My 2019 Life Experiments

Jonathan Swanson
9 min readJan 16, 2020

In my 2017 and 2018 experiments I tried adding habits, such as new types of exercise, meditation, productivity, etc. For 2019 I decided to experiment with removing things: working without a calendar, sleeping without an alarm, eating without meat, drinking without alcohol, living without a home, and launching a new startup without investors, an office, meetings…and lots of other things. 📆 ⏰ 🥑 🍹 🏠 💻

Ulysses was the original masochistic, self-experimenter (Ulysses and the Sirens)

For each experiment, I’ve laid out what I tried, what worked (and didn’t), and whether I recommend trying. Check out whichever ones interest you, and let me know what you’ve been experimenting with.

Working without a calendar: I love working, but I hate meetings. Getting into flow takes time, and meetings break flow. So this year I experimented with drastically fewer meetings. Not 20% fewer meetings — but 95% fewer. My goal was to have as many days as possible with zero meetings.

What I tried: First, I eliminated basically all recurring meetings except board meetings. Whenever I got meeting requests, I filtered them in one of four ways: 1) If the meeting actually required a call, I’d ask the person to shoot me a text or Whatsapp. A couple times/week I’d go on a walk, open my messages, and start calling people to connect. 2) If the meeting was necessary but didn’t require a live convo I’d ask the person to send me a voice note via text or Whatsapp with the problem/situation. Communicating asynchronously replaced 80% of meetings. 3) Any meetings that were absolutely necessary to schedule in advance, we’d batch into a block on the same day. 4) I ruthlessly eliminated the rest. For examples, at Athena we instituted a max one meeting per week policy. I also had my EA send me a calendar analysis once/quarter to track how many hours of meetings I had, which helped me get more ruthless over the course of the year.

What worked (or didn’t): It admittedly took some practice learning how to say no to so many meetings. Sometimes I felt bad not being more generous with my time. But, once I got over that, it was glorious! My productivity was higher because I had so much more focused time and so few distractions. And the impact on my happiness was even bigger. The biggest tactical win for me was moving meetings to async voice notes on WhatsApp. I found that 80% of hour-long meetings can be replaced with “send me a voice note on WhatsApp and let’s discuss there.”

Recommendation: If you’re managing a hyper growth startup with a huge team in an office, this won’t be possible for you. But if you can control your schedule, you should absolutely give this a try. You’ll find how few meetings you truly need. And if you’re not persuaded by me, check out Naval, Andreessen, and Paul Graham who all have all personally experimented with + advocated for killing meetings.

First week of December a couple years ago #endlessmeetings
First week of December this year #meetingfreedom

Sleeping without an alarm: Sleep is a core driver of health and happiness. But people typically schedule their sleep around the rest of their lives. This year I did the opposite: I never set an alarm in the morning. (Only exception was for a handful of flights and board meetings.)

What I tried: First I read Why We Sleep which lays out the importance of sleep, and how to get the deepest sleep. Then I tried everything the book recommends: don’t set an alarm (ever), keep your room cold (<68 degrees) and dark, use a white noise machine if the room is not totally silent, no caffeine, and no alcohol. In other words, Silicon Valley Mormonism. 😂

What worked (or didn’t): This experiment requires first doing the no-meeting experiment above or never setting morning meetings. But other than that this is about the easiest and most enjoyable experiment you will ever do. I found over time my schedule gradually shifted earlier and earlier towards the hours I’m most productive at work — by the end of the year I was waking up by sunrise without an alarm.

Recommendation: Many people obviously have inflexible schedules (e.g. parents) but if you can control your schedule, you have to try this. It’s the most enjoyable experiment I’ve ever run — I wake up every day rested, happy, and excited to work.

Starting a company without investors, an office, meetings…and lots of things: With Athena I wanted to build a company that was not just a new product or service but an experiment in company-building itself. Most new-company-design experiments fail (e.g. basically every startup that tries to get rid of managers or PMs 😂) but it’s important we collectively keep trying new methods because the winners can drive massive productivity gains across the economy. (To say this more explicitly: I think organizational/company design experiments are typically NPV negative for individual startups but very positive for the ecosystem.)

What I tried: We started Athena with lots of new constraints: we are building Athena with no investors (bootstrapped to profitability), no employees (all hourly/contract/project-based), no office (fully-remote), no meetings (max 1 per week), no 1-on-1s (informal catchups), no 360s (culture of ongoing praise + feedback), no team members we don’t love (only hire people we’d want as friends), and no customers we don’t love (fire customers who are difficult).

What worked (or didn’t): Building a company with so many constraints takes more work upfront. Also there’s a relentless gravity towards the default that you have to continually resist. Resisting this gravity was the hard part. For example, there were dozens of times where people I was interacting with wanted or expected (understandably) a more traditional workplace. But the purpose of putting these — admittedly unusual — constraints on ourselves was to liberate us to work faster and happier. And it worked! In our first year at Athena, we’ve grown the team to 75 amazing people, seven figures in ARR, a customer waitlist that is now 12+ months long, and a sustainable (=profitable) business that we can build for the long-term. And, most importantly, we’re enjoying the hell out of building a company on our own terms.

