10 Lessons from 4 Years Working Remotely at Automattic

Some really good advice here. I just hit my 90 day mark at Cisco, and our team is heavily remote, and even those of us local are primarily working out of home offices; I haven’t been in the office since I got back from Yellowstone, although I’ll get in this week.

It’s nice working on a virtual team again — but it requires a different mindset and you really have to worry about communication and coordination. My biggest challenge continues to be not letting things get buried in the inbox — I’m sure none of you have that problem, right?

One thing I did this week was follow the lead of Automattic and build out a team watercooler using their P2 Theme. This is specifically a place for those things where you think “some folks will be interested in this” followed by “but I don’t want to clutter their inboxes”. Now, that stuff has a home, which is overtly “not about business”. That you aren’t all in one office doesn’t mean the casual bonding and conversation isn’t important, I’ve found remote teams work best when you give that “side chatter” an official place and enable it within the team, and just because you can’t stand next to the watercooler in person doesn’t mean it’s not important to the work environment…

The Developer’s Dystopian Future

The Developer’s Dystopian Future

Ed Finkler (who I got to work with at Palm and is a really sharp and interesting guy) has hit that wall geeks hit when the challenges of keeping up the pace of a high technology professional meets your interest in doing things other than coming home from geeking all day and, well, spending all evening geeking.

I hit that point when I left Apple, where I had no idea what I wanted to do for a living but coding all day every day wasn’t it any more. There’s a reason why programmers seem to mutate into product managers, or in my case, a community manager (product management was my other path I considered).

The high tech world is a challenge to keep up with. The complexity continues to grow, the speed of change isn’t slowing down. I think to some degree this IS a young person’s game, partly because they have the energy of youth, but also because they don’t have the complications you get as you age — whether it’s spouse or children or mortgages or simply interests other than hacking.

And this is still very much an unsolved problem in the industry, which still to a dangerous degree depends on “we’ll replace him with another college kid. Cheaper, anyway”.

For those of you growing into this decision — and if you haven’t, you will, my answer is: don’t be afraid to reinvent yourself. Don’t be afraid to decide to specialize and take on only a piece of what you used to do — and become really good at it. Don’t be afraid to, every so often, take a step back and consider whether you want to go in a completely different direction. And don’t ever stop working to upgrade your skills and keep them fresh, or you’ll wake up and find yourself stuck in an eddy and unable to swim back into the current. That’s a scary place to be.

And even more than that, don’t be afraid to have a life. And maybe that life is outside of high tech. You don’t have to be a cute rat. If your interests run somewhere else, chase them. I’m lucky: I’ve been able to find a way to both stay relevant in high tech and chase my other interests. It can be done (but it’s not easy…)