For a young player, it can crush their dreams, a player in mid-career can find themselves at a crossroads, while a more experienced player can see it as the final nod towards hanging up their boots.
But with any decision, there is always that nagging doubt that it will come back and bite you on the backside.
It has happened countless times at the top level - there are players who have been let go by clubs for being too small, too slow, not good in the air, or whatever, only to go on and have good careers with other clubs, while sticking two fingers up at the manager who discarded them.
At a club like Cheltenham, the decisions get even harder.
Mark Yates is bound by a small budget, he has to divide it up as he sees fit, and this year five senior players, Dan Lloyd-Weston, Martin Riley, Frankie Artus, Jake Lee and JJ Melligan were deemed surplus to requirements.
Of those, arguably only Lloyd-Weston and Riley could come back to haunt Yates in the future - but time will tell on that.
Those decisions - Riley apart, I would hazard - were fairly clean cut.
At youth level, things get that bit tougher.
In recent years, Andy Gallinagh and David Bird have served as beacons for the club's youth policy, with Bird having made more than 200 appearances and Gallinagh around 150 since coming through the ranks, Birdy being spotted at Cinderford Town and Gallers at Stratford Town..
But their progression has been something of a rarity.
We have high hopes for Theo Lewis, who came on the scene at 16 with a pre-season friendly goal against Southampton, and last season made 22 appearances in League Two.
A summer in the gym and a big season in his career await him now.
Kyle Haynes played only in the last game of the season at Stockport, but had loan spells at Hednesford and Salisbury.
The youngest player ever to represent Cheltenham in League football, Kyle was 2009-10's League Two Apprentice of the Year - but like Theo needs a big season to stay on the right path... but that won't be easy with player of the year Keith Lowe blocking his way.
Coming into the pro ranks - provided he signs his deal and I understand Swansea are sniffing around - is Ethan Moore, an 18-year-old forward with a chequered history.
The boy from Stroud scored 21 youth team goals last season - but was at Cheltenham as an unpaid trainee having left Aston Villa under something of a cloud.
I have never really got to the bottom of it, but the tale is either of homesickness or a fall-out with some of the coaching staff - but whatever... it is to Cheltenham's advantage.
Someone at the club described him to me as 'a complex character' and the Villa history might bear that out, but Yates sees him as a risk worth taking - and considering Villa paid money at 15 to take him from Southampton there is something there.
In the games I have seen him play, Moore has shown himself to be a strong player, direct and a good finisher. He also has an aggressive 'Rooney-like' streak in him - a bit of a rough diamond if you like - so I get the impression that it will be interesting watching if he gets into the first-team reckoning.
When he played up front alongside the first-year professional Lee against Gloucester in the GFA Senior Cup, there was no comparison - Moore looked like the pro and Lee the apprentice.
Cheltenham Town are the sort of club who cannot give youth team players professional deals UNLESS they are going to threaten the first team.
This is the reason why goalkeeper Louie Barnfather, defenders James Fawke and Jamie Sauntson, forward David Waters and winger Josh Egan were let go.
Fawke sat on the bench for the first team at the end of the season and had a loan spell with Gloucester, and I thought the former Bournside School pupil would get a go.
I understand he may have a trial at Swansea, while the news has emerged that Egan - who scored 8 youth team goals last season, has been offered a contract by Blackpool.
Yes, Blackpool, trying-their-best-to-stay-in -the-Premier-League Blackpool.
So, you ask, how can he not be good enough for Cheltenham, yet good enough for Blackpool?
One answer, the old favourite... money.
As our head of youth John Brough told BBC Gloucestershire:
"We saw his potential but in our climate at the moment the club needs players that are ready for the first team when we get back for pre-season.
"Clubs like Blackpool have got the budget and can see potential like we have. Good players always come to the top and Josh is certainly one of those. Ability wise, he's one of the best I've worked with at youth level."
A shame, but it's hard to argue with what Broughy says.
It's a risk the club has had to take and that's why it's good to hear that there are moves to restore reserve team league football - cut by the previous manager - and good that we can play the games at Seasons if we get back in.
It's the only way that players like Josh Egan are going to get the chance to show what they can do and make real progress at our club, rather than going elsewhere.
It's a great opportunity for Josh, and I feel it is a feather in the cap for Broughy and Russ Milton that a club like Blackpool see potential in him, and can see that he has been taught the right way - but it's equally sad that we won't see any benefit if he makes it at the top level, unlike with the Arsenal deal for Jamie Edge.
But Egan could go the other way, and have to go into non-League football as the likes of Marley Watkins and Sam Foley have done - both doing well in the Blue Square Premier, and Cheltenham will face them both in pre-season at Bath and Newport respectively.
In League Two, another ex-Cheltenham youth teamer may play at Whaddon Road again for Crawley, and his story (thanks to Wikipedia...) gives hope to all of the released youngsters.
James Dance left us and dropped into non-league with Atherstone Town, he started to make his name however after a move to Coleshill Town.
He was awarded the captaincy at a young age and managed to lead his team to the Midland Combination Premier Division title, he progressed quickly up the pyramid arriving at Redditch United via Rushall Olympic.
It was at Redditch where he managed to attract the attention of Kettering Town by playing a starring role in an FA Cup match against them. Kettering wasted no time in snapping up the youngster, moving for the player only two weeks later.He then went on to Crawley and helped them to promotion.
I must confess I don't remember watching him for our reserves or youth side, or if I did he didn't stand out.
It might have been one of the easier decisions to let him go back then, and the manager at the time - John Ward I suspect - could not have predicted what would happen to him after he left Whaddon Road, such is the lottery of young players.
They can either be late developers or be prepared to work hard to get where they are, like Dance obviously has, or they just sink into oblivion.
In Josh Egan's case, we wait to see what happens with interest.