Sherwood's immediate future at White Hart Lane appears bleak as he leads Spurs into their final Barclays Premier League fixture of the season at home to Aston Villa on Sunday.
The 45-year-old has been staving off questions about potential replacements, with Ajax coach Frank De Boer heavily linked with the White Hart Lane job over the past month.
Southampton manager Mauricio Pochettino and Dutchman Louis van Gaal have also had their names mooted as potential successors to Sherwood, who is not sure what the future holds for him on a personal level.
When asked if he would definitely be a manager somewhere at the start of next season, Sherwood replied: "No, I'm not confident
"Having tasted standing in that technical area and being a manager, it is something I want to be long-term.
"I like doing it and until you've actually stood in there, no matter if you've been number two, number three, development coach, whatever, you don't appreciate what it's like."
Taking over from Andre Villas-Boas in December, the managerial role at Tottenham is Sherwood's first in top-level football.
The former Norwich and Blackburn midfielder, a Premier League winner in 1995, believes he has done well to start out at a club the size of Tottenham and that even poor results have been caused by issues out of his control.
"I think I've handled it all right to be honest," he said.
"It gives me a great bedding and experience for the future
I think you are judged on results and we have taken some beatings off some of the bigger teams but two of those beatings were against Man City and Chelsea, in which we got two red cards and they were both rescinded - I haven't started crying about that.
"We lost 1-0 to Arsenal at home and it was a one-sided game that we should have won
We got knocked out of the Europa League by possibly the winners, Benfica, who dropped down from the Champions League on 10 points and goal difference.
"So it hasn't been all bad when you analyse the thing
I think that Liverpool gave us a beating home and away.
"What I have learned is that you can't win unless you win
No-one wants anything dressed up
If you win, it covers over a multitude of sins."
Tottenham need just a point in their meeting with Villa to ensure Europa League qualification for next season but whether Sherwood will lead another charge into Europe remains to be seen.
Source : PA
Source: PA