That is not to say the forward has not felt at home since his move to the club two-and-a-half years ago. Nor that was he not comfortable with his storied step up from tier eight of the football pyramid.
But the 26-year-old admits the dawning of the new season has brought an increased confidence – something which has been reflected in strong performances in a deeper-lying role behind a lone striker.
May points to being handed a contract extension in January as the initial dose of validation he needed.
“It was massive,” he told the Free Press.
“I’d be lying if I said I wasn’t worried if I was going to get a new contract or will I get another club.
“I’ve never been in that situation before.
“When Doncaster spoke to me about a new contract, I was buzzing.
“I love the club, it’s excellent.
“To get it done early, I was very happy.”
If he needed a further dose of confidence, it was delivered over the summer, particularly following Darren Moore’s arrival when it became clear he would be a major part of the new boss’ plans for the start of the campaign.
May has made more substitute appearances than starts for Rovers since his arrival in January 2017 so to be handed a start in the opening two matches of the season was a considerable boost.
“The confidence is very high,” he said.
“The Gillingham games was the first time I’ve started the first game of the season. I’ve not started a season.
“I think it’s given me a lot confidence to just crack on and go and get it. Football is a big confidence thing.
“It’s massive and it’s down to me to keep the shirt. The lads behind me are wanting to rip that shirt.
“I’m not going to let it go easily.
“That goes around the whole starting XI. Everyone has got places up for grabs, so it’s good to have people behind you wanting your shirt.”
Starting games has come with a need to adapt for May, who has been deployed in a bank of three attack-minded players behind a lone striker.
As he looks to re-model his game, he is taking inspiration from a player who made a major impact at Rovers last season – Mallik Wilks.
“I feel like I touch the ball more, I can get the ball, turn and drive at players,” May said.
“Last year Mallik was the best at it. He was so strong, he used to turn and get at players.
“I said to myself that I want to try to get at players more. I want to have the belief to get at defenders.
“So I’m getting into little pockets behind the midfield, receiving it and I’m really enjoying it.
“Normally I would have been getting rid of the ball as quickly as I possibly can but now I’ve got the confidence to get at players.
“And there is a lot of fluidity with the system. Copps [James Coppinger] can go up there. Between me, Madger [Gomes] and Copps, we can all flit around.”