Nearly twelve years into remote work, I still value the flexibility and the time I’ve saved commuting. I also still have to work at knowing when to stop for the day.

I started working remotely when I joined InVision in December 2014. The entire company was distributed, and working with people I’d mostly see through a screen took some getting used to.

When people found out I worked from home, the questions were usually pretty similar. How do you stay motivated? Don’t you get lonely? Do you actually get dressed in the morning?

Yes, I get dressed. I covered that one in my original post about remote work.

I wrote that article in 2019, after about four years of working remotely. Reading it now, a lot still holds up, including the difficulty of leaving work alone when my computer is a room away.

Since then, I’ve watched remote work go from something that needed explaining to something people around me experienced for themselves during COVID. That experience made me more careful about recommending it to everyone.

Starting at a company that was already distributed

One of the nice things about starting at InVision was that remote work was already how the company operated. There wasn’t an office where decisions happened while the remote people tried to catch up. We were all working that way.

Slack was where we talked throughout the day, and meetings happened on Zoom. The people I worked with were spread across different time zones, so getting an answer sometimes meant waiting until someone was online.

The benefits were easy to appreciate. Before working remotely, I’d take two or three buses to get to work, spending about an hour and a half travelling each way. Waiting for a late bus in the middle of winter wasn’t something I needed much time to get over.

Being able to step away for an appointment or help with something at home made a much bigger difference than I expected too. Those things sound small until you think about how much planning they require when you’re spending most of your day away from home.

The pandemic changed the circumstances

In 2020, working from home went from something I occasionally had to explain to something people around me were suddenly doing themselves.

For me, the work setup was familiar. I’d already spent years collaborating online and getting comfortable with a workday that didn’t involve going into an office. I had a routine to fall back on.

But that only accounted for the work part. Having experience with remote work didn’t prepare me for a pandemic any more than it did anyone else.

I’d chosen a remote job at a company that was set up for it. People trying it for the first time were suddenly doing their existing jobs from home while dealing with school closures, limited space, and everything else happening around them.

When I wrote about flexibility in 2019, I mentioned being able to watch my son for an hour or two if he was home sick from daycare. Even then, that required some juggling. Trying to work while childcare was unavailable for an extended period was a very different situation for families.

I kept thinking about that when people talked about whether working from home was going well. There were so many things affecting the answer beyond where someone had their laptop.

Flexibility still depends on communication

I like being able to focus on a problem without someone walking over to my desk. Being able to plan work around an appointment or something at home still matters too.

Looking back at my time at InVision, being in different places didn’t stop us from building products together or taking ownership of our work.

There was a lot of communication involved, of course. You couldn’t assume someone knew what you were working on just because they’d seen you at your desk that morning.

That part of my earlier post is still relevant: give people context. Explain what you’ve tried when asking a question. Let your team know when something is blocked. It saves a lot of back and forth, especially when you don’t all work the same hours.

Meeting the people behind the screen

After all these years, I’ve come to appreciate meeting coworkers face to face more.

It’s a funny experience meeting someone in person when you’ve already spent so much time working together online. You know their voice, how they approach a problem, and probably what the room behind their desk looks like. But you’ve never actually stood in the same room.

There’s already a level of familiarity there, so you have plenty to talk about. At the same time, you get to know a bit more about them outside of whatever you’re building together.

A lot of remote conversations happen because someone needs something. There’s a question to answer, a pull request to review, or a meeting with an agenda. Meeting up gives you more room for the conversations that don’t need a reason to happen. You can grab a coffee, go for a walk, or sit down for a meal without needing to schedule another call.

I still value long stretches of time to focus at home. Spending time together in person gives me something I don’t get from those work conversations.

Boundaries still take effort

I wish I could say that enough years of working remotely automatically gives you good boundaries. In my original post, I wrote about spending a couple of extra hours at the computer after dinner and suddenly realizing I’d worked a ten-hour day.

Reading that again, I’m less inclined to brush it off because I happen to enjoy the work. There’s always another thing to look into, and having easy access to it doesn’t help you decide when you’ve done enough for the day.

I also wrote about occasionally missing the commute because it gave me some time to decompress. I certainly don’t want the three hours of buses back, but I understand that feeling. Finishing a workday and being available to your family involves more than walking out of your office.

Then there’s the effort involved in getting out of the house. Working remotely removes a reason to leave every morning. You have to make room for that elsewhere, and being aware of it doesn’t mean you’ll always be good at it.

I’d still choose remote work

In my earlier post, I said I saw remote work as the future. Having lived through it becoming so widespread during COVID, I’d be a little less sweeping about it now. People have different circumstances, and I can understand why someone would prefer going into an office.

For me, the flexibility and time saved have continued to outweigh the drawbacks. I’ve built my career this way, and I appreciate the room it gives me for life around work.

If I were considering a remote role today, I’d ask how the team shares decisions and handles questions when people are offline. I’d also think about where I’d work and what would help me leave it alone at the end of the day. Starting at a company built for remote work helped me with the first part. The second still takes my attention.