Memoir
One entry per year, newest first, back to 2001. The photographs are mine. The italic lines come from journals and notebooks I kept at the time, not written afterwards.
2026
Pictured Rocks, Michigan
Back in Seattle, building for myself.
- Growing World Tree into a small studio, an AI travel guide with local voices and cultural depth.
- Traveled to India, Thailand, and Sri Lanka.
- Summer on Lake Superior at the Pictured Rocks cliffs.
From my notes that yearWhen stuck, go back and assess why. Do you have the prerequisites? If not, go back and acquire them.
2025
Isle of Skye, Scotland
A turning point. The year I learned to work on my own terms.
- Lived in Sweden through the first half of the year, then left Supernormal.
- Drafted a book of essays, and did research at KTH on music-generation models in Bob Sturm's lab.
- Started World Tree.
- A van trip around the Alps, and the Roadjunky Festival of Creativity in the Czech Republic.
- Ran the Stockholm Marathon, my sixth and probably my last.
- New countries: Malta, Poland, Scotland, Ireland, Slovenia. Turned 49.
From my notes that yearTo solve the mystery of status while unemployed, simply work. Make your own work and pour everything you have into it. You will then transcend.
11 goals for 2025 Isle of Skye Granada & Valencia What I Learned Working at an AI Startup How We Moved to Sweden for a Year Six Years of Daily Habits
2024
Dubrovnik, Croatia
Moved the family abroad again, this time to Stockholm.
- Still Head of AI at Supernormal.
- In July we picked up the thread of the 2019 sabbatical and moved to Stockholm, to be close to the leadership team.
- Ran the Lidingöloppet.
- New countries: Sweden and Croatia.
From my notes that yearMoving somewhere new for a fresh start is a chance to reinvent yourself.
9 goals for 2024 Dubrovnik Kauai Costa Rica 2,000 Days Without Alcohol On Mountaineering You Must Change Your Life
2023
Vanua Levu, Fiji
Deep in the work at Supernormal.
- Head of AI at Supernormal.
- Fiji and Australia with the family, plus Spain, Portugal, and the Big Island.
- A brothers' trip to the Dolomites.
From my notes that yearIt ends. Remember that it ends. Don't waste your time, don't just try and get by. Have gratitude for each blessed moment. Beauty is everywhere, allow yourself to see it.
10 goals for 2023 Fiji & Australia Spain & Portugal Big Island Why Building On LLMs is a Gold Rush Reading 12 Books at Once Learning Something Every Day
2022
Arches, Utah
Left Stripe and started building my own thing.
- Left Stripe in February, after eighteen months on Radar.
- Launched Infeather as an AI-powered reader, starting in newsletter form.
- Rejoined the workforce in September as Head of AI at Supernormal.
- Ran the Seattle Marathon, my fifth.
- Brothers' trip through Utah; too many dudes in Tofino.
- Brought home a havanese puppy named Lola.
From my notes that yearMy greatest achievement is the work I have done on myself, and who I have become, compared to the immature and shy and dark person I was.
9 goals for 2022 Utah Tofino A Vision for Feather Software Infeather
2021
Iceland
Locked down, and making things.
- Work from home at Stripe; the office reopened in September.
- Traveled to Iceland.
- Kept up the synthy songwriting, and a coding side project that learns which links are worth sharing.
- Ran the Seattle Marathon, my fourth, in 3 hours 57 minutes.
- The most prolific essay year, four of them published in September alone.
From my notes that yearWhen I write all of this out it feels very real and alive, all of life happening around me, both the good and the bad.
10 goals for 2021 How they turned out Iceland Strategies for Generating Ideas Marcus Aurelius and Meditations Divergent Associations Restore, Don't Shame The Lamb Lied Down On Midi
2020
The Pinnacles, Western Australia
Stranded on the far side of the world when the borders closed.
- COVID hit while we were finishing the sabbatical in Bali. We made it into Australia days before the borders shut.
- Four months at Byron Bay, then Western Australia, and eventually home to Seattle.
- Started at Stripe.
- Started composing electronic music in GarageBand.
From my notes that yearWe were truly happy. The risk is that in Seattle we get overly preoccupied with our work.
10 goals for 2020 How they turned out Western Australia Byron Bay The first songs
2019
Ubud, Bali
After five years at Facebook, took a one-year sabbatical and moved the family to a rice field.
- Eight months in Ubud, Bali, and Southeast Asia around it: Vietnam, Singapore, and the long way around.
- Turned down a very good offer mid-trip in order to actually take the year.
- Tahiti, and a first pass through Australia.
From my notes that yearWhat will come? Will I lose my employability if I wait too long before getting a new job? Will I find a job I like in Europe? … Will we stay in Bali until April?
