Legacy: what will I leave behind?

What will I leave behind when I'm gone? What will be my legacy?

I'm not sure what is a "normal" amount to think about such things, but I do think about them.

Perhaps losing my father at a young age and then attending his funeral initiated some premature awareness that people could die and that there might be some variability in how they are thought of and remembered. As I came to terms with the existence of my own mortality, I more than occasionally wondered what might be said of me at my funeral, and how I would be known from that point on.

Of course it's an incredible privilege to even think about legacy, and dwelling too long on it can bring out the worst impulses of ego and self-importance. To have had incredible opportunities and access to resources over the course of my life and then still try to control how the world works even after I die...well, that would be crazy.

So I try to use any "legacy thinking" as a way to keep me focused, especially on the important things I want to do in life and the kinds of relationships I want to have, instead of as a vehicle for self-inflation or unnatural self-preservation. I also use it to keep perspective:

Big Picture

On a geologic time scale, I won't really have any personal legacy. I will be one of many billions of people who lived in a time when humans inflicted substantial, mostly harmful changes across the planet, killing off many other forms of life while altering the climate, poisoning the water, bringing up oil and putting down trash and toxic chemicals, and just generally making a mess of things while we wait for the sun to implode and swallow the Earth.

Hopefully I also live in a time where a shift in human attitudes about the planet we occupy eventually leads to some reversal of those trends, and maybe our descendants will despise us slightly less than they could have otherwise. But as much as I want to believe that I personally can make a difference in reducing this harm, I don't currently hold out hope that my lifestyle choices will be worth much when measured across the millennia.

Continue reading Legacy: what will I leave behind?

My new team at Automattic

Starting next week, I'll be shifting my focus at Automattic and joining our "WordPress Concierge" team.

It's a small group of talented folks who build custom WordPress sites for influential people and organizations across a bunch of different industries. I'll be creating and supporting the sites we work on while also helping to help the team scale up its internal tools and processes. I'm excited to flex a different mix of skills and ship some new kinds of things.

It's hard to believe that it's already been more than three years since I joined Automattic and began working with the VIP team, where I'm wrapping up my time this week. That role has been full of its own interesting and rewarding adventures that have taken me deep into the heart of the systems and tools that power the modern open web.

Continue reading My new team at Automattic

2016 Year in Review

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

Sky TrainWith 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.

Continue reading 2016 Year in Review

Figuring out what to write

I've started about five or six different posts this past week, but none of them have made it to "Publish." No matter how firmly I was convinced when I sat down to write that I would make it through to the end, one of these blogging insecurities always managed to creep in. I was even trashing drafts of tweets, sure that I would just waste some of the most frequently wasted digital space. Ugh.

I want to write about elections and politics in the U.S. But I have spent so much time reading other people's commentary and I'm in such a dark place about finding any hope in political systems that I just don't have anything all that constructive to say.

I want to write about the people I know who have recently died of cancer, or who are struggling with it right now. But I don't have the patience to find words that move through the anger and sadness toward something good, or even useful.

Continue reading Figuring out what to write

Parenting, year one

I haven't written much in this space about my experience of parenting so far. I suppose that's partly out of reluctance to claim any special insight in such a well established and oft-documented part of the human adventure. Partly it's because much of the time I've spent in the past on writing has instead gone to parenting itself, or recovering from the lack of sleep involved therein. And partly it's because I only have mostly gushing, positive things to say about it, bordering on the disturbingly hyperbolic.

But here I am at a year into the experience - we celebrated A.'s first birthday last week with family and cupcakes - so it seems important to acknowledge that milestone here too.

First I'll get some of the clichés out of the way:

  • Everything changes
  • It's a miracle
  • Sleep when they sleep
  • It takes a village
  • It gets easier
  • Just when you find a routine, things change
  • Hardest and most rewarding thing you've ever done

All of those have been true for us in some form or another. Details available upon request.

A point Kelly and I acknowledge often is how much harder parenting would be if it wasn't something you wanted or chose. We feel fortunate every day we get to parent A. because it is something we decided to do, knowing full well that it would be a challenge and a life-changing experience. My empathy for people who weren't ready to be parents, or for whom parenting is much different than they expected for whatever reasons in or out of their control, has grown significantly. For me and I think for Kelly, even on the hardest, most exhausting days of parenting, we still know and feel that there's no other way we'd want it to be.

See, gushing. I warned you. Ready for more?

Continue reading Parenting, year one

Working for someone else

This week marks two full years of my employment at Automattic. I was fortunate to celebrate in person with a number of my colleagues as we hosted a workshop for our clients and partners in beautiful Napa, California.

People who know that I co-founded and built my own tech business before joining Automattic often ask me what it's like to work for someone else. My short answer is usually:

  • I miss some of the joys and challenges that go with being ultimately responsible for the success of a business venture...
  • ...but Automattic is a place where I am trusted with a level of autonomy that I'd be hard pressed to find in many other employment situations, and
  • I am mostly just enjoying discovering new ways of doing things and being a part of a bigger team with greater resources available for innovation.

This post is my longer answer. While working at another company it has been useful and interesting to notice what it's like to have a change in my professional identity, not be "the boss," enthusiastically support something I didn't create, and try to balance the joys of "employment" with the inner itch to again be a "founder."

Continue reading Working for someone else