This month was my first time since early 2006 to be back in an office. Since 2006 I’ve been remote, and sometimes very remote. Over the last year or so, Stripe has opened engineering offices in Singapore, Dublin, and Seattle. Even I’m still a huge proponent of remote work, I joined the Seattle office and am excited to be an in-person part of the growth. I still believe supporting remote engineers yields strong competitive advantages, as it’s a forcing function for groups to be more deliberate which results in better choices.

This is a retrospective on my experience through January, and helping me setup for what to expect in February.

Disconnecting is much harder for me

As a result of habits built up over the years, at the end of the day I really need time to mentally put things away. I reserve the last hour of my day for “mental garbage collection” (credit to my bff, Cory, for the naming). This routine alone is not enough and my GC methods need to be adapted. At first, I suspected it was because I’m still around other people and tried hiding away in a corner at the end of a few days. This helps, but not quite enough. My commute of 15-20 minutes is enough time for my brain to put things in their place. I’m continuing to adapt on this. My wife and I settled on the term “fire gazing time” to describe this. When I’m mentally distracted I need to just stare into the fire until I can put things in their place and move on. Right now the best thing is coming home and starting to cook dinner, which I find mentally relaxing. Downside: I’ve made some fairly large, but amusing, mistakes.

Traveling in meatspace takes more thought

I was surprised at the mental overhead of worrying about where the next conference room is, where I need to go, and time to travel there. I am distracted at the end of a meeting or late to the next one. This is terrible for the people I’m meeting with but a simple tweak has fixed it. I do 45 or 50 minute meetings now and assertively hold to the end time. This gives me time to check email or slack so I’m not tempted to do it in a meeting, and if I need to be a human and use a bathroom I can do that, too. Less distractions means more attention. When I’m remote, there is zero cost to transitioning between meetings. I miss that.

Similarly, remote has no commute cost. I can start and stop working a few times a day, breaking my work day up to cover a variable schedule without spending time getting to and from work. When it takes 20 minutes to travel to work it isn’t feasible to come home and cook lunch. Having lunch with coworkers doesn’t feel like a split, but it is nice. To manage this, I’ve started going to the gym in the office. 45 minutes in the gym around lunch makes a big difference in how I feel.

Being close has value, but for how long?

I find it difficult to talk about the downsides of distributed work. People seem overly worried about this conversation, which frustrates me. Remote work isn’t perfect. It’s hard sometimes. It’s really, really hard sometimes. Everybody wants a highly gelled, bonded team and there’s a frequent attempt to design experiences that include remotes. This often takes the shape of an idea like “The folks in the office want to get together socially and watch a movie or play a board game!” They want to include remotes so they go to a conference room and setup VC, and remotes dial in and attempt to stay engaged. It never works out well. The remote folks are still at their desk where they do their work. It’s an uneven experience and creates an expectation that folks physically together should really reach out. I’ve been on the remote end of this many times, helping people and setting up social events that feel inclusive and fun (or not having them at all). My general guideline is pretty simple: Design an experience that works with one webcam per person. If you do that, everything is a-ok.

It’s clear that being in close physical proximity to other people is valuable. People get to know me and my behaviors more and that is really important. I frequently have people misread my emotion state (I have a special brand of resting jerk face, apparently). I hope by being around people more they can better read me, and I can read them better. I travel to our SF office frequently, and every trip I work to build up what I call “the social proof of existence”. Every interaction is an opportunity for the person to get to know me better, it’s more signal and higher bandwidth communications. That’s a good thing. Being in the office feels like it deepens this connection and hopefully I can also broaden it. It may have diminishing returns.

What didn’t change?

I’m not sure my kids noticed much of a difference with me being gone. My daughter greets me at the door, which wasn’t uncommon when working from home — both know I wrap up at 4pm. I still cook dinner and will continue, it seems critical to my GC routine since I find cooking mentally relaxing. I took one trip to SF, and my son forgot and only remembered when I didn’t come home by 5. I think that’s a good sign (although later in the week they had their own bouts of homesickness and sorely missed me).

I still love my job and can do my job effectively. I was worried I would be distracted and fall apart. I’m highly susceptible to environments and worried I would not able to complete any task. I still make my todo lists in the morning, figuring out the key things I must do, and I get those things done. A slight difference is I feel a slight urgency to the tasks. I’m more rigid about my time and I’m trying to never pull my laptop out at home (1 exception so far). The behavior and commitment is the same, but I approach it with more determination now.

Most importantly I still talk to coworkers all over the world. It hasn’t gotten heavily weighted to only interacting with my Seattle colleagues. This may change, and it’s up to me to prevent that. I’m optimistic my 7am - 4pm schedule will help.

After a month this feels like a good move. I’m excited what the future has in store. There’s going to be tremendous growth in the Seattle office. We’re hiring, and I’m happy to talk about what it’s like in more detail.

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