The Birmingham-born trade union leader was elected to the top job at the union representing actors and other creative professionals last year, a decade after he first joined as part of a varied career that included a stint as Press Secretary for the New Jersey Democratic Party in the US.
But one of his greatest regrets is having to leave Yorkshire and the Humber, where as an organiser for steelworkers' union Community he worked all across the region and even met his partner, who is from just outside the historic steel-producing town of Scunthorpe.
"It's a part of the world that is much derided, Scunthorpe, but actually I have an awful lot of affection for," he tells The Yorkshire Post's political podcast, Pod's Own Country. "I've never been in a stronger or more affectionate community. It's a really, really fantastic place.
"Actually going across Yorkshire with its incredible history of trade unionism, it always has an incredibly rich history of really deep and meaningful culture.
"Not only the range of actors and practitioners that have come from the region but also the way that you still have working men's clubs, the way that grassroots working class art is up there along with some of the best venues in the country for members to work in.
"The Bradford Alhambra is one of the best places to go to on the touring circuit. You've got an incredible creative scene in Sheffield and in Leeds, there's excellent community work that's happening in Bradford, there's some excellent community work happening out in South Yorkshire that's genuinely transforming people's lives.
"And when I was working up there, I was very conscious of that idea. I wasn't working for performers, I wasn't working in the entertainment industry but it's an inherently creative place. So I miss it."
It is workers in the theatres, working men's clubs, recording studios and TV sets of Yorkshire and the rest of the country that Mr Fleming, the first person in his family to go to university, represents now at Equity.
He was born in 1988, a year which also marked the end of the 'closed shop' which meant only Equity members could be an entertainment professional. And the restrictions brought about by the pandemic have left many of Equity’s 48,000 members facing challenges that are unparalleled in modern times.
Representing what he calls a 'highly precarious group of working people', he says those in the creative sectors are vulnerable to exploitation because of their passion for their work and their desire to make people happy and spark debate.
And he points out that many creative industries are among the most unionised in the country. Some 75 per cent of the cast of a touring musical are likely to be in a union and up to 70 per cent in soap operas, compared with 10 per cent in the private sector as a whole.
Among the union's roles, he says, is looking after people doing valuable work providing art and entertainment for those in care homes or combating loneliness.
"Children's entertainers who get paid in lemonade, or rocking up at a party and told they're not wanted anymore, or getting shouted offstage in a working men's club, those are the people that we're there to make sure that they have dignity in the work that they do.
"So the legacy of the closed shop is a strong union and the legacy of the closed shop is that high membership, which is a kind of an untold story in British trade unionism.
"If you talk about the most highly unionised people in this country, who would you think of? Steel workers maybe, or miners? Or would you think about nurses and teachers, but actually, some of the most highly unionised are the performers, the stage management, the creative team members whose work you enjoy every day, and whose work has got us through the lockdown.
"Where would we have been in the last 12 months if you hadn't had Netflix, with whom we have a union agreement, if you hadn't had the BBC, if you haven't had recorded productions from all over the country, including from places like the Crucible [in Sheffield] and so on, all working on union agreements?"
It's no secret that the creative industries have been hit hard by the pandemic as theatres, cinemas and music venues closed their doors during lockdown.
And while many will be reopening on Monday May 17, Mr Fleming describes "a real sense of terror about whether the industries will ever return in a way that we understood before, there is a worry about bosses taking advantage of this period of time".
The Government last summer announced that Britain’s "globally renowned arts, culture and heritage industries will receive a world-leading £1.57 billion rescue package to help weather the impact of coronavirus".Government officials say more than £1.2bn has so far been allocated from its Culture Recovery Fund (CRF). This includes over £100m to organisations and sites in Yorkshire to “protect thousands of jobs, stabilise organisations of all sizes and help them prepare to reopen”.
Officials say the CRF has had significant indirect benefits for freelancers, and that in round two of the scheme organisations were asked to estimate how many full-time employees and freelancers were protected by the fund until the end of June.
Collectively, applicants reported that 52,000 full-time staff and almost 100,000 freelancers would be supported until the end of June this year.
But according to Mr Fleming this fund, which has been handed out to thousands of organisations nationwide, is not designed to meet the needs of the sector, with 40 per cent unallocated and 40 per cent of his members not getting any benefit.
A large proportion of his members have also received nothing from the Government's job-saving furlough scheme or its equivalent fund for the self-employed, often because of their low wages or the sporadic nature of their work. His view is that the Government should have introduced a basic income guarantee for artists and adjusted the self-employed support scheme.
"Our industry, like any industry is fundamentally about people," he says. "You don't go to a theatre to see the seat or to enjoy the air conditioning, you go to the theatre to watch the work on the stage, to see the design set, to look at the costumes, to enjoy the music, to enjoy the performances that you watch, you go there to see people and stories you understand.
"And actually the Government is not allocating money for work to happen. And that is incredibly damaging, it is damaging for local economies. There are a lot of places in the hospitality trade who are going to struggle.
"If you think about somewhere like Bradford, that beautiful square that is in front of the town hall, it is alive because of the theatre that is in that square. If you think about Cast in Doncaster and how that revolutionised the nighttime economy and very often small independent restaurants, pubs, clubs, which actually depend on that happening.
"Now, if we're not given money as a sector to do work, which is what we wanted, actually all of those ancillary industries are going to suffer. And those are precarious people as well, they are people in hotels or the people in bars, pubs, clubs. So actually, they were not using it as a stimulus for the rest of the economy.
"They were using it [the Culture Recovery Fund] to basically prop up building projects, it was going into the pockets of buildings and bosses and not into the pockets of the workforce, or into culture, art and entertainment for people to consume. It gets even worse, if you're not one of those institutions.
"If you're a children's entertainer, if you're a club singer, those sorts of people and the places that they work are already under threat. In Yorkshire, the absolute heart of the working men's club, as far as I'm concerned, how many of them were under threat before coronavirus and how many are going to struggle when it comes back.
"Keeping live entertainment works and keeping those venues open and making them places you want to go, without a workforce to do that it's going to fail."