Keith Curle admits telling players their career at a football club is over is one of the big downsides of football management - and he has challenged all of those players released by the Cobblers boss go elsewhere and prove him wrong.
Town announced their retained list on Monday, and it was bad news for many of the squad, with eight out-of-contract players being released and a further three placed on the transfer list.
Long-serving left-back David Buchanan was one of those to be told he wouldn't be getting a new deal, with the others being Sam Foley, Dean Bowditch, Jack Bridge, Luke Coddingtom, Shay Facey, James Goff and Joe Iaciofano.
Former skipper Ash Taylor was one of three players transfer-listed, with the others being Joe Bunney and Billy Waters.
It was a pretty ruthless cull from the Town manager, who has been in charge since the beginning of October, and has had plenty of opportunity to run the rule of the entire squad at his disposal, and to make the judgments he has.
Curle sat down face to face with all of the players at the PTS Academy Stadium on Monday, to tell them where their futures lay, and he admitted: "It's not a day that I look forward to, because you build up relationships with players and personnel.
"But it is the nature of the job that some people have to go and find a different journey to go on and further their career.
"My job is make sure that I pick the right people to stay on the journey that I see this football club going on."
The released players as well as those transfer-listed will now set about finding new clubs for next season, and Curle says they have to use the disappointment of their Cobblers release as a motivation.
"It's similar to when you get the young scholars, when they come up to the decision time in their careers," said the Cobblers boss.
"There is nothing worse than when you have got an 18-year-old who has always had aspirations and dreams of being a professional footballer, and you have to shatter those dreams.
"But I always try and do it in a positive manner, in a positive vein, and leave them with positive thoughts in making sure they can go and prove me wrong.
"It happened to me at 16, when I was told in the manager's opinion I wasn't good enough and I wasn't going to be offered an apprenticeship.
"He didn't think I had the skill-sets to have a sustainable career as a professional footballer.
"That was the motivation I needed, and the driving force.
"My ambition was that I was going to be a professional footballer, and that is the message you have to get into some of the players.
"They have to go and continue their journey elsewhere.
"All the players, even though it is sometimes negative news, they will be given the opportunity to leave in a positive vein.
"I will say 'you are going on a different journey, but I wish you well on it'.
"They are people who have been good servants to the football club, but now is the time to find a new journey and be successful on that journey."