There are some decisions where you know what to do almost immediately. Then there are the decisions where you can spend days thinking about every possible outcome and somehow end up even less sure than when you started.

I’m in the second kind right now.

I have a decision in front of me where I can make a legitimate argument for both sides. I can explain why taking the opportunity could be great, and five minutes later I can give you an equally convincing explanation for why staying where I am makes more sense.

The question I keep coming back to is probably the same one you’ve asked yourself before: How do I know if I’m making the right decision?

I’m starting to think the answer is that sometimes you don’t.

There Might Not Be a Right Decision

This is probably the hardest thing to accept when you’re trying to decide what to do.

We want there to be a correct answer. If we think long enough, research enough, and ask enough people, eventually we’ll uncover the option that guarantees everything works out.

But most meaningful decisions don’t work that way.

You don’t know exactly what a new job will be like until you take it. You don’t know whether moving somewhere new will make you happier until you live there. You don’t know exactly what will happen if you take an opportunity, end a relationship, start something new, or leave something behind.

“There's really no right answer of what you do with your life or what you decide or what decision you make. There really only ever is what you do with that decision.”

I think that gets closer to the reality of making big decisions.

There may not be one path where everything works and another where everything falls apart. There might just be two different paths, each with its own opportunities, problems, and decisions waiting for you.

Stop Asking What Could Go Wrong

When I’m trying to make a big decision, my brain becomes extremely good at generating hypothetical disasters.

What if I do this and it doesn’t work? What if I regret leaving what I already have? What if I screw up something that’s going well? What if I say no and never get another opportunity like this again?

You can do this indefinitely.

That’s where a difficult decision can turn into analysis paralysis. The Cleveland Clinic describes analysis paralysis as overthinking a decision to the point that you struggle to actually make a choice. Fear of making the wrong decision can keep you searching for certainty that may never come.

There’s nothing wrong with considering what could go wrong. You should understand the legitimate risks of a decision.

But eventually you have to give equal attention to another question:

What could go right?

Maybe you take the opportunity and it opens doors you didn’t know existed. Maybe you try something new and discover you’re really good at it. Maybe the thing you’re afraid of changing ends up changing for the better.

You don’t know that either.

That’s the point.

Separate the Facts From the Hypotheticals

One thing I’ve noticed while going through this decision is how quickly something that could happen starts feeling like something that will happen.

There are facts about your decision, and then there are predictions.

The job pays this amount. That’s a fact.

You’ll hate the job six months from now. That’s a prediction.

Taking an opportunity requires you to give something else up. That might be a fact.

You’ll regret giving it up forever. That’s a prediction.

Those distinctions matter because anxiety can make hypothetical outcomes feel incredibly real. Psychology Today has written about our tendency to struggle with uncertainty and seek reassurance about outcomes we ultimately can't guarantee.

When you’re deciding what to do, try to separate what you actually know from what your brain is filling in.

You might discover that some of the strongest arguments against your decision aren’t facts at all. They’re fears.

Figure Out What You Actually Want

This sounds obvious until you try to do it.

When you’re making a big decision, your actual preference can quickly get buried underneath everything else. You start thinking about what your parents would do, what your friends think, what looks better, what feels safer, and what you think you’re supposed to want.

Eventually, you can lose track of your own answer.

This is something I’ve explored more broadly in How To Figure Out What You Want to Do With Your Life. You don’t need to have the next ten years mapped out, but knowing what matters to you right now gives you a much better place to make a decision from.

Try stripping everything else away for a second.

If nobody else knew about the decision, what would you choose?

If you knew neither option would end in disaster, which one would you want?

If you weren't afraid of failing, would your answer change?

Those questions aren’t perfect decision-making formulas. They’re ways to figure out how much of your indecision is coming from what you want versus what you fear.

Ask Whether You’re Learning Anything New

There’s a difference between thinking and overthinking.

Thinking gives you something new. Maybe you uncover an important piece of information, recognize a consequence you hadn’t considered, or hear a perspective that genuinely changes how you see the decision.

Overthinking is when you keep feeding the same information through your brain hoping it will eventually produce a different answer.

“One minute I'm kind of like, this is what I should be doing. And then the next I'm like, wait, but what about this?”

If you’ve reached that point, ask yourself whether another day of thinking is actually going to change anything.

If there’s important information you still need, get it.

If there isn’t, you might already know enough to decide.

Think About the Decision From One Year in the Future

One of the most useful things I’ve done with my current decision is imagine myself a year from now.

I try to picture that version of myself looking back at me today. What would he want me to know? What would he wish I had done?

The point isn’t to magically predict how your future self will feel. It’s to create some distance between yourself and the immediate stress of the decision.

Research into temporal distancing has looked at how considering emotional situations from a more distant future perspective can change the way we process them.

