I tried something new in 2017, which was to make a set of personal OKRs to fulfill throughout the year. OKRs (Objectives and Key Results) are typically used as a planning framework by companies (both Google and Twitter implement them) but I had never tried to structure personal goals in this way. I’m not sure it’s a general approach I’d recommend for anyone else, but I like the idea of taking a set of abstract goals and trying deconstruct them into measureable tasks.

I respect the effects of small adjustments to habits compounded over time. New Year resolutions have been effective ways for me to implement such changes. In 2014 I started making one-second-per-day videos (and have done so in 2014, 2015, and 2016 so far!). In 2015 I started regular Rosetta Stone lessons to learn Mandarin. In 2016 I tracked my weight and food every day with the intent of losing 30 lbs by the time my daughter was born. In 2017 I wanted to be healthier, happier, grow intellectually, and create things. I’m writing this as a postmortem on the process, and an accounting for how I think it went.


I generally understand OKRs as a mapping from higher-level and typically qualitative outcomes to a set of measurable key results which should work toward effecting the desired outcomes. I found a set of tasks I thought I could do (and track) which would contribute to my health, growth, and creativity. An important note is that I was trained that OKRs are meant to be aspirational - getting 100% is a sign that the target was set too low. So my rule of thumb is 70% or higher is considered a passing score. (And yes, people sandbag and fudge these numbers all the time.)

Objective: Be healthier and happier.

This seems somewhat redundant in that most things I do should further my own health and happiness, but I find it altogether too easy to neglect self reflection and care when my available time dwindles. Like a frog in a slowly heating pot of water I can find myself in a bad place without noticing how I got there. The intent of this objective was to make sure I kept my own state in a good condition throughout the year.

Key result: Interview at other companies

I once heard of a manager giving the advice that employees should periodically choose to continue working at their company instead of growing tired, complacent, or frustrated with their work. This meant interviewing at other places and making an explicit decision to stay or leave depending on what options were the most rewarding. By 2017 I was getting tired at Twitter and felt that I needed to decide to leave or stay to be effective. I conducted a long (for me) job search and eventually decided to leave Twitter and join Stripe, a decision I’ve been very satisfied with so far.

Key result: Complete home improvement / design projects.

This may seem out of place in the “health and happiness” objective, but I place a lot of value in having a space to live and work where I feel at ease and things are generally organized how I want them. Being comfortable puts me in a better mental state and makes me more effective. I set a goal for four home improvement projects to improve my living and work space at home. I completed three of them, leaving the most ambitious (installing cabinets and shelving in our dining area) for 2018.

Key result: Four six mile runs and one twelve mile run.

After my daughter Ada was born, my only real exercise dwindled down to a few miles of walking to work at Twitter every day. I felt myself getting out of shape and craved regular high-intensity exercise. I figured that I might start running by the end of the year, but wasn’t sure how much time I’d have. I set a pretty unambitious goal and completely missed it.

Stripe was too far away from my house to reasonably expect to walk every day, so I eventually dusted off my bike and started biking to work regularly. It’s objectively healthier, faster, and cheaper than alternatives like car services or Muni. I biked over 700 miles in 2017 over about 100 days of commuting. So I consider this one a success in spirit if not in letter of the intended result.

Key result: Write in a journal weekly.

I’ve been keeping a journal ever since reading Jordan Mechner’s notes on the making of Prince of Persia when I turned 30. Over time I’d gotten pretty lax about regular updates, sometimes taking months to write new entries. I set a goal to write at least weekly in the journal, getting into a regular habit toward the second half of the year and completing 38 entries in 2017.

Objective: Learn and grow intellectually.

As I’ve gotten older, I’ve grown more concerned about atrophy of skills, lack of intellectual growth, and a general tendency to avoid rigorous or challenging thinking. So I set a goal to exercise my brain more.

Key result: Finish 15 books.

As covered in my 2017 reading list, I wanted to read more in 2017. Tracking a goal here was very effective, as I completed 17 books (a good increase over prior years).

Key result: Finish 4 cinema club films.

I have a Cinema Studies minor from college. I’m both challenged and rewarded by the exercise of deconstructing art and writing about my interpretations—analyzing film expands my perspective. As I talked about in my Under the Skin post I found inspiration in the films the Kentucky Route Zero developers cited as references for their game, and started trying to write regularly about film in my cinema club posts. I wanted to pick up the pace in 2017 but fell a bit short of my goal of 4 films, writing a post about The Exterminating Angel but getting hung up trying to figure out what to write for The 400 Blows. So 1.5 films out of 4.

I think that the goal of writing an analysis about every film had the chilling effect of making me watch fewer films. In the future I think I may decouple the process of watching a film from writing about it.

