What Would You Do if You Knew You Could Not Fail?

Most of us have a dream that we are too afraid to pursue.

The question, “What would you do if you knew you could not fail?” is meant to bring that dream out in the open.

It’s a powerful thought experiment that can help you turn your life around. It’s also a bit scary.

Learn how you can overcome your fear of failure and why your passion is probably hiding in plain sight.

Factors To Consider

So, what would you do if you could not fail? Here are the most important factors to consider.

1. What Energizes You?

For every person, there are certain activities that infuse them with energy.

For my teenage me, it was playing a concert with my band. I have gotten a similar rush from talking to attractive strangers. These days, having coaching calls with clients gets me excited.

These energy-infusing activities are going to be different for everybody. The trick is learning to observe yourself. Whenever you get flooded with positive emotions, take a mental note. Whatever you just did is a contender for your one thing in life.

It’s important to be honest with yourself. What energizes you won’t always be flattering. For instance, all of the examples I gave about myself point to a high level of vanity. I enjoy being admired.

Morals don’t play into it, though. Whatever gets the juices flowing goes on the list.

2. What Did You Love as a Child?

As children, there was no ambiguity — we automatically did what we loved.

Your job then is to pick up where you left off.

However, what you loved back then was probably a premature manifestation of your passion. Still, it holds important clues.

For example, my first passion in life was reading. Between the age of 7 and 13, all I did was devour one tome after another.

But reading was just the seed activity. It was really about exposing myself to new, daring ideas. Eventually, I came to realize I should create content around such ideas myself.

You must revisit these formative years. Ask yourself:

  • What used to excite me?
  • What would make me forget the world around me?
  • What would I spend hours on?
  • What would the adults around me comment on? (“He is such a bookworm.”)

Uncover these clues and you will be rewarded with clarity. You will come to realize what “it” is that you should be doing.

3. Do You Love the Thing — Or the Idea of the Thing?

We fall in love with certain jobs from a distance. But there is a difference between fantasizing about a certain job and actually doing it.

The pro athlete who is always on pain medication is probably not enjoying himself as much as you think. Nor is the star pianist who is practicing the same few Chopin pieces for 6 hours a day.

For a while, I was entertaining notions of running a large agency and becoming filthy rich. I would imagine all the trappings of success — the penthouse, the parties, the women.

But the truth is, I am not cut out for it. I hate managing large teams. I would much rather be free.

So, when considering, “What would you do if you could not fail?” don’t be misled by what looks sexy on paper. Rather, think about who you are — your temperament, your inclinations.

Go with what actually makes you feel good, not some fantasy.

4. How Much Attention Do You Crave?

Different jobs come with different levels of attention.

If you become the next Eminem, you will receive a lot of attention. If you were to become a scientist, you would receive noticeably less attention.

It also matters whom you want to impress. Your bourgeois parents might applaud your cancer research but not your freestyling skills.

Be honest with yourself. If you want to enrapture the masses (or your parents), choose a profession that is suitable for that.

5. What About Money?

Different jobs come with different payouts.

You are more likely to make lots of money with a tech startup than as a freelance yoga instructor.

And while I am all for prioritizing passion over money, you still need to eat. Money is always going to be part of the equation.

What It Really Comes Down To

“What would you do if you knew you could not fail?” is a great thought experiment. But it is also a bit misleading.

The real question is not if you will fail or succeed. You will succeed at almost anything if you put the work in.

The real question is what level of success you will be content with.

When I was younger, I had aspirations of becoming a guitar hero. For several years, I would practice for four hours each day, never missing a day, even birthdays or Christmas.

However, I had little talent. I was making progress, but much less compared to other areas in my life.

I am positive that if I had given music another 10 to 15 years, I would have eventually been able to make a living from it. But I would never have excelled at it. I would never have become the next Jon Petrucci.

This is what you need to ask yourself — if I lack the natural talent for a certain activity, will I be alright with being decent at it, but never great?

For me, in the end, it was more enjoyable to choose a field that allowed me to blend passion with talent.

Fear of Failure

The question, “What would you do if you knew you could not fail?” implies that we don’t undertake our most meaningful work because we are afraid we might not succeed.

Enter Daniel.

Daniel’s life seems perfect. He has a Ph.D., works for a pharmaceutical company, and makes great money. His family is proud of him.

But deep down, he has a nagging feeling that he is missing out on something. Because before Daniel turned to science as a career, he used to draw underground comic books. And it was the best feeling in the world.

But could he have made a living from that? He doubts it. The market for artsy comic books is small, so only a few artists get to do this full-time.

Yet, on many Monday mornings, he wonders, “Could I have pulled it off?”

That’s the dilemma we are all facing — the uncertainty. If Daniel knew he would have made it, he would now be holding a pencil instead of a Bunsen burner.

Why Are We So Risk-Averse?

“What would you do if you knew you could not fail?” is about fear of failure. But why do we fear failure so much?

There are three reasons for that:

  1. Not wanting to waste resources
  2. Not wanting to let people down
  3. Not wanting to lose applause

1. Not Wanting To Waste Resources

Life is a game of limited resources. If you invest your limited time, energy, and money in the wrong project, you are going to lose.

Let’s say Daniel spends the next 10 years going to art school and building a reputation as an independent comic artist. Unfortunately, it does not pan out in the end.

As a result, he is now 50 years old and unlikely to find another high-paying job in science. He also has about $50,000 in student debt.

He will now be working low-level service jobs for the rest of his life, trying to pay his debt off. Not a great prospect.

2. Not Wanting To Let People Down

If Daniel went full in on the comic thing and didn’t make it, the people around him would be disappointed in him.

“You threw it all away — for what?”

Some people, like his parents or his wife, might become downright hostile.

