David Kershaw is on his third attempt at retiring. “My wife has given up on me, but I do mean it this time,” he says. Now 68, he first tried at 60, after 21 years at a school in the West Midlands, but came back to lead a school in West Yorkshire. Then he stepped down again, but was persuaded to become executive headteacher of two schools, this time in the East Midlands. And the reason he has twice shelved plans for an easy life has been to take up the challenge of turning around a failing school.

His appetite for transforming a school can be traced back to his headship at Coundon Court School and Community College in Coventry. In his two decades there, he oversaw a dramatic improvement in results. When he arrived, 10 per cent of GCSEs were at grades A-C; when he left, that figure was 70 per cent.

On retirement, he took up a part-time post as an educational adviser in Bradford and it was then that he was asked to step in as head of Bradford Cathedral Community College. “It was in dire circumstances and had just been given the worst exam results in the country,” Mr Kershaw recalls.

“Groups of pupils were just walking around the school, not attending lessons. There was a lot of aggression from pupils towards each other and the teachers.”

On the one hand, Mr Kershaw felt ready to slow down after starting his career at 19. On top of that, his family home was still in Coventry. But returning to the front line was a straightforward decision: “It was tough but I felt I had no choice,” he says.

During that first winter, a few months into his headship, he was at the school gates welcoming the pupils when it hit home just why he was there. “In Bradford you get very strong and icy winds from the North Sea,” he says. “It was snowing and it was cold and bitter. There were youngsters turning up, little girls of 11, in summer dresses and plimsolls.

“That’s why I was doing it. It was a moral imperative to break that cycle of deprivation and that cycle of helplessness, and to change those young people’s lives.”

Mr Kershaw is one of a small group of headteachers whose careers have taken an unusual turn. In the twilight of his career he has become dedicated - perhaps even addicted - to taking schools out of special measures.

For many teachers, even those with a passion for raising aspirations and helping children to achieve beyond expectations, the challenge of working in a school in special measures can seem daunting. Added to that, many of these schools are in deprived areas, compounding the scale of the difficulties.

Russ Wallace is no stranger to challenging days. “If it is a tough job, I’m really quite happy,” he says. “The more challenging it is, the better.”

The seasoned headteacher was drafted in to the Richard Rose Central Academy in Carlisle at the start of 2009, just after pupils went on strike and the school was placed in special measures. This was only months after the school opened its doors for the first time.

A few weeks before his appointment, Mr Wallace saw the television reports on the developing crisis at Richard Rose, including pictures of striking pupils streaming away from the school.

“I was sitting at home and I remember thinking, `Dear oh dear, what’s going on here?’,” he says. While some people would have sighed and shaken their heads, Mr Wallace received a phone call asking him to come on board. It was a call he could not resist. When he arrived, he realised the situation was as bleak as it had been painted.

“It was just desperate,” he says. “There were no systems and no one knew what was expected of them. I excluded a kid for telling me to fuck off before he had even got into school.” Originally he was contracted to do one term, although “that was five terms ago,” he says. “I was committed after 20 minutes, to be honest.”

Mr Wallace has been the headteacher of nine schools since 1997, four of which were in special measures. Despite undergoing over 20 monitoring visits from Ofsted, he still feels nervous when the inspectors arrive. The visits are “still pretty edgy,” he says.

But it was only in 2005, after working as a temporary head in three schools in Newcastle, that he decided to “grab the bull by the horns” and dedicate himself to school improvement. “You had to prove yourself,” he says, “so I took the first one that came along.”

That first placement was in Blackburn, where he had to oversee a school’s transition from a comprehensive into an academy in one term. “It was in a mess and, as is quite common for a school if it is closing, we had to be prepared to cope with incidents of arson,” he says.

The job took its toll personally as well. “Blackburn was not commutable, so I used to drive down very early on a Monday morning and stay in a hotel Monday through to Thursday. It was bloody awful.”

