My 2021 Life Experiments

Jonathan Swanson
8 min readDec 20, 2021

I’ve been running life experiments for a number of years now — but this year has many of my favorite experiments ever.

In 2021 I experimented with:

  • Creating a personal CRM to get 10x more leverage from my network
  • Setting up a Freedom Phone so I’m less distracted by my phone
  • Kindle-izing all my reading so I have zero distractions on my computer
  • Digitizing our nanny so we sleep more (black diamond delegating 😅)
  • Scheduling all my meetings on Tuesdays so the rest of my week is flexible
  • Delegating by voice only (no email) to increase efficiency
  • Moving 95% of my messaging from phone to the Texts desktop app
Ulysses was the original masochistic, self-experimenter (Ulysses and the Sirens)

For each experiment, I’ve laid out what I tried and what worked (and didn’t). Check out whichever ones interest you, and let me know what experiments you recommend I try in 2022! 😎

Creating a personal CRM: It’s a running joke in venture that someone needs to start a personal CRM startup. But it’s a joke for a reason: I’ve tried a half dozen now and they are all terrible. So I finally decided to just build a personal CRM for myself.

What I tried: We took my ~20k contacts and moved them into Airtable. Then we enriched the contacts with ~100 data fields from public/private sources. We added data like: how much venture capital has this entrepreneur raised, how many times have I emailed with the person, how many employees does the company have, how many twitter followers, what companies has the person invested in. Lots of the data could be pulled from LinkedIn and Crunchbase APIs, and some data required more manual data work (e.g. when was my last contact with someone).

What worked (or didn’t): I finally have the personal CRM I’ve been dreaming about. This new setup allows me to execute queries like this:

  • What CEOs am I connected with near London who have raised >$50M
  • Show me investors I know who invested in Notion, stack ranked by how many times I’ve emailed with them
  • Find me CMOs of enterprise startups with >250 employees stack ranked by Twitter followers

I finally have a CRM that allows me to search in the way I’ve always wanted. I’m using my new CRM all the time now. The biggest weakness we’re still looking to solve is Airbtable’s search is exact match only. So right now I have to search things like [title=CMO or Chief Marketing Officer or VP Marketing]. If anyone knows a tool that can make Airtable’s search more flexible, please let me know.

Recommendation: This was my 2nd attempt to build my own CRM. The first attempt got mired in over-complexity. So if you do attempt this yourself I highly recommend you start very simple and add complexity as you go.

It turns out you email your co-founders a lot. Between Sander + Marco they have emailed me directly ~50,000 times. That is 14 emails per day every day for the last decade+ 😅

Freedom Phone: I tried a phone sabbatical this year — 1 week w/o ever using my phone — and I loved it so much that I decided I wanted to do it more often. But the challenge with a pure phone sabbatical is it is only practical every so often. So to solve this I repurposed an old iPhone into what we now call the Freedom Phone.

What I tried: Factory reset an old phone and then only installed essential apps: Google Maps, Uber, and the Athena delegation app (no sabbaticals from delegating 😉). There’s no email, no messaging apps, nothing that could possibly distract or tempt you. And then the only contact I installed in the phone was Katherine’s phone so that if I need to call her I can and if she needs to find me she can.

What worked (or didn’t): Now when we go on dates we bring the freedom phone instead of our real phones. Or if we go for a hike on a Sunday afternoon we bring the freedom phone. I ended up also installing Google Photos so photos sync with my main phone.

Recommendation: Yes! If you want to be distracted less by email/messages while you’re with your friends this is really effective and yet still practical. I use mine multiple times every week now.

If you want to win the “what’s on your homescreen” game show them your Freedom Phone. Nothing!

Kindle-izing all reading: Every day I get emailed or messaged a dozen+ substacks or blog posts I want to read. But when I’m working at my computer I want to be in the zone and not be distracted by this endless rabbit hole. So I tried an experiment of not reading anything non-work-related on my computer and instead sending reading to my Kindle.

What I tried: Whenever I receive a Substack or blog post I’m excited to read, instead of interrupting my work I just forward it to my EA. She converts the content into a PDF and then sends it to my Kindle. (Every Kindle has a dedicated email address you can send PDFs to.) At night in bed I turn on my Kindle and a half dozen articles load up.

What worked (or didn’t): This has been awesome. I used to feel torn when I’d receive interesting stuff to read. Should I be productive on work or spend the next 18 hours reading Dan Romero’s crypto reading he just sent me? 😅

Recommendation: Yes. I’m way more productive on my computer, and every night my kindle is full of amazing stuff to read in bed.