Recommendation: There are lots of expectations for how to build a company. But the truth is there are many paths to building a massive, generational business: in my view, if you’re going to spend a decade+ on an endeavor, you should design your company to be a place you absolutely love.

Living without a home: When Katherine and I went deep-minimalist a few years ago we eliminated all possessions except what fit in carry-on luggage. We’ve been living for 3+ years now with <100 possessions each. When we first did this I was still day-to-day at Thumbtack so we lived in hotels in SF (crazy but true: we saved money on rent doing this). Since I moved to Exec Chairman at Thumbtack we are no longer tethered to SF so we’ve transitioned to being full digital nomads — working and living in a new place every ~month or so.

What I tried: We still work constantly but we’ve made the 🌎 our home/office instead of any one place. Puerto Rico is our home base and residency but every month or so we pick a new place to explore: the only guardrails are good weather and fast wifi. 😎 We worked at beaches (Puerto Rico, Tulum, Dominican Republic), mountains (Chamonix, Sundance), and cities (Oslo, Mexico City, NYC). We also did one month on a lake (Lake Muskoka) and one month in the bush (South Africa).

What worked (or didn’t): Making the world your office is incredibly inspiring. One of the awesome benefits of being a digital nomad is visiting places during shoulder season (example: a chalet in Chamonix in October is 80% less than during peak season). One surprising observation: It felt like time really sloooowed down since we started this experiment. 2019 felt like it was 2–3 times longer than a usual year. In the best way possible — it literally felt like Katherine and I squeezed multiple years out of 2019. I think it was the lack of routine combined with having more sunlight (we’re in New Zealand now and have 15 hours sun/day vs NYC which has 9 hours/day). There were only two challenges: 1) moving around takes lots of planning/coordination (Athena helps a lot but there’s still overhead) and 2) you have to be more proactive to see your friends (which is why we are building a traveling community).

Recommendation: This obviously requires deep minimalism and a flexible work environment, so it’s not for everyone. But it’s something we dreamed about having the freedom to do for years, and it has really lived up to our dreams. A few practical tips: A travel ergonomic setup is key. I use Apple wireless keyboard, Microsoft Arc mouse, and NextStand ergonomic laptop stand. We often stay in a normal hotel/Airbnb, but then head to the most expensive hotel in the area to work for the day. They generally have fast, free wifi and great atmosphere.

The real world is way better than WeWork!

Eating without meat: Last year I tried the keto diet. This year I tried a plant-based diet. I’m not going to wade into the debate (warfare 😂) between the keto and plant-based communities (tribes 😘) but every serious nutritionist agrees that almost everyone should be eating more veggies. So I figured testing plant-based was a good push to actually do that.

What I tried: First, I read How Not to Die which details which plant-based foods have the most scientific evidence for improving health and extending life. Then I downloaded the DailyDozen app (iOS, Android) which gives you a checklist of the healthiest foods you should eat every day. I tried to check off every item on the list every day (I typically hit 20–23 out of 24 total).

What worked (or didn’t): Eating plant-based felt very healthy but I’m lucky to feel pretty good on pretty much any diet. So I tested my blood before/after to see if there were meaningful changes in my blood work. The results were amazing: in just a month of eating plant-based my total cholesterol dropped from 227 to 171 and my LDL (“bad” cholesterol) plummeted from 151 to 102 (aka from high to healthy).

Recommendation: You should eat whatever makes you feel healthy. But eating more vegetables has lots of science behind it, and eating entirely plant-based (even if only for a month-long experiment) is a great way to build a habit of eating healthier.

Drinking without alcohol: While delicious (!) alcohol is a poison. So I figured I should at least experiment with eliminating it.

What I tried: No alcohol for the entire month of January.

What worked (or didn’t): This was one of those experiments that seemed really hard in anticipation. If you live in a city, it’s pretty easy to get in the habit of drinking 5 nights/week. And the first week of the experiment was admittedly annoying (“we’ve finished work and it’s 8pm: what should we do with ourselves?”) but there was a very positive and immediate effect: Katherine and I both started sleeping better than ever and waking up with a ton of energy. I didn’t realize how much even two glasses of wine hurt my sleep. This experiment also forced us to do more of the active things we love (e.g. play tennis or trail run after work) which was an added bonus.

Recommendation: While I’m not going full no-alcohol, this one month experiment led Katherine and me to drink probably 80% less than we would have the rest of the year. I also discovered the best way to avoid alcohol: stay in environments with good weather and where it is easy to exercise a ton (trail run, tennis, lift, etc).

I’m just starting to think about what my experiments should be for 2020. Send me your ideas!

High fives and happy 2020,




Jonathan Swanson

Co-founder & Executive Chairman at Thumbtack, former White House staffer, lover of life