After more than 5.5 years at Automattic, I recently decided that I am ready for something different, and today is my last day at the company.
The things about Automattic that excited and impressed me when I first joined in 2014 still excite and impress me today. The mission to democratize publishing and help people to better tell their stories. The pioneering of a distributed model for hundreds of people to work well together. The way even small improvements in a few lines of code could affect millions of websites. The focus on transparency and excellence in communication. Working with kind people from all over the world in a constant flurry of collaboration and creativity.
I recently joined podcaster Dave Albert to talk about my adventures with entrepreneurship, what it was like to start, run and eventually wind down a technology business, what it's like to work for someone else, the joys and challenges of distributed work, and some of the cool stuff we're doing at Automattic. We covered a lot and it was fun to look back on all of those different parts of my professional life.
My questioning has taken a variety of forms, including:
writing and editing for my high school and college newspapers,
hosting a weekly podcast with analysis of the local news,
blogging as a media critic,
serving on the local daily paper’s editorial board,
having letters to the editor accepted in local and national publications,
working professionally to advise and support some of the biggest news publishers on the web,
helping to organize a three-day national conference for publishers, and
researching business models for local journalism.
I’ve been rewarded and challenged in all of those things, and in most cases I’ve been told that I’ve made a positive difference. And yet...I feel more concerned than ever about the waning appreciation for journalism and pursuit of the truth in modern society. I also feel more drawn than ever to trying to do something (else) about it.
Thanks for asking. It was a lovely mix of world travel, puttering around the house, exercising, tackling fun projects or day trips with my daughter, visiting with friends, reading books, tinkering with my personal web presence and software projects, grieving my mom's death and working on her estate, volunteering for local organizations and political causes I care about, cleaning out my home office, watching movies, listening to podcasts and napping. (I did less writing and structured exercising than I'd hoped to, but I felt creative and in motion in other ways that mostly made up for it.)
And I learned, observed and realized some things during that time:
I recently returned from my first trip to Croatia, where I spent a week hiking, biking, kayaking, rafting, exploring and eating throughout the country. Between grieving my mom's death, working through her stuff, the busy-ness of work and trying to stay caught up on the rest of life, I hadn't had much time recently to do something purely for fun and purely for me. When my sabbatical was coming up this was one of the first things I planned, and I'm so glad I did it. (My mom also loved to travel and explore new places, so I think she would have encouraged it, too.)
I coordinated the trip through REI's Adventures program, which offers adventure/active travel and vacations around the world. I really appreciate that they focus on using local guides to facilitate small group trips full of context, history and authenticity in a true spirit of exploration, instead of just shuffling hoards of people through a standard tourist experience in all the standard locations. In Croatia this meant constant conversation with our two guides about the political and cultural history of the areas we visited, delicious home-cooked meals at the houses of everyday Croatian people, adapting our plans to the moods and weather of the day, and being able to linger in beautiful locations we had biked or paddled to, before and after the tour buses or cruise ships had come and gone.
This is my second trip with REI (the first being a week in the Galapagos Islands), and I felt fortunate that both times we had excellent guides (thanks Marin and Valentin!) and a group that was easy-going and enjoyable to spend time with. Celebrating our milestones and accomplishments over meals together each day was a real treat.
Croatia itself is just beautiful. The landscapes are so varied: lush national parks with waterfalls everywhere, open plains, islands dotting an amazing coastline, bustling cities. It has modern infrastructure and a high standard of living, but reminders everywhere of the not-so-distant periods of war and conflict.
Tourism is on the rise and is perhaps the country's main "export," and so they are wrestling with how to balance the many benefits that brings with the concerns of congestion and environmental degradation.
In addition to the joy of learning about a new place and getting outside my cultural comfort zone, the trip also served as a challenge to myself around physical fitness. The trip activities were rated as "moderately difficult" and I knew that I would need to do some preparation to go from my relatively sedentary lifestyle to being fully ready to take on a week of day-long physical exertion. Apparently I do pretty well with goal-oriented training; adjusting my diet, doing bike rides around town with a loaded-up trailer in tow and working out at the gym three to four times per week in the months leading up to the trip was a lot easier when I could do it in the name of not totally embarrassing myself in Croatia.
And it paid off! Each day I was more than able to keep up, sometimes even being the one who was pushing for a bit more speed or distance. Biking felt especially good and I think I was smiling for most of a 22-mile ride through the rolling countryside.
I know, I know. It's the end of March and it feels a little late to be reflecting on a calendar year that has been retired for three months now. But I've gotten in the habit of doing this - see 2017, 2016, 2015, 2014, 2011 - and there is part of me that needs any small bit of closure that writing this post might bring.
If you had told me a few years ago that 2018 would be the year I lost my mom, I wouldn't have believed it. But the year was indeed consumed by continuing to accompany her through cancer treatment, worrying about her health a lot when I wasn't with her, and then finally saying goodbye to her in December.