Digital Night Nanny: When people have kids they have to make a hard choice: Do I have my sleep destroyed by the new babe or do I pay $$$ for a night nanny so we can sleep? People with means will often get a night nanny but only for the first couple months. After that most parents will handle solo — and typically have their sleep interrupted a couple times/week. But Katherine had a genius idea: what if we could delegate this?

What I tried: We nominated one of our most trusted EAs in the Philippines to be our digital night nanny. She was given access to a Wyze camera in the babe’s room. From the app, the EA could see/hear the babe throughout the night. We then put the Freedom Phone (see above) next to our bed at night, and gave the EA this instruction: If the babe wakes up, cries for a couple minutes, and goes back to sleep: don’t call us. If the babe wakes up, and stands up or won’t stop crying: call us.

What worked (or didn’t): Katherine and I went from averaging ~5–7 hours/night of sleep to ~8–9 hours/night of sleep. Game changing! Our babe wakes up a couple times most nights and cries for a few minutes each time. This used to destroy our sleep. Now we only wake up when we’re actually needed which is very rare. When we first ran this experiment we just used our regular phones — but that means if you get a random spam call in the middle of the night you’re waking up. So we now use the dedicated Freedom Phone which no one has the number to except our EA.

Recommendation: A night nurse costs $200–300/night in most places in the US. That’s crazy expensive. But because our EAs are working in the Philippines they are already awake during our sleeping hours. And because they can do their regular work — with the babe monitor on in the background — we’re now getting 365 day/year night nanny coverage for no additional cost. This has been one of the greatest delegation experiments of our life. All credit to Katherine, and our amazing EAs in the Philippines. 🙏

Tuesday Meeting Day: In a previous experiment, I was successful at moving 95% of my scheduled meetings to asynchronous conversations (e.g. more voice notes on whatsapp). But meetings are still necessary for a few things. So to build on this experiment, this year I tried only scheduling meetings on Tuesdays. The rest of the week is for focus, deep work.

What I tried: Tuesday is my meeting day. No meetings on any other day.

What worked (or didn’t): I love having multiple days a week where I can focus on deep work without any interruptions from meetings. The trade-off is my Tuesdays are sometimes very long (e.g. 10 hours of back-to-back meetings) but for me it’s worth it because I am multiple times more productive when I have long stretches for deep work.

Recommendation: This isn’t for everyone — if you’re hyper scaling a startup as CEO you’ll probably need more meetings than me — but I’m personally way happier and more productive this way.

My schedule last week. Tuesdays are a little intense 😅 but the rest of the week is beautiful.

Voice only delegation: Delegating to your EA by voice is at least 3x faster (vs email or text). It also allows you to delegate while you are on a walk, at the gym, or jumping in an Uber.

What I tried: For three days I only delegated by voice. No typing email responses (voice delegated instead), no drafting docs (voice), no ordering things online (voice). The goal was to touch my keyboard as little as possible. To do this I used the Athena delegation app. After dictating a delegation, the app sends it to my EA, including an audio transcription, and adds a new task in our Asana project board. For delegating from my computer, I used Loom to make videos.

What worked (or didn’t): Delegating by voice is a muscle you have to develop, and the more you practice the better you get. Like going to the gym, the first few sessions are the hardest and it doesn’t feel natural…but with practice it starts to feel so good. Delegating only by voice really pushed my comfort level — I’ve gotten good at voice delegating email drafts, projects to research, and even outlines for documents I want to write. The level I haven’t unlocked yet — but I have a friend who has — is doing polished, essay writing by voice. This friend has written an entire book by voice. I have another friend who hasn’t written an email for years. #Goals

Recommendation: All of the top 1% delegators I know delegate a significant amount by voice. If takes practice but it’s worth the investment. I now measure my # of voice delegations every week and have competitions with friends to see who can push the limits the most.

Athena is building an app that is designed for voice delegation. Full version will launch early next year.

Superhuman for messaging. I’ve been wanting a Superhuman-like interface on top of all my messaging apps for years, and I’ve finally found it: Texts. This is — by far — my favorite new productivity app. I’ve moved 95%+ of my messaging off my phone because Texts is so much more powerful. Every morning for me now starts with Superhuman for email + Texts for messaging. The product is still v1 — it’s still a little buggy — but it’s increased my productivity dramatically and I’m addicted to it.

That wraps my 2021 life experiments. 😎

If you have suggestions for experiments I should try next year — especially radical delegation ones — please share.

Happy holidays everyone!



Jonathan Swanson

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