2018 in Review

Most of my year was spent in this room.

As I mentioned in 2017 (more historical data: 2014, 2015, 2016), I really only focused on two big things: Tom and I getting married and Dark. That continued into 2018, without the wedding part.

My primary goals were to:

1. Get a ton of work done for Dark.
2. Have the energy to support people in my personal life.

The good news was that I could work on getting better, rather than just making it through!

My two primary levers to do that were prioritization and maximizing my personal energy level. Using these techniques helped me to get through some extremely challenging personal and professional situations throughout the year. I had fewer milestone “achievements” this year, but felt great about my sustained output.

Prioritization

I dedicated more effort towards thinking about and working on the most important things this year.

I did this by recording one thing that I needed to make some progress on every day, which I called “most important thing.”

• I used a custom made date book that Tom got me last Christmas to write one thing down each day. Ideally I’d write it down before the day, but sometime I did it retroactively.
• I used this definition because the “most important thing” is likely to absorb all my mental energy until I do it, and that’s my best resource. In the most extreme cases, these items will wake me up at 3am and I’ll spend hours doing or thinking about them. The flip side is that sometimes an it’s a five minute phone call that I can quickly do at 9am, and then move on to other things.
• I have data for 339 days (I failed to track the data on 20 days, and there are 6 days left as of this writing). All numbers and percentages are based on 339, and I assume it will translate to the other 26 days.

Dark

As you’d guess, work was a huge part of my year. I loosely track the time I spend working, and it works out to 56 focused hours per week. That doesn’t count time like talking about work with friends, or thinking about work while exercising.

• 25% of my days (86), I prioritized building a strong team for Dark. Of those 86, on 56 I prioritized something related to our existing team, and 30 I prioritized hiring. We’re now a team of seven people, and going strong. We’re still looking an infrastructure engineer to join us.
• 20% of my days (65), I prioritized our product, customers, thinking, or writing. I group these because at this stage, they’re all directly related to building our product. Going into 2018, no one (including us!) had built anything on Dark. Now we’ve had multiple customers ship on top of Dark, and have validated some of our key product hypotheses. More to come, and if you want to try out Dark, sign up here and tell me what you want to build!
• 10% of my days (33), I prioritized the “startup” bucket. This is anything related to the company that isn’t people or product. This could be related to getting myself organized, investors or external advisors, compensation, and other projects. I’d like a little more granularity on this next year, but I feel great about the people we’ve surrounded ourselves with.
• 9% of my days (30), I prioritized speaking or a conference. This feels too high for me. The cost isn’t in the events, but in the fact that they require prep and recovery! While they can be good for connecting to users, there are other ways to do that, too. That cost is why I broke this category up from thinking, writing, and other customer activities. That said, I had the chance to speak at the CTO Summit in San Francisco, spoke at Harvard Business School, and got some awesome advice on giving better talks from Gibson Biddle (give sample talks, and request numerical feedback).

Personal Priorities

Everything I wrote down that wasn’t directly related to Dark, I lumped into “personal.”

• 11% of my days (37), I prioritized rest. This aligns to the fact that I feel good working 56 hours/week. I need about one in ten days off. I’m lucky, and I know this isn’t the case for everyone. I unfortunately was sick more often than usual this year, which upped this. If I don’t make this goal explicit by putting it in the notebook, I don’t do it.
• 9% of my days (31), I prioritized Tom. This is a fuzzy bucket. Sometimes this meant a full day (birthdays, vacations), but often I just knew I’d been heads down and had to point out how much I appreciated the support.
• 8% of my days (26), I prioritized a social activity. Hi friends! This was a huge range of stuff, including: a Taylor Swift concert, a Savoir Adore concert, making a lot of desserts (Petit Fours, Unicorn Barf, The Cookies), learning to cook pasta from scratch, co-working, pinball, and visiting gardens.
• 9% of my days (32), I prioritized thinking about or doing something. This is nebulous but includes all that #adulting stuff like “go to the dentist” and “make a budget.”

Interestingly, I rarely specified “travel” even though I did still do a bunch of that. Often it got lumped in the Tom bucket. Highlights included my birthday in St. Louis, Grand Cayman with my family, Canada for a friend’s birthday party (where I learned to water ski!), a company retreat to the North Bay, and Tom’s birthday in Western Mass/NYC.