10 goals for 2019 A Season in Bali Wanderings in SE Asia A Week in Viet Nam Tahiti Australia Singapore
The year my father died.
- Started work on the misinformation team at Facebook.
- Shortly after the mid-term elections, my father passed away of cancer.
Turned 40.
- Moved to the Search team at Facebook.
- An epic hiking trip in the Hornstrandir nature reserve, Iceland.
2015
Chloe, Jasmine, and everything we took
Jasmine was born, and we took her around the world at three months old.
- Three months of leave: Iceland, London, Crete, Sicily, the Canary Islands, and Japan, written up at The Traveling Klebans.
- Climbed Mt. Rainier.
- Recorded some sounds.
2015 goals The Traveling Klebans Keeping It Together on the Road
Left Microsoft for Facebook in January.
- Joined as a technical program manager in Seattle, working on ads.
- Went to the Sahara for a yoga retreat Tommy was running in Morocco. Ten years earlier he had told me where to find a hut in India; this time he sent directions to a desert.
Chloe was born.
- Sang Blackbird to her through Elizabeth's belly.
- Took her around the national parks at three months old: Yellowstone, the Grand Tetons.
- Program manager at Microsoft, working on Bing search.
Finished the doctorate, and lost a friend.
- Finished my Ph.D. in electrical and computer engineering at UC Santa Barbara. I had gone for one year, to make myself employable again. I stayed five, because search and retrieval turned out to be magic.
- Co-organized the Road Junky travel film festival in Berlin, the end of the site Tommy and I had run for six years.
- My friend Charlie died while I was there.
- Joined Microsoft as a program manager and moved to Seattle.
- An amazing thru-hike in the Sierra Nevadas, with Dmitry and Katya.
Elizabeth and I married in Santorini in July.
- Honeymoon through the Greek islands, Turkey, and Hungary.
- Married a second time in Santa Barbara, for everyone who could not get to Greece.
Got engaged in Alaska.
- Travelled in Taryn and Todd's truck, got lost in the forest, and fished from a canoe.
Spent the autumn doing research at Microsoft Research Asia in Beijing.
- Started an Olympics lodging site on the side, finding apartments for people coming to the Games the following summer.
Breckenridge, then Japan, then Santa Barbara.
- Six months in Breckenridge, Colorado, working in a restaurant and learning to snowboard.
- In May, went to Japan to see Elizabeth, who was living there. We hitchhiked from Kyoto to Tokyo.
- Asked her to come to Santa Barbara.
- Moved there in July, destroying my brother's car on the drive out from Colorado.
Manly Beach, then Asia, then home.
- Lived at Manly Beach in Sydney for a couple of months.
- A surfing accident, then a Krishnamurti book, then a week that rearranged how I saw things.
- Solo through Southeast Asia.
- Three months in Himachal Pradesh, in a mud hut above Vashisht that Tommy had told me about. When I found the hut there was an eighty-year-old man with a flowing beard meditating inside it. He made me tea and offered to teach me yoga. I climbed the mountain to him every day that monsoon season, and wrote a book about the trip in journal form.
- Home in July with a sitar, by way of New York.
- Took the GRE and was accepted at UC Santa Barbara with a fellowship.
- Started Roadjunky late in the year with my friend Tommy.
Roadjunky The festival it became Keeping It Together on the Road
Left with a backpack and kept going.
- Was accepted to a Ph.D. at UT Austin and given a year's leave from Intel. Sold everything I owned, bought a one-way ticket to Mexico with no plan and no prospects, and took the road instead.
- Left Phoenix in May 2002.
- Taught English in Guadalajara for 35 pesos an hour, and learned Spanish doing it.
- Fourteen months overland through Mexico, Central America and South America, all the way to the tip of Argentina. Failed on Cotopaxi. Hitchhiked across Chile with a man I met on the side of the highway.
- Met Tommy in Panama City, through my friend Joe. We bonded over Tom Waits. Two years later he emailed about starting a website.
- Learned to play guitar. Learned to surf.
- Lived in Buenos Aires for a few months in 2003.
- In October, flew to New Zealand with my friend Joe Brana, bought a van, and toured both islands. Australia by December.
Working at Intel in Phoenix. Then Peru.
- Flew to Peru alone right after 9/11 and hiked the Inca Trail to Machu Picchu.
- Met Elizabeth.
Things you can try
- World Tree, an AI travel guide with local voices and cultural depth. The 2002 trip, two decades later.
- Infeather, an AI reader that finds the best writing on the web each day.
- Quizzal, a spaced-repetition Chrome extension. Retain what you read; earn your feed-scrolling time.
- The albums: every trip above, photographed.
- The music: what came out of the lockdown years.
- What I'm reading, and everything I've written.