A bi-weekly roundup of writing the rules last. June 13 - June 26 Practice Beats Paperwork I had to tell my friend and client Krysta this week that the policy she wanted to publish doesn't exist...and then tell her she was already ahead of companies ten times her size. This exchange took place after the second session of my AI Fluency for a 100% Human Workforce program for her BuildingPPL team. Specifically, I had just sent over the Gut-Check Card from Tuesday's session and 90 minutes later,...
23 days ago • 5 min read
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...
about 1 month 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 2 months 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...
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...
3 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...
4 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