What mental models help founders decide between equally good options?

Two Great Options, One Terrible Choice

You've got two options on your desk. Both make sense. Both could work. And you're sitting there staring at them like they're going to magically tell you which one is "right."

I've been there. The weird thing about being a founder is that sometimes too many good options is worse than having one obvious choice. At least with obvious choices, you can just do the thing. With equally good options, you have to actually think.

Why "Equal" Options Are Never Actually Equal

The first thing to understand is that truly equal options don't exist. They just look equal because you're not asking the right questions. Most founders get stuck because they're comparing features instead of comparing consequences.

5 Ways to Think Through Options When Your Brain Won't Pick

1. The "Can I Undo This?" Test

Some decisions are doors. Some are tattoos. Figure out which one you're making.

• If you can easily reverse it, pick fast and adjust later
• If you can't undo it, take time to think it through
• Most founder decisions are doors, not tattoos

2. The "What Am I Giving Up?" Question

Every choice costs you something. The question is what you're willing to lose.

• What opportunities disappear if you pick Option A?
• What about Option B? What goes away?
• Sometimes the thing you're giving up matters more than the thing you're getting

3. The "80-Year-Old Me" Test

This one's cheesy but it works. When you're old and looking back, which choice would you regret not trying?

• You'll regret the chances you didn't take more than the ones you did
• Which option scares you in an exciting way?
• Which one feels safe but boring?

4. The "Math It Out" Approach

Sometimes you need to actually run the numbers instead of just having feelings about it.

• Best case scenario for each option: what's the upside?
• Worst case scenario: what's the downside?
• Most likely scenario: what will probably happen?
• Which numbers you can live with?

5. The "How Would This Fail?" Exercise

Imagine each option went wrong. Really wrong. What would be the most likely reason?

• Which failure would be easier to recover from?
• Which failure would you see coming?
• Which failure would be entirely your fault versus bad luck?

The Questions Most People Don't Ask

Which Option Keeps More Doors Open?

When you can't predict the future, pick the choice that gives you the most options later. Flexibility beats optimization when you don't know what's coming.

Which Option Would Your Team Actually Execute?

The best strategic choice is worthless if your team can't get excited about it. Sometimes the "worse" option wins because people actually want to do it.

Is This the Right Time for Either Option?

Perfect timing beats perfect choices. Sometimes both options are good, but the market isn't ready for either one. Or you're not ready for either one.

When You're Still Stuck After All That

If you've run through these questions and you're still stuck, you might be dealing with decision paralysis, not a decision problem. Sometimes you need someone who isn't emotionally invested to point out the obvious thing you can't see.

Or maybe you're stuck because both options actually are bad, and your brain is trying to save you from making a mistake. That's worth considering too.

FAQ: Choosing Between Good Options

Q: What if I pick the wrong option?

A: Most founder decisions are reversible or adjustable. The real risk isn't picking wrong—it's not picking at all and missing the opportunity entirely.

Q: How long should I spend deciding between options?

A: Set a deadline. If you can't decide within a week of serious thinking, you're probably overthinking it or the options aren't as different as you think.

Q: What if my team disagrees about which option is better?

A: That's normal. Get everyone's input, but make sure someone (preferably you) has final authority. Teams can provide perspective, but founders make decisions.

Q: Should I always pick the less risky option?

A: Not always. Early stage companies often need to take bigger risks to create bigger opportunities. The "safe" choice might be the riskiest long-term choice.