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The Power of Accountability
A timeless lesson from a legend

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Now, onto Issue 31.
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3 lessons from The Captain
Derek Jeter’s first contract was worth $0.
It was a contract with his parents.
He signed it every year as a kid.
Before each school year, his parents would outline their expectations.
They’d put them in a contract with clauses such as:
No drugs
No alcohol
No arguing
Respect girls
Meet curfew
And Derek would have to sign it.
If he violated the contract, there’d be no baseball.
Jeter would go on to become “The Captain,” a New York Yankees legend and MLB Hall of Famer.
These contracts are how it started.
This is one of my contracts from high school… my parents were tough negotiators. #TheCaptain
— Derek Jeter (@derekjeter)
2:02 AM • Aug 12, 2022
There are a few timeless lessons we can learn here:
Lesson: Success isn’t an accident
As a kid, Jeter didn’t understand the contracts.
They were a hokey thing his parents did.
But over time, he saw the intention behind them.
“It built the framework for success,” he said.
He learned that successful people aren’t that way on accident.
Lesson: Accountability is nurtured
Everyone would agree accountability is essential.
But you’re not born with it.
It’s a character trait that’s taught and nurtured.
This was the primary purpose of the contracts, Jeter said.
Accountable people become successful people.
Lesson: Stay grounded
Jeter quickly blossomed in baseball.
By 18 years old, he was one of the best prospects in the country.
The Yankees drafted him No. 6 overall in the 1992 draft.
But his parents didn’t let that get to him.
Even as a high school senior, he had to obey the contract or he wouldn’t play.
“It taught us to stay grounded,” Jeter said.
The Power of Accountability
All three of the above lessons are grounded in a common theme:
Accountability.
There are two primary types of accountability:
Accountability to yourself
Accountability to others
Let’s briefly discuss each and how you can develop them.
Being accountable to yourself
Our goals are meaningless without a commitment to do the work.
That commitment is built on personal accountability.
So, how do you develop personal accountability?
A few common strategies:
You can have an accountability partner who helps you stay accountable to yourself
You can make your goals public to create a sense of social pressure to hold you accountable
You can use frameworks like the Eisenhower Matrix to manage more your time effectively
I like to use a concept behavioral psychologists call stimulus control.
My unscientific description of it: your environment influences your behavior.
If I want to be more accountable to my goal of exercise, I need to manage my physical (and digital) environment to remind me of that goal and hold myself accountable.
Scheduling time on my calendar to exercise
Staging my workout area in my home gym
Setting an alarm on my phone to remind me
Whatever strategies you use, being accountable to yourself is essential.
Do what you say you will do, and do that consistently.
Being accountable to others
Being accountable to others creates trust.
Trust is the foundation of all relationships.
In a team, you’re accountable to your teammates
In a family, you’re accountable to your spouse and kids
At work, you’re accountable to colleagues and customers
Specifically, you’re accountable to fulfilling your responsibilities.
When you do this, you become dependable.
Jeter’s contract is an example of him being accountable to his parents (although I’m sure their goal was to develop personal accountability, too).
Training hard during summer conditioning is you being accountable to your teammates
Doing high-quality, detailed and professional work is you being accountable to your customers
Following through on projects is you being accountable to your colleagues
Nobody becomes their best without a team.
Uphold your commitments to others.
Summary
Let’s quickly recap.
3 timeless lessons from Derek Jeter:
Build a framework for success
Hold yourself accountable to it
And stay grounded
These are rooted in personal accountability and being accountable to others.
Build the discipline of being accountable.
Accountable people become successful people.
Teddy’s Recommendations
My favorite biography is The Rise of Theodore Roosevelt by Edmund Morris.
It won the Pulitzer Prize and National Book Award in 1980.
I’m reading it again right now, and it’s reminding me of how great it is.
Roosevelt is one of history’s most fascinating people — can you imagine a sitting president going on hunting trips to the Badlands, and nobody being sure where he is or if he’s alive? — and this book makes him come to life.
It’s a biography that reads like fiction.
If you like reading or learning from world-class people, get this book.
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See you next Sunday.