They invested in him. His parents paid his way through graduate school. His wife chose Daniel over other attractive suitors when she was at her sexual peak. These investments have now been lost.

Daniel will get to feel their disapproval.

3. Not Wanting To Lose Applause

Daniel will also lose the applause he is currently getting.

At this moment, Daniel has parents who are proud of him. His wife considers him a good “catch.” His friends from college tell him he made it. When strangers learn that he has a Ph.D., they look at him with respect.

All of this feels very good.

But if he left his current career and started drawing comic books, that applause would fade. Even if he did make it as an underground comic artist, the best he could hope for might be a few nerds celebrating him at Comic-Con.

Your Choices Have Consequences

Fear of failure is not some irrational impulse. When you stray from the trodden path, there are risks to face.

Van Gogh comes to mind. He took a risk and became a painter when he was already 27. It didn’t go well. He was notoriously broke, misunderstood by many of his contemporaries, and sold very few paintings during his lifetime. Eventually, he killed himself.

Granted, that is an extreme example. You probably won’t shoot yourself in the chest if you don’t make it as a yoga influencer or a guitar hero. But you might have to move back in with your parents and work at Starbucks. Also not great.

For every choice we make, there is a price to pay. Asking, “What would you do if you could not fail?” should not make light of that fact.

Go For It Anyway

Having said that, what is the alternative? Is it worth foregoing your dream by avoiding all risks? I would argue not.

The dying notoriously come to regret their caution. They will lament that they always played it safe.

Vice versa, you will come to cherish the risks you took.

I observed this firsthand with my German grandmother, who was an adventurous woman in her youth. When she was dying of lung edema, the one thing that would pull her out of her misery was reminiscing about her travels.

There were risks then too. Traveling communist Russia or exploring LA as a female solo traveler in the 1970s, she could have easily gotten robbed or worse. She knew these dangers but did it anyway.

Understand — anything worthwhile comes with risks. If you think big enough, there is a good chance that you might fail.

But in the face of death, it’s still better to have tried. And if you do succeed with your dream, you will exult over it until your last breath.

How To Overcome Fear of Failure

Here are five strategies to deal with your fear of failure.

1. Frame Failure as a Steppingstone

Embrace failure. You hast just learned one more way that doesn’t work. This will improve future decisions.

2. Outline the Worst Possible Outcome

We tend to blow the consequences of failure out of proportion.

To counteract this, write down what the worst possible outcome of your quest might be. In many instances, it won’t be that bad.

3. Remind Yourself of Your Mortality

Once you are dead, within a short few years, you will be forgotten. It will be like you never existed.

What sounds depressing at first is actually a blessing. It means you are free to try whatever you want. Since your successes and failures alike will be forgotten, you might as well go for it.

4. Enjoy the Process

It is tempting to fixate on the outcome, the success you are aspiring to. But if you learn to enjoy the process that will be reward in itself.

If you draw comic books for the next 10 years and in the end do not become an iconic artist, you will probably still have had a lot of fun along the way.

5. Stop Playing the Age Card

Many people are worried about age. “I am already 38, I am too old. I should have started earlier. “

Understand — 10 years from now, you will think the same thing. “Oh, I should have started when I was still in my 30s.”

Stop playing the age card. Ray Kroc was 52 when he started McDonald’s. If he was able to start a multi-billion dollar business at that age, you can still become a yoga influencer.

Where Did This Thought Experiment Originate?

The question, “What would you do if you knew you could not fail?” is often attributed to First Lady Eleanor Roosevelt, but actually goes back to American pastor Robert H. Schuller.

In a self-help book published in 1973, he asked the reader, “What goals would you be setting for yourself if you knew you could not fail?” Variations of this question appeared in Schuller’s subsequent works.

Regina Dugan, at the time director of the Defense Advanced Research Projects Agency (DARPA), popularized this thought experiment in a TED talk she gave in 2012. However, she came at it from a technology angle, not a personal development angle.

The Wrong Way To Look at This

The question “What would you do if you knew you could not fail?” is meant to help you find your one thing in life, your work of passion.

But ask this question, and most people will resort to avoidance strategies. Let’s look at these, so we don’t fall for them.

Category 1 — The Philosophers

One camp is concerned with life gone easy. “If I could succeed at anything, there would be no sense of accomplishment.”

And while this is technically true, it is beside the point. The question is meant to help you find your calling, not speculate about alternative realities.

Category 2 — The Idealists

This group of people would solve the energy crisis, end world hunger, and cure cancer.

These are certainly noble goals. But after making the world a better place, you would still not know what to do with your life.

Category 3 — The Multitaskers

“I would start the next Facebook, get ripped, climb Mount Everest, date Margot Robbie, and record a platinum album.”

“What would you do if you knew you could not fail?” is not about succeeding at 100 different things.

It is meant to bring more focus to your life. What is the one thing you would do if you could not fail? That’s where it gets interesting.

Category 4 — The Bank Robbers

Predictably, most people, if they could not fail, start thinking about robbing banks and having threesomes with models.

Here, the avoidance strategy is hedonism. And while sex and drugs are undoubtedly enjoyable pastimes, they don’t provide long-term fulfillment.

If an Employer Asks You This in an Interview

“What would you do if you knew you could not fail?” is also a popular question in job interviews.

If you answered truthfully, you would probably have to say, “Not this crap here.”

But this is not about the truth; it is about what your future employer wants to hear.

So, play the game.

“If I could absolutely not fail, I would find a solution for the energy crisis, as I consider that the most pressing issue of our times. That’s why it’s important for me to work here at [company X] since you are well known for advocating sustainability.”

Of course, you will have to tailor your reply to the company you are applying to. But the formula is the same. First, make yourself look good. Second, flatter them.

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