The first came as "a boy" in Bendigo when, while working in his family hotel's bottle shop, Geelong recruiter Bill McMaster and Colin Rice, a Cats premiership player, walked into the room, introduced themselves and told Sheehan he was good enough to play for the Cats.
Sheehan was stuck in Carlton's recruiting zone but was widely regarded as one of the best players in the Bendigo league who just couldn't break onto the Blues' strong list. So, as a 20-year-old, he took his chance with the Cats and went on to play 102 games in nine seasons with the club.
The next came break came three years later, when Sheehan was approached to be the first full-timer at Geelong. He took that chance, too, holding a promotions role and learning more about football beyond the boundary while still playing within it.
It was the third big opportunity, though, which will define Sheehan's place in the Australian game.
In 1983, Sheehan joined the then VFL as its first full-time development officer.
Thirty years on, Sheehan is still full of passion, energy and drive in his position as the AFL's national talent manager. After taking his own opportunities, he's helped and pushed hundreds of others to do the same.
Last Saturday, he was announced as a recipient of an Order of Australia Medal for his service to the game.
"I'm quite chuffed by it," Sheehan told AFL.com.au.
"It's not something you think about or even dream about, it's just not on the radar. But when it does come about it's a tribute to all the people who have worked in game development and have done for the last 30 years.
"There's been so many great foot soldiers out there who have been unrecognised and I'm happy to be a representative of them."
The achievements within Sheehan's time in the game pile up like notes on an office desk. He played a key role in growing the game into a national competition. VicKick, then AusKick, was part of his charter for youngsters, and he played a big role in scrapping the 45-year club-based under-19 competition to establish the TAC Cup, now a staple of the talent pathway in Victoria.
The under-16s and under-18 championships have been established and developed, as has the AIS-AFL Academy, which nurtures and guides some of the country's most promising prospects.
Throughout Sheehan's time the draft camp – now Combine – has become a staple event of the football calendar, as has the national draft, which grew from humble beginnings to be a live-televised and highly anticipated annual event.
Sheehan's contribution, says AFL chief executive Andrew Demetriou, has been enormous.
"The AFL is extremely proud of Kevin Sheehan and delighted that his work with junior talent and young players over more than three decades has been given wider recognition," Demetriou said.
"Kevin has helped many thousands of young players, from every part of the country, pursue their dream of playing our game at elite level and his constant passion for the game shines out in everything he does.
"At our national championships, at both under-16s and under-18s, Kevin is a constant presence and a regular source of inspiration for young players and his knowledge of talent is unmatched in the game.
"His Australia Day honour was thoroughly deserved and we look forward to him continuing to champion the prospects of young players coming into the AFL environment."
Sheehan celebrated his honour at Wellington Stadium in New Zealand as the level one AIS-AFL Academy team defeated New Zealand by 43 points. Fitting, he thinks, given international expansion is his team's next big focus.
"It worked out well. I couldn't think of being in a better place than being with the Australian team, on Australia Day, and seeing the game expand," Sheehan said.
"Ninety-five per cent of those in the AFL will probably always be young Australians, but there's no reason why there won't be more coming from the South Pacific, from Ireland, from America and from other parts of the world."
Follow Callum Twomey on Twitter at @AFL_CalTwomey.
