There’s one question that can make almost any big decision significantly harder: What if I fail?

You can be excited about an opportunity, know that part of you wants to take it, and see all the ways it could make your life better. Then you start thinking about what happens if it doesn’t work.

What if I take the job and regret it? What if I try something new and I’m not good at it? What if I give up something comfortable for an opportunity that goes nowhere?

Suddenly, the decision isn’t about what you want anymore. It’s about avoiding the possibility of getting it wrong.

I’m dealing with that right now. I have a decision to make, and one of the biggest things making it difficult isn’t that I don’t see the potential upside. It’s that I can also imagine what happens if I take the chance and fail.

The more I’ve thought about it, though, the more I’ve realized that fear of failure might be influencing the decision more than failure itself should.

Why Does Fear of Failure Make Decisions So Hard?

Failure is uncomfortable because it doesn’t just feel like an outcome. Sometimes we turn it into a judgment about ourselves.

If I take this opportunity and it doesn’t work, what does that say about me? If I try and I’m not successful, was I wrong to think I could do it in the first place?

That’s almost exactly where my mind went during this decision.

As I said in the episode:

“What will that say about me or where will that put me then?”

That’s a much bigger question than whether an opportunity works out. Now you’re attaching your identity to the outcome.

The American Psychological Association defines fear of failure as anxiety about not meeting a goal or standard, often accompanied by concerns about the consequences of failing. When those consequences start feeling enormous, avoiding the decision altogether can seem safer than risking the possibility of being wrong.

But not trying doesn’t necessarily protect you from regret. It just gives you a different kind of uncertainty to live with.

Separate Failure From the Worst-Case Scenario

One of the first things I think you have to do is define what “failure” would actually mean.

We use the word so broadly that it can start representing every negative outcome imaginable. You take a new job and don’t like it. Failure. You start something that doesn’t become successful. Failure. You take a chance and eventually decide it wasn’t right for you. Failure.

But are those actually failures?

Maybe you take the job, realize it isn’t what you expected, and find another one. Maybe the thing you start doesn’t work, but you meet someone through it who leads you somewhere else. Maybe you try something for six months and discover that you don’t want it nearly as much as you thought you did.

Those outcomes might be disappointing. They aren’t necessarily catastrophic.

Fear can take a possibility and turn it into a permanent future. Before you let that future determine your decision, ask what would actually happen if the thing you’re afraid of happened.

A lot of the time, you’d deal with it.

Ask What Happens If You Don’t Try

Fear of failure naturally makes us focus on one side of the decision.

What happens if I try and it goes badly?

That’s a fair question. But there’s another side that deserves just as much attention:

What happens if I don’t try?

Maybe nothing happens. Maybe you stay where you are and you’re genuinely happy that you did.

Or maybe six months from now you’re still wondering where the opportunity could have taken you.

This is one of the biggest things I’ve been thinking about in my own situation.

“If I, you know, don't even give myself the chance to try, then I'll never even give myself the chance to fail.”

Failure is only one possible cost.

Regret can be another.

The goal isn’t to scare yourself into taking every opportunity. It’s to make sure you’re evaluating both sides instead of allowing fear to make the decision automatically.

Figure Out Whether You Don’t Want It or You’re Scared of It

This distinction has been really helpful for me.

Sometimes you don’t take an opportunity because you genuinely don’t want it. Maybe it doesn’t align with your goals, the timing is wrong, the downside is too significant, or you simply prefer what you already have.

Those are legitimate reasons to say no.

But sometimes you want something and immediately start constructing reasons you shouldn’t do it because wanting it means accepting uncertainty.

Ask yourself: If I knew I couldn’t fail, what would I choose?

That hypothetical shouldn’t make the decision for you because failure is possible. But your immediate answer can tell you something about what’s driving your hesitation.

If removing failure completely changes what you want to do, then fear probably has a pretty significant role in the decision.

That’s also why How To Overcome Analysis Paralysis matters here. Once fear enters the equation, you can spend endless amounts of time trying to find enough information to guarantee that nothing will go wrong.

That guarantee probably isn’t coming.

Stop Treating Failure Like a Final Outcome

We tend to tell stories about failure as if they end immediately after the bad part.

You take the risk.

It doesn’t work.

The end.

Real life keeps going.

You respond to what happened. You learn something. You make another decision. Maybe you try again. Maybe you change direction entirely.

Research on resilience from the American Psychological Association emphasizes adaptation in the face of adversity rather than the complete avoidance of difficult experiences. That distinction matters because the goal of making a decision isn’t to create a life where nothing ever goes wrong.

That’s impossible.

The goal is to become somebody who trusts himself to deal with things when they do.

Think About What Failure Would Give You

Obviously, nobody takes an opportunity because they’re hoping to fail.

You want it to work.

But if it doesn’t, you probably still leave with something you didn’t have before. You might have more experience, more information, a better understanding of what you want, new relationships, or proof that something you thought you wanted actually isn’t for you.

