The Drive To Succeed

Competitive, resilient and full of heart, Jackie Stiles shares how she's been able to find alignment after a basketball career that took her all the way to the WNBA. Now, her time on the court is on a pickleball court, so we met for a game of pickleball at Classics Yard and a chance to chat.

What was your earliest inspiration?

I knew exactly what I would do. I told my second grade teacher I was going to play professional basketball—and the WNBA didn't exist then. I just had that vision, that basketball is what I was meant to be good at.

Strategic play

I just follow my heart and what I'm passionate about, and then try to make a living from it.

Coach or be coached?

Oh, I love being coached. I love having somebody help me be better than I could be on my own.

What do you like to do when you aren't working?

Pickleball is one of my greatest passions. And I like to do game nights with friends. I love Mexican train dominoes. That's my favorite game because you can socialize, as it's not really intense.

What makes you proud?

I'm proud of making the Final Four for Missouri State, because everybody thought that was an impossible dream. Now it's definitely opening my business. You just have to have the courage to do it if you really are passionate about it. You will learn as you go. Don't be scared that you don't know everything up front, you will learn it. And if you make mistakes, you'll just correct them, and it'll be okay.

Work hack

I can't stand sitting at a computer for hours on end, so I found a way to do all of my emails and business work on my phone [while I'm] on the elliptical. I might spend three hours on the elliptical a day, but I'm also getting my work done and all my emails answered.

Favorite thing about work

I love the relationship with the client. I've just always been curious about other people's stories. I like to know who they are, what makes them happy, and what makes them tick.

Keeping score

I'm the scorekeeper in pickleball. I literally say the score for both teams, but I joke that the score is the only kind of numbers I can keep. My business numbers... who knows? I hate looking at numbers and analyzing those kinds of things. Thank goodness, I have good people.

On her competitive drive

Our strengths are also our weaknesses and my drive is definitely a strength, but it also ended my basketball career. So I have to keep that in check.

Retiring before age 30

I was so focused on being the best basketball player I could be, for years. I was close to 30 when I realized I couldn't play anymore. I had perfected a skill that didn't work for me anymore. In the second half of my career, it's more about significance over success. How can I align my gifts to help the most people? I have always had a huge passion for fitness. And now for the first time in my life, I feel like I'm truly aligned professionally.

Building a team

It's so awesome because that's what sports taught me. It's putting people in positions to do their best work, finding their strengths, and highlighting them. I want to be the boss who helps people love their jobs.

Word to live by

You don't have to be great to serve, but to be great, you must serve. And greatness is not what we have, it's what we give.