I stumbled on an email from my friend Peter last week while searching for a totally unrelated message in my inbox. It reads like a public newsletter, but it was sent directly to a small group of friends through Gmail. It’s broken into a handful of sections, each capturing a slice of life, tied together by a consistent heading structure.

One heading is labeled the “Much to Learn Department,” filled with notes from an intimate conversation. Another section features the “Heaven on Earth Department,” complete with a photo of an idyllic cabin and some reflective questions. The final section, “Trendy Fam Fails Department,” is a collection of recent family photos, including one of his young daughter crying beside a KitchenAid mixer that splattered frosting everywhere.

I don’t usually dig through my Gmail archives in search of delight, but landing on this email sparked several:

1. Organizing life into metaphorical departments is fun and unexpected. I’m borrowing that for this update (sorry not sorry, Pete).
2. I often feel pressure to have a thesis or grand, unifying purpose when I write. This format is a reminder that I don’t need one.
3. I like the idea of newsletters for friends. Not in the dystopian everyone-as-an-influencer way, or the you-forgot-how-to-talk-in-person sort of way, but in the warm feeling of receiving a Christmas card way.

So in that spirit, here are a few departments of life I’ve spent time in recently.

Department of Digital Gardening

For anyone who’s counting (no one is counting), I haven’t released a “Build Mode” update since Update One, which was 15 days ago. The truth is, I haven’t been “building” as much as I expected. I’ve been writing and wrestling with some big insights and self-discoveries (more to come).

I’ve been in my head a bit. Thankfully, I stumbled on the concept of digital gardening this week. It’s both a metaphor and method for cultivating ideas. It recognizes that ideas move through different phases, from seed to fruit. Historically, I’ve been stuck in the seed stage, trying to hold and make sense of too many ideas at once. I’m working to bring more of them to fruit as tangible expressions.

Tactically, that means having a better system for cataloging what I find interesting and shaping it into something concrete. Personally, it means taking more time to reflect and sharing openly.

Department of the Cozy Web

“I’m working on re-building my personal site.”

A sentence my ghost will utter to haunt future descendants, alerting them of my presence.

Designing and building a website for yourself is hard. It forces you to stare at yourself for too long and use words like branding and packaging, which feel better suited to software or sparkling beverages.

My current site is fun and creative, but it’s old and tied to a time when I was trying hard to sell myself as a freelancer. At this stage in life, I feel I have less to prove and more to show, so I’m tearing it down to the studs.

While looking for inspiration, I came across the idea of the Indie and Cozy Web, which frames personal websites as valuable real estate outside the reach of big tech. Here are a few of my favorites:

• https://ohhelloana.blog/
• https://www.marco.fyi/
• https://maggieappleton.com/
• https://busterbenson.com/
• https://craigmod.com/
• https://tomcritchlow.com/

They can be visually expressive or simply serve as containers for creativity. In my case, I want people to come to my website for the flowers, not the vessel holding them.

Department of Random Date Nights

Renee and I have a tradition of going on a random date night on the last Thursday of every month. The rules are simple: one person chooses the restaurants and drives, the other is along for the ride and the surprise. It’s an act of planned serendipity, if that’s a thing. We plan ahead by placing a block in the calendar, but then let fate determine the experience, rather than optimizing for places with the best reviews.

Lately, I’ve been wondering if I can share that same spirit of randomness with others. So I built Grub Roulette. It fetches nearby restaurants from Google Maps, based on a set of parameters, and returns a random result.

Try it here 👇

https://grub-roulette.replit.app/

It’s a small way of inviting surprise into your life, and letting go of the illusion that you can only find interesting and fun things through planning.

P.S. If you end up using Grub Roulette, reply or comment with your experience. Try not to cheat and stick to the first new result. 🧘‍♀️ Breathe in the smell of hole-in-the-wall Thai food. Breathe out the illusion of control.

Department of ‘So What Do You Actually Do’

This week I built an automated matchmaking tool for a startup community here in Maine. Most of the people closest to me have no idea what I actually do or what my skills are, so here’s a tangible example. You can watch the video I sent to the team after I finished it.

It draws on years of experience using Airtable, along with some new experiments with Slack bots. This project was fun because it used my skills in service of IRL connection, which feels good. Good work should feel good.

Department of Recognizing Beauty

On Saturday afternoon, I was doing what most men in their early 30s do: clean the house while listening to Broadway singalongs. Dear Theodosia from Hamilton came on. I’ve listened to the Hamilton soundtrack a few times before, but for some reason, the song hit differently this time.

As I often do when I find something I like, I went down the rabbit hole and discovered other beautiful covers and versions. I love this low-quality, phone-recorded jazz version because of the prelude and its intimate feel.

I am not a trendsetter. I have no shame sharing a video that’s seven years old from a musical that’s well past its hype cycle. It’s a great song.

Department of Old Poetry

Here’s a poem that’s been napping in my notes since 2021. This newsletter feels like a good time to include it.

Let the pen move without knowing how to fill the whitespace. Life is not planned five words in advance. It can be, but would you stumble on the insights of unencumbered thought? Would you feel the humor in putting words to paper that barely make sense?

Rejoice in not “getting it right” all the time. Treasure the feeling of stepping off the ledge, unsure whether your next word will land on solid ground or a chunk of jello.

If you can write without judgement, you can be more free. Realize that moments are sometimes just moments. Words are sometimes just words. Not everything is a strategic move. Throw a word on the page. If it doesn’t fit, move on.

Release your words from the filter of expectations and edit later. Ramble because you can and don’t let anyone stop you, especially yourself.