Caldwell and Pressley played alongside each other for Celtic and Scotland
“I’ve become a full-time painter and decorator,” laughs Steven Pressley.
His former team-mate Gary Caldwell, meanwhile, has turned his hand to gardening.
Both men lost management jobs in the first half of the season and have spent the intervening months without a full-time role.
Coming out of the relentless world of football is a big adjustment, especially during these uncertain times.
So what’s it like to go from the whirlwind of club management to unemployment?
Losing your job
The first stage is the most painful. The news no manager wants to hear, but knows the likelihood is they will at some stage of their career. Often it’s expected. When results are poor and supporters are restless, many coaches are just waiting for the inevitable, though it can arrive as a bolt from the blue.
There is little consistency to the approach from clubs who move to relieve a manager of their duties. Football is known as a brutal industry, and managers often bear the brunt of that.
When Caldwell was at Chesterfield in 2017 he could sense the end was nigh, and he was right. Kind of. A 5-1 defeat by Stoke City resulted in a pitchside conversation with the club’s chief executive, who told him the owner had “had enough”, which Caldwell accepted.
“After that, the analyst came out the dressing room and said the players wanted to speak to the chief exec,” the former Scotland captain says. “He said: ‘We’d better go in.’ I said: ‘I ain’t.’ He went in with the director. I knew exactly what was going to happen.
“I went back into the manager’s office. Ten minutes later he came out and said: ‘The players are behind you. They take responsibility and want you to stay on, so we’re going to keep you on.’
“Looking back I should’ve just said ‘stuff your job’,” he laughs. He was sacked the following Saturday after a defeat followed a midweek draw.
Pressley too is familiar with the harsh reality of the industry. He was dismissed by Carlisle in November of last year and says, six months on, he has yet to be told exactly why.
‘You go from 100mph to zero’
Working as a manager is relentless and all-consuming. From coaching and analysis to budgets and transfer deals there is rarely a free moment. At clubs with greater resource, the burden is lessened by more staff, but not all have that luxury.
“I spent a lot of my time at Carlisle with no analyst,” Pressley says.
“So not only did I have to watch all the games, I had to cut the games, prepare them and present to the players. I could be up to 1 o’clock in the morning doing this.
“And then it goes from that, to nothing. And that’s the difficulty.”
Caldwell has experienced the same empty days.
“You go from 100mph to zero pretty much,” he says. “You get time with your family which is nice, but you lose your identity a little bit.
“Football has been my life since I was 16 years old. I left school and went to Newcastle and I’ve never done anything else.”
Trawling Wyscout & meeting Simeone
Coming back a better manager is an oft-repeated phrase, but how easy is it to improve when you are out of the game?
Pressley would sit down with assistant Neil McFarlane, who is now head coach of Brentford’s B team, and do a “debrief” on what was right and wrong during their last spell.
Caldwell trawls through Wyscout – a programme that lets you watch games from all over the world – and analyses teams and players.
Both attend games at various levels to profile players for future jobs. They both also advocate exercising regularly.
And then there are the visits to clubs to try to learn from the best.
Pressley has arranged trips to watch Atletico Madrid manager Diego Simeone in action, as well as Quique Sanchez-Flores, David Moyes, Brendan Rodgers and others.
The union for managers in England – the League Managers’ Association – also sets up events, including question and answer sessions with Pep Guardiola, and coaching ‘masterclasses’ with elite managers.
These help bring some purpose and structure, but the support network is not always extensive.
“It can be [tough] trying to motivate yourself at times because the job gives you that motivation,” Caldwell says.
“One thing I’ve learned is you have to pick up the phone yourself. Every manager or coach, is so welcoming, everyone wants to help you and be there for you. Because I think everyone understands that at some point, they’re going to lose their job and need that support.”
Pressley adds: “The life of an unemployed football manager can be very lonely.
“There are a lot of days where I’m on my own. And I don’t want anyone to feel sorry for me. There are people in much worse situations than myself. But still, they are challenging.
“I’ll run five times a week. I think that’s important because I believe a fit body gives you a fit mind. I try to keep on top of that. Media work keeps me involved too.”
Getting another job
The key aim for any unemployed manager is to get back into the hot seat. Despite the pressure, criticism and often brutal disposal, the touchline fix is the only high that comes close to playing.
Football is a small world and often the same managers move around clubs. But it is not always as straightforward as it seems to get back into management. Caldwell estimates he is now into double figures for interviews, having been offered the Wigan job without doing one.
He describes one for the post of under-23 manager at Manchester City as his toughest. It was three hours long and involved three tasks, supervised by about nine staff. In one room, Caldwell had to give a presentation on himself, and one on how to motivate and develop young players.
Then, to another room where he had to pick cards with different scenarios on them and explain how he would deal with them.
“The first one I picked up was about motivating a player that didn’t want to train,” Caldwell recalls. ” There were about four people in the room and I looked at them and thought ‘I know the answer they want to hear, and I know answer I’m going to give.’
“And I thought ‘do I stick by my principles or do I really want the job?’ I gave them my honest answer and I could see them looking at each other. I knew straight away as soon as a came out that room.”
The final step involved analysing 10 minutes of clips and explaining how to set up a team for two different matches. It’s a far cry from Claude Anelka rocking up at Raith Rovers.
“I go in with everything now,” Caldwell explains.
“From the budgets to players I would look to sign, to a squad analysis, to my way of my man-management, coaching style, training. I go in with the full package.
“I can show them exactly how I want to play football, how I’ll train the players to do it, what players I need to recruit to make that happen. It’s then about the budgets and how, as a club, we can work and make that a reality.”
Caldwell was sacked by Scottish Championship side Partick Thistle in September
‘Some managers need the money’
Pressley was this season’s 19th managerial casualty in the English football leagues when he left Carlisle on 13 November 2019. There have been 19 since.
Eleven of Scotland’s 42 senior clubs have changed manager this season, Caldwell being one of those after being sacked by Partick Thistle in September.
“I’m not in a position where I can select any job I want – I’m aware of that,” Pressley says.
“But I would rather not work for three years now than take on a job that I didn’t think was aligned to me. That’s been my biggest learning curve.
“At the top level if you’re paid off you’ll get enough money to see you by for many years. But for other manager that’s not the case – they have to go back to work quickly because they need the money, so the choices they make often aren’t for the right reasons.”
Caldwell has also been stung by jumping back in too quickly at Chesterfield after leaving Wigan.
At 38 he has managed three clubs but only one full season, when he won League One with the Latics. He regrets the shift in attitudes towards managers and the faceless cries of social media.
“You are only judged on the result and more often than not there’s more to it,” the former Hibernian and Celtic defender says. “I understand it’s a results business and winning is the most important thing but there’s so many other things go on within a football club.
“Chesterfield was the only one I felt ‘yep, it is the right decision, no progress here, I can’t see a way out’. But in my other two jobs I felt, whilst it wasn’t perfect, there was progress being made.”
His advice to other young managers who will almost inevitably get the sack in the future?
“Don’t ever take it personally, and don’t fall out with people.
“Try and leave and be respectful. But once you leave try and learn the lessons from the job you’ve just been in.
“Take the best and the negative from that and try and improve so every time you come back you come back a better manager.”