Category Archives: Personal

Life updates, reflections, and everything that doesn’t fit neatly into another category.

Sabbatical Wrap

Audrey, Automattic, Personal

Today is my first day post-sabbatical, getting back in the swing of things with Automattic. W.org, all the things. What a unique experience! I found the lead up to the sabbatical and planning process to be infinitely valuable, the sabbatical itself to be interesting experentially, and I’m curious to see what the post-sabbatical effects are. I have that nervous excitement like it’s the first day of school, which I haven’t felt in years. What should I wear? Who will sit with me at lunch?

I could now give a much better talk about the value of sabbaticals, having finally done one myself vs observing the hundreds that have taken place at Automattic. Like having a kid, it’s something you can understand intellectually but the direct experience is profound in ways that are hard to articulate.

There’s so much to catch up on and it’s kind of delightful to check in on progress of things after a few months rather than day-to-day like I normally do. If I had one bit of advice it would be to not get a big surgery (I had a sinus one) or plan for other major health things during a sabbatical, that should be on a different track if you can help it.

At the beginning I allowed myself two goals around sailing and chess. Sailing I decided to postpone to take advantage of a peak opportunity in July, but chess has been a fun incorporation into my daily habits and also incredibly humbling playing with folks who have been at it longer. The thing I didn’t plan for that became actually really important to me was getting back to the saxophone, not even trying to perform but the ritual and zen of long tones and practice is incredibly grounding in a way I didn’t know I was missing.

A few bullet point highlights:

  • Rowed to Alcatraz.
  • Got Covid the 4th time.
  • Went to Super Bowl.
  • Spent time at my alma mata University of Houston.
  • Toured the modern cathedrals of datacenters.
  • Did a ton of health scans, blood tests, doctor meetings.
  • Got my DEXA body fat down to 17.9%.
  • Skied Big Sky and Yellowstone Club.
  • Went to friend’s 40ths and 50ths.
  • Got a major sinus surgery.
  • Hosted an epic eclipse party from a plane with 100+ flash talks.
  • Studied Qigong and yoga.
  • Spent time in Houston, San Francisco, Big Sky, Austin, Orlando, Tokyo, Taipei, Amsterdam, Paris, and Mallorca.
  • Cleaned up a ton of personal projects.
  • Read a ton.
  • Swam in the ocean.
  • Played saxophone at 40k feet.
  • Equine therapy.
  • A lot of progress on renovation projects in Houston and San Francisco.
  • Hiked many places, walking in general more than normal.
  • Tweaked my back. :/
  • Couple of podcasts and interviews, a few meetings.
  • Binged Three Body Problem.
  • Did a lot of solo time and introspection.

Also, there was actually a lot of Automattic stuff happening most notably the acquisition of Beeper! I wasn’t able to unplug as much as I hoped, but I did definitely reverse my normal priorities. One thing I really missed was that I had very high hopes to see a lot of people, but a lot of stuff came up so outside of the events it was probably smaller social circle than I normally have.

It does make me think about apophatic theology or how Nassim Taleb talks about via negativa. Whatever you’ve been doing, it’s nice to try the opposite for a while, just to see what happens.

Mouth Biohacking

Personal

I’m not one to shy away from random things I find on the internet, so when I came across the Scott Alexander article on a discovery in the 80s about people who don’t get cavities, my first thought was “how far is Honduras from Houston?”

So on February 28th, my friend Rene and I became the 50th and 51st people to get our normal mouth bacteria scrubbed away and hopefully replaced by a genetically modified strain of Streptococcus mutans that doesn’t turn sugar into lactic acid. A nice sabbatical jaunt.

In the 9 weeks since, no teeth have fallen out, I haven’t gotten any cavities, really the only noticeable change is that I seem to have less bad morning breath, though I still wholeheartedly recommend SmartMouth mouthwash and travel packets.

The company is working on making it more widely available without travel to another country, and if that works it will be interesting to see how long this takes to spread. Will it be adopted quickly or be like the lemon juice cure for scurvy that took 42 years to become policy? In the meantime, the weather in Roatán is warm!

