The fates of Martin Lawlor and Tommy Lynch over the past couple of seasons might have deterred him but, five days before his young and inexperienced side travel to the Brandywell for their first Eircom-sponsored Premier Division game, Longford Town boss Stephen Kenny is in no-regrets mode.
A couple of years after taking over the struggling midlands outfit, the Dubliner has taken the plunge into full-time management. Staking his future on a group of players that very few people outside of the town are giving much hope, the former St Patrick's Athletic coach grins at the thought of the risk involved in giving up the small business he has run in recent years in order to devote more time to the club.
"They could sack me," he half laughs. "I know that, but I'm really not thinking about anything like that. It's a very exciting time around the club and I think we're going to surprise a few people." In truth, he admits, he is about to start learning as much about the group of players he has assembled and much more about himself than any of the rivals from other clubs who will be attempting to size up the new arrivals over the coming few weeks.
While Bray and Kilkenny return to the top flight with a good number of bodies that have travelled this road before, Kenny has passed up the chance to draft in a few older heads, opting instead to stick with his policy of cherry picking youngsters and those who have failed to break out of reserve-team football at the big Dublin clubs.
Eight new faces will be around Strokestown Road over the coming campaign while only one of last year's first-choice 11, Richie Parsons, has departed. Kenny is certain the new panel will be good enough. Of the new arrivals at the club two are strikers with Robbie Farrell - who scored 17 for Home Farm/Fingal last year - and Niall Byrne both presenting their manager with new options. It's at the other end, Kenny admits, that things just might start to get a little bit sticky.
The manager has refused to see a shift from attacking tactics as part of the inevitable price of promotion, pointing to the club's defiance of conventional wisdom in their successful first division campaign. "A couple of years ago everybody was telling me that I needed to get in a load of big lads because the only way to get up was to kick your way out of the first division and what we did was prove that that was absolutely not the case. Now we're looking to prove everybody wrong again and maybe it's just that I'm too close to the thing here but I genuinely think that we can do it."
There are some drawbacks to the club's steadily improving status, however, as Kenny readily admits when asked about last year's rare and best forgotten run in with Premier Division opposition - the 7-1 defeat by Finn Harps in the cup.
"Well, before the current board came in things could be a bit of a struggle at the club and one of the things that would generally be a concern was getting a bus for the away game. I remember we had one that was a bit rough for the trip down to Cobh last season but out turned out great, everybody was playing cards, sitting around chatting and the effect on team spirit was terrific. Then, for the Harps game - which in fairness was the craziest game I've ever been involved - we got this beautiful bus with videos for everybody to watch on the way up. It was terrible, nobody said a word to anybody, they all just sat there watching the box and we went out and got hammered."
The days of travelling in comfort are over for the Premier Division new boys. From here on in they'll save the style for those critical 90-minute spells between bus journeys.