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A bi-weekly roundup of ways to quench smoldering feelings of shame May 11 - May 24 Everyone Has A Personal Dumpster FirePart of my goal when coaching business leaders is for them to feel safe enough to flip open the cover to their personal dumpster fire to help them acknowledge and fix the secret flaming garbage inside them. In a nutshell, this is learning & development. L&D's function is to figure out what someone does know, doesn't know, needs to know, and then get them that necessary skills and knowledge as quickly and permanently as possible. My job for 15+ years was to get people to feel safe enough to lower their façade of "I have my shit together" and share their reality, "I have this shit together but I struggle with that important shit." The lesson I learned: Everyone struggled with something. Learning professionals like me know that humans hide their weaknesses, intentionally and unintentionally. We've got strategies to Analyze, Design, Develop, Implement, and Evaluate (ADDIE) the important shit you don't know but need to know, whether you know or don't know that you don't know it. You struggle with something, regardless if you are aware of it. When I transitioned from corporate L&D to running Learn to Scale providing coaching and consulting, it wasn't surprising to hear how many entrepreneurs are living in their own personal dumpster fire (and how often they're unaware of the fire but can feel the heat). To be more specific, here are the kinds of unsurprising problems I've heard:
In the vast majority of cases, there's deep feelings of shame, guilt, embarrassment, and failure that accompanies these admissions. They look at their challenges as personal garbage. It's not garbage. It's just skill gaps. Everyone struggles with something. An almost universal challenge I've seen small business leaders have is around communication. Sometimes a leader is aware that team meetings aren't efficient or that a team lead doesn't write clear emails. More often, a leader can feel a sense of disconnect or low morale but assumes its normal. Poor communication at small organizations is normal, but it's a piece of garbage that can be thrown out of your dumpster relatively easily and will have a clear positive impact on the business. It's just a skill gap. Everyone struggles. Nothing to be ashamed of. That's why I created the guide, "Drive Your Business Forward With Powerful Communication." It's full of examples of how communication problems look and feel- so you can actually SEE the garbage in your dumpster- and how to throw that garbage out. For something very actionable, skip to page 20 for the SBI approach to feedback. TL:DR- Everyone struggles with something. It's just a skill gap. Nothing to be ashamed of. You can do something about it.
A TL;DR from the CROMy intern, Finn, struggles with impulse control. -Roman Noodles, Chief Ruff Officer New Blog Post: Do the Most Important ThingsAnother thing a lot of leaders struggle with: time management and prioritization. Escape the burnout trap and conquer your entrepreneurial to-do list with these time management and prioritization strategies. Read more... Roman Noodles has a friend staying with me for the weekend, Finn. Finn's seven months old and ten pounds heavier than Roman, but they're pretty equally matched during playtime. Sure, Finn's got energy, but Roman's got speed and agility. Letting them loose in the field, Roman instigates Finn into a chase but her dopey seven-month-old legs just can't get her up to Roman's top speed, let alone pivot and turn like a poodle. However, the sunshine on Roman's black curly hair and all the sprinting-dodging tires him out, which is when Finn finally catches up and tackles him. Watching this, I asked myself: if Roman represents success, am I Finn? Should I keep chasing the poodle of my dreams, hoping it will get tired? Or do I need more years of growth and development and then it will be Roman trying to keep up with me? Then I remember- I'm standing in a field in the afternoon watching two dogs play. This is success, right here. Relishing dog walks, Dan from Learn to Scale Opt-out from the newsletter | Unsubscribe from all emails | Update your Preferences | www.learntoscale.us, Boston, MA 02119 PS. Michael Bolton ain't no dumpster fire, just a cinephile |
I help organizations build AI fluency and governance that actually changes behavior — not the kind that lives as a PDF on a Notion page. 19 years onboarding humans to strange new places (startups, scaling tech, enterprise agencies like GroupM and WPP) gave me a head start when AI showed up as just another strange new place. The TL;DR is my biweekly newsletter for leaders thinking through what AI means for their people.
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...
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...
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...