The TL;DR, Craving A Little Pain


A bi-weekly roundup of carrots and sticks
February 18 - March 3

It Hurts So Good: A Love Affair With Pressure

I had the honor of being interviewed by a student regarding my personal entrepreneurial journey and she created a report that hit like a punch in the gut.

On its face, it was a pretty typical assignment: interview an entrepreneur and ask them questions about how and why they started their business. Being able to read the report, though, was like seeing myself through a fun-house mirror, the revealing kind of mirror that accentuates your pimples, smile, and awkward hands. It really made me question myself.

That questioning opened up an uncomfortable insight: I’ve been feeling a lack of pressure in my professional life.

I'm too comfortable.

Growing up as a musician, having a natural achiever drive, AND surviving the pandemic (a pressure cooker in more than one way), I have spent a lot of my life living under pressure. Trying to meet expectations, striving for status, securing financial stability, and investing in future success have all been sources of pressure that has pushed me to grow and learn.

What surprised me from the report are my results from this lifestyle of pressure. A few one-liners that jumped out and slapped me in the psyche:

  • “Dan has spent more than ten years researching the most effective methods for helping individuals learn and develop”
    • This sounds like a product of Achievement pressure where I was trying to do my best work at my job
  • “Dan believes [employees should have] creativity and freedom to contribute within any area while working with passion”
    • Growing up in the arts, this Cultural pressure has shaped my personal values to cherish the woo-woo inside all of us
  • “[Dan believes that] advancements in technology…creates more competition and can make it challenging…to maintain market share”
    • I'm obsessed with the First-Mover Advantage and the pressure to learn fast has helped me become someone who produces fast results
  • “Dan's vision is driven by a belief in talent development’s power to drive success and help individuals reach their full potential"
    • Pressure from our Hustle-Culture Western Self-Improvement Trope, framed by my early career in charter schools, has shaped my Fundamental Why: Everybody Learns
  • “Entrepreneurs often face challenges and setbacks, so it's important to be able to bounce back from these and adapt to changing circumstances.”
    • Fear of being labeled as a failure is a core piece of my Fear Motivation drive

For most of my professional career, I rarely had to seek out pressure. For a long while, trying to do my best, get promoted, and attain status was pressure enough. As an Obliger personality type, extrinsic accountability was all I needed to bounce out of bed.

As an entrepreneur, my first true pressure was financial: if I didn’t make money, I didn’t have money. That pressure pushed me to try new things, work late into the night, build relationships, and foster my own skillset.

Once I secured financial stability, that pressure dissipated. Over the years, the other pressure sources also receded (or I just habituated to them) until they were barely noticeable.

Now what?

I’m scared to be mature enough to seek out pain (i.e. a source of pressure) to re-motivate myself. Who willingly chops out their legs from underneath themselves to encourage themselves to go to the gym? Who puts a short deadline on themselves to prevent themselves from wasting time?

I’m afraid that by intentionally putting pressure on myself that I am going backwards in life.

Part of why I'm sharing this in a newsletter is that I believe these feelings and thoughts are normal. Being afraid and scared is probably a good thing when you're truly a learning-focused person.

TL;DR- I ain't got this all figured out.

But...

...you probably don't have it all figured out either.

Wherever you are in life, you too may be existing under pressures. Social, financial, professional, cultural, physical, emotional- all kinds of constantly changing sources of pressure. You might be too uncomfortable facing down financial pressure or you might be too comfortable and starting to get bored with your work.

Whatever it is, you're not stuck and you're CERTAINLY not alone.

I invite you to chat with me about your pressure. Talking out problems may be all you need to reframe the pressures in your life. Hearing how other people are grappling with their pressure may help me find what I need to reach my next level.

This is a team effort, here. Let's learn together.


A TL;DR from the CRO

I deal with pressure by spending time with my friends.

-Roman Noodles, Chief Ruff Officer


New Blog Post: What's a Corporate Offsite?

If you didn’t do a post-pandemic offsite, you missed a big opportunity.

The good news is that you can still organize a low-cost high-impact business ritual that carries little to no risk. But if you never ran or organized an offsite, it can be intimidating to start and you may not know exactly why you should have one.

Five whys, coming right up.


You know what kind of pressure I am still thoroughly enjoying?

Rock tumbling. It's dumb and it's delightful.

I've got some Fancy Jasper that's going into the tumbler for the next 4-6 weeks. This is the last batch of stones I purchased on a late night whiskey-fueled shopping spree a few months back.

Fancy Jasper, for the people out there who know when to expect the next full moon, is about healing and focusing on the present. Fancy Jasper allegedly amplifies feelings of well-being.

There's a certain poetry that I'm grappling with my identity right when it's time to tumble a stone associated with focusing with the present.

It also sounds like Fancy Jasper is a healthier way of feeling good about yourself than late night whiskey, but we wouldn't be talking rocks without Glenmorangie and the r/RockTumbling subreddit.

Getting high on rocks over here,

Dan from Learn to Scale​


​Opt-out from the newsletter | Unsubscribe from all emails | Update your Preferences | www.learntoscale.us, Boston, MA 02119

​PS. If gemstones and booze aren't your preferred pressure relief, how about cheering on a marble rally?​

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
Toddlywonks, a chaos gremlin cloaked in flames

A bi-weekly roundup of underwhelming SOUL.md files September 19 - October 2 Enthusiastically Parliamentary Meet Toddlywonks. He's a chaos gremlin with a lazy eye and a degree from a for-profit college that went out of business in 2019. According to TW, he's a 'Licensed Arsonist.' Toddlywonks lives in Muse, Meta's new AI personal agent product, and I only allowed it context data about my personal life. Longtime readers already know Tiddlywinks, my Claude-based thought partner, who is all...

a man running over a very small hurdle saying "Wait, that's it?"

A bi-weekly roundup of reliving that first time feeling September 5 - September 18 You Never Forget Your First When I started my entrepreneurial journey in 2019, I did what all the good podcast ads tell me to do: launch a website on Squarespace. For almost seven years, that was good enough. Sure, there were lots of weird workarounds I had to bang together to get all my different tools working together (I'm looking at you, Code Embed Block), but overall, it got the job done. Part of why I...

a scale weighing time and done, with done weighing down the balance

A bi-weekly roundup of sycophancy in 9 minutes August 22 - September 4 Remembering How To Human Quick note: September 16-18th I'll be at HubSpot's UNBOUND conference, doing tarot card readings about AI fluency/anxiety. I've set up a Braindate listing if you're going to be there, or just look for the guy in the Learn to Scale hat and ask for your fortune. I learned how to design trainings way back in my first job after college, in an AmeriCorps program at a charter school. Through a blend of...