While on sabbatical…

I’m incredibly fortunate to have had several weeks of paid leave at my job. It’s a perk of working at Etsy after 5 years, though I took it after 6 because it lined up better with plans to buy a house and coordinate with my wife’s summer breaks. I haven’t had more than 2 weeks away from work since 2004 when I graduated from college and…just didn’t have a job yet.


It’s also something I’ll be unlikely to have any time soon, if ever, until I retire many decades from now. I’m also terrible at taking breaks, so I can imagine even in retirement keeping myself very busy. I had to learn how to relax again, or at least unlearn putting myself through a ringer scheduling as much as I could within a day to maximize getting things done. This being such a rare occurrence, I’d be crazy to let pass any kind of reflection upon it.


As mentioned, I’m not very good at vacations. Lots of other folks who go on sabbatical, at least at Etsy, have done big trips: flown to Australia for several weeks, taken an RV around the US, or hopped country to country around Europe. Those are all fantastic and well worth the time/money spent. I was looking inward a bit for mine, as I can attest I was burning out at work. With everything happening outside my sphere of influence at Etsy and so many of my coworkers departing, that loss of control and, frankly, a bit of loneliness was leading me down a pretty bad spiral of cynicism and apathy.


Having just moved into a house, I wanted to give myself a bunch of projects surrounding that life event – a form of nesting, I’m guessing. In and out of work, I love checking things off lists, it’s one of my big stress reliefs. Smarter people than I have almost certainly written about it, but I’m sure there’s a psychological connection between people who pile stuff upon themselves (yup, that’s me) to then dig themselves out as a reward. At least in this case, it was proactive towards a long term investment, the place I’d hopefully live for quite some time or means of self improvement. Looking forward to this sabbatical for a while, I’d come up with a huge list of things to work on. I was going to

  • paint every room in the house
  • put in a fence
  • build my own arcade cabinet
  • set up a home media center to stream throughout the house
  • pick up piano lessons
  • go running every day
  • read/listen to several unfinished or unopened books, blog articles, and podcasts I’d accumulated
  • write a big portion of a book of my own (!)

And these were just a few I had written down.


Of course, I didn’t get all of these done. It’s a ton of work putting together everything around a house! There was no way I’d complete all of these in the time I had.


Reading up a bit on topics surrounding this, I came across an article on the Planning Fallacy (which pretty much every software engineer in the world can attest to succumbing to) highlighting three reasons we tend to overestimate how much we can get done in a given period:

  1. We tend to assume new tasks are unique and unrelated to previous tasks, ignoring how long they have taken before
  2. We assume best case scenario, forgetting that stumbling blocks will slow progress along the way
  3. We assume the task as a whole instead of individual parts to break down the task, and therefore don’t accurately account for the combined cost of all the parts.


This is one of the reasons I’ve felt so refreshed from my sabbatical and why it was so critical to give myself this time off. I’ve finally given myself the freedom to think about these sorts of issues. I’m a chronic multitasker, despite my awareness of many different articles showing its detrimental nature. I especially liked this blog post from trello noting a “Brain-off Duty” Strategy:

Everyone has tasks that are necessary to do, but don’t require much critical thinking. Tackle those when you realize it’s the best you can do. Focusing on a mundane task actually centers your brain, and allows you to start thinking more clearly again. As Kevan Lee of Buffer says, “You have to eat a lot of frogs. It’s easier if you start breaking them into tadpoles.” Touche.

Half way through my break, I came down with a fever for 3 or 4 days. It wasn’t warranting of a trip to the emergency room, but I recognized the telltale signs of aches and sluggishness surrounding it. I was exhausted . The first half of my sabbatical I spent moving into the house, hosting my family for several days, and trying to work through my entire sabbatical list of todo’s. I wanted so badly to utilize this time perfectly that I’d completely lost the thread on what it was for – recharging from the daily grind. I was out of practice on knowing when to stop.


So for a week I didn’t touch the book. If I played piano, it was songs I’d already been familiar with and nothing new. Running was only enough to get a low impact jog in. Otherwise, I did one thing – I painted a single room. I would flip open my laptop in the morning, throw on a podcast, and do just a little bit of painting each day. It would be a distinct subtask with well bounded constraints every time – “Today is taping the trim around the walls” or “one coat of paint on the ceiling”, then I was done. It was of course frustrating to think there were things left to do with time to spare, but forcing myself to put them down made the back half of my break much more relaxing.


Now that I’m back into the 9-5, I’m trying to make sure I’m not jumping back into burning myself out tackling every project that’s in front of me. Long term, I’m going to get more done (and be happier about it) by reducing that context switching that’s been killing me for so long. My career isn’t going to suffer from doing less. If anything, keeping my job to working hours is making that that time in front of a terminal all the more productive.


The trick, I suppose, is how I’m going to make sure I keep to this.