CS and the City Sean Lynch

The plan

As of May 1st, I'm on a two month sabbatical. I'm grateful for Dropbox being down with me taking time off and giving me the opportunity to reflect and explore.

I'm trying to figure out what's next "work"-wise. ie how I want to spend my working time for the next few years of my life. Of course, the non-work aspects of life are just as important and will weave into this process regardless. But I'm a worker, I love the work I do and the people I work with. Getting this side of the house in order is fundamental.

(I'll tackle the elephant in the room: there's an assumption that this means I'm leaving Dropbox. That's not how I'm looking at it. There's a whole world of possible answers to the question of what's next, and Dropbox is the best place in a world for a whole lot of them. It's possible that it's not for some, but I'll cross that bridge if I get there.)

Two months is both a huge amount of free time and a period that will blink by in a moment if I'm not careful. And my biggest fear is that I'll end up at the end of the two months and not have made any progress in my thinking. So I've been trying to be really structured with that the time.

I started putting together a TODO list, but after a few years at TapEngage and Dropbox, I'm accutely aware that laying out a plan in uncertainty isn't useful any further than a few weeks. So I boiled down my TODO into a few themes that, in theory, I can aim to repeat every day. And, as a initial goal, I propose doing each of these things for at least 30 minutes each day.

Sean's really overwrought sabbatical framework:

  • Talk with potential users/customers
  • Write thoughts and reflections (like this!)
  • Code and build things
  • Exercise

So, how am I doing so far?

Exercise Talk Write Code
5/2 - Sat Yep
5/3 - Sun Yep Yep
5/4 - Mon Yep Yep
5/5 - Tue Yep Yep

tl;dr - Not a single day where I did all four, and right now, averaging only two per day. On my own version of this table, I've added a fifth column: "What actually happened?". Everything on that list is important (so far), but it does limit the 'Yep's in the table.

It's only four days in, but I already figured a few things I need to improve in order to get to a Yep in each category. Follow along and I'll report back every week until the end of my time. Hopefully I'll have some interesting lessons as a result.