The Scrabble Pieces of 2016

Reflections on 5 years of social experiments

December 2021

While rereading notes from my previous end-of-year reflections, I came across this gem, titled "The Scrabble Pieces 2016."


  1. Ambitious, driven, analytical people are often disadvantaged when it comes to close ties. The pursuit of excellence not only demands sacrifice; it's isolating. Fewer people can relate to or understand you, and those who can are equally busy or inaccessible.

  2. Close ties are really, really important. See Triumphs of Experience.

  3. My friends scattered to different corners of the globe in our 20's, and increasing local "gravity" conspires to keep us separate.

  4. The world is small, but the distances are great. Proximity doesn't guarantee strong ties, but distance makes everything more difficult.

  5. It takes an increasing magnitude of excuses to bring distant people together. A wedding, a 10 year reunion, an extravagant hippie / Mad Max thing in the desert, etc.

  6. Certain peak experiences rapidly forge close ties. Man vs nature, physical challenge, awe-inspiring environments, etc. These imprint strongly onto identity and promote a lasting sense of "being on the same team."

Putting it all together, this is a puzzle for our 30s and 40s...


"Scrabble pieces" referred to the fact that I knew the ingredients, but didn't know how best to combine them.

Five years later, I still don't have a satisfactory recipe, but I've learned a few things along the way...

  • Short collaborations was my most promising prototype. The original products we built at Ultraworking captured some of the magic I had envisioned, although I ultimately wasn't able to steer the company towards that destination.
  • Career-life integration was a mixed bag. Startups are great for forging team bonds but terrible for nurturing outside ones.
  • Long form letters were a partial success. Conversations.txt, for the right group of people, could be a powerful nexus. Unfortunately, the time and practice required to engage deeply were natural limits to its reach.
  • Repeating calendar invites were the best effort-to-value ratio of anything I did during COVID. It's astounding how much a few simple calendar invites can shape behavior.
  • Finally, time spent in nature remains as reliable as ever. Camping always feels like a hassle while preparing beforehand, but a miracle cure-all afterwards.

And that brings us to present day.

I must admit to a newfound sense of urgency this time around the sun. A sense that the next decade will be faster, with fewer time-outs, and fewer chances to adjust course.

There are still unclaimed triple word bonuses on the board...

But I feel the pressure to play my Scrabble pieces soon, lest I be stuck with a hand of jumbled letters.


As we once again approach the collective, aspirational planning exercise known as "New Year's resolutions," I have one piece of unsolicited advice for you:

Don't start with yourself.

Instead, try letting your gaze drift outward — beginning with your inner circle of family, friends, and tribe. Let it settle for moment on your close community and the faces of people you've spoken to recently. Continue backwards through time, lingering on each name that holds, or once held, significance.

Now imagine yourself on stage, on full display — all of their expectant eyes watching and waiting for your next move.

How will you make a difference for these specific people in 2022?

And how can I help?