Gary Waddock described his decision to move from Aldershot to Wycombe as the, "hardest decision I have ever had to make."
After a couple of successful seasons in Hampshire where he led them back into the Football League and established the Shots there, the club are currently sixth after an impressive start to the new campaign.
The decision to move to League One strugglers Wycombe arguably resembles more of a gamble for Waddock than his new club therefore.
After promotion last season, Peter Taylor failed to help the Buckinghamshire side adjust to life in the third tier. Just one win in their first 11 games sealed the fate of the former Leicester manager, including successive home losses to fellow strugglers Tranmere and Leyton Orient.
Another defeat at the weekend, this time to Gillingham, another side promoted from League Two last season, means Waddock's new side find themselves six points adrift from safety already.
For a man whose only previous managerial spell above League Two was an unsuccesful stint at QPR, there will be no time for Waddock to get to grips with the task of managing a step-up.
The reality is that Wycombe's problems run deeper than simply who picks the team. After a blistering start to last season, Wanderers barely stumbled over the finishing line to secure promotion on goal difference.
However, after failing to strengthen the squad over the summer, and rumours of a fall-out between club owner Steve Hayes and Taylor, they appear to be ill-equipped for the challenge of League One.
Barring loan signings, Waddock will be unable to recruit any permanent signings until January, by which point an immediate return to the basement division may already be on the horizon.
A relegation on your CV is something no manager wishes to experience, failure to keep Wycombe up and that's exactly what Waddock will have, even if his responsibility is minimal.
In the words of Roy Keane, Wycombe's failure to prepare means they have risked preparing to fail. Waddock has gambled on his ability to turn around their fortunes.
He has also gambled on his ability to translate the methods which proved so successful at the Recreation Ground to the current group of players at Adams Park.
Expansive, attacking, passing football has been the order of the day at Aldershot. It's a stark contrast from the more dour and cautious approach which saw Taylor lead Wycombe to promotion last term.
Can Waddock adapt a team designed to be more industrious than imaginiative into playing good football and achieving results?
Will, in attempting to get the side to express themselves more, they be left more open to the more clinical forwards at League One level? 35 goals have been scored in league games involving Aldershot this season - Wycombe fans are in for a culture shock.
Finally, it represents a long term risk for his career prospects. After a poor spell at Loftus Road, Aldershot represented a chance for him to rebuild his managerial career, he grasped it with both hands.
Failure at Wycombe and he may find himself facing his old employers, or even seeing Town passing Wanderers as the two sides move in opposite directions in the pyramid.
Remaining at Aldershot and continuing his work there could have seen a bigger and arguably easier job coming his way in the future. However, with his stock probably at its highest point, could he be sure such opportunities would ever arise again?
Waddock has taken his chance.