Three lessons from a mastermind, the science of why we keep feeding what almost works, and one card to run this week.
· 6 min read
I just got back from a mastermind, and one line from Eric Zimmer has been sitting in my head since.
"You can never get enough of something that almost works."
He said it is a saying from addiction medicine. I have been sober since May 15, 2015, so I felt that one in my chest. But he was not talking about substances. He was talking about everything.
The things that almost worked
I have a list. Things I tried in my business that almost worked. I kept trying. I kept tweaking. I kept telling myself it was close.
None of them ever scaled the way I wanted.
Here is what I know now, sitting with it honestly: I knew internally why. Every one of those ideas was out of alignment. I was forcing something my gut already knew was wrong, and calling the effort hard.
Nothing ever took off until I locked in on Hard or Wrong and Send It. The thing that was actually mine. The thing I could not stop doing even when nobody was watching.
You probably have a list too. I will not ask you to read me yours. I will ask you to be honest about what is on it.
Why we keep feeding it
There is a name for this. Psychologists call it the sunk cost effect. In the classic study, people were asked about a failing project.
When they were told millions were already spent, most said keep funding it. When they were told nothing had been spent yet, most said walk away. Same project. The only difference was what was already sunk.
That is the almost-works trap. The more you have fed it, the harder it is to admit it is not food.
The lab version of this has been argued about for decades. Fair enough. But you do not need a lab to see the pattern. You have your list.
Getting out of my own head
The second thing the mastermind handed me was a mirror, held by Laura Gassner Otting.
I have been walking around with this belief that I needed a physical deck of cards before I could take Send It to corporate. A real, hold-it-in-your-hands deck. That is what a launch looks like, right?
Laura looked at me like, no. That is just hesitation. Corporate is going to want digital anyway.
She was right, and I knew she was right the second she said it. I was using the physical deck as a reason to wait.
Then I told her I was thinking about offering the first session for free, and she said, absolutely not. Why was I assuming people would not want to pay for it?
Fair question. I had no good answer.
Planning is the most intelligent way to procrastinate
So here is what I am doing now. I am done negotiating with my own limiting beliefs about this. I am taking Send It to teams and companies, digital-first, paid from day one. This only works at scale. Selling a deck of cards one at a time is not the business. The business is getting rooms full of people to play the game, over and over.
Michael Bungay Stanier opened the day with a question for the whole room: what is quietly whispering to you from the future? Mine was not quiet at all. Yo, I got to go B2B. I know I have to. Being guided through the whole day by people like that was amazing.
And I am going to build that part in public. All of it. The workflows, the processes, the ups, the downs, the ideas that win and the ones that do not. I will show you how I am making it work, and how I use AI to help.
But I want to be clear about something: AI is not the center of this business. I got clear on who I am first. Now AI amplifies that and makes it easier. Most of the actual work happens in person.
The ONE Thing
Jay Papasan, the author of The ONE Thing, was in the room too. His book has a line I have known for years: until the one thing is done, everything else is just a distraction.
My one thing right now is booking my first corporate training. That is the quest. Everything else is a distraction until that is done.
This is where I have to really focus instead of just filtering. Filtering is saying no to bad ideas, or to opportunities I was never going to take in the first place. That is easy. Focusing is saying no to things I would actually like to do, because something larger needs the energy and the thought.
For me, that something larger is the corporate work.
And to be clear: I do want to sell these cards to individuals. But at the volume that would take, I would need to run ads or greatly increase my audience, and I do not feel like doing more right now. I know I have enough. I want to embrace the essentialism approach and do less, but better.
What keeps me honest
Michael Bungay Stanier, the Coaching Habit author, put a question on the table from his book, The Slippery Weasels Guide to Kind Accountability. The question: what kind of accountability is typically how you have worked in the past?
I gave him three honest answers.
One: fear of going back to who I was before I quit drinking. That is why I work out so hard. It is also why I am not lazy at work. I want to be a hard worker because I do not want to not be a hard worker.
Two: fear of failing publicly at that image. I built a life I am proud of, and I do not want to embarrass it.
Three: I do stuff I love. I show up at the gym because now I love it. Creating content, working out, helping people, talking to people. These are things I actually love doing. Showing up is easy when the showing up is the reward.
Here is the part I want you to hear. My best-performing content has always been the vulnerable stuff about my past. The drinking. Losing everything. Starting over. You already know those stories.
Now I want to get vulnerable about what is happening in the future. Not in a read-my-diary way. In a let-me-help-you-out way. I am building this thing in real time, and I am going to show you the whole thing. The wins and the misses. Because the miss you see me own might be the one that saves you six months.
That is going to be a lot of fun.
You're wrong about your limits
For years, the science said willpower works like a battery. Resist the cookies now, make worse decisions later. It was called ego depletion, and it gave every one of us a perfect excuse: I'm too drained for the big thing.
Then 23 labs ran the biggest replication ever attempted, over 2,000 people, and found nothing. The battery might not exist, at least not the way we were told.
So the next time you tell yourself you don't have the energy for the larger thing, check the story. You probably have more in the tank than the old science gave you credit for.
What you will actually regret
Two researchers, Gilovich and Medvec, spent years studying regret. Their finding: in the short term we regret the things we did. In the long term we regret the things we did not do. The failed attempt fades. The chance you never took sticks around.
So the kill is not the thing to fear. The kill is the thing you will be glad you did.
This week's card: WHAT ALMOST WORKS
Name one thing in your business that almost works. The thing you keep feeding because it is close. Now run it.
What is the goal? Is it hard, or is it wrong? What is the move?
Keep what is hard. Kill what is wrong. Then send it.
Play guide: Write the thing down. Do not pick the safe one. Run the three questions on it, out loud, to someone who will not let you lie. Then post the card and tell me what you are killing. Report the kills, not just the wins.
Now it is your turn. What almost works in your world?
Originally published in Better Problems on LinkedIn.