How to Get the Most Out of Your Failures


Rick Carabba
If failing is cool... consider me Miles Davis! (Billy Madison voice)
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Updated On: 
Oct 15, 2020
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Everyone fails.

Not everyone is a failure.

When you fail you feel embarrassed, depressed, like you’d rather jump off a cliff then have others see you fail.

However, failing is the best thing you can do to succeed.

Many greats are quoted saying that they credit their successes to their failures: Michael Jordan, Oprah Winfrey, Thomas Edison, J.K. Rowling.

You’re in good company.

The more you try the more you fail, the more you fail the more you learn, the more you learn the more you’ll succeed.

So how do we reframe our failures from “embarrassment and fear” to “embracement and success”?

Reframing a “Failure”

The dictionary says to “fail” means:

to be unsuccessful in achieving one’s goal.

This is the definition we’ve been working with since the 1600s.

In the past 400 years what we’ve learned about failing has changed drastically. The irony is that in order to succeed, we need to fail, and fail a lot.

“Success is stumbling from failure to failure with no loss of enthusiasm.” — Winston Churchill

So what is a “failure”?

A failure is the inevitable first step to accomplish something. A failure is an opportunity to learn.

To fail is to try. To try is to learn. To learn is to succeed.

Many people think that failing is losing. However it’s actually the opposite.

3 Assets You Gain From Failures


“The only real mistake is the one from which we learn nothing.” — Henry Ford

Every time you try something, you need to identify what it is you’re trying to learn. Consider a simple example: Asking someone on a date.

When you first ask someone, you have an idea of what you’re going to say. The guy that asks a different girl on a date every day of the week is inevitably going to become a master at asking girls on dates.

He may fail early on but his success rate is only going to improve with each iteration. In his failures he’s going to learn what worked and what didn’t work. What you say and what you don’t say. What they like to hear and what they don’t like to hear.

With each iteration you’ll sharpen your approach, your delivery, and your message. Ultimately stacking these many failures on top of each other and gaining information out of each one on how to improve will lead to success.

It’s your job to get the right information out of every failure.


The Dictionary describes “confidence” as:

A belief or conviction that an outcome will be favorable. Belief in the certainty of something.

Confidence comes from being able to predict an outcome with a high level of certainty.

When you fail repeatedly at something you start to gain confidence. I know this sounds backwards but consider our date example. The first time you muster up the courage to ask someone on a date, you have an idea of what to say (whether it works or not).

Your confidence may dip slightly in the beginning if you get rejected. However now you have information on how to improve. The next time you ask someone on a date you’ll be able to implement what you learned and predict how it will go.

Part of the fear that comes with trying something is in the unknown of what could happen. As you continuously fail and learn the unknowns start to disappear.

With each iteration your ability to predict the outcome will increase and so will your confidence.


When you fail you gain experience. We use experience as the metric to grade skills, knowledge and worth.

You are valued by the sum of your experiences.

Take your resume for example. It’s a total of all your best experiences.

Under each experience on your resume you provide metrics from your performance, skills you acquired, and knowledge you gained.

Experiences grant credibility, authority, knowledge, and validation of skills. We are our experiences.

You can’t get experience until you fail. Until you try something.

Experience is earned. With each new experience you earn, you gain access to more opportunities.

Opportunities that only someone “experienced” can get.

Experiences stack up on top of each other like bricks building a house.

So when you attempt something new, keep in mind what you’re trying to learn, what skills you’re trying to acquire, and how you’re going to use those new assets to build up to your goals.

5 Steps to Plan a Successful Failure

I believe that if you know how to design your “failure” then you will never truly fail.

The assets you gain will always outweigh the cost of failing with successful preparation.

Step 1: Define

Define what you’re trying to learn. You need to go into your attempts knowing what information you’re trying to get out. You’ll use this information to design the next “more successful” failure.

Step 2: Do a Negative Visualization Exercise.

Visualize all the ways in which it could go wrong. All the ways it won’t work. Then write them down. Ask “What does the worst possible situation look like? Would I be able to handle that?”

The reality is that 9/10 times, the worst thing that could happen is not as bad as we think. Pull those hesitations and fears out of your mind, slap them on paper, and call them what they really are, “nonsense”.

If the fears that survive that test actually hold some weight, plan for them. Ask “What can I do to ensure that these scenarios can’t happen?” or "How can I reduce the damage if they do?".

Step 3: Crowdsource

Talk to people who are doing what you’re trying to do. If you’re trying to start a business talk to the people who are successful in your industry. Tell them what you’re setting out to do, ask what common failures and pitfalls to look for.

Ask them about your hesitations from step 2. They’ll have some insight.

Incorporate the learning into your plan.

Step 4: Act

This step need not be longer than a couple sentences. Go do what you’re trying to achieve and get the information you need to improve.

Step 5: Recalibrate

“Failure is only the opportunity to begin again, only this time more wisely.” — Henry Ford

Analyze the information that you got, reflect on what worked and what didn’t. Recalibrate your plan with the newfound information then try again.

Each attempt will get you closer to your ultimate goal.

Go Fail

If you plan for your failures this way you will never truly fail. The only failure is not learning from each failure and using that learning to adapt and try again.

Failing is an opportunity.

Your opportunity diminishes every day you wait and compounds every day you act.

Don’t overdue the planning, the learnings from failing will allow you to improve faster than if you would have spent that time planning.

Time is of the essence. Go fail.

“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” — Michael Jordan
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Rick Carabba is the Author.