This sense of dislocation is a familiar feeling for Mr Kershaw. His second headship in Bradford involved considerable personal sacrifice. “I had pangs of guilt about being away from home,” he says. “At first I stayed in a hotel which I didn’t like. ”

Colleagues from his consultancy work made the weekdays in Bradford easier, and eventually he bought a flat in the city. “The education community in Bradford welcomed me with a warmth and a care that was tremendous,” he says. “And for the first time in my life - which is a terrible condemnation on me - I was cooking meals for other people. But the community there did support me, which was just as well because we had some challenging days, by Jove.”

Mr Kershaw is now executive headteacher of two schools in Leicester, helping them come out of special measures, and is a serving school improvement partner and National Challenge adviser in Barnsley.

But the decision to work in a challenging school is one many teachers - perhaps naturally - want to avoid. A survey for the Training and Development Agency for Schools (TDA) earlier this year found that only one in 10 teachers and heads would consider working in schools in challenging circumstances.

The prospect of wanting to work in a school where standards are low, behaviour is challenging and the pressure is considerable would be off- putting to many. But for heads, the stakes are even greater.

Levels of accountability mean the pressure on heads has never been greater. According to figures put together by the Association of School and College Leaders, about 150 heads and deputies lost their jobs in 2008, up from 30 just four years earlier. Falls in exam results, or even results not improving quickly enough, and poor Ofsted inspections, are frequently the spur to resignation or dismissal.

Taking over a failing school can also bring with it an intense level of scrutiny. When Carole McAlpine resigned 18 months into her headship at Firfield Community School in Newcastle in 2000, it raised questions over a key government policy. Ms McAlpine was the first headteacher appointed under the Labour government’s Fresh Start scheme to turn around struggling schools, but when results fell she quit.

It is not only outside pressure to perform that can be a potential source of anxiety. Often, attitudes within the school among colleagues and pupils cause problems. “The first thing staff will do is put your name into Google,” says Mr Wallace. “They will have done their homework, and the kids I guess will do that as well.”

Sir Dexter Hutt, executive headteacher of Hastings Federation of Schools in East Sussex has turned around four - “almost five” - schools, and has been through more than 15 Ofsted inspections.

Despite the potential pitfalls and difficulties, he relishes the risks. “I thrive on it,” he says. “I enjoy the challenge.” But turning round a failing school often involves making difficult decisions, and Sir Dexter has also experienced the dangers of this approach.

In 2007, when he was head at the International School in Birmingham, a teacher won a case for unfair dismissal against the school, and the resultant publicity included criticism of the school’s management and behaviour policies.

“There are all sorts of issues to do with, shall we say, the human condition and personalities,” Sir Dexter says. “But that’s the expertise that we have to have - knowing how to solve those.”

Programmes such as Teach First and Future Leaders aim to prepare teachers and headteachers specifically for working in schools in challenging circumstances. But they do not just appeal to a teacher’s sense of social justice - they aim to attract ambitious individuals.

Teach First positions itself as a competitor for the best graduates with the private sector and expects many of its recruits to use the scheme as a launch pad into a more lucrative private sector career.

But risk-taking is only appealing when there is a certain amount of confidence that it will pay off. As a result, heads need determination in abundance and the conviction that they can make a difference, says Iris Cerney, headteacher of Whitmore Junior School in Basildon, Essex.

Mrs Cerney describes her attitude as a “thirst for school improvement.” This is her second headship of a school in special measures, although she has worked with eight more schools in special measures as part of the local authority’s school improvement team. She also leads a resilience group for headteachers in Basildon through CK Academy, a health and fitness training provider.

When she arrived at Whitmore, there were children out on the roof and pupils who would come in and out of school at all times during the day. But it did not put her off. “It was highly enjoyable,” she laughs.

“I have really strong views on pupil entitlement and equality of opportunity,” she says. “Schools in difficulty are often in areas of areas of socio-economic deprivation. My belief has always been that if we can provide a school that is safe, secure and a stable environment, then children will have a greater propensity to flourish and do well.”

As part of her MA in school improvement, Mrs Cerney researched the personal qualities headteachers working in special-measures schools need to have. Experience and knowledge of the issues involved are fundamental, of course. But being a successful school improvement headteacher comes down to an absolute conviction that they can make a difference, allied to the patience to follow that through.

