And the 28-year-old winger got his wish on Deadline Day, when he joined Everton.
Indeed, the wide man got his wish on Deadline Day, with the club that took him on loan last season, Everton, eventually prising him away from Tottenham.
But Lennon says he was frantically waiting all window long for a move to materialise, painting the picture of a man who was simply desperate to leave White Hart Lane.
The new Everton winger is quoted as saying by the Mirror: "Around four o’clock I started getting a bit nervous!
"I was rushing around London at that point and you’re just hoping it all goes through, with all the paperwork and everything, and I was so happy once it got done.
"Once the paperwork was all done, it was happy days and I just couldn’t wait to get up the motorway. I was hoping it got done throughout the summer, I was just waiting, waiting - last night, just about 8 o’clock or so, I was on the motorway as an Everton player and that was a great feeling."
Judging by Lennon's quotes, he never stood a chance of breaking back into Mauricio Pochettino's Tottenham team. That's interesting, though, considering the poor form of his competitors so far this season.
Patience has now run out with Erik Lamela, while Andros Townsend is also off form when fit - and has been unfit of late. Alex Pritchard isn't yet fit, either, making Lennon a perfect alternative for Spurs.
That would have been if the 28-year-old was going to stay at White Hart Lane, of course, which it is now clear was never the case. Everton fans, meanwhile, were left underwhelmed that Lennon was the sum of their attacking signings on Deadline Day, although they were pleased with the winger's recruitment itself.