Sheedy, back at the club for the first time in 30 years after winning four flags as coach of Essendon, told the players the important thing was to believe they could do it.
The Tigers have made the finals just twice in the last quarter-century, and Sheedy asked them to have a good hard look at what they wanted from 2009.
"Why not this year? Why not?" Sheedy asked at Wednesday night's season launch at the Regent Theatre.
"When you reach deep down into yourself, how do you want to see this year? You do have an exciting opportunity.
"You've got enough experience. You've definitely got enough youth.
"For God's sake, you have to have the hunger – it's a quarter of a century.
"Don't just roll out another footy season like the last 25, because you have a chance.
"Could you win it this year? I think you could.
"Because I think everyone might drop their guard. If they drop their guard and you lift 5 per cent and they drop 5 per cent, it's a very even ball park."
Sheedy drew on history – both Richmond's and his own – to make the point that in sport, anything can happen, no matter how unlikely.
"In 1993 no one thought Essendon could ever win a premiership – but they did.
"They were 50-1 and given no chance, with a few senior players and of course, lots of young, talented players.
"In 1967 it was the classic, because it's very similar to Richmond this year.
"If you could take something from the past and history and look at it, then you may have a wonderful opportunity if you want it to be.
"Ron Barassi has always said: 'If it is to be, it's up to me', and I think the players have got to realise that."
The 61-year-old said there were a number of reasons Richmond could pull off the seemingly-impossible.
"Number one is the draw – it could be a good draw for us. You don't often get that.
"Secondly, I think that everyone will talk about Geelong and Hawthorn (for the flag) – it doesn't have to be like that.
"That's where your willpower comes into it.
"So when you see yourself sitting down in 10 years, like the great Kevin Bartlett and the great Richmond players looking back at their life, they can honestly, justifiably say, 'I tried my absolute 100 per cent best'.
"We may have missed one or dropped one here or there, but I can tell you now, I want to know what you're going to think in 10 years time."
