The TL;DR: There's A Saboteur Inside Your Success


A bi-weekly roundup of entrepreneurial fears in short form
September 16 - September 29

Fearlessly Promotional

What does your saboteur whisper to you?

When the pandemic first started, I ended up delivering dozens of free workshops to co-working spaces, networking groups, and industry associations as an attempt to get my name out. They needed to provide value to their now-absent communities and I wanted new clients. The workshops were great; people loved them.

Clients closed: zero.

Looking back at some of those workshops, it's partly my fault that I didn't convert anyone into a paying customer. I didn't make it easy or clear as to what attendees should buy. My background in education and internal learning and development didn't teach me how to give away something for free that makes people want more. I didn't know how to effectively sell myself.

When I accepted that this promotional strategy wasn't working, I tried to copy the coaches and gurus who marketed themselves so strongly to me. They're doing something right...right? I'm a fan of failure, so I was open to the possibility that my previous approach was wrong and the gurus were right.

I did a six month program, studied diligently, and marketed myself tenaciously. I followed the instructions. I used the templates and frameworks.

Clients closed: four.

However, there was something that felt wrong. Little clues started to pop up. I wasn't looking forward to my conversations with prospects. I started to see my clients as upsell opportunities, rather than people. The hustle-culture language was coming easier and easier ("Limited time only! Finally feel free! Number seven will shock you!").

There was a middle ground that I sprinted over when going to the other extreme of marketing. I became the gurus that I hated.

Gaze long enough into the abyss, and the abyss gazes into you.

The behavior that was the tipping point was that I became too flexible with my offers. I was trying to chase the deal, rather than be fearlessly confident with my featured service. I would get glowing customer testimonials, but I kept returning to hustle-culture marketing techniques to mask the imposter syndrome-

-that my happy customers were lying to me.

Lord, the mind games we entrepreneurs play on ourselves.

I've walked back from that hustle-culture marketing extreme to a place where my value, my offer, my service, and my social proof are anchored a little bit more firmly in objective data. I'm happy to give away 30 minutes for free, but I'm also happy to let someone walk away when my real work is more expensive than free. I've survived long enough to start to see those not-now leads are coming back with the realization that you get what you pay for (and when you pay for nothing, you get nothing).

That voice, though, still whispers. The Forever Empty that knows exactly where your worst fears wait to be triggered.

During the pandemic, I worked closely with two other entrepreneurs and we talked all the time about these kinds of mind games. We dreamed up starting a podcast about having people you could confide in. We met every Friday, virtually, and we would crack open our businesses and psyches to shed light on the anxieties and issues we were facing. It made things a lot easier to process.

One of the things we created was a neat infographic about setting better goals. Number one on the list: Disarm your inner saboteur.

Number three will shock you.


A TL;DR from the CRO

My biggest deep-seated daily anxiety is what's for dinner.

-Roman Noodles, Chief Ruff Officer


New Blog Post: Building or Outsourcing Learning & Development

What are the pros and cons of building vs buying your organization’s next training initiative? Employee engagement, cost, exclusivity, time, effectiveness, business impact, and more.


ROCK TUMBLING UPDATE:

When I was digging up the photo at the top of this email from my archives, I realized that I don't share many pictures of my "setup" for my day-to-day work. In that vein, here's what my rock tumbling setup looks like in my basement:

  • The white pellets- that's the ceramic media- helps cushion and wear away the rough edges on rocks.
  • The black round container is the tumbler, where the stones, water, and the ceramic media go to rumble-rumble for a week at a time.
  • I usually drain the rock sludge from a used tumbler outside, using the red strainer (though in the winter I might throw it off the second floor balcony).
  • The four clear tubs with black dust in them? That's the grit- four stages, from rough to fine, that helps polish the stones.
  • When I'm transitioning stones between the 3rd and 4th stage, I usually brush them with the toothbrush to clean out all the grit.
  • Oh, and the pink light is from a grow light where I'm trying to keep cacti alive before they end up in terrariums.

Everyone's got weird hobbies, ok? It's not much, but it's honest work.

Go find yourself a dumb hobby,

Dan from Learn to Scale


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PS. That sounds...familiar

Dan Newman

Your agency doesn't have a sales problem. It has a people problem. I spent 15+ years building teams, from scrappy startups, to scaling tech companies, to huge agencies like GroupM and WPP. Now, I give small agency owners the SOPs, frameworks, and hard truths they need to build high-performance cultures that run without them.

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