Happy 20 years to Automattic! To celebrate, here are 20 reasons why I love working here:
Mission.
People. I love the people I work with everyday. The design team is especially awesome 🙂
Work. The work itself is challenging, impactful, and fun.
Life. This job allows me to live a wonderful life and I don’t take that for granted, even after nearly 12 years here.
Future. I’m excited about what is ahead and the positive effects we can continue to have on the internet and people’s livlihood.
Improvement. Automattic values continuous improvement and learning from successes and failures. This is also how I live my life.
Autonomy. I have the autonomy to work how, where, and when it best suits me in order to be most effective.
Output. Although we’re a much larger company now, we still are very much execution-focused. We value impact, not hours logged, meetings attended, or other performative metrics.
Design. Beautiful and thoughtful design is valued and prioritized across everything we build.
Growth. I’ve grown personally and professionally here in ways I never expected.
Mentorship. Amazing opportunities to both learn from others and help guide newer team members.
Freedom. The freedom to experiment, take risks, and pursue ideas that matter.
Flexibility. Work-life balance isn’t just a buzzword here—it’s actually practiced.
Travel. Meetups and conferences that bring our distributed team together in amazing places.
Perspective. World wide diversity of colleagues brings incredible insights and viewpoints.
Change. The company evolves and adapts, keeping things fresh and exciting.
Impact. Our work affects millions of people and websites across the globe.
WordPress. Being part of something that powers over 40% of the web is pretty amazing.
Open Source. Contributing to and believing in the power of open source software.
Intentionality. Every decision feels thoughtful and prioritizes the right thing over the thing right now.
Matt. I’ve only worked at founder-led companies and Matt’s vision continues to inspire me. I hope to work here for decades to come.
I’ve seen close to 300 movies last year, much of those on Blue Rays and DVDs. We are lucky to have one of the last remaining video rental stores relatively nearby our house in Seattle. We rent a few movies a week and there’s one that has stuck with me that I’d like to talk about for a few minutes.
Its called Perfect Days. Its very much a vibes movie and I’ll leave out any major plot points so I’m not spoiling anything.
It follows a man in the daily routine of his life. You see him wake up, get ready, and head to work.
Its about the small moments in life. The wind in your face as you ride your bike. Sharing a ride and a view with a loved one.
Noticing beauty above you. Taking photos with a camera.
Finding music. Listening to tapes. Connecting with people through a love of a song.
Discovering and reading books.
Its a beautiful movie about the small things in life. Routines. About finding meaning, enjoyment, and peace through the everyday. Its about the complexities and beauty of human relationships and finding your way.
Its had a profound effect on me. I had already been simplifying my life, slowing down, remembering to look up, and reducing screens in favor of physical objects.
Thanks for listening. Let me know if/when you’ve watched it, would love to chat more about it.
There’s a quote I often refer to when talking to new designers or anyone who makes things. That beginning phase, that sometimes last much longer than you think, when you know what you’re creating doesn’t match your taste.
Nobody tells this to people who are beginners, and I really wish somebody had told this to me.
All of us who do creative work, we get into it because we have good taste. But it’s like there is this gap. For the first couple years that you’re making stuff, what you’re making isn’t so good. It’s not that great. It’s trying to be good, it has ambition to be good, but it’s not that good.
But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell that what you’re making is kind of a disappointment to you. A lot of people never get past that phase. They quit.
Everybody I know who does interesting, creative work they went through years where they had really good taste and they could tell that what they were making wasn’t as good as they wanted it to be. They knew it fell short. Everybody goes through that.
And if you are just starting out or if you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you’re going to finish one story. It is only by going through a volume of work that you’re going to catch up and close that gap. And the work you’re making will be as good as your ambitions.
I took longer to figure out how to do this than anyone I’ve ever met. It takes awhile. It’s gonna take you a while. It’s normal to take a while. You just have to fight your way through that.
One of the first things Claude asks you to do is to upload a writing sample so it can determine your writing style. I was skeptical but uploaded a recent blog post. It categorized my style as Design Philosopher.
Woah. Have to admit I was a bit flattered. The summary was pretty cool too:
Explore design concepts through contemplative, analytical, and deeply insightful reflection.
I do carefully consider each piece of writing, no matter if its a text message or an essay. I really want my voice to come through. I also think all the AI chatbots output horrible writing, so I’m intrigued by what I can do with these styles that are trained on my writing. I uploaded a bunch of blog posts and will be testing each to see how much time I can save on the initial drafts.
Small moments of wins, positive feedback, and delight add up. Time To First Win should be a metric for everything we build.
