His rise to the top level of Scottish football has been far more rewarding.
It might have felt a good deal steeper at times too, with Ashcroft having played only boys club football before winning a contract at Rugby Park. Even then an offer was only made after he had carried out a two-month trial at the club during which he trained with the under-19s team.
The defender was well into his teens, arriving in the club's academy system just one rung below the first team. Ashcroft has taken a road less travelled in modern football, but it is a journey he has since learned to appreciate, given that it has taken him into the centre of Kilmarnock's defence. He can expect to line up against Hearts tomorrow.
"I played with Barrhead Boys Club most of my life then Hillwood for a year, which included the Scottish Cup final," said the 20-year-old. "I didn't play pro-youth, I played boys club until turning full-time. I was straight into pre-season training then games with the 19s. I was in for a couple of months before they offered to sign me.
"It was a big step but I've loved it. I was a bit nervous when I first came in but once I got used to it everyone was great. Don't get me wrong, this is a lot of pressure at this age because of the situation we are in but it's just good to be out there playing every week. It's nerve-racking at times but once you play in the games that disappears."
The Rugby Park side have just three fixtures remaining this season if they are to avoid the unsettling experience of a play-off against a side from the SPFL Championship. Kilmarnock occupy 11th place at the moment but Allan Johnston remains sunny about their prospects.
"We've got to go for it, we've got to go and get wins, be really positive and get on the front foot," said the Kilmarnock manager. "We want to get the win and we need the win. There are two points between us and seventh place and that's where we want to finish."
Hearts are not able to set their sights quite so high - the Edinburgh side are already relegated from the top flight - but they are able to clutch menacingly at the clubs above them. Confirmation that they will drop into the Championship at the end of the season has given the Tynecastle side a sense of freedom and they are now content on making life as uncomfortable as possible for teams like Kilmarnock.
"I'm sure people looked at us on the fixture list earlier this season and thought, 'that's three points'. We were on a bad run," acknowledged Scott Robinson, the Hearts midfielder. "But now we have completely turned things around and I'm sure teams now don't look forward to coming to Tynecastle and playing us.
"We have nothing to lose. We can express ourselves and just play our normal game. People have been saying Hearts are the team who will drag others into it. But really we're just looking to finish on as big a high as we can by winning every game until the end of the season."