Today, his diary is still full of theatre-related appointments, but now they are appointments about his own plays.
The poacher-turned-gamekeeper has fulfilled a life-long dream and become a bona fide playwright, with one hugely successful run of a p
lay under his belt, a slot in this season's theatre brochures, and two other plays on the go.
Windass, 41, left his day job – theatre critic for the Hull Daily Mail – in May last year, as rehearsals for his first professionally produced play, Sully, got into full swing.
"I took a couple of weeks off so I could be there for the final rehearsals, and just never went back," says Windass.
"It got to the final week of rehearsals and I was having an absolute ball, loving every minute of it – they wanted me back in the office, but I realised that where I really wanted to be was in rehearsals, doing what I was doing, so I just decided that I didn't want to go back.
"It was one of those moments where you get an opportunity to do something and you have to take it. If I hadn't done it, I think I would have regretted it forever."
And so he stayed.
A week later, Sully opened. It's the story of Clive Sullivan, the Hull rugby hero who captained Great Britain. Although Windass had picked a subject which would have local audiences on his side, he admits: "I have never been so nervous.
"It was a strange feeling because I've spent so long going to first nights of plays, but only ever as a critic. This time I was seeing it from the other side."
The production was a roaring success, audiences staying behind to talk to the author and actors, grown men admitting they had been moved to tears, and the applause as loud as it was long.
"It was the greatest feeling, the reaction that first night, just something it is impossible to describe," says Windass.
But the play was booked at Hull Truck Theatre for only a short run, and when it was over, Windass found himself without a job. Able to live on some savings and money earned from the success of Sully, the new playwright was delighted when Hull Truck Theatre told him that they wanted to re-stage it this coming season.
"I think we realised it was going to be a popular play, but no-one really realised just how popular it would be," he says.
"People were ringing up and trying to book tickets as soon as they had seen the show, only to find it had sold out. The theatre told me they wanted to bring it back almost as soon as it was finished."
With Sully booked in for another run, Windass set out on the path of his new career as a full-time playwright.
Attempting to maintain the discipline his previous job demanded, he would make sure he was at his computer in the morning, writing something, anything – even if it was just his weblog.
"I found that mornings and evenings were the best times for me to write, so that's when I get my work done and I have the afternoons off. It just means that I live to a slightly different timetable – now my afternoons are my evenings!"
Further meetings followed with Hull Truck, and Windass was soon commissioned to write another play.
He can't talk about the new project but he expects to have the first draft finished soon and the theatre will look to programme it.
Late last year, he also secured a £4,500 Arts Council grant, which he is using to help develop a play based on the life of British film mogul J Arthur Rank.
The man who presided over a glorious period in British cinema began his life as an East Hull lad, working
as a flour-miller before establishing the most successful studio in the history of British film.
Windass was walking near his home when the idea came to him.
"I was passing by this battered old house that I must have walked past hundreds of times, and saw that there was a blue plaque on the wall," he says.
"I stopped to have a look at it and found out it was the house where Rank was born. I started researching his life and I couldn't quite believe that
no-one has told this story before. It is an incredible tale of someone from Hull who became one of the most powerful men in movies.
"The Arts Council award means that I can concentrate on researching the play and getting it finished. I've actually completed a first draft and now I'm going to start refining it and getting it right."
Once the play is at a state where Windass feels it is ready, it will be given a public reading before he develops it further.
"I still have deadlines and I still have the habit of leaving things to the last minute, but it really is a dream come true to be working full-time as a playwright."