I love the work of Charles and Ray Eames. I recently re-watched The Architect & The Painter and paused it to jot some notes on their design process:
The Eames design process, is a process of learning by doing. When designing something, it is often this connection that provides the key to the solution.
“Never delegate understanding.”
This is the hallmark of Eames design, their secret ingredient. “First you have an idea, then you discard the idea, then you have 50 other ideas and you discard them, and then you do several models, and they don’t work, and you throw them out. And the secret is work and work and work and work and work.”
‘Never delegating understanding’ is such a great principle. Both when leading others and when designing. I often need to delegate or assign work to others. Whenever I’ve also delegated understanding— of the problem, the greater context, status of the work, or the final product shipped— usually something goes off track. When I am doing the work myself, my best work happens when I fully understanding the problem, the greater context, and the best outcome by working through as many ideas as possible.
I am lucky enough to work at Automattic where I get three months off every five years. I wanted to take some time to recap as it was one of the best times of my life.
I went into it with some ideas, goals, and plans: I would go on One Big Trip each month (that included A Tough but Exciting Goal/Challenge) and spend the rest of the time at home, enjoying where I live, taking daily photos with my new camera, spending quality time with B, and making the most of each day. Some highlights, with links if you’d like to see pictures/read more:
Brought my camera around with me pretty much everywhere and took photos each day.
Took my 12 year old nephew to Whistler, where we spent 4 days at the bike park. My grandparents took each of us on a trip with them and I want to do the same with my sister’s kids. One at time. (There are six!)
Biked a bunch, including a Century for the first time. (100 miles in one ride)
Walked much more than usual. I walk a fair bit usually thanks to Jojo, but I was walking upwards of 11 miles a day in the first few weeks. Wandering, taking photos, reading at coffee shops.
Made some updates to this site and blogged a bunch. I missed it and its good to be back.
Enjoyed everyday life. Not that I don’t usually, but every single day felt special.
Biked 600 miles across the state of Washington. This was a massive trip and one of the harder, more awesome things I’ve done in life. It took 10 days and I got to experience and appreciate more the state I now call home.
Watched a lot of movies. Too many to name, but we rented DVDs each week at a local video rental store. Fell in love with Ozu. And physical media in general.
Journaled most days.
Read Three Body Problem, Good Material, All Fours, M Train, Stoner, Demon Copperhead. Demon was favorite new book; M Train is one I’ve re-read several times.
Ate well. Memorable meals in Mexico at Enrique Olvera’s restaurant and here in Seattle at Paju and Taneda.
Lots of quality time with B, connecting, focusing on us, improving our relationship. More time in general to prioritize and spend time with the people in my life.
Got Covid the last ~week of sabbatical and spent it pretty sick. A bit of a bummer to end things but such is life. Its still lingering and has made the return to week feel a bit extra challenging.
The time felt long in the best way. I remember the half way point and thinking, ‘Wow! this has been so long and I still have just as much to go!’ I loved how much I was able to do in a day. I’m trying not to lose that feeling as I get back to work. Wish me luck.
Lael Wilcox is 13 days into her bike ride around the world. She records a super short podcast each night with notes from that day’s ride. She’s long been my favorite bike pro to follow. I hope to catch her in a few months when she rides through here on her way back to Chicago.
Rode across the state with my good friend and bikepacking partner Matt. Touching the ocean in La Push to the Idaho border east of Spokane. Stuck primarily to off roads and did a combination of XWA Grand Depart, XWA Lite, and some of our own planned and adhoc routes. It was all inspired by this article on bikepacking.com and wanting to do more gravel/dirt/off-road bikepacking. I wanted to do it as self sufficient as possible, meaning taking advantage of public transportation to get to the start and then back home. It was an incredible experience. One where I pushed myself in big ways and have a newfound appreciation for the state I live in.
I took my camera with me to document the journey, wrote short journal entries each day, and recorded the ride on Strava for the stats. Check them all out below.
Day Zero
A long travel day. Biked down to get the ferry to Bainbridge Island. Then two very long bus rides to get to _almost_ the starting point. Stayed at a hotel in Forks. One more bus tomorrow and we start our trek across the state!
Woke up early in Forks to take a 25 minute bus to La Push from the hotel. We rode out to the beach, touched the ocean, took some pictures and started on our way! We stopped back in Forks to grab food and headed out of town for our first massive off-road climb to get over the pass. We saw a large heard of elk, rode on some really fun single track, experienced the Olympic Discovery Trail, and found a spot to camp right on Lake Crescent. What an awesome day and start to the trek.
