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Building Confidence, Prolonged Failure, & Learning to Hedge Failure
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Wednesday Wisdoms

Building Confidence, Prolonged Failure, & Learning to Hedge Failure

Wednesday Wisdom’s for July 17, 2024

D.A. DiGerolamo's avatar
D.A. DiGerolamo
Jul 17, 2024
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Building Confidence, Prolonged Failure, & Learning to Hedge Failure
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Welcome to Wednesday Wisdom, our 3x3 Newsletter where I distill worldly advice for better living with 3 quotes, 3 observations, and 3 questions.


Building Confidence

🤨 Quote

“The benefit of failure is an objectivity that success simply can't offer. If you win right away—if your first foray into any new area is a runaway success—you'll have absolutely no way to gauge if you're really just that brilliant or it was a total fluke and you got incredibly lucky.”

Maria Konnikova
Source: The Biggest Bluff

Observation 🧐

Sometimes we fear failure because we have not yet built confidence in ourselves, we haven’t yet proven we can overcome the task at hand.

But by starting off with small wins—accomplishing something such as showing up for the meeting you have to present at or practicing for the speech you have to give—you provide yourself small wins which help boost confidence and diminish fear.

More often than not, if we look at our past failures, they were never really as bad as we initially thought they were. Is failure truly such a bad thing? Does fearing failure truly provide anything but regret to our lives?

We often fear more in imagination than in reality the Stoic philosopher Seneca once observed.  

Perhaps it is time we stop fearing failure and instead start counting the “wins” we make on our way toward the thing we fear.

Confidence is only a few wins away.

🤔 Question

What is the number one technique you turn to when you are afraid you’re going to fail?


Prolonged Failure

🤨 Quote

“If failure is a necessary part of change, then the way people understand failure is critical.”

Chip and Dan Heath
Source: Switch

Observation 🧐

We don’t necessarily fear failure itself, but we do fear prolonged failure.

Failing at one thing is a single time, it is a micro-spot on the lifetime of our existence. When we fear of failing, however, we often fear of failing multiple times.

We project into the future a single fear and say to ourselves, “I’ll never not fail at this” or “I’ll never overcome this.”

But these are just internal messages we provide ourself and hold no truth in the matter.

Success does not come with a bang, it comes through small actions that taken as a whole lead to success. It is about small incremental wins that align us for the big wins.

And this is good because it means we can fail at some feats and still succeed at the big stuff. You fail five out of a hundred times, it’s the 95 wins that count.

We lose when we allow a single failure to write our mental models for what we can achieve.

🤔 Question

How do you allow yourself to let go of failure?

What the? A paywall?!

Fear not!, you can read the entire Wednesday Wisdom (and all my premium content including the archives) by dropping a few dollars in the cookie jar🫙

We explore the wisdom of Annie Duke for our final Wednesday Wisdom.

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