It's a question that awaits every athlete, but for Chris Bosh it came not with his on-court abilities in decline, but while he was still near the peak of his talents — just 31 years old.
In his acceptance speech Saturday at the Basketball Hall of Fame in Springfield, Mass., the 11-time all-star reflected on being forced to choose between "risking my life every time I stepped on the court or retiring from the game" due to blood clots.
A tough choice for someone who dedicated their life to reaching the pinnacle of the sport — and did so twice with two titles alongside LeBron James and Dwyane Wade with the Miami Heat — but one that taught him an important lesson about life beyond basketball.
"After finally making it to the mountaintop with so much more to do, in my mind, so much more to prove, suddenly it all stopped," he said.
"By now I don't have to tell you there were plenty of tears that day, and in the days since, but in going through those crossroads I eventually came to realize that we all have it in our power to make the most out of every day despite what happens, to turn setbacks into strengths."
Bosh's first battle with blood clots came during the 2015 All-Star Break, when he felt ill during a vacation and was later ruled out for the rest of the season. After returning the following campaign — earning his 11th and final all-star nod — Bosh was diagnosed with a clot in his leg with his final game coming on February 9, 2016.
The fourth pick in the 2003 NBA Draft by the Raptors, Bosh established himself as a star during his first seven seasons in Toronto before forming the "Big Three" with James and Wade in Miami in 2010.
While often playing in the massive shadows cast by James and Wade, Bosh played a pivotal role in the Heat's two championships during the "Big Three" era, highlighted by his rebound and pass to Ray Allen for the unforgettable game-tying three-pointer in Game 6 of the 2013 NBA Finals vs. the San Antonio Spurs as well as his clutch block on a Danny Green three-point try at the buzzer to protect Miami's lead. The Heat won Game 7 for their second straight title.
Bosh averaged 19.2 points, 8.5 rebounds and 1.0 blocks per game over the course of his 13 seasons in the NBA. He was inducted into the Hall of Fame as part of a 16-member class — its biggest ever — alongside Paul Pierce, Jay Wright, Ben Wallace, Rick Adelman, Chris Webber and Yolanda Griffith, among others.