Striker Kayden Jackson won a competition to land his first professional contract, but says he never expected the jackpot to be a career that would span more than a decade.
In 11 years, Jackson has been signed by 10 clubs, once commanded a £1m transfer fee, won promotion to the Premier League and now tops Derby County's goalscoring charts on their return to the Championship.
It is fair to say the 30-year-old's journey has been anything but ordinary.
After failed attempts to join academies at Leeds United and Bradford City, he outperformed 5,500 other prospects in a nationwide competition aged 19 to earn a contract with then League One club Swindon Town in 2013.
"Crazy" is how Jackson describes the experience of going through rounds of trials in Leeds and Manchester before competing for just two professional deals in an exhibition match.
"It was literally the dream - anyone wanting to become a professional footballer had this opportunity," Jackson said.
"Thankfully I came through it and was one of the lucky two that was given an opportunity to go into professional football."
That contract, however, lasted only a year. But it was the start of a career that has meandered from the National League to the Championship.
He started at non-league level, which included a season at Wrexham that led to a 2016 move to Barnsley – a then Championship side that he never featured for.
A loan stay with Grimsby was followed by another move to Accrington Stanley, which earned him a £1m switch to Ipswich Town, where he would stay for six years and win back-to-back promotions from League One to the Premier League.
However, he did not head to the top flight with the Tractor Boys, and joined Derby County after being released.
"Everything, my experience, what I've learned and my route into the game - that’s what has helped shape me," Jackson told BBC East Midlands Today.
He has been quick to make an impression at Derby, scoring three goals and providing two assists in 11 appearances.
Jackson has started eight games in the Championship this season - one fewer than he managed across the entire league campaign last term.
For Jackson, it adds to his story of perseverance.
"I had trials at Bradford and Leeds, but didn’t quite make the grade, but those experiences were eye-opening for me because beforehand I looked at professional footballers as these godlike figures and I could only dream of being in their shoes," he said.
"I’ll be honest, I didn’t think I was good enough. I didn’t think I had the ability because I never really had that academy learning - players are technically taught so much and I literally had my family there guiding me, saying you can do this better and that better."
That guidance and existence outside the traditional development pathway has given Jackson an unusual perspective of what it takes to sustain a career in the game.
"I thought I missed out on a hell of a lot of coaching, and because of that I wasn't sure how far I could actually go," he said.
"So when I was told something, I took it on board. I didn’t think I knew everything, whereas in football nowadays kids think they know everything. They think they can get through the game without listening - without taking information on board.
"Work ethic, humility and the constant want to keep improving can get you further than ability alone.
"It wasn't the conventional route into football, as much as I'd have liked it to be. I was patient, but thankfully I persevered and I'm sat here today."
It is at Derby's Moor Farm training base that Jackson opens up about his remarkable journey, and yet he is quick to say that he is "not one to keep looking back" when asked about the success his final two years at Ipswich brought.
Instead, he is more interested in focusing on his future at Derby, who sit mid-table after a solid start the campaign.
"In terms on reflecting, you don't get much time," Jackson said.
"I want to keep looking forward because we have a job to do here."