The Northern Irishman will not die wondering.
That much was obvious in the way he released the shackles at Doncaster Rovers; Darren Ferguson's caution replaced by freedom and flair. It nearly worked in spectacular style.
Moving to Hull City, a club up for sale and with well-documented issues, might seem like the biggest risk yet in the 39-year-old's short managerial career.
But McCann will see only the opportunity and not the risk: an opportunity to prove himself in the Championship, an opportunity to keep his career on an upward trajectory.
He is a fiercely ambitious person who lacks nothing in self-belief. He will back himself to build on the foundations laid by his mentor Nigel Adkins in a similar fashion to the way he was able to get Rovers moving through the gears following Ferguson's rebuild.
Absolutely key to this is that McCann's stock as a manager has never been higher.
It may never be this high again - things can change very quickly in football - and he has seized the moment.
He deservedly won acclaim within the game for leading Rovers to the League One play-offs and FA Cup fifith round despite the club's modest resources.
But, looking ahead, next season already seemed tougher on paper even before this week's unexpected turn of events.
There was a genuine camaraderie among the players last term which almost carried them to Wembley but that bond has been broken. Rovers are almost starting from scratch again.
It is a possibility that McCann might have felt he had taken Rovers as far as he could; that last season would be difficult to top. Talk of a top two push certainly seemed far fetched.
But it is more probable that Hull simply made him offer that he just could not refuse.
Rovers fans have every right to feel disappointed. Some will feel let down, betrayed even, given the content of some of McCann's final interviews as Doncaster boss.
But for him this is an opportunity that, had he turned it down, may never have come again. For McCann it is obviously a risk worth taking.