Key result: Work through Statistics textbook.

As a programmer, I’m regularly reminded of how much more I could know about math and statistics. I believe practicing these disciplines would have a positive impact on my work and ability to work effectively. I bought a copy of this Statistics textbook as a reference for a class I took a few years ago, but never got too deep into it. I wanted to work through the book and challenge myself to complete the exercises in each chapter but never scheduled the time necessary to do so. A complete miss, unfortunately.

Key result: Finish referaat.

The Estonain fraternity I belong to has two classes of members. Junior members are expected to write a dissertation on the topic of their choosing and defend it in order to advance to full membership. I’m well past the age where it would have been reasonable to complete this task, but I never did it. It’s a point of shame in my life and every year I intend to finish this up (but never really get around to it). Another year with little progress.

Key result: Practice Mandarin regularly for at least one month.

My wife got me a copy of the Mandarin Rosetta Stone program as a present in 2014. I practiced this in 2015 but didn’t keep it up over time. I’d like my daughter to grow up bilingual and wanted to pick this up again in order to try and speak some Mandarin at home. The negative trend of “Learn and Grow” continued, however, as I did not get even a month’s worth of practice in.

Objective: Create things.

From software, to art, to food, I feel a strong compulsion to make things. I wanted to focus on being more prolific in 2017, spending less time on more things and practicing finishing more often.

Key result: Eat from the garden every season.

After some work in the back yard in 2016 we had a functioning garden in 2017. I wanted to make sure I was putting time into tending that patch and set a goal to eat a meal out of the garden every season.

Spring started off well, with a salad of radishes, pickled greens, and butter lettuces. Summer was a little more sparse. We didn’t do anything for fall, but pretty much all of our Thanksgiving herbs came out of the garden in the winter. It’s a bit of a stretch to call that 3 meals, so I’m giving myself 60%.

Key result: Paint every day in January.

I joined a group of friends to try and create a painting every day in January. This was a great success and I think it kickstarted a good habit of painting regularly and getting out of my comfort zone creatively. Finishing a painting every day forced me to cap the amount of time I spent, and I had to get used to the idea of shipping each piece without agonizing over details for very long.

Key result: One painting a week from February - December.

I wanted to keep the inertia from painting every day, so I pledged to make a painting every week after January passed. I dusted off my old Instagram account to share my progress. I’ll be honest that I didn’t feel like sharing everything I made, but I finished 30 paintings in 2017, out of 48 remaining weeks in the year.

Key result: Publish a game, make $1 from someone I don't know.

I’ve been working on various half-finished games for a while. My prior efforts to compete in Ludum Dare have been successful, but I haven’t found an equivalent success in polishing a real game to the point where I’d feel comfortable charging for it, and someone I didn’t know would pay for it.

My closest effort is a project I’m calling Tiny Patch, which is more of an interactive experience than a structured game. It’s something I wrote because I wanted to make a toy my daughter would enjoy playing with and I thought it would be relatively quick to wrap up. She does enjoy playing with the prototype, but I didn’t make it past my requirements for a beta release before the end of the year.

However, part of the reason I picked up painting in 2017 was to get better at art so that I’d feel comfortable making assets for games. As I shared my paintings online, I got an offer to do a comission from a friend-of-a-friend. I didn’t feel comfortable charging a real fee for the painting, but I did ask for $1, as I thought that making a dollar from someone I didn’t know for a piece of art satisfied the spirit of this challenge.

Key result: Write 10 blog posts.

I’ve never really felt like I have been prolific enough on this site. I’m always impressed by writers who can regularly generate compelling articles for a personal blog. I think I tend to overwork things and spend too long on posts. I put some effort into trying to finish more this past year, with some success. I wasted a lot of time fiddling with the blog generation software and writing React components for the Timebox post. But I also published more posts in 2017 than I have in any year since 2013, reaching the ideal 70%:

Reflecting on 2017

I’m currently reading The Score Takes Care of Itself by Bill Walsh. He talks about turning around the San Francisco 49ers football team not by focusing on winning games, but on helping the team build an inventory of skills “both attitudinal and physical”. These skills would lead to improved execution. Better execution would lead to better performance on the field. Only with better performance on the field would the team win more (hence, “the score takes care of itself”).

Do OKRs work the same way? In 2017 I did feel healthier and happier. I felt that I learned and grew intellectually. I created things. Were these outcomes the result of an inventory of skills earned through rote practice? It’s probably too early to tell, but I like the model and don’t think I disproved its effectiveness. So I’m sticking with it, have a new set for 2018, and am making progress against it (even at this very moment).

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