For people at the top of their game, whatever that game may be, the road to retirement and beyond can be a scary one. The “game” can be a sport, a profession, a business – it doesn’t matter.

Matt Dickinson’s excellent piece in The Times yesterday, “Wiggins proves hardest task for elite is moving on”, spells it all out for one of Britain’s top sportsmen, Sir Bradley Wiggins.

The “scary void” that replaces the organised days (and for blocks of training and recovery time just replace with chargeable and non-chargeable hours) can lead to “anger, confusion, plummeting self-esteem”. There is a subsequent quest for purpose (which Wiggins finds on the back of a motorbike commentating on some of the big bike races – he is good at it). His career as a top cyclist had many triumphs, yet, as Dickinson says, he now spends so much time explaining why he doesn’t want to be defined by them.

Coaching in business frequently draws on sporting parallels. The road from the top of the mountain, as with any descent, can be navigated with care and thoughtful planning. Becoming an “Ex” (with thanks to Herminia Ibarra’s “Working Identity”) can be an exciting and energising process, one to relish, rather than fear.

At Milestones we have the road miles under our belt – indeed a lot of us have been on the ride.

If this resonates with you, and you want to know more about how to face up to the challenge of a new career, then please get in touch. Call Nick Holt on 07802 885 363 or Tim Musgrave on 07802 481 124 or email us at