Leadership

How I make difficult decisions when there isn’t an obvious right answer

How I make difficult decisions when there isn’t an obvious right answer

Some decisions are easy because one option is clearly better. The difficult ones aren't like that. Both choices have upside. Both have risk. You can build a convincing argument for either one, which is exactly why you've been thinking about it for three weeks. I've had to make plenty of those decisions—as a founder, executive, business owner, employer, and person trying to figure out my own next chapter. I don't have a formula that guarantees the right answer. I do have a process that helps me get clearer.

Some decisions are easy because one option is clearly better. The difficult ones aren't like that. Both choices have upside. Both have risk. You can build a convincing argument for either one, which is exactly why you've been thinking about it for three weeks. I've had to make plenty of those decisions—as a founder, executive, business owner, employer, and person trying to figure out my own next chapter. I don't have a formula that guarantees the right answer. I do have a process that helps me get clearer.

Separate facts from fear

I start by writing down what I actually know.

Not what I think might happen.

Not the worst-case scenario my brain created at 2 a.m.

What do I know?

Then I write down what I'm assuming.

Seeing those two lists separately can change the entire decision.

Ask what each option costs

We tend to focus on what we'll gain.

I also want to know what I'm choosing to give up.

If I take this opportunity, what becomes harder?

If I stay, what am I sacrificing?

If I start the company, what does it require from my family, finances, and time?

If I make the career change, what security am I giving up?

Every meaningful decision has a cost.

Pretending otherwise doesn't make the decision better.

Decide which consequences are reversible

This has helped me enormously.

Some decisions feel permanent but aren't.

You can take a job and leave.

You can test a business idea before committing everything.

You can try consulting.

You can take three months to explore something.

When a decision is reversible, I try to lower the pressure and gather information through action.

Pay attention to the answer you're secretly hoping for

Sometimes I ask myself:

If someone I completely trusted told me Option A was definitely the right choice, would I feel relieved or disappointed?

That reaction is information.

It doesn't mean you should blindly follow it.

But it's worth understanding.

Stop looking for an option with no downside

This is where people get stuck.

They're waiting for one option to become obviously correct.

Often it won't.

Choosing one career means not choosing another.

Starting your own business means accepting risks that employment may not have.

Staying somewhere safe can mean giving up an opportunity to grow.

The goal isn't to find the choice with no downside.

It's to decide which combination of upside, downside, risk, and possibility you're most willing to live with.

Think about the person making the decision

Finally, I ask:

Which choice feels more aligned with the person I'm becoming, not just the person I've been?

That question matters because our decisions often lag behind our lives.

We keep choosing based on priorities, identities, and fears that made sense five years ago.

Sometimes the hardest part of a decision isn't figuring out which option is better.

It's admitting that what you want has changed.

And when there truly isn't an obvious right answer, I don't think the goal is certainty.

The goal is enough clarity to choose—and enough trust in yourself to handle what happens next.

Want to talk it through?

Want to talk it through?

You don’t need all the answers before you begin. We can start with a real conversation about what’s next.

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