Novak Djokovic is closer to the end of his career than the start as he chases down a collection of incredible milestones

Novak Djokovic finds himself at a career crossroads as he approaches his 38th birthday next month.

The 24-time Grand Slam champion is wrestling with thoughts of retirement whilst pursuing two significant milestones that would further cement his legacy.

Djokovic remains one title shy of his 100th tour-level trophy and is seeking a record-breaking 25th Grand Slam.

The Serb recently missed the chance to reach his century of titles after losing in the Miami Open final just a week ago.

Novak Djokovic missed out on his 100th career title at the Miami OpenReutersDespite recent struggles with motivation, Djokovic’s run to the Miami Open final has renewed his inspiration to continue competing at the highest level.

The current world No. 5 had endured a difficult start to 2025, including a three-match losing streak after the Australian Open in January.

His performance in Miami, though ending in defeat to Jakub Mensik, has silenced some of the doubts in his mind.

“The performances I had in Miami, when I’m playing that way, obviously it gives me more inspiration to keep going,” Djokovic said.

“It just feels great on the court when you’re striking the ball well, when you’re winning matches,” he continued.

The 37-year-old admitted that maintaining motivation has become increasingly difficult.

Novak Djokovic finds himself at a career crossroads as he approaches his 38th birthday next month.

The 24-time Grand Slam champion is wrestling with thoughts of retirement whilst pursuing two significant milestones that would further cement his legacy.

Djokovic remains one title shy of his 100th tour-level trophy and is seeking a record-breaking 25th Grand Slam.

The Serb recently missed the chance to reach his century of titles after losing in the Miami Open final just a week ago.

Novak Djokovic missed out on his 100th career title at the Miami OpenReutersDespite recent struggles with motivation, Djokovic’s run to the Miami Open final has renewed his inspiration to continue competing at the highest level.

The current world No. 5 had endured a difficult start to 2025, including a three-match losing streak after the Australian Open in January.

His performance in Miami, though ending in defeat to Jakub Mensik, has silenced some of the doubts in his mind.

“The performances I had in Miami, when I’m playing that way, obviously it gives me more inspiration to keep going,” Djokovic said.

“It just feels great on the court when you’re striking the ball well, when you’re winning matches,” he continued.

The 37-year-old admitted that maintaining motivation has become increasingly difficult.

“When you start to play less good, start to lose early in the tournament, that’s when more questions appear,” Djokovic revealed.

“More, I guess, inner voices which are bringing doubts and conversations of whether you should keep going and how much and so forth.”

He described his challenge as finding “a nice equilibrium between the professional life and private life.”

Djokovic acknowledges there are those who believe he should retire at his peak.

Novak Djokovic has admitted doubts over his future in tennis

Reuters“I know that there’s a group of people that thinks that I should leave tennis on a high, which I understand,” he said.

Some suggested he should have retired after winning Olympic gold last year in Paris.

“If you tell me I’ll win a 100th title in any of the Slams this year, I’ll sign right away, no problem,” Djokovic stated.

However, he remains confident in his abilities, saying: “I still feel like I have some gas left in the tank.”

Speaking ahead of the Monte Carlo Masters, Djokovic explained his dilemma further.

Novak Djokovic is desperate to win a 100th title

Reuters

“I don’t think I would quit before pushing to achieve my goals, but you never know,” he said on Sunday.

“It’s a big mountain to climb and I’m hoping for the best.”

The Serb now stands as the last actively competing member of tennis’s famed Big 4, following the retirements of Roger Federer, Rafael Nadal, and his current coach Andy Murray.

“I’ve proven that I can still play at a high level,” Djokovic insisted.