What Would You Do If You Knew You Couldn't Fail?

"What would you do if you knew you couldn't fail?" is a question that appears on posters, in speeches and in countless coaching sessions. It can sound like a cliché. But used well, it's a powerful tool for discovering what you really want and what's holding you back.

Why the question works

Fear of failure quietly shapes many of our choices. We avoid applying for jobs we might not get, starting projects that might flop or trying activities where we might look foolish. Over time, the list of things we don't attempt can grow longer than the list of things we do.

Asking what you'd do without the possibility of failure temporarily removes that fear, so you can see your wishes more clearly.

Step 1: Write your honest answers

Take ten minutes and write freely. Don't judge or edit. Some prompts:

What would I do with my career?
What would I create?
Where would I live?
What would I learn?
What conversation would I have?
What adventure would I take?

You may be surprised by what comes up. Some answers will be wildly unrealistic; others will be things you could start next week.

Step 2: Notice the themes

Read through your answers. What do they have in common? Perhaps many involve creativity, independence, helping others or adventure. These themes point to values that may be underrepresented in your current life.

Step 3: Separate fear from real risk

Now bring failure back into the picture, but examine it honestly. For one of your answers, ask:

What exactly am I afraid of? Embarrassment, losing money, disappointing others, discovering I'm not good at it?
What's the realistic worst case? How likely is it?
Could I recover from that worst case? How?
What's the cost of not trying?

Often the fear turns out to be about looking foolish or feeling disappointed, which are uncomfortable but survivable. Sometimes the risk is real, such as financial or health risks, and deserves careful planning.

The cost of not trying

Research on regret is relevant here. In an influential 1995 review, psychologists Thomas Gilovich and Victoria Husted Medvec found that in the short term, people tend to regret actions that turned out badly. But over the long term, people more often regret things they didn't do: chances not taken, words not said. Inaction regrets seem to linger.

That doesn't mean every risk is worth taking. It does suggest that the pain of having tried and failed often fades faster than the nagging question "what if?"

Step 4: Design a safe first step

You don't have to leap. Choose one answer and design a small, low-risk first step:

Want to start a business? Sell one product to ten people.
Want to write a novel? Write for fifteen minutes three times a week.
Want to move abroad? Spend a holiday there and research visas.
Want to change careers? Take a short course or shadow someone.

Small steps let you test your dream without betting everything.

Step 5: Reframe failure

Failure is usually less final than it feels. Most failures are temporary, recoverable and full of information. Many people who achieved something meaningful failed along the way. Our overview of J.K. Rowling's speech on failure explores this.

Try this

Write your answers to the question, choose one, identify your biggest fear about it and take one small step this week.

Sources and further reading

Gilovich & Medvec (1995), The experience of regret: what, when, and why, Psychological Review