Doubt Plague

I’ve sat across the table from an opportunity that looked perfect on paper, where

• the numbers made sense,

• the timing felt right,

• and everyone around me was nodding.

So I moved, fast & decisively… and I got burned for it.

I was left crawling from the wreckage of that opportunity, trying to figure out what happened.

The opportunity wasn’t the problem, so what was?

The answer was both simpler, and harder, to admit: I didn’t stop long enough to ask myself 1 question, “What could go wrong?”

Here’s what I’ve had to learn the hard way (more than once if I’m honest): if you can’t name what could go wrong, you don’t have a plan.

“What could go wrong?” is the question most founders skip past, even though most of them know deep down that it matters.

Founders skip the question because asking it feels like they’re doubting themselves and their ability to make decisions decisively.

And in business culture, doubt’s treated like the plague.

Founders are left to protect themselves and the people they lead from getting the “doubt plague”.

I’ve seen founders walk into decisions like they’re bulletproof, their chests puffed out, voice steady, and delusionally convinced they’re about to make the right call.

And some of them got the call right (even a broken clock is right twice a day). Most though were being arrogantly ignorant… they were steering blind.

I’ve been that founder too, the one who ignored the itchy feeling at the back of his head. That uncomfortable, nagging feeling that something wasn’t right, and pushed forward anyway.

Feeling confident about a decision, and being prepared for it, aren’t the same thing (not even close).

Confidence is an emotion. Preparation is a discipline.

When founders mistake confidence for preparation, they don’t find out they were wrong in a meeting or on a spreadsheet.

They’ll find out the way I did, when the whole thing comes crashing down on them like a tower of bricks.

Founders take medication to keep the doubt plague out. Their medication is being bold, backing themselves, and being decisive.

But if you look closer at these founders, you realise their medication comes with some nasty side effects:

1. they treat questions as weakness, because naming what could fail feels like admitting it might,

2. they build a whole identity around never flinching and always moving,

3. they let their pride, ego and arrogance do the thinking for them instead of strategising,

4. and they sell decisions to themselves by justifying them, explaining them away and smoothing over the parts that don’t quite fit.

None of those side effects make them feel like they’re getting sicker… they feel like their medication’s working.

The decision gets made, everyone’s nodding, and the risk no one names just sits there… and waits.

Then, 3 months down the line, with everything committed, the risk shows up, leaving the founder with

• no plan B,

• no breathing room,

• and no good options,

only damage control.

I’ve taken the same medication. I know the side effects. Pride, ego, arrogance… they drove my decisions.

There was no strategy and no rationale behind my decisions. Just my unwillingness to admit that maybe, just maybe, I didn’t think this next decision all the way through.

Then I realised something that changed how I make every decision: the right decisions are the ones where you don’t need to convince yourself you’re making the right decision.

Bulletproof founders will read that statement and still swear by their medication, and they’ll push back hard:

“Doubt spreads! If you stop to list everything that could go wrong, you’ll talk yourself and your whole team out of every deal worth doing.”

And I’d push back just as hard.

I’ve made moves that looked reckless from the outside, but those moves were backed by preparation, by understanding and by a genuine willingness to be wrong.

But knowing the difference between a calculated risk and a gamble isn’t catching the doubt plague.

If you sit down and name the risks right there on the table, and strategise your game plan, you cure your doubt plague.

And doing so is what earns me the right to back myself with genuine confidence, instead of medication.

Because if you can’t name what could go wrong, you don’t have a plan.

Before you make your next decision, ask yourself 1 question: “What could go wrong?”

Try it this week, on the next decision you’re about to commit to.

Name what could go wrong specifically, concretely and honestly. “It might not work out” doesn’t count as an answer.

You don’t need a massive risk register or a consultant running a workshop for this.

Sit down, on your own or with your team, leave your ego at the door, and name the things that could break your current game plan.

If you’ve felt that itchy, nagging feeling that something isn’t right, the feeling is usually the question trying to get your attention.

And if asking the question feels like catching the doubt plague, that’s probably just your withdrawal talking.

Once you can name those risks, they stop being threats to your plan. You can plan for them, build around them, or decide, with your eyes open, that you’re willing to accept them.

When you can’t name the risks, whatever you commit next (your money, your time, or your reputation) could be riding on a guess.

Guesses don’t build businesses. They break them.