Whiteman had long been planning for a career away from professional football. On days off and during afternoons after training, he would meet directors or producers for coffee, or help assist on set as a runner.
He has his own radio show, first appearing under his mother's surname to keep a low profile before deciding "just to be myself".
"Everyone was like 'wow, you're a footballer and you listen to jazz, this is crazy!'," he smiles.
Fans discovered his Letterboxd profile, where he has reviewed more than 200 films, but Whiteman also spent free time working on photography projects and taking acting lessons.
One summer, while his team-mates set off for Dubai or the Maldives, Whiteman appeared in a play in Holborn - an experimental art piece where he played a "really cheesy, over-the-top boyfriend". "So it was quite easy," he jokes.
"All these little things were edging me closer to taking this step into this unknown," says the 27-year-old. "I knew I didn't want to be in football when I was done.
"I was trying to teach myself and learn, so that when that day came I wasn't at zero. I was quite unhappy for a while and thought I would rather try something else when I am young."
Whiteman has always been culturally engaged, his father was a jazz musician, but in his youth some team-mates would call him a "hippie". He says there used to be a feeling inside professional football that doing anything else on the side was a "distraction".
He was living a very different life to the stereotype of a footballer - Whiteman didn't play golf and would ride his bike or get the train to training. He lives close to the stadium, so would walk to home games.
"If you get kids from such a young age and put them in this bubble it is inevitable that everyone becomes a product of the environment and reflections of each other in the changing room," he explains. "And I lived that as an early teen. I was desperate for the monogram Gucci washbag."
But he came to separate his work from his personal interests: "I love the craft of playing football and being a keeper and rolling around on the grass, it's great, getting hit with the ball.
"But I also love these other things and [thought] one day I would like to try those. I didn't feel they really went together, hence why I had them running alongside.
"All my team-mates were great and we got on really well, but it was work. I was always a little bit... slightly different."
In the end, football was effectively stopping him being able to pursue opportunities presented in the creative industry, caught in a "never-ending cycle of season-holiday-season-holiday", to Whiteman that felt "kind of the same thing all the time".
