Novak Djokovic reveals toll of continued pursuit of greatness – ‘I feel I am imprisoning myself’

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After winning 24 Grand Slams, Novak Djokovic would be entitled to have a near limitless supply of self-confidence. And yet, in a new documentary on Amazon Prime, the Serbian tennis icon admitted he is his own "number one doubter."

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Nobody has won more Grand Slam singles titles than Djokovic, who is matched only by Margaret Court on 24.

And the 39-year-old achieved most of his success while competing against two of the other all-time tennis greats in Roger Federer and Rafael Nadal.

Federer won 20 Grand Slam titles, while Nadal claimed 22, of which 14 came at the French Open.

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But Djokovic outlasted his two greatest rivals and is still routinely making major semi-finals at almost 40.

But, in a side to him that is rarely seen, Djokovic admitted he is not satisfied with what he has achieved.

"I cannot say I feel content with what I have and who I am," Djokovic said in the Amazon documentary.

"I am always looking to be more - better, faster, stronger. Oftentimes I feel I am imprisoning myself."

He adds: "I'm the number one doubter. I'm trying to prove myself wrong more than anybody else."

In his career thus far, Djokovic has won the Australian Open 10 times, three French Open titles, been crowned Wimbledon champion seven times, and won the US Open on four occasions. He is also an Olympic gold medallist, having beaten Carlos Alcaraz in the men's singles final at the Paris 2024 Games at Roland-Garros.

But the last of his Grand Slams titles came in 2023 and there has been a clear challenge for Djokovic to get over the line against the now dominant duo of Jannik Sinner and Alcaraz.

And Djokovic is realistic. At 39, he is aware he cannot go on forever.

But he also knows nothing other than tennis, the sport he has been at the very top of for almost 20 years.

His wife Jelena, who has been loyally by his side for the majority of his career, with the pair marrying in 2014, adds that as well as doubt, her husband’s hunger will never be satiated.

"He definitely has mixed feelings about his retirement," she said. "He carries that burden that he's never enough.

”No matter how much he does, it will never be enough.

"Tennis is a fulfilling place for him - a place where he feels worthy."

The 2026 US Open represents another big opportunity for Djokovic to do what nobody has ever done before and win a 25th major singles title.

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It was at this very tournament in 2023 that he last got over the line in a Grand Slam, beating Daniil Medvedev in the final at Flushing Meadows.

His recent defeat in the Cincinnati Open did not exactly bode well for glory, but there is a chance that neither Sinner or Alcaraz will be present.

Sinner missed the ATP 1000 event in Cincinnati with a knee injury, while holder Alcaraz has been out of action since suffering a wrist injury at the Barcelona Open in April. That ruled Alcaraz out of the French Open and Wimbledon, with a return date still unknown for the Spaniard.

So, while self-doubt might still linger for Djokovic, the 2026 US Open could yet prove his best chance of getting his hands on that elusive 25th Grand Slam.

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