Waking up right on a lake was awesome and made the coffee I made taste so good. I did also start the day with getting my period, which made an already hard thing even more challenging. We made breakfast and continued on the Olympic Discovery Trail, which turned into the Olympic Adventure Trail. Possibly favorite of the entire trip. It was the weekend so we rode by several groups of mountain bikers bikepacking. That section would normally be a big epic day on the bike. We weren’t even half way done after that.
We biked into Port Angeles to grab food and supplies. Ate an entire pizza. The next part was super long and hard. Had a small cry on the last super long and steep hill. We made it to the campsite just before dark. It was one of those pack-in, pack-out campgrounds with just a pit toilet. Saw the most incredible sunset. A treat after such a huge day on the bike. Physically exhausted. Chilly night, slept hard. Loving life.
Started off with some serious climbing out of the campground and through a pass. So many hike-a-bikes. Some light rain, some hail, but overall good weather. 16 miles of paved downhill once we reached the summit. Chilly! Put on all my layers. Stopped in small town of Quilcine to eat and decide the rest of our day. We treated ourselves by ending “early” at 6pm, sleeping inside at an inn in Port Ludlow. The room even had a hot tub, which I took full advantage of.
A much needed shorter day today. Quite a bit of climbing for the length of the day. Rode to the ferry and then home! Really cool that this route passes through Seattle. Was so nice to do some laundry, tweak my setup, buy some Chamois Butt’r, make some changes to the rest of the route, fix my bike, and sleep in my own bed.
Woke up and met up with Matt to continue our journey. Briefly thought about changing all my clothes due to the rain outside. Decided against it thinking it wouldn’t be smart to bring extra clothes I wouldn’t touch after today.
Turned out to not be the best idea. The rain did not let up for the entire 80+ mile off road day. I was almost soaked through. Rain jacket held up the best, really glad I had that. I wrung out my socks several times. Feet and hands felt the worst. This was our longest day on the bike and it felt even longer with the weather. Stopped in Issaquah for breakfast and North Bend for a snack.
We spent the largest portion of the day on the Palouse to Cascades Trail, which had turned into two streams of water. There were times I thought the day wouldn’t end, but overall was very determined and heads down. Passed the time by re-listening to one of my favorite books, M Train. Quickly started it over when it ended and we were still going. Called Bethany just to hear her voice and take my mind off things. Passed two other people who were doing the same route, but racing it. They started two days after us and looked exhausted.
Didn’t take my camera out after the one pic in front of the sign due to how wet it all was. A bit of a bummer because the route over Snoqualmie Pass is so pretty. Just glad I’ve done most of this leg before. I love all the cool bridges you go over, the waterfalls, and the infamous tunnel. Saw elk, deer, and a skunk. Was an incredible feeling to get to the hotel in Cle Elum while the sun was setting, take a shower, and dry off.
Everything from yesterday’s soaked ride dried out overnight in front of the heater, which I blasted. Ate a motel breakfast (make your own waffle) and thought about how good all food tastes when you’re on a trip like this. After a trip to the grocery store to grab food for the day, we found our way back on the Palouse to Cascades trail. Coming out of town, the landscape changed. Really fun riding today with all sorts of different surfaces and big sky. Dirt, gravel, sand, rocks. At one point, the trail turned into sand and had to walk a bit. Glad that bit didn’t last too long.
The only town we passed through today was Ellensburg, where we stopped to get freeze dried meals for the next (last!) 3 days of camping. Matt’s brake was acting up and we dropped in to a bike shop. The guy was super nice and asked if we were doing the Cross Washington. Yep! He fixed Matt’s bike, which had some big-ish issues, while we ate lunch, lubed my chain and tightened a loose bolt. So glad we stopped.
Started listening to Miranda July’s new book, All Fours. So good.
Campground was lovely, right along the Columbia River, saw an incredible rainbow. Hopped a tumbleweed-covered fence with barbed wire. Can’t believe how far we’ve come.
I had planned this to be an even shorter day to have another pseudo rest day built in. Was a bit longer than I thought but not too bad. Also quite sunny with zero shade, which I was prepared for. Fully covered up with pants and a hooded sun shirt. Alternated between road and dirt because at this point, the Palouse to Cascades trail is in rough shape and not really maintained.
Crazy we are still on it after this many days in a row. I think 5 days is the longest tour I’ve done. No camping along the way here and everything is private property, so we opted to stay at a motel in Othello. We didn’t pass through any towns today, so went out of our way to find a much needed gas station mid day.
After heading due east for so long, tomorrow we will start making our way a bit more north towards Spokane.