If you’d like to learn more Cremiux Recueil also has a pretty good deep-dive.

Beeper & Texts

Automattic, Marketing, Open Source, Personal

It’s such a delight when a plan comes together and unfolds, especially when it’s something you’ve been working on for many years. Today the announcement went out that we’re combining the best technology from Beeper and Texts to create a great private, secure, and open source messaging client for people to have control of their communications. We’re going to use the Beeper brand, because it’s fun. This is not unlike how browsers have evolved, where solid tech and encryption on top of an open ecosystem has created untold value for humanity. Eric Migicovsky has written well about the plan going forward.

A lot of people are asking about iMessage on Android… I have zero interest in fighting with Apple, I think instead it’s best to focus on messaging networks that want more engagement from power-user clients. This is an area I’m excited to work on when I return from my sabbatical next month.

On StellarWP Podcast

I’m still doing some podcasts as sabbatical-Matt, especially with the WordPress community which for me isn’t really work, it’s building relationships in our community of practice. If you know me, I can wax poetic about WordPress for hours! It’s what I do for fun. Here’s my first post-sabbatical interview with Michelle Frechette. Another unusual thing about this interview is I was quarantining with Covid!

It’s hard to pick a favorite tenor player, but the GOATs that come to mind are Dexter Gordon, Sonny Rollins, John Coltrane, Michael Brecker, and I’m missing people but if I had to pick someone to express the human condition and soul, it would be Joshua Redman. He has such incredible fluency with the horn you get an amazing emotional experience with his vibrations. He’s probably the greatest living tenor saxophonist. He just did a Tiny Desk concert, and the audio and visual capture was impeccable. I watched this full-screen on an Apple XDR and listened with Airpods Max—the chords they’re using, the subtlety of the interactions— the experience was exquisite. (Also peep HSPVA grad Paul Cornish!) I can’t embed because it’s not on Youtube yet.

What if this VR is training our brains to compute in a different way? How we perceive our thoughts to train the models. We are reconfiguring our model of reality to process things in a way we couldn’t before.

If I were President for a day, the first thing I would do is instruct our national security to patch and secure every American technology company, as they are our gems in the world. I would burn every zero-day I had on a US company and help them patch it. The rest of the world would know our immense defense budget was now being used to secure our companies as well, as China does. Apple, Meta, Google, Microsoft, Intel, Cisco, Arista, Unifi, Qualcomm… I’m probably missing a few, they should all have the shield of our national security defense. Right now each company has to create their own defenses, and they are getting eaten and pillaged by foreign companies with state backing.

Samattical

Automattic, Events, New York, Open Source, Personal, Travel, Video, WordPress.com

Today is the day! The first day of my sabbatical. What an experience it has been. On Thursday I delivered my very first Ignite talk on the subject! Here it is.

The Ignite format is a tricky one as a speaker! I will do better next time. My friend Connie has delivered seven Ignite talks now and I thought hers and Adam Savage’s were the highlights of the ones I saw. (I didn’t see everything because I was popping in and out.)

Preparing for this sabbatical has been the most fun I’ve had working at Automattic, ever. It brought so much clarity to things, we’ve been able to resolve in hours things that have lingered for months, including two acquisitions, several hires, big strategies, and more.

After this talk I caught a redeye to NYC to meet with the WordPress.com leadership team and hand off my leadership there to Daniel Bachhuber.

It is a beautiful symmetry that the first-ever sabbatical taken at Automattic was by its CEO at the time, Toni Schneider, which gave me the opportunity to step in and try on being a CEO, and it’s an incredible gift that Toni is returning to be CEO of Automattic while I’m out for the months of February, March, and April.

What am I going to do with all this free time? Blog a ton. So follow along if you want to see this journey. I’m going to try to open source all the things. 😇

Update: I ended up extending this to May 15 since it got a late start.

Proprietary software is like creating art which no-one can see. Open Source elevates software engineering to a collaborative art form. Code is poetry.

— Tom Willmot

Some choice words from Tom Willmot, who was watching Kirby Fergusen’s Everything is a Remix, which I’ll check out now.