Energy Level

For the second, I kept careful track of what impacted my energy level and ability to do an important activity and many other activities.

Sleep

(I get really frustrated when people insinuate that I must not sleep. I sleep eight hours per night!)

Sleep is the most reliable predictor for if I’ll have a a good day. This also goes on the list of things that I’m lucky with: I fall asleep quickly and wake infrequently. At the beginning of September, I started using a Whoop band to track and see what that really looked like.

• On average, I spend slightly more than eight hours in bed.
• All the data is strongly clustered around 7–9 hours (say, 80% of it).
• About once per week, I sleep less. That’s typically when I’m taking a late night or early morning flight. Most of those nights are still 6+ hours.

People

I’m at introvert (more on that), but as is clear from the “important” items, I spend a lot of time with people. People time has a huge impact on me. It’s important, but it’s like a battery, and when it drains I’m less present for our team. Because of that, I invested the time to build a personal CRM in Airtable, based on Danny Crichton’s description of his system. I made modifications as I went.

• I recreate my data from my calendar and my memory every morning. When I find an error, I fix it, but I’m sure some things slid by.
• Seeing someone and catching up for 15 minutes at a party counts as one (but 30s wouldn’t), and so does spending an entire day with a friend who is staying at my house 🤷‍

With those caveats:

• I met with 654 distinct people this year, nearly two new people per day, all year (I use distinct people as a proxy for energy because seeing new people takes more energy than seeing someone I see frequently).
• I saw about 30% of those people (201 people) more than once.
• I saw about 15% of those people (100 people) more than twice.
• I saw about 5% of those people (33 people) more than 5 times. That’s a weird mix of personal friends, founders who have advice that I value, investors, and people I just happen to run into a lot. The data actually made me re-evaluate how I think about my friends!
• I saw Nikki the most (no surprise). That said, I’ve only seen her 15 times, despite our goal to have dinner every Tuesday.
• There are eight people I see nearly every day and don’t bother to track: Tom, and everyone at Dark.

This felt pretty sustainable, but I don’t think I could do more social interaction and still perform as well at other tasks.

Routine & Overlapping Activities

I found the more I could get into a routine the better. My ideal morning means that I get to exercise, meditate, wear something I like, writing morning pages, and then start working. I also found the more I can interlace tasks (folding laundry while making a call, doing a face mask while meditating) the happier I am.

Food, Alcohol, Exercise (not tracked: Coffee, Water)

People think my obsessive spreadsheets are weird (it’s true) but I have learned a lot from them over time!

• I drank 6% less alcohol in 2018 than in 2017, which sounds pretty stable. That said, I drank 35% less per day after mid-April than before mid-April in 2018, which is a huge change. Looking at data over multiple time periods is important. (My Whoop also helped me validate that drinking has the a big impact on my sleep).
• I exercised 137 times in 2018 (a bit more than once every three days), or 10% less than 2017. There was more variety: hiking was more frequent, and water skiing made its first appearance!
• I started tracking food in 2018. I haven’t gotten any interesting data out of it yet. I’ve been tracking the food item and the diet (Omnivore, Pescatarian, Vegetarian). I also try subjectively tracking how I felt about the food. Maybe next year I’ll have something interesting to share from that.

I don’t track my caffeine or water consumption. I would guess I have 1–2 cups of coffee per day, and a lot of water.

Books

Along with everything else on this page, books are a huge part of what helps keep me feeling emotionally stable.

• I read 158 books this year, one book more than my previous record of 157 in 2016.
• More importantly, that’s 23% more books than 2017 (like I said, I’m getting better again, not just getting by!)
• 77% of the books I read were by women, and 23% were by men.
• 69% of the books were fiction, and 31% were nonfiction.

I’ll get the full list of book recommendations up soon! I’m also excited to share this small project I did to share books throughout the year.

Conclusions & Looking to 2019

I’m genuinely proud of the work that I did this year. I care a lot about doing good work on an ongoing basis vs. just looking from success to success.

Going into 2019, I’m expecting more of the same. I’m excited to keep working on Dark with our team and our customers. Outside of Dark, I’m excited to continue to see and support my friends.