Derek Jeter wearing a hat

Meet Derek Jeter

Derek joined the American Family Insurance brand ambassador family after retiring from the game in 2014, inspiring dreamers everywhere.

Welcoming Derek to the Family

a man wearing a hat

Achieving Your Goals

When you hear the name “Derek Jeter” what do you think of? You might think about a signature blue and white striped jersey with the number two on it, some of the countless records and awards he’s earned. Not only is Derek Jeter one of the top professional baseball players, he’s also dedicated to philanthropic work including his own charitable foundation and the business ventures he’s undertaken, including being the CEO of a professional baseball team. But what do all of these things have in common? They all demonstrate Derek’s leadership on and off the baseball diamond! Derek joined the American Family Insurance brand ambassador family after retiring from the game in 2014, inspiring dreamers everywhere.

Learn more about Derek and his dream pursuit (and achievements) and see why he’s an inspiration for dreamers everywhere.
Blue doodle of quotation marks
When it comes to pursuing your dream, don’t let anyone outwork you, don’t let anyone tell you that you can’t achieve it, surround yourself with a great support group and believe in your dream. You have to believe it! - Derek Jeter

About Derek Jeter

To achieve a dream, you have to work at it.

Kathy Ireland: This is American Family Insurance ambassador, Kathy Ireland, welcoming you as we break through to dream fearlessly.

On screen: Break / Through logo, presented by American Family Insurance.

Kathy Ireland: Please welcome, to Break Through, Mr. Derek Jeter. Welcome, Derek.

Derek Jeter: Thank you. Thank you very much. Thanks for having me.

Kathy Ireland: Derek, there's a legendary story about you being away from home, the first time, being very homesick. And it was a time where you could either break down or break through.

Can you share with us how you chose to break through?

Derek Jeter: I was drafted when I was 17. I left the day after my 18th birthday and, really, the only time I've been away from home was when I went to see my grandparents in New Jersey.

So, here I was going from Michigan down to Tampa, Florida, and struggling for the first time because, I never really struggled before.

Kathy Ireland: What was the struggle?

Derek Jeter: I got there and I was completely overmatched playing against the best players in the world. And constant phone calls at night, crying every night, being away from home, homesick — I didn't give up. I kept fighting, kept battling. And, you know, anytime I struggled from that point forward, I always used to say to myself, well, it's not as bad as when I first started.

So, you need to experience success, but I think, more importantly, you need to experience failure.

Kathy Ireland: Right — right. So, what would you say to a young person who is going through similar struggles and considering just giving it up?

Derek Jeter: Keep fighting. You know, you have to have a short memory. And everyone's been there. And if they're telling you that they haven't, then it hasn't meant enough to them and they're not telling you the truth.

Kathy Ireland: Derek, Sharlie shared with me that she was diagnosed with cancer in her senior year of college. And so many families are facing that tragedy. What can you share that will inspire, and encourage, people who are going through such challenges.

Derek Jeter: Yeah, my sister — right before her 21st birthday — she was diagnosed with cancer. And when I was growing up, you heard someone had cancer, it was an automatic death sentence.

Kathy Ireland: Terrifying.

Derek Jeter: And that was it. But her strength that she had, instead of taking time off and going through her treatments, she wanted to have her treatments and still continue to go through school. I thought that it was very powerful. I thought it was encouraging to me. But she fought hard.

And, you know, just to be there as a family. I miss my sister — I left when she was in the eighth grade — so I wasn't home when she went through high school, and then she's dealing with this. And you know, I'm in New York playing. So, we had a lot of phone calls at night. A lot of conversations that went very, very late. But any time I would struggle, I'd always say, well, how can I complain about what I'm doing on the field when I have my sister that's battling cancer?

Hard Work Pays Off

Derek Jeter grew up in Michigan with a dream of making it to the big leagues. But Derek understood from a young age that wanting something to happen is never enough. To achieve a dream, you have to work at it.

And work at it he did! Derek remained focused through high school, college and finally the minor leagues before making his baseball debut at the professional level in 1995. But even with his winning mindset and eagerness to succeed, Derek still faced obstacles along his dream pursuit.

At just 18 years old, Derek had to deal with being homesick and experienced self-doubt as he faced challenges in the minor leagues. He broke through this adversity and learned that sometimes your failures can be just as valuable as your successes when it comes to achieving your dreams.

Throughout his 20-year professional career at shortstop, Derek never stopped working to accomplish the next feat, the next goal or the next championship. His hard work paid off, and Derek’s legacy will live in baseball history forever as a 2020 Hall of Fame Inductee.

But Derek’s leadership didn’t stop off the field. He was CEO and part owner of a professional baseball team from 2017 to 2022.

 

 

Blue doodle of quotation marks
Being a good leader means putting what you say to action, and more importantly, get to know who you are leading. – Derek Jeter

Derek Jeter's Foundation

logo, company name

Turn 2 Foundation

Derek also used his ability to motivate and lead others through philanthropy and charity work with his very own foundation Turn 2 Foundation. The Turn 2 Foundation is an initiative started by Derek and his father with the dream to encourage young people to turn away from substance abuse and “Turn 2” healthy lifestyle choices.

Inspire Leadership

Ready to become the leader you’ve always dreamed of becoming? Check out these leadership resources inspired by influential individuals like Derek.
a hand holding a red and white card with a white symbol on it

10 Skills of Effective Leaders in the Workplace

From communicating effectively to delegating work, we’ve developed a list of 10 essential leadership skills with tips to help you strengthen each one.
a close-up of a laptop

How to be an Effective Nonprofit Board Member

Volunteering on a nonprofit board could be what you’re looking for! It’s a great, hands-on way to make a real difference in your community and grow certain skillsets.
a group of people looking at a laptop

Stop Networking, Start Connecting

Networking — it’s an activity that even the most extroverted among us dread. Although the idea behind it seems promising, the way in which we go about it can feel unnatural and uncomfortable.

Meet Our Other American Family Insurance Brand Ambassadors

Now that you’ve met Derek Jeter, consider meeting the rest of the family! Learn more about how they help us inspire dreamers everywhere.
Jonathan Silver Scott, Jonathan Silver Scott smiling

The Scott Brothers

Drew and Jonathan Scott are dedicated to designing and creating safe, quality homes for people all across the county. Learn how these charismatic brothers have inspired millions to dream big, roll up their sleeves and turn houses into homes.
Learn More
a baseball player holding a bat

Christian Yelich

Making it to the big leagues in baseball takes more than athleticism or skill — Christian Yelich had to stay disciplined, humble and persevere to achieve his dream. Here’s how he worked his way to the top and the lessons he learned along the way.
Learn More
Kathy Ireland with long hair

Kathy Ireland

When one of the biggest supermodels in the world decided she wanted to launch her new business with branded socks, many said it couldn’t be done. Learn how Kathy blocked out the naysayers and grew her company to become a multibillion-dollar brand.
Learn More
Steve Stricker wearing a white hat

Steve Stricker

Steve Stricker may be known for his successful golf career, spanning over 25 years, but what makes Steve an inspiration to all dreamers is what he does on and off the green. Learn about Steve's dream journey and how he's used his success to give back to others.
Learn More