Reflecting on a Year Off

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Reflecting on a Year Off

(This note is an edited version of a thread I wrote on Twitter that got way too long; yay, freewriting!)

Today [October 19th, 2020] marks one year of taking time off. I deeply realize I have been very fortunate to have this incredible privilege, but I must say that I genuinely didn't feel its importance until about 3-4 months ago.

Making The Decision

Whenever I've talked with people about taking time off, the immediate question is: "How did you decide to take time off?"

The story this brings to mind is that I decided against it twice. First, I almost left FB at the start of 2017 because my team and I had just finished a big project, and I was tired. And (2) I had no plan to join a company immediately after my time at Facebook. In both cases, my attention and focus were wavering, but I could do these focused sprints that were so productive it seemed I was perfectly fine... until I wasn't.

Facebook gave me the freedom to work on efforts that hadn't had a lot of design attention before. This allowed me to be out of the line-of-sight of a release cycle. I got to do some super nerdy fun work and build teams that worked on internal tooling and privacy. However, my engine was sputtering, and I wouldn't stop.

In one instance, I was able to design work far enough ahead that I could take six weeks off (a company perk they called recharge) without much operational impact at all. When I came back to work, I had a bit of renewed energy, but it waned fast. Work was unfocused, and my life was unfocused. Yet, I couldn't at the time see my attention, my relationships, and my optimism slipping away. But I kept going, even though I couldn't get a good mental picture about what I was doing and why anymore.

Cue the departure from Facebook and a fantastic opportunity in New York at Glossier. I continued to follow a path I had laid out: aim to do great work, with a heavy focus on design, team, and company fundamentals (solving problems in predictable, systematic ways, consistent communication, career tracks, performance management, transparency etc.)

Lo and behold, my lack of energy caught up to me. (Lesson learned: even with all the optimism and excitement, I can do about 9-10 months of this) Again, my focus and the consistency of my output were waning. It became clear that I should have taken time off, but "I signed up for this, and I'll be damned if I don't deliver." So I focused on hiring some of the smartest people I could find and delegated the work away that led to me having to context switch constantly.

Whenever you find a way to increase your efficacy dramatically or delegate large parts of your work (also known as "hiring yourself out of a job"), there is often this great Y-split that you create.

You can either:

  1. define a new role and break open new scope, or
  2. make a lateral move, or walk away.

I'd done both at different levels of scale but never truly walked away entirely before. So there came this moment where I had the title, I had the seat, and grown my team, and delegated my role enough that either I could decide to double down and define a new scope or take myself out of the picture. And I did not have the energy to double down.

Taking Time

A year ago, on this day, I had my first proper day off in 15 years. A day without a company I ran or a job I was responsible for—even if only in the back of my head. Immediately I started doing a ton of traveling to see friends all across the world. This was an absolute blessing and also the best distraction. It wasn't until I got back home in January that I forced myself to sit in quiet and open up Pandora's box of how deeply I had affected my energy and brain. I didn't want to get out of bed, I had absolutely no feelings of inspiration or creativity, and I generally disengaged from everything.

Two months later, the pandemic hit. I should have taken as a hint to embrace doing little to nothing. Yet, every day, with the smallest bit of energy, I had my 'productivity' brain fighting my 'you-need-a-break' brain. Every day, it was "You should do something!" vs. "I don't want to do anything." This ended up lasting months.

I had to allow myself to do nothing, and trust to come out the other side with a clear mind. Which... is a stupendously hard thing to tell yourself.

To make sure I wasn't jumping off the deep end without any tools, I had my weekly therapy check-ins, kept up on calls with friends, ran on the West Side Highway (yay, those little mask cups that allows you to run with a mask), and implemented some basic structure to keep my sanity alive. But that was about as much as I could muster in a day.

A few months into the pandemic, it became clear I had to leave the concrete jungle and find some sunlight on the coast I had moved from. San Francisco would offer me more daylight, and I could take my car anywhere to feel a sense of movement and see the beauty around me.

On The Upswing

Slowly but surely, even with a city in lockdown, my regular conversations with friends, not asking too much of myself, and keeping somewhat of a structured day, gave me the desire to want to make things again.

A great opportunity came along, so—of course—I immediately jumped on it and started doing work. After a few weeks, it became clear this was too early, and it wasn't the right fit. However, this was the first time I felt my optimism, focus, and productivity come back.

This optimism was what made me finally accept that it was okay for me not to work for a bit. As soon as that became clear, my mood shifted. I focused on my personal life, which in turn (patently obvious, by the way) started tickling my creative and technical brain again. We're now at 12 months and a day, and while I don't feel that I need to work on something immediately, I have not felt this sharp and energized in about 3-4 years.

Lessons Learned

The biggest lesson for me among all this was—and this may sound 'woo-woo': seeing a structured day, a quiet cup of coffee, or a workout not as a task but as something to relish. There are these things in our lives that we know we 'should' do, but if we don't find a way to appreciate them truly, it will forever be a struggle to integrate them.

Be it working out, being mindful of your diet, meditating, managing your attention, and in this case—for me—it was challenging my assumptions and getting off of this career hamster wheel. Even though fear will tell you otherwise: with a little turbulence, you can always get back on.

However, I don't just want to write this without acknowledging the situation we are in right now. It's a cliché to say this, but times are crazy; there is macro-level stress, day-to-day life has been upended, and—on top of that—you're likely in too many (video) calls every day.

If you have the opportunity to protect your time by taking a long stint of time off, especially after many years of work, please consider it. Plan it out, budget it, consider the consequences, learn how much it will affect your retirement, all those things.

In all of us lies this subconscious stress that we can manage, and manage, and manage until we cannot. It's like dehydration for your energy: when you figure out that you are thirsty, it's way too late.

If you made it here, thank you for your time and attention. If you want to talk more about this: my DMs are open.


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