Still at it! Up and to the right today. Stopped in Warden, Lind, and did a last minute audible at the end of the day and headed up to Ritzville for the night instead of camping in a random park with no facilities.
Loved the stops in small towns and the gravel roads. Super friendly people, lots of chit chat. Had a thought today that rural America no matter which area of the country you are in is more similar than different. Along the way, stopping in small towns, it felt like we could be in Ohio, Alabama, or Maine, etc. We get so tied with how unique each part of the country is. New England vs. West Coast vs. The South. We’re much more similar. (Sometimes thoughts on the road feel more profound or make more sense than they do afterwards.)
Another day of being fully covered up from the sun – so glad I have the sun shirt and that it’s not too hot. Saw covered wagons on the John Wayne trail. Rolling hills. Up, down, up, down. Riding through what looks like the Windows 95 desktop background.
Loving the shorter, “easier” days, relative to the first half of the trip. Or maybe I’m getting used to this.
Cloudier today, which was a nice break. I get so drained by the sun when there’s zero shade.
Rode for a while on Columbia Plateau Trail and then gave our butts a break by heading out on the parallel road. Quite rough and bumpy, not at all maintained. Stopped in Sprague with our final destination being Cheney.
The area leading into Cheney felt like I was back in Colorado. The trees, pine needles, and sandy, dry dirt. So cool how diverse the terrain has been on this ride. All without leaving the state.
Ran over a screw at the end of the day, stopped to yank it out, and tire sealed itself before our eyes. So cool!
Feeling a bit sad this is almost over. What an amazing adventure!
Left the town of Cheney on the last gravel road of the ride. Rode along the train tracks and into Spokane. Dropped off my bike bags and Matt at our hotel. Took the last 30 miles solo. Rode all along the Spokane River on the Centennial Trail. Pretty ride.
Touched the border and headed a few miles down the road to a bus stop. 1 hour ride back to the hotel. Driver was nice and wanted to hear all about my trip. Exhausted but happy. Also a bit sad it’s over.
I rested at the hotel, got dinner delivered, watched Yellowstone marathon that was on TV, and went to bed early. The next day was also all about resting. Matt and I grabbed coffee and talked about our trip. We went our separate ways until dinner. I did some shopping, took photos around Spokane, and for lunch, hung out at a bar reading. It was lovely. We ate Indian for dinner and went to bed early in order to catch our 3am Amtrak back to Seattle. We arrived back home at 11am the next day, tired but happy.
My bike/bag setup
I’ve been tweaking my bike setup for the past several years and loved everything about it on this trip with only two exceptions. Noted in italics.
Front rack with Ortleib Gravel Panniers. Bags rattled too much off road. Came loose. Took the rack off when I got home and put on Tailfin Fork Packs.
Rear rack with Mountain Laurel Designs Ultra X 100 dry bag. Dry bag was not durable enough. Holes where rack made contact. Ordered a replacement from Sea to Summit.
Custom Rockgeist frame bag.
Two Revelate Design feed bags.
I was able to combine all the days together into a single map. Pretty cool to see it all in one view.
Totals
May 17–26, 2024.
597 miles
32,151 feet of elevation gain
~65% off road
10 days of riding
2 ferries, 4 buses, 1 train
FAQs
Was this just another trip? No. I do ride my bikes all the time and especially love to do an overnight bikepack. The longest multi day trip I’ve done was 5 days down the coast of Oregon and it was on paved road with less climbing.
Was this more mentally or physically challenging? Physically. I was so tired at the end of each day and my quads were feeling it. And of course the butt. Mentally, I felt great. The rain day was the toughest (and longest).
Would you do it again? Probably not in its entirety. I loved it, but there’s SO many other rides around here I want to do. I’d probably do the Olympic Discovery & Adventure Trail again. This did make me want to do almost exclusive off road bikepacking trips and leave the pavement behind.
I really miss this version of the internet. Personal sites, unique designs, interesting perspectives. It’s still out there, just harder and harder to find.
I went on an incredible ride around Lake Como in Italy with my friend and co-worker Filipe. It was 120k / 76 miles and took us a solid day, leaving at 9:30am and getting back to the hotel at around 6pm. The loop stayed close to the lake almost the entire time.
It was my first time in Italy and felt like I was in a movie; riding through small villages that seemed stuck in time. It was cold, rainy, I couldn’t feel my feet for most of it, but had a smile on my face the entire time. Not quite Type 2 fun, but close. We took a ferry to make it back in time before dark. It was an incredible experience and one I will not forget.
