But, for some of the players currently in his charge, just getting past their first anniversary in the Hoops is proving to be a serious challenge.
Clinching the 2013-14 SPFL Premiership title will, effectively, mark the end of the campaign for several in his team.
For a few less settled, getting over the line will be the starting point for determining in which direction their career now heads.
While Scott Brown, Efe, Emilio Izaguirre, Adam Matthews, Anthony Stokes and a clutch of others revisit that champion feeling and begin thinking about planning for another tilt at qualifying for the Champions League, doubts are already hanging over whether Fraser Forster and Virgil van Dijk will still be at the club when next season kicks off.
It's widely accepted Georgios Samaras will be departing with his fourth league winner's medal safely tucked away.
But it is unlikely he will be alone in heading for the exit door.
In an occupation that has become more and more transient by nature, some will welcome the opportunity to start afresh.
For others, the prospect of being cut adrift by Celtic is much less palatable.
Two who definitely come into that category are Teemu Pukki and Steven Mouyokolo.
The former has had his first year at the club wrecked by loss of form and confidence.
The latter has seen his season destroyed by a ruptured Achilles tendon.
Pukki, at least, has the reassurance of another two years on the well-paid contract he signed when he joined from Schalke for £2.5million in August.
Mouyokolo's situation is much less secure.
Having impressed in two trial periods either side of the summer break, the 27-year-old Frenchman was rewarded with a deal for just 12 months.
His history of knee injuries prior to turning up at Lennoxtown dictated understandable caution on the part of the club, who did not want to commit beyond that period.
But, while their circumstances differ, Pukki and Mouyokolo are united in their determination to make the next few weeks count.
Lennon has tried cajoling the introverted Finnish international. He has put his arm around him, eased him into games when the points have been won.
Each time Pukki has scored - something he has done five times - the manager has hoped that would be the cue for the gloom to lift and the confidence to soar.
However, Pukki still cuts a disconsolate figure whenever he is sent into battle, as he was again at the weekend when the win against St Mirren was in the bag.
The fact he had two decent opportunities to score - pulling a shot well wide, then making poor contact when afforded a free header - only served to add to his angst.
Lennon feels his pain, and looks for any and every crumb of comfort with which to try and replenish the under- nourished self-esteem of the man who turns 24 on Saturday.
"Strikers feed off goals," said the Hoops boss as he attempts to understand what ails Pukki.
"But, Teemu keeps getting in there, and that's the important thing.
"He could have scored three or four in the period he was on against St Mirren.
"That pleased me because we felt, with him coming on and St Mirren tiring, there would be gaps, and he exploited them very well.
"He just couldn't add the finishing touch."
Lennon plans to persevere, and is not prepared to yield to those who reckon they have seen enough of Pukki.
"He just needs goals," Lennon insisted. "And, if he keeps putting himself in those positions, he will score.
"But it does affect his confidence when he misses."
Amido Balde was another raw striker brought in last summer who, like Pukki, has spent more time on the bench than on the pitch.
But the 22-year-old from Portuguese club Vitoria Guimaraes did not have the same depth of CV as the Finn.
As a result, Balde - who still has scope to develop, both physically and professionally - is expected to be given more time to prove he has something to offer.
Leigh Griffiths has shown both Pukki and Balde what it takes to arrive at Celtic and hit the net and the ground running.
But Lennon accepts it is not comparing like with like as the January signing from Wolves arrived with a distinct advantage.
"Leigh has come in and added that bit of spark to us that was missing," said the manager.
"He was accustomed to the environment, and had played with a few of the guys in the Scotland squad.
"Leigh's family is here, and there is a comfort there as well. He also knows the pace of the game."
Mouyokolo appeared to have got to grips with all of that when he settled into the club last summer.
Indeed, in the initial few games, he looked to be more comfortable than another new Bhoy, Van Dijk.
But while the Dutchman's profile has rocketed, for Mouyokolo it has only been his infamous injury reputation which has been enhanced.
After proving his fitness and worth to the team in the first month of the campaign, the misfortune which has blighted Mouyokolo for the past couple of years tracked him down to Lennoxtown where he suffered a horrendous Achilles rupture during a training game.
The courage he has shown to battle back through another lengthy rehabilitation, spent both in France - where he underwent surgery - then in Glasgow, has further endeared him to Lennon.
But in the cut and thrust of today's game, there is no room - or spare cash - for sentiment.
With the clock running down on his contract, it is what Mouyokolo produces on the pitch from now until the end of the season that will determine his future.
Lennon is sympathetic to his plight as he oversees the final few days of Mouyokolo's recovery and said: "I'd like to see Steven get some games because he has worked very, very hard to recover from his injury.
"It will be an important run in for him. But we will have to be very careful with Steven because it was a horrendous injury."