How's Your Relationship With Failure?

Scott Asai
April 29, 2025

Not exactly motivational content, right? But hear me out…

Fact: the most successful people don’t fail less, they fail more.

How is that possible?

Because they don’t let failure stop them from trying again.

One of my favorite quotes is:

“No risk. No reward.”

If you don’t try, it’s impossible to succeed.

Now I’m not saying to fail on purpose.

But I am saying fail with purpose.

Use is as a learning opportunity, a teachable moment.

You see, most people don’t like the sting of making mistakes (who does?), so they stop trying.

Yet the cost of doing nothing is high.

Some perceive avoiding risk as playing it safe.

I understand risk management.

Taking calculated risks is different than being reckless.

But allowing your past to dictate your future is dangerous.

(I promise this is not a therapy session.)

I’ve made plenty of mistakes in life (I will continue to make more), but I try to learn and not repeat them again.

As a parent, my wife and I allow our kids to try different activities.

If they commit to something, we expect them to complete the season then they can stop if they choose.

I mean how else are they going to figure out what they truly have a passion and strengths for?

The common theme here is: learning through trial and error.

We’d all love to succeed on the first try, but that rarely happens.

Let’s use metrics from professional sports as context:

If you translate those to grades in school, they’d all be failures.

The real takeaway here is: how do you respond to failure?

As a leader, how you deal with failure on a personal level will dictate how you teach it to others on a professional level.

People will follow your example.

Understand, most victories are preceded by losses.

Often life hits you at a crossroad, then you have to make an important decision.

Keep going or stop.

In some instances, the wise move is to pivot in a new direction.

But that presupposes you processed the information, then used that data to move forward.

See, it’s still your response to failure that determines your future.

So now it’s time to evaluate your relationship with failure.

How you respond to it will make you or break you.

If you felt like this post was speaking to you (I needed to hear this too) reply to this email and let me know.

God Bless,

P.S. Want to know what great leaders do?👇