“You have to have high aspirations and high expectations,” she says. “I thought of my own childhood a lot when I was doing this. I grew up in Wales, I’m from a normal background, but the one thing my parents and family rewarded was education.

“I would be rewarded for reading and my parents had high expectations. I had a great belief I could achieve anything.” This helped to shape her own attitudes, and in turn fed into her motivation for teaching, to instill that same level of self-belief in her pupils.

Heads who take over failing schools also have to fight against the now- largely discredited “superhead” label. In the late 1990s, when Labour’s zeal for improving schools was at its height, politicians and the media latched on to the idea of the power of a single figure to transform a school. High salaries and media scrutiny followed, but the results did not always live up to expectations.

As well Ms McAlpine’s brief tenure at Firfield, one of the highest-profile superheads was Torsten Friedag, appointed at the new Islington Arts and Media School in 1999 on a then-unheard of, and widely publicised, salary of pound;70,000.

His arrival was attended by David Blunkett, the education secretary at the time, along with TV crews and newspaper reporters. Seven months later, Mr Friedag resigned, claiming that the board of governors had blocked his attempts to improve the school.

Perhaps not surprisingly given these high-profile precedents, many heads who specialise in taking schools out of special measures are reluctant to use the term “superhead” and largely stay out of the limelight. “Some people think that to do something like I did, you need to be an extrovert, or a larger-than-life personality,” says Mr Kershaw. “I don’t think you need that. All you need is a driving ambition to change young people’s lives.”

But he acknowledges the lure of being seen as the leader who is calling all the shots. “My personality type is quite attracted to it, frankly,” he says. “It gives you a great sense of power and audience, but it is not in the best interests of the staff and the students because superheads come and go.”

Such a label is also superficial, he says. “What I’m after is changing young people’s lives and teachers’ practices, and you do that through partnership and teamwork. I’ve got experience, but I don’t have all the answers.”

The terminology may have changed, but the Government is still keen to emphasise the importance of a school leader, says John Bangs, former NUT assistant secretary. “There has been a deification of the role of the headteacher,” he says. “You can headhunt and pay a headteacher as much as you like, but to ask an individual to achieve the Holy Grail is like asking for the Moon.”

Even the idea that a school in special measures can be turned around in the space of a year puts too much pressure on headteachers, says Mr Bangs, and this also affects the teachers involved. “In a sense, headteachers in special measures schools are victims of unreasonable expectations.”

But it is not always about instant success. Taking on the role of executive headteacher involves bringing about change within a leadership team who will be there for the long haul, says Sir Dexter. He does not believe in taking on short-term headships as a “superhead”.

“I think it is a dangerous misunderstanding of the role,” he says. “If any school should fail to improve, accountability would be shared between the head and me. But you almost have to get the headship role out of your mindset.”

An executive head role means dealing with strategy more than the “nitty gritty”, he adds. But this in turn can be a difficult transition to make for a head used to having a hands-on role.

“I missed it deeply, especially at first,” he says. “But it is something that I have had to come to terms with. It is almost a sacrifice you have to make to do this kind of work. Sometimes I’m envious of it.”

While many headteachers would hesitate to put their reputations on the line, it is a belief that they can make a difference that makes a handful return to schools in special measures again and again. This is why they put up with living away from home and getting used to different colleagues, as well as the additional pressure and media circus that can surround their appointment.

“I was born and brought up in a council house estate in Dundee and I am no different, other than being older, than the vast majority of kids I am head to,” says Mr Wallace. “I was really lucky. I had supportive parents and teachers - I had somebody help me in that situation.”

Despite the publicity surrounding Richard Rose when he took over, he says the focus of the job is straightforward.

“It is about giving young people the best possible chance you can, to have a good life,” he says. “That sounds dreadful - but I actually believe that. These kids are the salt of the earth. They just need a little bit of structure to their school lives, a little bit of guidance. And they blossom from it.”

• Orignial headline: Hooked on special measures