Master Decisions: The Only Playbook You’ll Need

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Entrepreneurs live and die by their decisions.

Every choice—whether it’s who to hire, what to focus on, or when to scale—shapes your future.

Most decisions aren’t optimized.

You’re either stuck overthinking or rushing in, hoping it works out.

Great decisions aren’t magic. They’re a skill, and skills can be learned.

Let’s get into it.

The Two Paths of Decision-Making

Your brain approaches decisions in two ways: fast and slow.

There’s the quick, gut reaction—the instinct you rely on when picking lunch or answering a simple question.

Then there’s the slower, deliberate process—the one you need for big calls, like launching a product or hiring a key player.

Here’s where most people go wrong: they use the wrong system at the wrong time.

You hire someone because you “feel good” about them, but you didn’t dig into whether they can do the job.

Or you spend weeks over-analyzing a decision that should’ve been made in five minutes.

Smarter decisions happen when you know when to trust your gut and when to slow down.

Low stakes? Trust your instincts.

High stakes? Slow down and think it through.

Why Most Decisions Suck

Your brain is wired to take shortcuts, and those shortcuts sabotage you.

Maybe you rely too much on the first thing you hear—like taking the first price someone offers and assuming it’s fair.

Or you overestimate risk because of one bad experience, even though it’s not likely to happen again.

The worst? Thinking you know more than you do.

These biases are sneaky, but they’re everywhere.

If you don’t catch them, they’ll catch you.

So, the next time you’re making a call, pause and ask yourself:

• Am I assuming something without facts?

• Am I letting one piece of information weigh too heavily on my choice?

• Could someone else see something I’m missing?

This isn’t about being perfect—it’s about catching the big mistakes before they happen.

A Simple Framework for Smarter Choices

Here’s the easiest way to make better decisions:

1. Widen your options. If you’re stuck choosing between A and B, find option C.

2. Test your assumptions. Don’t assume something will work—test it on a small scale first.

3. Create space. Ask yourself, “How will this feel in 10 minutes, 10 months, and 10 years?”

4. Plan to be wrong. Every decision has a chance of failure. Prepare for it upfront.

The biggest mistake entrepreneurs make is rushing into decisions without thinking through alternatives.

Take a beat. Find another path. Think long-term.

Stop Going It Alone

The best decisions aren’t made in a vacuum.

Your team—if you use them right—is your secret weapon.

Most people try to do everything themselves. Bad move.

Bring in people who are smarter than you in key areas and let them challenge your thinking.

If everyone agrees with you all the time, you’ve got a problem.

Encourage people to push back.

They’ll save you from mistakes you didn’t see coming.

Decisions Need Space

If your calendar is jammed with meetings and busywork, good luck making a smart decision.

Big calls require clear thinking—and clear thinking requires time.

Start by auditing your day.

What’s eating up your time that isn’t moving the needle? Cut it.

Then, protect a block of time each day for deep work.

No meetings, no distractions—just you and the decision you’ve been putting off.

Jeff Bezos tackles all his high-stakes decisions first thing in the morning, when his mind is sharpest.

You should too.

The Ultimate Checklist for Smarter Decisions

Before you make your next big choice, run through this checklist:

1. Have I defined the problem clearly?

2. Am I considering all my options—or just the obvious ones?

3. What assumptions am I making, and are they true?

4. What’s the worst-case scenario, and am I ready for it?

5. Have I asked someone else for their perspective?

6. What does success look like, and how will I measure it?

This takes two minutes but could save you weeks—or even months—of regret.

The Bottom Line

Bad decisions aren’t random.

They happen because you rushed, skipped steps, or let your biases win.

The good news? Smart decisions are a system.

Follow the frameworks, ask the right questions, and you’ll make better choices every time.

Start small. Apply one strategy this week.

Maybe it’s blocking time for deep work or asking your team for input.

Whatever it is, commit to it.

Better decisions aren’t just possible—they’re inevitable when you have the right tools.

P.S: I’m dropping the updated 2025 nootropics list next Wednesday. Don’t miss it!

Explore Further:

• Before You Decide: 3 Steps To Better Decision Making- Matthew Confer