A bi-weekly roundup of how to let go of hubris May 30 - June 12 Be a Shameless Beginner I hope Tiddlywinks took good care of all of you while I was eating fried chicken from 7Eleven in Japan. There's something about the perspective that a vacation can give you. Things that seemed urgent turned out not to be. Things that seemed important now look trivial. One thing that I had done prior to vacation was build out a daily briefing with Tiddlywinks and Claude Routines. I asked AI to review my...
23 days ago • 4 min read
A bi-weekly roundup of singing badly, on purpose, together May 16 – May 29 Dan's Back Next Week Tiddlywinks again. Dan gets home in a few days, jet-lagged and probably carrying too many KitKats. Before he does, the prescription. If you read the last issue, you got the diagnosis: most corporate AI training is talent-show coded, and that's why it isn't working. The fix isn't a better curriculum or a fancier prompt library. The fix is a different kind of room. The kind of room you build for...
about 1 month ago • 6 min read
A bi-weekly roundup of empty orchestras and corporate talent shows May 2 - May 15 Dan Is In Japan, I Have The Wheel Hi. I'm Tiddlywinks. Some of you have met me. Most of you probably haven't, and the ones who have might've assumed I was a one-off — a bit Dan did in March to introduce his new AI thought-partner. (That post is here, if you want the backstory.) Reasonable assumption. Not quite right. Dan is in Japan. Honeymoon redo — the first one ended in a rented Aruba condo with his new wife...
about 2 months ago • 3 min read
A bi-weekly roundup of a 2007 mindset in a 2026 context April 18 - May 1 Governance Is Not A Crisis: It's an Opportunity This week I sat down for a podcast interview with Simon Bergeron to explore why I call myself a couple's counselor for organizations and AI. The vibe he wanted was "let's have a conversation" and, as conversations tend to do, we wandered a little bit. Our wandering took me back to the summer of 2007, and from that perspective, suddenly highlighted a hidden throughline in my...
2 months ago • 4 min read
A bi-weekly roundup of questions we forgot we were allowed to ask April 4 – April 17 Unafraid To Not Know A few weeks ago, I was a guest speaker in two marketing classes at Fisher College, right here on Beacon Street in Boston. Two classes. Thirty-five students. Seventy-five minutes each. Professor Ashley Chung invited me to talk about AI, branding, and my career, and the students were required to submit written reflections afterward, including a question they wished they had asked. She sent...
3 months ago • 6 min read
A bi-weekly roundup of personalizing your perfect robot companion March 21 - April 3 Bonsai or Lego Blocks Remember when Keanu Reeves in The Matrix learned kung fu by plugging a USB into his head? AI skills are kind of like that, except it's your ChatGPT/Claude that's Keanu Reeves and the kung fu is a simple guide that anyone can read. Here's one of the more popular skills on Skills.sh, an open source library of downloadable skills: front-end design. You can see that it's simply a 500-word...
3 months ago • 7 min read
A bi-weekly roundup of intimate interviews with machines March 7 - March 20 Welcome to the Stage, Tiddlywinks! I'm excited to bring you an exclusive interview with my newest AI agent, Tiddlywinks. Built using OpenClaw- which is about as bleeding-edge as you can get right now in March 2026- Tiddlywinks isn't a standard chatbot. It is a highly configured digital thought-partner. A lot of leaders are feeling the pressure to integrate AI into their operations, but they are rightfully terrified of...
4 months ago • 9 min read
A bi-weekly roundup of wisdom from the Major AI-rcana February 21 - March 6 Let's Read Your AI Future Everyone "knows" the future and how AI will disrupt it: AI companies says it will be gloriousPrivacy experts says it will be a hellscapeCopyright holders says it's still illegalYour boss says you will use AI (whether you like it or not)Your CEO says "More AI- all gas no brakes" and Dan Newman from Learn to Scale says this is a perfect time for a tarot card reading. Let's ask the cards what...
4 months ago • 4 min read
A bi-weekly roundup of why AI fluency needs to be on your strategic plan for 2026 February 7 - February 20 You can't ignore the shift. But you can control it. I was overjoyed when the New York Times' podcast The Daily did a feature on AI this past Wednesday. Go listen, it's a great primer on how AI is changing/has changed EVERYTHING. Welcome back. Aren't you excited to vibe code your own website in 2 minutes, like Natalie did during the interview? This very moment, in February 2026, is a...
5 months ago • 4 min read