The TL;DR, Acknowledging Personal Dumpster Fires


A bi-weekly roundup of ways to quench smoldering feelings of shame
May 11 - May 24

Everyone Has A Personal Dumpster Fire

Part 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:

  • A serial entrepreneur who struggles with building a company
  • A senior people leader who struggles with managing their people
  • A senior sales leader who struggles to make sales
  • Countless coaches who think they're not good enough at coaching
  • Countless business owners who think their competitors have it all figured out

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 CRO

My intern, Finn, struggles with impulse control.

-Roman Noodles, Chief Ruff Officer


New Blog Post: Do the Most Important Things

Another 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

Dan Newman

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.

Read more from Dan Newman

A bi-weekly roundup of money-saving hacks in iambic pentameter July 11 - July 24 A Poem For FinOps For next week’s monthly Show Me Something Cool With AI, I issued an optional challenge to get AI to write a poem that sounds like you in the FEWEST number of words/prompts as possible. This challenge is both a curiosity of mine and my forecast where AI Fluency is headed next. First, the forecast: people are using AI. According to Pew Research, about half of Americans are using chatbots in 2026,...

an AI machine vomiting slop into a slopifying news digest

A bi-weekly digestible digest about digests June 27 - July 10 AIndigestion You know what’s an “easily AI-automate-able task” that felt utterly boring? News digests. Back before the Slop Era, newsletters were how I curated my own personal knowledge base. There were a few publications that I treasured for their selection (personal favorites, The Educator’s Notebook and Offbeat) and I trusted them to keep me sharp and informed on my professional and personal interests. It’s actually what...

a tiger made of paper, roaring

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,...