The Family Outing

Rethinking work, life and meaning for the contemporary age

I’ve written a book! It arrives on shelves this fall, and I hope you’ll pre-order it.

And no, it’s not about tech. This is the story of how every member of my family—Mom, Dad, Sister, Brother, Me—came out. It starts with a serial killer in 1969, and ends with a big gay post-pandemic family vacation, and I’m nervous as heck for you to read it. But also, I’m excited to share it.

Six years ago when I began sending this newsletter, I was a technology writer, full-stop. I scrambled to get to the up-and-coming founders before my peers. I endeavored to decode their ideas for readers, to find the ways their inventions were relevant even when their companies sometimes tanked. I’d been at it for more than a decade, working for BusinessWeek, and then Fortune, and then Wired. And I’d recently joined Steven Levy, incredible mentor and good friend, to help create the publication that embodied the best of all of this work, Backchannel.

But things have evolved, and so have I. The companies I chronicled are no longer upstarts; they’re the establishment. The magazines I wrote for are no longer thriving as their parent companies continue to tread water in a declining industry. More centrally, my own curiosities have shifted. I’ve always been drawn to the people within the stories, their motivations and their drive. What has interested me most is the way technology is shifting the context in which we live, the way it has opened up new lines of communication. I’ve been interested in the choices we have made about how to use it, and the paths that have become available to us because of it.

Then a few years ago, everything changed for me. I still can’t articulate exactly why. In a short period, I became a parent. I left magazines to work on podcasts at LinkedIn. And the pandemic emerged. I had to reimagine every major aspect of my identity. For awhile, I couldn’t write. I had no words. I couldn’t even pretend to conjure the interest I once had for tech’s inventions, or its most significant personalities. I couldn’t map language to the changes I saw happening around me, or inside of me. I could barely keep the baby fed.

If you’ve kept up with this newsletter for awhile, you saw the change in course. When I found my voice again, I could only write—infrequently—about the human experience of navigating the present moment. I found myself thinking deeply about my most important relationships. I began to reflect on my family. We hadn’t had an easy time of it, growing up. (That is, perhaps, a euphemism.) But these were the people I spoke to every day during in 2020, the people I cared most about.

This is the origin of The Family Outing. That spring, I pitched the idea of The Project. I would, in effect, interview each member of my family about coming out. I would try to weave our narratives into one story, a tale that described how we ended up in our closets, the impact of those closets, and what it has meant to find our way out of them.

There is no one narrative of a family, as any one who has ever been in one knows, but instead of tangle of differing perspectives and failing memories. Even so, my gracious family allowed me to attempt to record this one. If any of them had attempted something similar, the story would be completely different.

To be clear, this isn’t a book only about being queer. I take a broader view of what it means to come out. We’re all born into a set of expectations set for us by our families, our culture, our society. These expectations are rarely in line with who we really are. We live in a moment of great awakening, a moment that inspires the technology that we create, and is informed by it, a moment in which we can all move toward more authentic expressions of ourselves. That is what this book is about.

🎙What comes next

Now that I’m no longer working daily on the book, I hope to return to writing here at a semi-regular cadence. The work will be influenced by the guests and listeners on my show and the people in tech to whom I still speak frequently, among other things. I’ve always seen this newsletter as the place where I can engage in active conversation with people whose curiosities resemble my own. Feel free to unsubscribe if it no longer feels relevant to your interests. Otherwise, look for another letter in the next few weeks.

🎙Things I’ve made

I’ve recorded about 50 episodes of Hello Monday since I last wrote. I hope you’ll check out the archives. In this episode on caregiving, I spoke with writer and activist Angela Garbes about the work involved in caring for others, and how we weigh it against the work of our careers.

In this episode on how to find your purpose—to figure out what you want to do and how that intersects with how you make your living—The Good Life Project’s Jonathan Fields offers up a path for knowing oneself more deeply.

🎙All things audio

Earlier this year, I helped launch the LinkedIn Podcast Network. Imagine a future in which every conversation about business, careers and anything that intersects with these topics is powered by LinkedIn. For our pilot, we began with 12 great shows. Shout out to the hosts like Morra Aarons-Mele and Reid Hoffman and Rufus Griscom and Leah Smart, among others, who also happen to be newsletter readers. We plan to expand in coming months!

🎙Post script

My last letter arrived two days before our daughter was born. We were, in so many ways, expecting. Alice Camille Clayton made her grand entrance on March 18, 2021. She walked early and refused to sleep for most of the last year, but it’s clear she has big plans for the life ahead of her, and we’re ecstatic that she’s here.

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