Forty!

Birthday, Personal

Birthdays are so great because they’re about generosity.

The act of giving, helping, is so generative.

It’s what we can all do for ourselves and each other.

But accepting is really hard, too! Gosh! Let it in.

Sometimes we don’t let the gifts in.

Approaching forty has felt impossibly light and heavy at the same time for me.

It’s so cool to be typing this into something we made together. I want you to really think about that. Ponder the enormity of all that came before that allowed you to be here today, and I want you to get a little bit excited, in that sacred hidden part of your heart that yearns for more.

Let’s keep doing that. And let’s make it better and share it so everyone can enjoy it. We make the world.

I’ve been enjoying so much all the posts coming in for the birthday gift. I’m reading them as fast as I can.

Specifically, my failure mode is I share too much. I’m too generous. I like to err on the side of open. Here’s some amazing code I wrote that you have a legal license to use however you like. If you ask those closest to me how I mess up, it’s that I over-extend myself and try to do too much.

I’ve never shared this publicly, but when the Bay Lights wasn’t going to make it the first time, I mortgaged my apartment and used that money to get it over the line. My personal finances were messy for years after that. I think a lot about being impeccable with my word.

I want people to give the smallest $10 donation to the Bay Lights and encourage others to do the same so that we can all share in feeling that together, we can build things. And every time you see the light or bridge or think of San Francisco, you’ll think of that sacred hidden part of your heart that yearns for more, wants to leave everything better than you found it.

Add some light.

Let the gift in.

This is the part where the sounds come in and you hear it’s the remix.

I find myself returning, again and again, to the Automattic Creed, especially the first line:

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.

I’m having the most amazing day reading everything that people are sharing. I want to re-share the quote I shared on Tim’s podcast from Will Durant:

Health lies in action, and so it graces youth. To be busy is the secret of grace, and half the secret of content. Let us ask the gods not for possessions, but for things to do; happiness is in making things rather than in consuming them.

All birthday posts: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42.

Books 2020–2023

Books, Personal

I’m a few years behind in posting my book lists, and past few years a good amount of my book reading time shifted to other mediums. I have been rediscovering the joy of books so here’s what I read the past few years as a motivation to myself to pick it up more in 2024.

2020

  1. The Gift by Hafiz
  2. I hope this reaches her in time by r.h. Sin
  3. Essentialism: The Disciplined Pursuit of Less by Greg McKeown
  4. Exhalation by Ted Chiang
  5. Deceiving the Sky: Inside Communist China’s Drive for Global Supremacy
  6. Zero: The Biography of a Dangerous Idea by Charles Seife
  7. Caves of Steel by Isaac Asimov
  8. High Growth Handbook by Elad Gil
  9. The Naked Sun by Isaac Asimov
  10. What You Do Is Who You Are by Ben Horowitz
  11. Gideon Falls 1: The Black Barn by Jeff Lemire
  12. Gideon Falls 2: Original Sins by Jeff Lemire
  13. Gideon Falls 3: Stations of the Cross by Jeff Lemire
  14. What if I Say the Wrong Thing? 25 Habits for Culturally Effective People by Vernā Myers
  15. The Most Important Thing: Uncommon Sense for the Thoughtful Investor by Howard Marks
  16. Wool by Hugh Howey
  17. Trillion Dollar Coach by Eric Schmidt and Jonathan Rosenberg
  18. Powerful: Building a Culture of Freedom and Responsibility by Patty McCord
  19. Awareness: The Perils and Opportunities of Reality by Anthony de Mello
  20. How to Know Higher Worlds by Rudolf Steiner
  21. No Rules Rules by Reed Hastings and Erin Meyer

