The surprise announcement that Adrian Anderson had decided to walk away from his position as the AFL’s chief football manager of operations, and the not so surprising retirement of former Australian captain Ricky Ponting, does leave the dilemma of when exactly is the right time to retire.

For most AFL players, their playing career ends with a whimper as they succumb to injuries or that poor from leads them to be delisted. There is always the lingering issue of when it is best to retire, and even though a player may be still contributing effectively to the team, a sudden decline in his output may see him end his playing days mid-season, as opposed to walking away completely on their terms.

For Sydney’s Jude Bolton , he weighed up the pros and cons of continuing on versus hanging up the boots and has elected to play on in 2013. Fellow Swan veteran Adam Goodes will also continue his career, and his form in 2012 certainly justifies doing so. However, these two 300-game players had a unique opportunity to leave the game at the best possible time, while basking in the glow of premiership success.

Memorably, former Hawthorn captain Shane Crawford’s last moments as a player were spent celebrating a successful 2008 Grand Final, and while he contemplated playing on into 2009, he ultimately made the right decision and is remembered for his exclamation of “That’s what I’m talking about” as he celebrated winning his only premiership in a 16-year AFL career.

Of course, the flip side of this is that for a player that plays on for one season too long, as was the case with former West Coast and St Kilda star Fraser Gehrig, they can be remembered for their poor last season.

Gehrig, who memorably kicked 100 goals in a season in 2004, played his last game against the Tigers in 2007 and performed well in a Saints’ win. He was carried off the ground like all retiring greats of the game and looked to the next phase of his life.

Unfortunately, he changed his mind over the next few weeks and chose to play on in season 2008, and his career at the Saints ended mid-season as his form slipped to such a degree that his selection in the senior team was no longer viable.

It is a very rare case when a player gets to retire with dignity and on their own terms, and while Bolton and Goodes may well prove that playing on was the correct call, history is littered with cases of players going on for one season too many and the chances of them having another go at leaving the game while experiencing the ultimate in AFL football is long odds against.

Even if the Swans are successful next season and win back-to-back flags, the chances that both Bolton and Goodes will be fit and firing on Grand Final day are unlikey.

Perhaps the best way of looking at when to retire is for a player to ask themselves whether they want people asking why they retired as opposed to them questioning why they waited so long.

One thing that’s for sure is that when a player plays on too long, it puts a dampener on the hard-earned respect built up over the course of their career.