Sometimes You Have to Take One Step Back to Take Two Steps Forward

I had one of those moments this week that every owner dreads and needs.

I got the first demo of OwnerRx from my developer. Months of work. Tons of excitement. Finally seeing it come to life.

And my first thought was: "This is kind of boring."

The Gut Check Moment

I was testing the initial assessment I'd built back in February – something I hadn't really looked at in months. As I clicked through it, I realized I didn't love it.

That's a problem when you're building something you want tens of thousands of people to use.

So I did what I always do when I'm stuck: I called in my Board of Titans.

The Board of Titans Breakthrough

The Board of Titans is a GPT I built that gives you advice from six legendary founders, each bringing a different perspective: Bezos on customer obsession, Jobs on design thinking, Buffett on moats, Frank Slootman on execution, etc.

I explained what I was trying to do with the app. Then the Jobs character said something that stopped me cold:

“Our assessment should feel like an interactive story, not a survey."

Holy shit. That's it.

Then I thought, “Make the assessment feel like the unfolding of the owner's story as they're taking it."

The Reframe

My original assessment was just business questions. Boring. Functional. Forgettable.

But what if it told a story? What if taking the assessment felt like uncovering your unique journey as an owner?

I'd been working on owner energy separately – helping people identify what gives them juice versus what drains them. Suddenly I realized: these things need to be together.

The assessment of your business AND the assessment of your energy. One story.

The Rebuild

I went back to the drawing board. Completely rebuilt the assessment. Instead of just focusing on energy or just business metrics, I created something that weaves them together.

Now it doesn't just tell you where your business stands. It identifies patterns: "This business is in a no-growth slump" or "This business is ready to scale" or "This owner is burning out."

Then I rethought the entire notification system. How do we keep people coming back daily? How do we make each interaction valuable?

The Developer Call

Friday morning I met with my developers expecting to deliver bad news about delays.

Instead, they said: "This is way better. And because of how we built it, it's not a huge delay."

Sometimes good architecture saves your ass when you need to pivot.

The Forcing Function Trap

Here's what I learned: There's a difference between "don't let perfect be the enemy of good" and "don't ignore your gut when something feels wrong."

We're always under pressure to ship. To get something out. To hit deadlines.

And most of the time, that pressure is good. It forces decisions. It prevents endless tinkering.

But sometimes you hit a moment where your gut says "this isn't right" and you have to listen.

How do you know when to push through versus when to step back?

Ask yourself:

• Am I forcing this because of external pressure or because it's actually right?

• If I saw this for the first time today, would I be excited about it?

• What's my gut telling me when I strip away all the sunk cost thinking?

• Is this solving the real problem or just a symptom?