The TL;DR, Previewing A Big Change Before My Business Birthday


A bi-weekly roundup of insights from six years of failure
September 20 - October 3

Stitching A New Birthday Suit

Next week, Learn to Scale turns six years old. I've been a professional failure for almost six years.

I don't know about you, but birthdays make me reflective. It's a special event that connects you to previous versions of yourself: the person who used to believe one thing is the same person that you are today, but you've changed what you believe.

And every year, the Dan from six/five/four/three/two/one years ago thought that now, NOW, I've figured out what was wrong and will finally get it "right" this time.

In recent years, I've leveraged AI to help me reflect. And before you go all "Don't trust a syncophant machine!" think back to the last time you sat down for hours and written out your deepest fears and had an infinitely patient person process it all and help you reframe things without having to pay an hourly rate.

Oh, you can't remember that moment? Probably because few of us sit down and truly reflect. AI isn't a perfect coach, but at least I'm doing the good work to try to understand what's running through my head.

Every year through this reflection practice, I come to some perspective-shifting conclusion:

  • Year One: Being an entrepreneur is a lot harder than I thought...especially in a pandemic.
  • Year Two: Selling a cohort-based learning program to HR people is really hard.
  • Year Three: Selling something without tangible outcomes and deliverables is wicked hard.
  • Year Four: Balancing sales and marketing and networking and financial security is pretty hard.
  • Year Five: Startups, as a market, is a hard market to build a business around.

(In case you're curious, this newsletter has been taking snapshots of this learning journey. Ever since I switched from Hubspot to Kit, I've published every TL;DR for web reading so you too can retread this journey of lessons learned.)

The lesson going into Year Six is this: being a generalist in a sea of specialists is hard.

Laugh it up, because Dan from any of the previous years would have said that's a no-brainer...but here I am, watching myself try to grow a generalist consulting business for marketing agencies, not self-aware of my own positioning sin.

I'm proud, nonetheless, for recognizing this as another lesson and not giving up.

Or maybe I'm stupid enough to think that now, NOW, I've figured out what was wrong and will finally get it "right" this time.

I'm recruiting you to help me confirm that I'm heading in a better direction.

I'm making a small-but-meaningful change.

I'm retiring the "general scaling consultant" hat to focus exclusively on the problem I'm uniquely built to solve: the messy, human challenges that actually stall agency growth.

No more general advice. I'm doubling down on what I do best: acting as a fractional Agency People Officer to help founders build resilient teams, train their next generation of leaders, and fix the cultural issues that lead to burnout.

These are the kind of issues I love to solve: Decision-making, burnout, leadership rituals, imposter syndrome, fixing team culture, entrepreneurial dread, remote work, and more.

As a first step in this new direction, I've completely rewritten my story to reflect this focus. I would be honored if you'd take a look.

My business birthday is next week, and this is just the first of several changes I'll be rolling out. Your feedback on this first step would mean the world: feel free to reply to this email with your thoughts or slide into my DMs on the social platform of your choice.


A TL;DR from the CRO

We all go through change and it changes us, just like a good grooming.

-Roman Noodles, Chief Ruff Officer


On Monday the 6th (four days before the birthday), there will be a full moon. Whenever a full moon was due, I often jokingly reminded people to put out their crystals to charge in the full moon light.

I don't really think some mystical energy reflected off the moon's regolith is going to get stored in crystalline structures created by glaciers millions of years ago...

...but I like the idea of it.

I like the imagery of capturing a special power that only comes around every 28 days and then using that power to give me a little extra vim and vigor for whatever I'm trying to achieve.

Again: I do not believe it's actually doing anything, but I kinda want to manifest the feeling that this woo-woo ritual can conjure.

With this pivot, I could use some extra vim from the moon.

So the other big question you can answer alongside your feedback on my brand refresh:

Which crystals are the best for capturing and harnessing full moon energy?

Asking for a friend,

Dan from Learn to Scale


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PS. What they never tell you when you're eleven is that you're also...

Dan Newman

Entrepreneur, Professional Learner, & Proud Failure. Writes about sales, marketing, and entrepreneurship from the eyes of a learning and development nerd. Lead teams, manage people, scale a business, and learn better through the biweekly irreverent newsletter, the TL;DR.

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