(briandoddonleadership.com)
One of the hardest decisions any leader ever faces is knowing when to walk away. Whether it is an executive stepping down, a pastor transitioning, a coach resigning, or an athlete retiring, the moment of release carries equal measures of grief and gratitude.
A Hall of Fame Pitcher
Few stories illustrate this tension better than Clayton Kershaw’s decision to retire from Major League Baseball after 18 unforgettable seasons with the Los Angeles Dodgers.
Per this article, one year, 11 months, and 11 days ago, Kershaw believed he was finished. His body was broken. His shoulder required surgery. His pride was wounded after being shelled by the Arizona Diamondbacks in the 2023 postseason. And perhaps most crushing of all, his spirit was drained. Exhaustion replaced joy. Pain replaced passion.
“I’m done,” he told his wife Ellen.
But the next morning, Kershaw went back to work. Why? Because he still loved the game and was not ready to give in to self-pity. His inner standards demanded one more try. That is what leaders do. They rally, recommit, and push forward.
Now, nearly two years later, Kershaw has chosen to walk away — not from a place of despair, but from a place of peace. He will leave the game as one of the greatest pitchers to ever step on a mound. His record includes 220 wins, three Cy Young Awards, an MVP trophy, 11 All-Star appearances, and a World Series championship.
5 Ways for Leaders to Know When it is Time to Walk Away
From Kershaw’s journey, leaders can draw several valuable lessons about knowing when it’s time to walk away.
1. When the Cost Outweighs the Reward
Kershaw’s body absorbed a lifetime of punishment. Herniated discs, damaged elbows, fragile shoulders, even injured toes and knees — each year demanded more than the year before. Leaders, like pitchers, have a finite reservoir of energy. When the physical, emotional, and relational cost begins to outweigh the reward, it may be time to step aside.
2. When You’ve Accomplished the Mission
In 2020, Kershaw finally hoisted the World Series trophy that had eluded him. He checked the last box on his Hall of Fame résumé. Leaders also must ask: Have I done what I came here to do? If the answer is yes, then walking away is not quitting but rather completing the assignment.
3. When You Can Exit with Dignity
Many athletes limp across the finish line. Kershaw did not. In his final year, he went 10–2 with a 3.53 ERA. He was not the dominant ace of his prime, but he was still highly effective. Leaders, too, should strive to leave before their influence wanes to the point of ineffectiveness. Exiting with dignity preserves your legacy and blesses those who follow.
4. When the Organization No Longer Depends on You
The Dodgers’ future rests with younger arms — Shohei Ohtani, Yoshinobu Yamamoto, Blake Snell, Tyler Glasnow. Kershaw recognized the shift. A wise leader does not cling to relevance. Instead, they celebrate the next generation’s rise, cheering them on rather than competing with them.
5. When You Can Walk Away in Peace
The difference between 2023 and 2025 is stark. In 2023, Kershaw considered walking away in bitterness, sorrow, and regret. But in 2025, he chose to retire with joy, satisfaction, and peace. Leaders should aim to leave not when they are broken, but when they are whole — grateful for the journey and hopeful for what lies ahead.
Conclusion – The Value of Legacy
Kershaw’s greatness is not only statistical. It is relational. Former opponents like Paul Goldschmidt, Gerrit Cole, and Madison Bumgarner hailed him as the best pitcher of his generation. Teammates admired his discipline, intensity, and faithfulness to his craft. Younger players studied his habits. The Dodgers relied upon him more heavily than any team relied on any other player. His impact will reverberate in Los Angeles for decades.
Leaders, your legacy is not the trophies you accumulate or the awards you receive. Your legacy is the people you influence, the standards you establish, and the culture you leave behind.