That’s what I keep coming back to with my decision.

“If I try and I fail, then then at least I have that experience of trying.”

I don’t think we give enough value to that experience.

Trying something gives you information that thinking about it never can. You can imagine how something will feel for months, but actually doing it might teach you more in a week.

Failure can hurt and still be useful.

Both can be true.

Don’t Confuse Fear With a Warning

Being scared doesn’t automatically mean you shouldn’t do something.

Sometimes fear is a legitimate warning. If a decision could put you in serious financial trouble, damage an important relationship, jeopardize your safety, or create consequences you genuinely can’t absorb, you should take those risks seriously.

But fear can also simply mean you’re leaving something familiar.

The Cleveland Clinic notes that fear of failure can contribute to analysis paralysis, where worrying about making the wrong choice makes it harder to make any choice at all.

That’s why it helps to ask what exactly you’re afraid of.

Is there a specific consequence that you need to address before moving forward? Or are you uncomfortable because you can’t guarantee the outcome?

One is a problem you might be able to solve.

The other is uncertainty you might have to accept.

Talk to Someone Who Knows You

When you’ve spent too long thinking about a decision, your own arguments can start sounding equally convincing.

That’s when I think you should talk to somebody.

A close friend, sibling, parent, partner, mentor, or somebody else you trust might be able to recognize something you can’t see because you’re too close to the situation.

You don’t have to ask them, “What should I do?” Explain the decision, explain what you’re afraid of, and see what they notice.

That’s something I’ve written about in How Do I Stop Doing Everything on My Own? You don’t get extra points for figuring out every difficult moment in your life without letting anyone else into it.

Just remember that advice is information, not an instruction.

You still have to make the decision.

Think About Your Future Self

This is probably the exercise that has helped me most with my current decision.

I imagine myself one year from now looking back at the version of me making this choice today.

What would that guy wish I had done?

Maybe he would be glad I didn’t unnecessarily disrupt something that was already going well. Maybe he would tell me that the opportunity wasn’t worth it.

But when I actually imagine him, I keep thinking he’d be more interested in knowing what happened than wondering what could have happened.

That doesn’t mean your future self will tell you to take every risk. It means changing the perspective can help you see past the immediate fear.

The decision that feels enormous today might look very different when you imagine it as one moment within an entire year of your life.

Trust Yourself to Handle Failure

Maybe this is the bigger goal.

Instead of trying to become certain that you won’t fail, become more confident that you can handle it if you do.

Those are completely different things.

One asks you to control the future. The other asks you to trust yourself.

That’s part of what I mean when I talk about How To Gain Confidence As A Man. Confidence isn’t believing everything you attempt will work. If anything, that’s unrealistic.

Confidence is knowing you can try something without having your entire sense of self depend on the outcome.

If it works, great.

If it doesn’t, you’ll be disappointed. You might be frustrated. You might need to change plans.

And then you’ll figure out what to do next.

Remember That Doing Nothing Is Still a Decision

This is easy to forget when you’re scared.

We tend to treat taking the risk as the active decision and staying where we are as the neutral option.

But staying is a choice too.

If you turn down the opportunity, that has an outcome. If you don’t have the conversation, that has an outcome. If you never start the thing because you’re afraid it won’t work, that has an outcome.

Doing nothing might still be the right choice.

The important thing is that you choose it because it’s genuinely what you want, not because fear made it feel like the only safe option.

And Here’s The Thing

You can’t make a decision without accepting the possibility that it might not work.

I wish there were a way around that. I wish you could think about something long enough that eventually you knew exactly what would happen.

You can’t.

You can understand the risks. You can talk to people. You can think about what you actually want and what your future self might wish you had done.

Then eventually you have to choose without knowing the ending.

I’m still working through that myself.

But I keep coming back to the same idea: I’d rather make my decision based on what I want my life to look like than exclusively on what I’m afraid could go wrong.

Maybe I try and fail.

If I do, I’ll have to deal with that.

But at least I'll know what happened.

Frequently Asked Questions

How do I make a decision when I’m afraid of failure?

Identify what you're specifically afraid will happen and separate realistic consequences from hypothetical worst-case scenarios. Then consider both the cost of trying and the potential cost of never trying at all.

Why does fear of failure stop me from making decisions?

Failure involves uncertainty and can feel like a reflection of your abilities or worth. That can make avoiding the decision feel safer, even when doing nothing has consequences of its own.

Should I take a risk if I’m afraid of failing?

Fear alone doesn't mean you should or shouldn't take the risk. Consider the actual downside, whether you can reasonably handle it, what you stand to gain, and whether fear is the primary reason you're holding back.

What if I make a decision and fail?

Failure doesn't have to be the end of the story. You can learn from what happened, adjust your plans, use the experience you gained, and decide what to do next.

How can I stop being so afraid of making the wrong decision?

Stop requiring yourself to guarantee the outcome beforehand. Focus instead on making the best choice you can with the information you have and building confidence that you'll be able to handle what happens afterward.