Three days after being handed an 18-month contract to succeed Andre Villas-Boas, Sherwood led Tottenham to a 1-1 draw against struggling West Brom at White Hart Lane.
Christian Eriksen scored a stunning free-kick to give Spurs the lead, but Jonas Olsson equalised less than two minutes later.
Tottenham's defence looked vulnerable at times and at the other end of the field they lacked a cutting edge.
A smattering of boos rang out at the final whistle to sum up how the home supporters viewed the performance, but Sherwood remains optimistic about his chances of success in the long term.
"It's a gamble because I've never done it before," the 44-year-old said.
"But there are a lot of good managers who had never done it before and become a success.
"I was never a professional footballer until I stepped on to the field."
Sherwood was appointed caretaker following the dismissal of Villas-Boas and he delivered an encouraging win over Southampton last weekend.
The former Spurs midfielder laid out his unconditional commitment to attacking football in that match and he repeated that stance at White Hart Lane on Boxing Day.
Still, there it was hard against a well-drilled Baggies defence and Sherwood knows the fans were right to be unhappy.
"The fans will be disappointed, obviously. I understand that," Sherwood said.
"We are at home and with respect, against West Brom you should be winning.
"It's a game we should have won. We should have played better and we are capable of playing better.
"I thought we could be a bit more adventurous around the penalty box and show a little more guile."
On paper this was a perfect first league match for the newly-appointed Tottenham boss.
West Brom, who sacked Steve Clarke two weeks ago, arrived in the capital having failed to win any of their last seven games, but caretaker boss Keith Downing would have come away with a win had Hugo Lloris not pulled off two top saves.
Pepe Mel is favourite to succeed Clarke, but it looks unlikely that the former Real Betis manager will be appointed in time for this weekend's crunch match against West Ham.
Downing is furious that the game against the Baggies' relegation rivals has been scheduled for Saturday lunchtime - around 44 hours after the clash against Spurs ended.
"Less than 48 hours is ludicrous," said Downing, who made seven changes from the side that drew 1-1 against Hull last weekend.
"I just don't understand it. Obviously the TV take preference but asking players to play in less than 48 hours and provide the quality and entertainment..."