I've written some about what that loss and grief has been like and so I won't repeat that all here. But there was little I did, planned, thought about or worked on that wasn't somehow affected by the constant low-level stress and anxiety of knowing a loved one was facing tougher and tougher odds for survival. I wrestled with finding the right balance of dropping everything to have meaningful and special experiences with mom while I could, and living my own life as fully as I could knowing that she found comfort and pride in hearing about our adventures and accomplishments as a family.
Those struggles and that grief brought out some of the best moments, too, when it comes to the love and support shown by friends, family and community. I still can't fully believe or begin to recount the incredible ways that people have reached out and, through gestures big and small, helped make life easier for us during the hardest times. I am so grateful for this and yet I've felt woefully incapable of expressing that gratitude while the fog of grief still swirls around me.
Parenting a preschooler continued to be an almost all-consuming experience. The year started with me entertaining her with puppet shows and craft activities and now she entertains us by breaking into song, dancing on her homemade stage, telling us the latest scuttlebutt from school and amusing us with endless creative scenarios and ideas for play. Helping a human develop, figure out the world, absorb language and deepen her emotions has been incredibly moving and wonderful. Exhausting! But wonderful.
I was thrilled to have a couple pieces of my writing included in publications beyond my own websites, and I still want to get back to doing more of that.
Happy New Year. As arbitrary Gregorian boundary conditions go, I've been really looking forward to the end of 2017. And as I've done in the past I'm posting a few thoughts from the year. (Previously: 2016, 2015, 2014, 2011.)
Though I know the machinations of U.S. politics and culture are not a primary concern for many people in the world, it felt like a year where I could not get out from under the dark cloud of the current presidential administration and the things we are naming and learning about ourselves as a society. I'm someone who usually follows news and politics closely, so it was tough to balance awareness, engagement, activism and appropriate amounts of anger with self-care, long-term thinking and finding any kind of focus or calm. I don't think I did very well with that process, and I've watched it take a toll on me, people I love and communities that I care about.
On top of that I spent a lot of time and energy this year accompanying my mom through her cancer treatment and related medical adventures; it was a source of always-present, low-level (and sometimes high-level) stress that was never too far in the background. I was of course always honored to bring care and support where it was needed, but it was hard watching her be consistently miserable while wondering when or how things could get better.
It was a year of incredible growth for our daughter, going from a barely walking toddler with a relatively small vocabulary to a whirlwind of a kid who runs through the house asking us hard questions, telling stories and expressing strong opinions. A day doesn't go by that I don't look at her in amazement, or that my wife and I aren't asking to each other, "did you know that she can do that??" Witnessing and participating in literal child-like wonder has been a special bit of grace in these times.
Friends have been kind to say that "you don't look forty" (whatever that looks like) and thankfully I don't feel "old," even if I don't often feel young any more.
I do notice the occasional sign of what might be aging.
I find myself increasing the font size on my various devices and apps, and at an appointment this week my eye doctor used the language of "you can't outrun it forever" instead of the past variations on "you're young, no worries."
A few weeks ago I butt-dialed two different people over two days.
The distance across which I can walk to retrieve or do something without forgetting why I started walking in the first place is decreasing. If it involves going to a different floor of the house, forget about it.
My hair has more strands of grey than ever before.
And my ability to sleep through the night without needing a visit to the restroom is all but gone.
With another year gone by, I'm again sharing a few reflections on how 2016 went. (Previously: 2015, 2014, 2011.)
New house, staying in Indiana
With a big shift in my wife's professional life and an intentional wrapping up of most of my local commitments that required regular attendance at in-person meetings, this year found me as physically untethered to the city of Richmond, Indiana as I've been since I first came here in 1995. We spent much of the year asking whether we should stay, or take the opportunity to explore living in new places outside of the U.S. midwest. (Someone even started a rumor that we'd already moved away.) I reflected a lot on why I've stayed in Richmond this long, what we'd be giving up if we did go, and what we'd gain by living somewhere else.
There are changes happening locally and regionally that concern us, and there are times we want our daughter to have more diverse experiences than we can find in Richmond, so we know we'll keep considering these questions. But we decided that our wonderful community of friends and family, the difference we feel like we can make locally, and the opportunities we still have to see and live in other parts of the world all added up to staying in Richmond right now.
Friends, there is a miniature human being living in my house now.
There are many things about that experience I could go on about -- the adoption process, being in the delivery room for her birth, the incredible support and help we received from our friends and family, figuring out how to care for a new person and getting some sleep along the way, watching my wife become a wonderful mom and navigating a huge change in our life together, implications for our home automation setup, and much more -- and I'll try to blog about all of that as I can. For now I can say that being a father has been magnificent.