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The greatest attribute of an entrepreneur is often their achilles heel.

Mine was decisiveness. In startup circles, "analysis paralysis" is the insult reserved for people who think too much and act too little.

I avoided overthinking like the plague, yet found myself a victim of a different disease = being a lazy thinker.

The big problem with under-thinking strategic decisions isn’t the short-term impact. It’s that the cost of a wrong decision compounds and shows up 6–12 months later, when it’s almost impossible to reverse course.

That's exactly how my last start-up, DealBuilder, ended up with five products with almost zero revenue. We would have a “great” idea, often accompanied by a “How hard could it be?” question. After a few minutes of deliberations we’d go, “I don't really see the downside” and get to work. This process makes me cringe when I think back on it.

Our delusional optimism came from failing to use a simple framework - best put by Jeff Bezos: one-way door and two-way door decisions.

A two-way door decision is easily reversible. For example: changing your company logo. If your customers hate the logo, it’s pretty easy to revert back to the original (take note: Jaguar).

A one-way door decision is hard or impossible to reverse. Lowering your pricing (good luck raising it back) or the big ones: taking on a business partner, signing a long-term lease, or selling your company.

Bezos says to walk through two-way doors with speed and comfort, and to treat one-way doors slowly, deliberately, and carefully.

Our mistake at DealBuilder was treating every door as a two-way door.

This is a mistake I have been desperate to avoid with Breakwater. We have been deliberate in slowing our growth - to ensure sustainability of our core operating model. At each pivot turn over the last year, we’ve tested whether the decision we are making is a 1-way or 2-way door.

So how do you test this? We’ve found the best filter is a one-sentence test.

Explain the idea to a colleague and let them ask one question: "What's the end goal?" If you stammer out a long-winded answer with four different objectives, you're off track. If you can answer in one confident sentence, you might be onto something:

In contrast, when I ask many business owners, “What would be the purpose of that decision?” many do not have a concrete answer. I'm guilty of this more than anyone.

This is what I've spent the past year doing at Breakwater. Deep, slow, deliberate thinking on the one-way doors. My younger self would have laughed at it as overthinking… which is also why my younger self was broke 😅

You should answer every big decision in your business within a single sentence. If you can't, your thinking is half-baked, which is the fastest way to go broke.

I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that's of interest, make sure to subscribe:

Credit: ideabrowser.com

DoorLog - the decision registry for SMB operators

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14-minute AMRAP:

Strength + conditioning. 5 rounds:

Rest 2 minutes between rounds.

Clip breaking down the 1-way vs. 2-way door framework:

every second counts