The midfielder hasn’t played a lot of football since making his first team debut at the tender age of 16.
That high he experienced coming off the bench against Scunthorpe in April 2017 was only bettered when Gary Caldwell started the youngster in the opening game of the 2017/18 season.
He admits life at the Proact hasn’t exactly been a barrel of laughs in the two years that have followed.
“It’s been up and down, to sum it up in a few words,” he said.
“Since I made my debut against Scunthorpe when I was 16, I was high then, and started the first game of the season against Grimsby.
“That season I was doing well, playing well in the youth team.
“I got my first main injury in February and that kept me out for the rest of the season.
“Last season was difficult for me, I didn’t play many games.
“I went on loan to Sheffield, played a few games but got brought back and didn’t play many games before the end of the season.
“There’s been two relegations.
“I’ve experienced it all in the space of two years really.”
Wakefield was tipped for big things by Caldwell, who remained an admirer long after his own Proact departure.
The Spireites academy product recalls the buzz he got running out in front of almost 8,000.
He insists there was no complacency, however. He didn’t take first team involvement for granted.
“I was excited, I was definitely nervous starting the first game.
“I didn’t think ‘this is it’ I just wanted to try and impact the game as much as I could, like I did in the youth team.
“I didn’t think I’d made it, that’s not what you can think after playing one game.”
A pair of EFL Trophy appearances were the full extent of Wakefield’s first team action that season.
In fact he hasn’t featured again as a senior player.
And chances to play any kind of football at all have been few and far between, with no reserves in place for the past two seasons.
“Last season was particularly frustrating,” he said.
“I couldn’t play many games.
“It wasn’t so much the season before, because I could still play Under 18s football every week and I was enjoying myself still.
“Last season I went on loan but after a handful of games got brought back.”
That recall from a loan spell at Sheffield FC occurred when the world’s oldest club failed to start Wakefield in a match and Spireites boss Martin Allen responded by cutting his stay short.
Looking back, Wakefield wishes he’d been allowed to remain at the Northern Premier League side.
“I didn’t know what he was thinking at that time, if he was bringing me back to involve me more,” he said.
“If I knew I wasn’t going to be involved I would have liked to stay there, get some games and carry on.”
Despite the lack of time on the pitch, Wakefield believes he’s grown and improved since playing in League One.
Adversity, disappointment and frustration have forged resilience.
“I’ve learned a lot, mentally.
“I’m a lot stronger mentally than I was a couple of years ago, just through what I’ve been through injury wise, being in the team then not playing.
“I’ve developed as a player as well, since the new gaffer came in - he’s helped me a lot.”
Sheridan’s arrival appears to have been timely for Wakefield and his Chesterfield career.
The boss spoke positively in the press about his young midfielder and handed him a new contract.
His encouragement on the training ground has helped lift Wakefield’s morale.
“He brought the confidence back into me, just by speaking to me, helping me a lot more in training.
“I’ve got a lot more confidence now than I maybe had at the start of the year.”
And, crucially, Sheridan is opening up the possibility of regular football for Wakefield and the rest of the club’s young prospects.
A development squad, playing matches under the watchful eye of newly appointed head of recruitment Charlie Williamson, will help fill the void between the youth team and the senior side.
“I think that’s really important,” said Wakefield.
“I had it in my first year of scholarship and that helped a lot of the lads from the Under 18s and young pros who weren’t involved in the first team, we’d get games in every week to play in and develop.”
There’s a marked difference in the teen’s tone when the talk turns from a frustrating last two years to what the future could hold.
He’s excited once more about his football and determined to impress Sheridan.
“Because we finished the season so early we’ve had a long time off so I can’t wait to get back.
“I can’t wait.
“(I’m doing) a lot of gym, a lot of running, football sessions, working on technique.
“But the main thing is to stay fit and make sure you’re fit for the first day you come in.
“You’ve got to make sure you’re near the top of the group in all the running, be strong in the gym sessions.
“This is a big season for me, to prove what I can do, like I did before.
“I’ve got to start pre-season strong and do well.
“I want to prove to the manager I can play in the first team.”
Having watched from the sidelines as his club suffered back to back relegations and, initially, struggled in the National League, Wakefield hopes to finally experience the good times at the Proact.
He’s got an inkling they might be just around the corner.
“I’ve got a good feeling about it all.
“We finished the season very strong, since the new gaffer came in.
“I think it’ll be a good season.
“I’ve only really experienced the relegations, it hasn’t been good, so it’ll be nice to have some good times.”