I could have started Piper Co 18 months ago.

I didn't.

I wasn't sure what I wanted to do, so I kept taking executive roles I didn't want. For 18 months, I ran scenarios in my head. Talked myself out of things. Talked myself back in. Reread the same notes. Rewrote the same offer page I never shipped.

Rumination masquerading as strategy.

The tell is always the same. You say "I need to think about it." What you actually need is a decision, by a deadline, that you've been avoiding because committing to it feels worse than being stuck.

There's a name for this disease. And I see some version of it in almost every founder I work with. Including, obviously, myself.

My name is Chris. (Hi, Chris.) And I'm a chronic overthinker.

Been that way since I was a kid. Learned behavior from growing up in an environment where mistakes were expensive. You learn to play every scenario forward before you move. It keeps you safe. And it slows you down for the rest of your life.

A few years ago, a friend reframed it. I was walking him through some business situation, mapping out scenarios and downstream effects, diving a few levels deeper than anyone asked me to, and he stopped me.

"You're not an overthinker. You're a methodical thinker."

That was a gift. "Overthinker" carries shame. Implies something broken. "Methodical thinker" sounds like a feature, not a bug.

But is calling overthinking "methodical thinking" really different from calling alcoholism "committed drinking"?

Two sides to the same coin.

Upside: I don't make many stupid decisions.

Downside: I've paralyzed myself for weeks on decisions that deserved about 11 seconds.

Methodical thinking, at its worst, assigns the same weight to every decision. The $200k strategic hire and the email subject line get a similar rumination cycle. A pricing restructure and which Notion template to use get the same analysis treatment.

When everything requires the full process, one of two things happens. You slow to a crawl. Or you avoid. The task sits... idle but open... because engaging with it means committing to finishing the thinking.

When I finally decided to launch Piper Co, I did it in a weekend.

Updated my LinkedIn. Published an offer page on Notion. Sent out a few texts. That was the launch.

A week later, I had a basic website and this newsletter. $800 all-in. Didn't obsess over positioning, messaging, UX, or what platform to use. Fuck it, ship. (The site is... fine. I'm not proud of how it looks. I'll redo it when there's a business reason to.)

Why the sudden speed?

My daughter was two months from arriving. Could've come early. "Let me think about it for awhile" was no longer a sentence I could finish.

The newborn was my deadline. And the deadline did what a year of thinking couldn't: forced a decision.

Here's the part that still annoys me. The tech debt I created, the imperfect brand, the website I still wince at... none of it mattered. Literally no one cared. There are a million reasons shipping ugly was the right call.

The thinking I did for over a year added nothing that the first month of actually operating didn't teach me 10x faster.

So what's the fix? Underthinking?

Nope. I work with companies on that end of the spectrum too. Different flavor, same dead-end.

The chronic underthinker moves fast and calls it "strategy". Every decision gets treated like it's disposable. Every new data point becomes a reason to change course. Every meeting ends with a new plan that doesn't resemble last week's.

One company I worked with was growing toward eight figures. Smart founders. Good team. But every quarter brought a new answer to the same question: what is this company, actually?

New positioning. New offer architecture. New core metric. New agency to fix the new thing. The strategy deck got rewritten so often the team stopped internalizing it.

Each pivot made sense in isolation. But nobody in the company could cleanly describe what the business actually was, because the answer kept moving.

One of the co-founders said it plainly in a session: "We're not really sitting with the problem long enough."

He wasn't wrong.

The cost wasn't just the money, although there was plenty of that. Each pivot came with a rebuild. New tools and briefs, new people to run the new thing. And every pivot burned a little more of the team's faith that this time was the time.

Nothing stayed in market long enough to produce real signal. Nothing stayed in the company long enough for anyone to master it. That's a tough environment to succeed in.

Shiny Object Syndrome isn't about objects. It's about moving before you have enough signal to tell if the last move was right.

The overthinker can't close a loop.

The underthinker can't let a loop stay open long enough to learn from it.

Same ceiling. Different route to get there.

There's a mental model I come back to constantly. Credited to Bezos for years now.

One-way doors are decisions you can't reverse. Or at least can't reverse without real cost to money, reputation, or relationships. Shutting down a product line. Signing a long-term lease. Letting your head of sales go. These deserve the full methodical process. Sit with them. Think through the second and third-order effects.

Two-way doors are decisions you can undo. Contractor not working out? Find another. Tried a new offer page and it flopped? Change it this afternoon.

More decisions are two-way doors than you think. Nearly everything that eats your calendar... tactical calls, small hires, messaging tweaks, pricing tests... can be reversed if they turn out wrong.

The problem is when you apply the wrong weight to the wrong door.

My 1.5 years of not launching Piper Co? I was treating a two-way door like a one-way door. A LinkedIn headline, a Notion offer page, a website I could rebuild in a weekend... all reversible. The monster in my head was a framing problem, not a real one.

The founder pivoting every 30 days? Treating every door like a two-way door. Churning through hires, burning through positioning, eroding customer trust. Some of those decisions had consequences he couldn't walk back.

Both are mistakes. Opposite directions.

I still catch myself spiraling on a decision I should've made weeks ago. Or sitting on something I know I need to do.

When I notice it, I ask one question.

Is this a one-way door, or a two-way door?

If it's two-way (and most things are), I probably already know enough to walk through it. The additional analysis isn't making the decision better. It's making me feel better about not making it.

Methodical thinking is a genuine asset. I'll take it over the alternative most days.

But it needs a filter. Without one, it quietly kills your business over the course of a year you can't get back.

You have to make decisions.

Inaction is never an option if you want to win.

— Chris Piper