There are many downsides to this approach (for obvious reasons). I was almost never available for impromptu catch-ups, I had to miss some important meetings, the difference in workday meant that I only overlapped with my colleagues for 4 days a week. Over time, I don’t think that’s a sustainable approach, particularly in a highly collaborative work environment like an early-stage startup.

But as it turns out, there’s a lot to like about working weird hours. And I’m still trying to figure out how to bring some elements of my “Australia life” back to my new normal in NYC.

Originally published at Dry Erase.

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Bethany Crystal

Bethany Crystal

2.9K Followers

A little bit web2, a little bit web3… Today’s projects: @Bolster & @Zeitgeist_xyz , board @CompSci_High ; ex @USV , @StackOverflow , alum of @Northwes