The Three Questions That Actually Matter When Making Big Decisions

I used to be the worst decision maker you'd ever meet. Seriously. I once spent three weeks deciding whether to switch email providers. Three. Weeks. For email.

I tried everything. Pro/con lists that went on for pages. SWOT analyses for personal decisions. I even bought one of those decision matrix apps. You know what they all had in common? They made simple decisions complicated and hard decisions impossible.

Then I missed out on the opportunity of a lifetime because I was too busy analyzing it to death. A partnership that would have changed my business trajectory. By the time I finished my "thorough evaluation," they'd moved on to someone who could actually make a decision.

The Framework Graveyard

After that disaster, I looked at every major decision I'd made in the past five years. The good ones and the disasters. I wanted to find a pattern.

What I discovered surprised me: The best decisions I'd made were usually the fastest ones. Not impulsive—fast. There's a difference. The worst decisions? The ones I'd agonized over for weeks or months.

"Analysis paralysis isn't about being thorough. It's about being afraid."

The more frameworks I used, the worse my decisions got. Why? Because I was using complexity to avoid responsibility. If the decision went bad, I could blame the framework.

The Three Questions That Changed Everything

I threw out all the frameworks and boiled decision-making down to three questions. That's it. Three. I've used them for everything from hiring decisions to life-changing moves, and they've never let me down.

Question 1: "What's the real downside if I'm wrong?"

Not the catastrophizing, anxiety-driven downside. The actual, realistic worst-case scenario. Write it down. Be specific.

When I was deciding whether to leave my corporate job, my anxiety said the downside was "I'll end up homeless and everyone will think I'm a failure." The real downside? "I'll have to find another job in 6-12 months if it doesn't work out."

One of those is terrifying. The other is manageable. Guess which one was true?

Question 2: "Will I regret not trying more than failing?"

This is the regret minimization framework, stripped down to its essence. When you're 80, looking back, what will you regret more—taking the shot and missing, or never taking it at all?

I've never met someone who deeply regretted trying something that didn't work out. I've met plenty who regret not trying.

Question 3: "Am I making this decision from fear or from opportunity?"

This is the killer. Most bad decisions come from fear. Fear of missing out, fear of looking stupid, fear of losing what you have. Fear makes you play defense when you should be playing offense.

Opportunity-based decisions have a different energy. They're about building something, not protecting something. They expand your world instead of shrinking it.

What This Actually Looks Like in Practice

Last month, I had to decide whether to invest $50K in a new business venture. Old me would have created spreadsheets, called advisors, and probably missed the opportunity. Here's how it actually went:

• Real downside? I lose $50K. Painful but not life-ending. I've recovered from worse.
• Regret factor? High. This was a chance to work with people I respect on something meaningful.
• Fear or opportunity? Pure opportunity. I wasn't running from something, I was running toward something.

Decision made in 24 hours. Not because I was reckless, but because the three questions gave me clarity.

The Part Nobody Talks About

This framework isn't magic. It won't make all your decisions correct. What it will do is make them yours.

The hardest part isn't answering the questions—it's being honest with yourself when you do. It's admitting when you're driven by fear. It's acknowledging the real downside might be smaller than your ego wants to admit.

Also, this doesn't work for every decision. Choosing a health insurance plan? Use a spreadsheet. Deciding whether to have kids? Maybe talk to more than three questions. But for business decisions, career moves, and opportunity choices? These three questions cut through the noise.

Looking Back (And Forward)

I still occasionally catch myself overcomplicating decisions. Old habits die hard. But when I notice it happening, I stop and ask the three questions.

The partnership I missed out on all those years ago? The founders sold the company for eight figures two years later. That lesson cost me millions. But it also taught me that perfect decisions are the enemy of good decisions.

Now I make decisions in days, not months. Some don't work out. Most do. But they're all mine, and I can live with that.