It's a question which should be occupying the thoughts of the men who employ him at Celtic.
The cut-and-thrust of the Champions League action is over for another season, and will not be reintroduced to Lennon's life until July - provided the Hoops retain their league title.
That's when the increasingly difficult and fraught qualification process begins again.
In the meantime, the second half of a league race which already has the look of having been run, the defence of the Scottish Cup and the pursuit of players Lennon hopes can allow him to be more competitive in Europe next season is all that will be there to keep his mind here and not wandering elsewhere.
In March, the 42-year-old will have been in the Parkhead hot-seat for four years, and he is now the longest-serving manager at any club in the SPFL.
That can feel like a lifetime for someone asked to deal with the unique challenges of leading this club from the front - on and off the park.
Lennon has shown no outward signs of believing he's had his fill, or that he considers he is reaching the end of his shelf-life in his first managerial position.
But without the added thrill and major pre-occupation of European football, it could be a long, difficult winter for him, during which it would only be natural if a period of introspection took place.
Should he give any indication he would consider beginning a new chapter in his managerial career, there will be no shortage of owners and chairmen interested in speaking to him.
England, with the vastly-superior funding which keeps the game afloat down there, is an obvious next port of call.
With two league championships and two Scottish Cup wins, plus a place in the Last 16 of the Champions League, Lennon has already carved out a very good CV.
However, it is unlikely to open the door to one of the very big clubs down south, and a "bridging" move would appear to be the best approach to getting where he would ultimately like to go.
He was being touted for the position at Wigan recently made available when Owen Coyle was relieved of his duties. But that has since been filled by Uwe Rosler, who made his reputation with Brentford in Division One.
Whether or not the position at the DW Stadium would have interested Lennon, it was another reminder that so much more credence is given to managers who have made some kind of impact in England.
When Paolo di Canio was given the chance to step up from Swindon to replace Martin O'Neill as Sunderland boss, Lennon couldn't help but comment on how it appeared you only had to do something with a lower division club down there to be given your chance with a Premiership side.
However, against all of this, the student that is Lennon has not missed the fact the jobs only become available as often as they do in England because managers are sacked at an alarming rate.
This season alone, 19 league club managers have gone, two resigning and 17 being sacked.
Seven of them were given their cards between November 25 and December 2 as owners got the lust for blood.
Even proven bosses like Martin Jol and Dave Jones have not been safe, though at least they had been given some time at Fulham and Sheffield Wednesday respectively.
Lennon half-jokes his mentor and the man who brought him to Celtic, O'Neill - himself a casualty at Sunderland last year - warned him that the only thing you are guaranteed in this job is the sack.
But it is something which he has to considered seriously as he looks to his future.
Unless something hugely untoward occurs, it is highly unlikely Lennon's bosses at Celtic would come to the conclusion he had to go.
But if the man himself feels he can't suppress an urge to test himself in a more competitive environment, Lennon is fully aware he that would be swimming in very dangerous waters.
NEW owners from business and abroad ploughing money into clubs down south want results - instant results - because they can see the rich rewards available for success.
The average term of office for a manager in the four leagues is currently just 19 months, a figure hugely skewed by Arsène Wenger's 17 years in charge at Arsenal.
Lennon has watched it all happening from afar, and has his own strong opinion on why jackets down south have never been hung on shooglier pegs.
"Unfortunately, it's not surprising as owners are becoming less patient with managers," he said of the sack race in England.
"There are some cracking managers. Dave Jones has been in the game a long, long time, as has Martin Jol.
"It's a results-driven business and, unfortunately, it's the precarious nature of the job. Some don't get the opportunity to bed in.
"I don't know why some of these owners bring them in because they don't give them the opportunity to actually put in place what they want to do.
"So it just shows how precarious the job can be, and I'm just thankful I have had the experience and the time here to gain all the knowledge and work with some very, very good players over the last four years."
Lennon does not believe this instability is a new phenomenon which is infecting the managerial species.
It is perhaps just becoming faster-acting and more virulent.
Asked if it is worse now than before, he replied: "It's always been that way.
"I remember Martin used to say to me the only thing you are guaranteed in this job is the sack. So I don't think it changes that much."
Lennon can see where the problem is most acute, and knows the reasons why.
"In the Championship, the pot of gold at the end of the rainbow is huge for these owners of clubs," he told Celtic TV. "You get a few adverse results, three or four defeats, and they seem to press the button very, very quickly.
"I think that's where the imbalance is. There are Championship clubs who are going okay, then they see this money at the end of it.
"If they can get into the Premier League, it can change lives, change fortunes of clubs for years, and it's so important for them.
"There's a desperation there sometimes.
"That's probably one of the reasons that the Championship, more than any other, is the most dangerous water for a manager to swim in."
And a reason why he might think twice about taking the plunge.