My 2018 Life Experiments

Jonathan Swanson
7 min readJan 2, 2019

--

In 2018 I doubled down on my favorite experiments from the year before and also tried new experiments with delegation-by-voice, meditating on ideas, eliminating news consumption, and daily goal check-ins. 🎙🧘🏼‍♂📰🎯

Like last year, 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. 😎

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

Delegation-by-voice: Like most people, I historically have done most my work by tapping my fingers on a keyboard. The problem with tapping fingers on a keyboard (or worse: thumbs on a phone) is: 1) it’s slow and 2) requires you to be sitting and looking at your computer. In contrast, dictation is way faster (you can talk 2–3x faster than typing) and allows you to work away from your computer.

  • What I tried: My friend Denis helped me create an app for our phones that instantly starts recording upon opening. One touch to open, start talking, one touch to end, and the audio + a transcription is sent to your EA.
  • What worked (and didn’t): Voice is fantastic for delegating tasks on-the-go (“Marni, pls book me a flight to Chamonix”) , writing emails (“Hey Marni, I just met with Cameron; pls send him an introduction email to Ed”), drafting letters (“Hey Marni, I need to write a recommendation letter for Ken; I’ll dictate some thoughts for the next few minutes and then pls pull together into a draft”), and even brainstorming (“Hey Marni, Katherine and I are going to brainstorm a new business idea for the next 20 minutes; pls synthesize non-idiotic ideas into an outline”). Besides being faster, voice makes it easier and more enjoyable to delegate: you can dictate while you walk between meetings, are jumping in an Uber, or strolling at sunset.
  • Recommendation: This is awesome for both productivity + happiness but it takes practice. Most of us are used to only working in front of a computer or phone. It sometimes feels unnatural at first. So when my EA sends me emails I asked her to add a note to the bottom that says “remember you can dictate your response” to help me develop the habit of using voice. But the more you practice the more natural it gets. My friend Korok has been doing this for years and he has written an entire book by voice!

Daily Goal Check-ins: I started doing daily check-ins against my quarterly goals in 2017 but I’m re-sharing because this system continued to be game-changing for me in 2018. If you only try one thing from this post you should do this.

  • What I tried: Every 3 months when Katherine and I have our “Life Board of Directors” meetings we set 3–4 goals we want to work on in the quarter ahead (both personal/professional). Then we have our amazing EA in the Philippines send us a daily check-in on those goals on WhatsApp. At the end of each week we get a summary of our stats for the week. (Screenshots: daily check-ins & stats summary.)
  • What worked (or didn’t): This is the most successful experiment I’ve ever tried. It didn’t just help marginally; it helped me significantly with every personal and professional goal I put into the daily check-in system. Because of these daily check-ins in 2018 I exercised 226 times, meditated 182 times, read a new book every other week, stopped cracking my knuckles, and a bunch of other personal goals.The system is powerful because: (1) it is easy to record progress (<10 seconds/day) (2) the check-ins are daily and (3) there was relentless accountability (Katherine and I saw each others’ results each week).
  • Recommendation: If you’d like to do this yourself (or leverage the voice delegation system above) check out Athena, a new company I’m helping get off the ground. Athena will recruit you a high-caliber EA based in the Philippines and train you to delegate 10x more.

Meditating on ideas: Last year Katherine and I started a meditation practice which we both love. But this year I also wanted to try something a bit different: meditating on ideas. There are things I know about the world intellectually but that I haven’t integrated into my moment-by-moment thinking and living. Examples: I believe free will is an illusion, our minds evolved to deceive us, and we will all die. And yet: I don’t have universal empathy for everyone I meet (you should if there’s no free will). I typically assume my chain of reasoning is–if not unbiased–at least transparent to myself (but our minds evolved to confabulate). And my gratitude for life is deep but far from unbroken minute-by-minute (but it should be if you really reflect on the brevity of life). All of these truths–if understood not just intellectually but also felt and experienced and embodied–offer the doorways to peace, understanding, empathy, and even levity. So I wanted to see how far through the doors I could go…

  • What I tried: At the end of normal meditations, I would spend the last minute or so reflecting on one of these truths. If I was thinking about free will I would just imagine all the humans around me not as people but rather as tornados (since if free will doesn’t exist humans are effectively complex weather patterns). If I was thinking about death, I would imagine myself dying and reflect on how grateful I would be to have even one more day with the people I love.
  • What worked (or didn’t): I’m only 1% of the way to integrating these ideas fully but even that small progress has given me glimpses of deeper gratitude, freedom, and peace. To me, these ideas feel like cheat codes for life. It’s also clear, though, that our brains are designed to reject these cheat codes. Which is why I believe wisdom is often not discovering how to live but rather habituating what we already know to be true. So this is definitely an area I want to go deeper on. I want to reprogram my mind to fully embrace these concepts so I can get their full power. I’d love recommendations from others on how to go from 1% to 2%. 🙃
  • Recommendation: I certainly recommend but with a caveat: Reflecting on free will is a bit like peering over a metaphysical cliff. Some people can find it unmooring so I wouldn’t jump off the cliff if it feels too scary. For me personally, it felt uncomfortable at times at the beginning but now it only invokes a sense of freedom and peacefulness that is quite profound. I’ll leave you with my favorite quote from Seneca: “It is clear that no one can lead a happy life without the pursuit of wisdom. Yet this conviction needs to be strengthened and given deeper roots through daily reflection. You have to persevere until the will to good becomes a disposition to good.”

Eliminating news consumption: Last year one of my experiments was a deep digital cleanse. I deleted all social networks from my phone, turned off all (all!) notifications, and this year Katherine and I started a habit of never bringing phones in the bedroom. This has been amazing. But what I discovered was that eliminating those junk foods from my digital diet led me to binge on the digital crack cocaine of 2018: reading the news. I was probably checking the New York Times or Axios a half dozen times/day. 💉 So in 2018 I completely redesigned my news consumption.

  • What I tried: I eliminated all news consumption (New York Times, Wall Street Journal, Axios, etc) and replaced it with more substantive sources: I listened to podcasts, read way more books, and subscribed to a few industry newsletters (e.g. Stratechery).
  • What worked (or didn’t): Just attempting to not check the news on my phone didn’t work for me. My White House background + a certain US president made the digital crack too irresistible. What I had to do was literally update my browser settings on my phone to block all news sites. So if you send me a link to a NYT article on Whatsapp I would have to go to my computer to read it. 💉Extreme addiction requires extreme measures. 😂 But it worked! And what’s been most interesting is that I actually feel more informed about the world: I scan the headlines on Memeorandum a few times/week from my laptop and in just a few minutes get all the understanding I need of the drama in DC. And with all the time this frees up I’m getting way more substance from podcasts, books, and industry newsletters.
  • Recommendation: Checking the political gossip on CNN doesn’t make you a better citizen. Thomas Jefferson summarizes my view: “The man who reads nothing at all is better educated than the man who reads nothing but newspapers. I do not take a single newspaper, nor read one a month, and I feel myself infinitely the happier for it.”

I’d love to hear what experiments you tried (and loved) in 2018. Happy 2019!

High fives,

Jonathan

--

--

Jonathan Swanson

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