2021

  1. Broken Stars by Ken Liu
  2. The Body Keeps Score by Bessel van der Kolk
  3. Broadbandits by Om Malik
  4. How to be Antiracist by Ibram X Kendi
  5. The Reason I Jump by Naoki Higashida
  6. Billionaire Wilderness by Justin Farrell
  7. Antarctica: What Everyone Needs to Know by David Day
  8. San Fransicko by Michael Shellenberger
  9. Antarctica: An Intimate Portrait of a Mysterious Continent by Gabrielle Walker
  10. At the Mountains of Madness by H. P. Lovecraft
  11. Delirious New York by Rem Koolhaas
  12. This Is How You Lose the Time War by Amal El-Mohtar and Max Gladstone
  13. Fallen Leaves: Last Words on Life, Love, War, and God by Will Durant

2022

This year I ended up mostly reading AI and machine learning academic papers, attempting to “learn AI deeply” as I asked people at the State of the Word that year. Started a bunch of other books but these were the only two I finished.

  1. 4000 weeks by Oliver Burkeman
  2. A Wizard of Earthsea by Ursula K. Guin

2023

  1. Tomorrow and Tomorrow and Tomorrow by Gabrielle Zevin
  2. Belong by Radha Agrawal
  3. Excellent Advice for Living by Kevin Kelly
  4. On That Note by Michael Wolff
  5. Unreasonable Hospitality by Will Guidara
  6. Surely You’re Joking, Mr Feynman by Richard Feynman
  7. Permutation City by Greg Egan
  8. Seven Brief Lessons on Physics by Carlo Rovelli
  9. Damn Good Advice by George Lois

All book years: 2017, 2018, 2019, 2020–2023.

