Could the curtain finally be closing on B.J. Penn’s legendary career? It appears the UFC Hall of Famer is coming to the realization that’s a strong likelihood.

Although Penn (16-14-2 MMA, 12-13-2 UFC) has etched out a legacy that includes becoming the first in UFC history to win titles in two weight classes, the past decade has been an ugly downturn for the former welterweight and lightweight champion.

In the cage, Penn has only struggled. He hasn’t won since a quick knockout of Matt Hughes at UFC 123 in November 2010, and his current seven-fight UFC losing skid is the longest in the promotion’s history. Matters haven’t been better outside of the cage, either, with Penn experiencing a bevy of legal issues, some of which were allegedly violent in nature.

At 41, Penn, who has retired twice before, said the idea of preparing for a high-level fight is a task he’s not currently – and may never again be – ready for.

“It takes a lot of work,” Penn said on a recent Instagram Live chat with longtime coach Jason Parillo. “It takes too much. Too much (expletive) work. At this age, it just takes too much (expletive) work. You never know what’s going to happen, but it takes so much work.”

Penn said that he’s asked daily what his fighting future holds, and it’s always mixed feedback.

“There’s so much people telling me to fight again,” Penn said. “Other people telling me don’t fight again. It’s a lot to take in.”

If Penn were to compete again, it wouldn’t be under the UFC banner. Penn’s most recent incident in February saw him hospitalized after flipping his vehicle in a possible DUI. That came roughly five months after UFC president Dana White finally released Penn from the organization shortly after he was caught on video fighting in the streets of Hawaii.

Following his previous retirements, Penn said he was lured back to the sport because it was one of the few things in life that made him feel fulfilled and happy. It gave him something to work toward, even if he wasn’t getting the winning results.

It appears some of that feeling still remains, because Penn admitted he’s still having a tough time finding his next step after fighting.

“If I can get anything else going it would be nice,” Penn said. “If I could get anything else going in life than just a fist fight, it would be nice. But it’s so fun and I love the process and all those things about it. Then you get in the gym and start doing good with active fighters and next thing you know you’re trying to fight and biting off more than you can chew. You might be, you might not be. But the process itself it’s a lot to just do a camp or whatever.”

Penn most recently competed at UFC 237 in May when he suffered a unanimous decision loss to Clay Guida. There’s a good chance that ends up the last fight of Penn’s career, and if that’s the case, he appears to be content.

Despite still having a part of him that loves to throw fists at another man’s face, Penn has seemingly accepted his position after fighting professionally for more than 19 years.

“I guess when you have something to prove that’s when you can fight the best,” Penn said. “It’s like, ‘Hey man, you already proved yourself.’ It’s not about proving myself, I just really like doing this. But you can’t go out and keep getting hurt. That just don’t make sense to anybody.”