Tottenham striker Harry Kane is at a crossroads and must make sure he does not waste his career, says Teddy Sheringham.
Kane's future has been a source of speculation in recent weeks after he hinted he could leave Spurs if he did not see clear signs of progress in the future.
The England captain has been linked with Manchester United, while Barcelona are claimed to have shown an interest, despite Spurs having no intention of parting with the 26-year-old.
Sheringham made the switch from White Hart Lane to Old Trafford in 1997, a decision that was vindicated by three Premier League titles and Champions League and FA Cup winners' medals, and he believes Kane will have a similar decision to make in the coming years.
"There are similarities [between myself and Harry Kane] but you've got to look at where Tottenham are now compared to where they were when I was playing for them," he added.
"The ambition had been sucked out of the club when I was at Tottenham, we weren't going places. At least with Tottenham now they are challenging for the top four and were in the Champions League final not so long ago.
"Kane has got to weigh up his situation and whether he wants to leave. Is there going to be top players coming to Tottenham to play with him, or is he going to have to go elsewhere to play with top players?
"At the moment, his career at Spurs has been on a steady forward trajectory, but I think he may be at a crossroads. If not this year, if they haven't won anything or don't look like they are going forwards next season, there could be changes.
"Harry has only got one career and he wants to win things. My advice would be that you only get one career, make sure you make the most of it."
Sheringham: Pogba lacking Keane factor
Paul Pogba lacks the Roy Keane factor Manchester United so desperately crave and a replacement with the right mentality and desire must be signed, says Teddy Sheringham.
Former United striker Sheringham appeared on Tuesday's edition of The Football Show to mark the 21st anniversary of the club's Treble-clinching Champions League final victory in 1999.
France international Pogba continues to attract criticism for his performances at Old Trafford and Sheringham says his mentality is holding United back.
"People mention top players and captains," Sheringham told Sky Sports. "When things weren't going right in our time, Roy Keane put things right. He would drive our team on, he would dig deep and make sure we had a say in every game we played in because of his desire.
"When you look at Pogba, yes, he may be a talented boy, but does he have the same mentality? Does he really dig deep and get Manchester United out of the mire when the going gets tough? For me the answer is no.
"He gives off the wrong vibe as a Manchester United player. Yes, it's good to be cocky and arrogant at the right times, Dwight Yorke had that as well, a big smile on his face when he played. But Yorke had a desire to do the right things at the right times. You've got to have that, and I don't think Paul Pogba gives you that.
"He would be one that would need to go so that you can get someone in with the right mentality and desire to drive Manchester United out of the position they are in."