When I do that, one thought keeps coming back to me:

“I'm glad I at least tried because now I know what would have happened.”

Your future self might tell you something completely different.

Maybe that version of you is glad you didn’t abandon something good just because another opportunity appeared. Maybe he’s glad you waited. Maybe he wishes you had taken the risk.

The useful question is: Which decision do you think you'd rather have made when you look back at this moment?

Listen to Other People Without Letting Them Decide

I think you should talk to people when you’re making a difficult decision.

I’ve done it throughout this process. Sometimes just explaining what’s happening to someone else forces you to organize the thoughts that have been bouncing around your head.

That’s also why How To Stop Trying to Do Everything on Your Own applies here. Asking someone for perspective isn’t the same thing as asking them to make your decision.

But there’s a limit.

If you ask enough people, eventually somebody will validate every possible option. Then instead of deciding between A and B, you’re deciding whether your friend who said A understands the situation better than your sibling who said B.

That’s just analysis paralysis with more participants.

Get the perspectives you need, especially from people who know you well. Then bring the decision back to yourself.

Ask Which Decision You’re Making Because of Fear

Fear doesn’t automatically mean you shouldn’t do something.

Sometimes fear is useful. If something presents a serious risk to your finances, relationships, safety, or future, you should pay attention to that.

But there’s another kind of fear that simply comes from not knowing what happens next.

Fear of failing. Fear of regretting your decision. Fear of being uncomfortable. Fear of leaving something familiar.

That’s the fear I’ve been wrestling with.

At a certain point, I started asking myself whether I genuinely believed I shouldn’t do something or whether I wanted to avoid it because doing nothing felt safer.

Those are very different reasons.

This is where How To Gain Confidence As A Man becomes relevant too. Confidence isn’t always knowing that something will work. Sometimes it’s trusting yourself enough to act without that guarantee.

Consider Whether the Decision Is Reversible

We have a tendency to treat big decisions as permanent.

Some are. Many aren't.

If you take a job and eventually realize it’s wrong for you, you can look for another job. If you move somewhere and hate it, moving again might be difficult and expensive, but it’s possible. If you try something new and it fails, you can decide what to do with what you learned.

That doesn’t mean decisions don’t have consequences. They obviously do.

It means you should evaluate the actual consequences instead of automatically treating every decision as something that determines the rest of your life.

One decision rarely eliminates your ability to make another one.

Remembering that can take a huge amount of pressure off the choice you’re making today.

Make the Best Decision You Can With What You Know

Eventually, you have to stop.

Stop researching. Stop asking people. Stop creating new hypothetical scenarios. Stop waiting for some final piece of information that will make you completely certain.

You have to make the best decision you can with what you know right now.

That’s an important qualification: with what you know right now.

Six months from now, you’ll know things you couldn't possibly know today. Judging today's decision using tomorrow's information isn't fair.

A good decision can lead to a bad outcome. A questionable decision can sometimes lead somewhere unexpectedly great. You don't control every variable that comes afterward.

What you control is whether you seriously considered your options, understood the risks, listened to yourself, and made the choice that seemed right with the information you had.

And Here’s The Thing

Maybe the better question isn’t “How do I know if I’m making the right decision?”

Maybe it’s “Do I trust myself to handle what happens after I decide?”

Because I’m not sure there’s always a way to know beforehand.

You can think everything through. You can consider the risks. You can ask people you trust. You can imagine what your future self would say and pay attention to what your gut keeps telling you.

Then eventually, you choose.

And once you do, the decision stops being hypothetical. You get new information. You have new experiences. You learn whether the things you were worried about were real and discover things you never could have predicted.

If it works, great.

If it doesn’t, you adjust.

You make another decision.

Maybe knowing you can do that is as close as any of us get to knowing we're making the right one.

Frequently Asked Questions

How do I know if I’m making the right decision?

You may not be able to know with certainty before you make it. Focus on whether the decision makes sense based on the information you have, aligns with what matters to you, and isn't being driven entirely by fear.

Why do I keep second-guessing my decisions?

Second-guessing often happens because you want reassurance that you won't regret your choice. When no option can provide complete certainty, you can get stuck repeatedly reconsidering the same information.

Should I trust my gut when making a big decision?

Your instincts can be useful alongside facts and careful consideration. Pay attention to which option you consistently lean toward once you've separated legitimate risks from hypothetical fears.

What if I make the wrong decision?

A decision that doesn't work out doesn't necessarily mean you ruined anything. You can learn from the outcome, adjust your plans, change direction, and make another decision with information you didn't have before.

How long should I think about a big decision?

Give yourself enough time to understand your options and their meaningful consequences, but notice when thinking stops producing new information. If you're repeatedly analyzing the same possibilities, more time may simply create more overthinking.