What’s in My Bag, 2023

In My Bag, Personal
  1. 16” M3 Max MacBook Pro, with all the memory and storage. I went from carrying two laptops earlier in the year, a 14” as well to just this. I like the Space Black color because it’s novel but might go back to silver next time. Brand new so just a few stickers so far!
  2. Black Magic Mouse, steady and useful when I’m doing lots of emails. Looking to replace this, as it uses Lightning. At home I’ve been using the Mojo Pro Performance Silent Gaming Mouse because it’s wired and quiet when you click, so something wireless and quiet could be nice for when on the go… I do like the gestures of the Magic Mouse though. I’ll be testing out some new mice over the holidays.
  3. Universal Airplane Phone Holder, also good along with #4 for mounting an iPhone for using the Continuity camera or selfies (after taking that he said “please don’t go to jail”). Also super cheap, <$20 for two.
  4. Capstone Continuity Camera mount for MacBook laptops, easy way to mount your iPhone to your laptop to use as a webcam. Looks amazing, but a bit of a pain, which is why I’m excited about #6.
  5. Anker 655 USB-C 8-in-1 Hub. I use this mostly for Ethernet, but since everything is USB-C now I can also use this with either phone or the iPad. I seem to have bad luck with USB hubs, I’m always burning through them, but this one has lasted a while. This thing is heavy! I could go smaller/lighter here.
  6. Opal Tadpole webcam, this is the Opal product everyone has been waiting for. Quality close to iPhone at a smaller size, plugs in via USB-C so you don’t have to worry about connectivity or charging, doesn’t need any special software, looks amazing. Only fits a laptop though, not a bigger monitor. The way the cable works is really clever, great design.
  7. This is one of my most delightful new additions, a Pixel G1s RGB Video Light, it can cast warm light for a Zoom call or you can send it to a specific color to enhance the ambience of room for a party. It can rotate through a rainbow of colors. I ended up giving this to all my friends, and now when we’re in the same place we can instantly vibe out a room with two or three of these devices, and turn off any unpleasant default lighting a space may have. It charges via USB-C, natch. Hat tip: Robb Walters.
  8. UE Premier custom headphones. The best aural experience you can have. Invest the time in visiting an audiologist to get earphones and earplugs customized for your ears.
  9. Belkin Rockstar headphone splitter, great for sharing audio with others, especially if they have #8.
  10. Small USB-C to 1/8th inch converter, to be extra though upgrade to this one from Belkin with power.
  11. Rolling Square inCharge XL 6-in-1 Multi Charging Cable, nice compact all-in-one I’ve been playing with. They make some other interesting accessories. A 100w Swiss army knife of cables, and the thing they do combining Lightning and Micro-USB is so cool.
  12. Baseus has made a retractable 100w/5a USB-C beautiful cord. This is probably the one you’ll want to carry around. Someday it will replace all other cables when we achieve USB-C nirvana.
  13. Chafon USB-C multi-cable is my ultimate workhorse, what I use the most. It’s available at different lengths. I like the way the attachments can be moved around, but there is some fragility being entered at every connection so I like to travel with these not linked so they don’t bend or break.
  14. Tiny Miisso 6000mah battery pack with cables built in.
  15. Pixel Fold. I always try to have an Android device for testing and the pixel fold has been a interesting one, because I found myself using it in ways that feel like sci-fi. Reading a book on the Kindle where you can turn the pages it’s really nice. It’s just a fun tool.
  16. Pixel Buds Pro, they sound remarkably good. Airpods for Android.
  17. Airpods Pro, now with USB-C as God intended. I have a little robot on mine. Just amazing, and how great that you can buy them anywhere in the world. This is the first thing I’d replace if I lost it.
  18. iPhone 15 Pro, now that it has USB-C, my favorite iPhone ever. No notes.
  19. Maruman N196A Nemosine Notebook, great paper. I have a small Pilot Couleur pen tucked into the spiral binding. Both brands are Japanese and I think I picked them up on a trip there, probably at the amazing Daikanyama T-Site.
  20. OHTO Needle Point Knock 0.7mm pen, a nice daily driver. I was carrying around a Montblanc Heritage Egyptomania Doué ballpoint pen but I lost it somewhere.
  21. Notecards from Ugmonk Analog. I really enjoy everything they make, great company, I keep these on every desk as well. These cards are often what drives my day.
  22. Kindle Paperwhite Signature Edition, finally with USB-C! I prefer the Oasis, but they inexplicably haven’t updated it to be USB-C, so I carry the Paperwhite instead.
  23. 11-inch iPad Pro, always great in a pinch. I have the pen in case I magically develop an ability to draw and the keyboard and alway-connected 5G makes this great for hopping on Slack or Texts.
  24. 35w dual USB-C charger, from Insignia I probably picked up at Best Buy. Here is a 40w Amazon alternative I recommend and usually carry. This is one of the items I give away the most, so I must have given away my Highsay version.
  25. Ugreen 100w 4-port compact charger, this is what I break out when I want to charge my laptop quickly.
  26. Belkin 37-Watt Dual USB Car Charger, I use this very rarely now but it’s great in a pinch, especially on older cars that have very weak USB ports.
  27. Epicka travel adapter. Nice that it has some built-in ports, but I rarely use them. I probably should switch back to the smaller and lighter Muji adapter.
  28. Still my favorite power cable: Baseus 60w. I tried the higher watt models, they didn’t always work on planes. This is a 6-foot extension cord and can charge a laptop directly. Really a joy. When they do an all-USB-C version I’ll probably upgrade..
  29. Apple Watch Magnetic Fast Charger, of course with USB-C
  30. This year, I’ve been focused more on my overall health. As I’m getting into the habit of moving my body everyday, the Apple Watch Ultra 2 has been motivating because it’s great at letting me know how much I don’t run. Jokes aside, I’m a data person so seeing the numbers of my habits have helped me optimize my goals. 
  31. A candle can make a space feel cozy. Though I don’t travel with my own candle, I like to have my trusted Rechargeable Candle Lighter. Light fire with USB! 
  32. Swiss Army Card, let’s talk about cool gadgets. I use every feature of this card on a regular basis during my travels. It’s incredibly compact and slim. I’ve had to reorder this card a couple of times because they will confiscate the tiny knife. 
  33. Petzl e+LITE Headlamp, as a former boy scout, I’m always prepared for anything including a potential blackout.  
  34. Lockpick set.
  35. Carabiner is always good to have on hand.
  36. You know, a Disposable mask is just good practice. This mask shape is my favorite and very comfortable. 
  37. Immunity Throat Spray was recommended to me by Paul Stamets. I’m not sure if it’s a placebo, but I haven’t gotten sick. Thus, 3 sprays twice a day will keep the doctor away… for me at least. 
  38. Lately, I’ve been curious about the quality of air. I carry the Aranet4 CO2 monitor to gain insight about different spaces. Higher CO2 literally makes your brain slower!
  39. Winter is coming… BioDerma Chapstick is my go-to for dry lips. 
  40. I must admit I don’t really eat the mints from this Marunao Mint Case. However, I have a high admiration for this elegantly crafted case. It has a soft finish feel and a satisfying magnetic closure.
  41. Kikkerland Red Plaid Earphone Case is where I store my custom molded ear plugs. 
  42. SmartMouth travel packets was the best recommendation I received in 2019. It really tackles mouth hygiene well for all day freshness. 
  43. Cloth card holder / wallet, simple minimalist way to carry some extra cards and a few bills. I believe Tim uses one of these as well.
  44. WordPress ring.
  45. Sea2See Sunglasses. Sunglasses made from recycled plastic collected from the ocean. I discovered this from a goodie bag at the Brilliant Minds conference and have since purchased more to have it everywhere I go.
  46. Small plastic holder I got from my sister that helps me carry around stickers without them getting crinkled.
  47. Hermes business card holder. There are some occasions where exchanging business cards is a ritual. Also great to wedge it in a door jamb to keep it from autolocking. 
  48. Passport, never leave home without it. Always be ready for adventure! My passport photo is actually AI-generated, because, why not? We live in the metaverse.
  49. Eye Mask. I like these because the material feels nice on the skin and the wraparound is excellent for blocking out the light and some sound since it covers your ears. Great for sleeping or just needing a moment away from overstimulating environments. Similar one here (the version I have doesn’t appear readily available outside of Europe). 
  50. REI Goretex mittens. They’re shell liners, lightweight and water resistant. The ones I have are an older version and no longer in stock. Version 2.0 available. There’s no bad weather, only bad clothing.
  51. Gloves, nice in the winter but I carry them year round in case I need to carry wood or something. Also the fingertips have the conductive material that makes it touchscreen compatible for devices.
  52. This is a grey wool buff, which works as a scarf, a hat, or an eye cover if I’m trying to sleep. I tried this out because of one of Tynan’s also-great gear posts.
  53. Gore Thermo Beanie, my favorite feature are the slits by the ears for sunglasses. Kept my eyes and ears protected while in Antarctica with Tim. He and I recorded a podcast episode in our tent talking about our personal fears, bucket lists, and more. Have a listen!
  54. Aer Fit Pack 3 backpack, embroidered black-on-black with Automattic and WordPress logos. I upgraded this year from version 2 to 3, which changed some of the interior pockets a bit, and most notably added outside side pockets, which I have found super useful. This is the bag that makes it all work.

