Some players you know are going to just nail it. They are going to hang up their boots and move seamlessly into post-retirement life, embrace it and thrive.
Usually, but not always, those who make the best transitions from professional rugby to civvy street have accepted early that the day would come when they wouldn't be able to earn a living playing rugby.
That realisation drives an attitude of being prepared - of thinking and planning to enable maximum control over what that new life will look like.
It also enables players to appreciate they have to enjoy what they have when they have it: to respect the lifestyle they have been afforded as a professional player and understand there's no entitlement.
It's easy enough to pick which players get it, to forecast who will do well when they walk out of the changing room for the last time.
It is no surprise at all that Richie McCaw has moved away from rugby and appears to be living his life to the full. He gave everything for 15 years but he had other outlets in his life - his flying and his various business interests - and knew that he would leave one challenging environment to immediately enter another.
Conrad Smith, when he finally gives it up, will be another who most likely won't give rugby a second thought. He's a qualified lawyer, pays attention to the "real world" and is prepared and equipped to live it when the time comes.
But what's become apparent in recent weeks is that it's firstly best not to assume anything when it comes to players and their ability to successfully transition out of the game. The tragic death of former Wallaby Dan Vickerman showed just how difficult post-retirement life can be for players.
Outwardly, Vickerman appeared to be perfectly set up to thrive away from rugby. He'd pursued educational opportunities while he was still playing, was well connected to his peers and social networks, was employed, married and seemingly settled in family life. However good things looked for him, he clearly didn't feel the same way.
The second point to realise is just how hard it can be for players to give it all up. That no matter how many rewarding endeavours they push into their post-retirement lives, sometimes they just can't replace the depth of feelings and fulfilment they used to know when they played.
The sense of camaraderie, of being on a mission with like-minded teammates, is hard to replace. There is the loss of kudos and social standing. As a professional player, there is social currency. In retirement, the doors don't quite open the way they used to; there's not so many people interested in catching up for a chat and that sense of purpose and energy dwindles.
There's also the emotional emptiness that can occur as a result of not having such highs and lows built into the working week. Just as military types miss the adrenaline rush that comes with war, so too do rugby players find it hard to cope without the elevated stress of playing in front of millions.
Some players simply can't redefine themselves once they stop playing. They can't see themselves as anything other than a rugby player - it's from that which they gain their self-worth and self-confidence.
There are multiple challenges on multiple fronts for rugby administrators around the world, but this challenge of helping current players become former players sits as one of the biggest.