Not pictured: Flipper Zero, which was actually in my pocket and I forgot to put it in the photo. I have found this device really handy and fun to play with, just a delightful piece of technology.

Here’s what I was rocking earlier in the year:

I’m not going to label it all, just posting for posterity. It’s mostly the same except I gave up on carrying around the Airpods Max, the grippy tripod, and haven’t found a great disco phone light yet.

Wowza!

Personal

Okay, I’ve seen a lot of things in my life, but this has me fairly floored. I was at an EcoAmerica board meeting dinner and afterward instead of calling an Uber like I usually would, I tried a self-driving car, a Waymo. (The name inspired by my friend, Jaime Waydo.) As I got home I was so excited to tell my Mom what just happened.

I feel like every cell in my body is charged, it’s like the first time I got a script to run, or committed code into b2/cafelog, this is definitely a before and after moment. Here’s a video as the car arrived and I got out. I’m really at a loss for words. The “wow” you hear me say in one of my most genuine in my life. The thing is I know these self-driving cars exist, I’ve seen them around San Francisco forever, but the experience of being picked up and dropped off by a robot navigating the tricky SF hills and streets just hits different.

“The future is already here – it’s just not evenly distributed.”

William Gibson

One thing that always brings me back to San Francisco is you feel like you’re living in the future. Tonight was no exception.