This year, Roundabout is proud to mark a remarkable milestone: Ben Keegan’s 20th anniversary as our Chief Executive.

When Ben first joined the charity in 2005, the landscape looked very different. He recalls joining outreach teams on the streets of Sheffield and struggling to find any rough sleepers at all. Today, sadly, visible homelessness is on the rise in both Sheffield and Rotherham.

Yet, despite these growing challenges, there’s one thing that’s remained constant under Ben’s leadership:

“The thing I am most proud of is that we don’t have anybody sleeping rough under the age of 25 and that’s because of Roundabout’s work,” he says.

Two Decades of Dedication

When he first took on the role, Ben told his interview panel he’d probably stay for only five years. Twenty years later, he’s still here – and more committed than ever.

“Roundabout is a great organisation and every year is a great challenge,” he explains. “It has grown so much and my job is not the same as it was when I started – every week is different.”

Ben brought with him a decade of frontline experience, starting in 1995 at a large 60-bed city centre hostel in Manchester, followed by time working with rough sleepers in London and later in Sheffield. What drew him to Roundabout was its progressive approach to involving young people in shaping their own futures.

“The thing I liked most about Roundabout was that it was always renowned for involving young people in decisions, helping young people to have a voice, which was ahead of its time,” he says.

Ben pictured outside Roundabout’s Homeless Prevention Centre.

How Roundabout Helps Prevent Youth Homelessness

Founded in Sheffield in 1977, Roundabout supports young people aged 16–25 who are homeless or at risk of homelessness.

We currently support over 400 young people every day through a combination of accommodation, support, and life skills services designed to help them gain independence.

At the heart of our work is prevention – ensuring young people never have to face the trauma of sleeping rough.

Our Homeless Prevention Service, launched in 2014, offers advice and support to young people facing family breakdown or other risks. Mediation, early intervention in schools, and one-to-one support all contribute to keeping young people safe and housed.

In the 2023/24 period:

> 1,245 young people were supported through our prevention and support services

> 2,107 school students engaged with our Peer Education programme, hearing first-hand experiences of homelessness from those who’ve lived it

“At Roundabout, we understand the importance of providing a high level of tailored support to our young people and helping them reach their full potential,” says Ben.

“That’s why we’ve developed our range of services that meet the unique needs of each individual and our aim is to provide an inclusive and dynamic environment, where all our young people can access the support they need to achieve a brighter future.”

Ben playing swing ball with one of Roundabout’s young people.

Adapting to New Challenges: Growth, Innovation and Impact

In Ben’s 20 years at Roundabout, our services have grown significantly in both size and scope to meet the increasingly complex needs of young people facing homelessness in South Yorkshire.

Some of the most vital services and innovative developments during this time include:

> Peer Education, developed by Deputy Chief Executive Tracey Jackson, where young people who have themselves been through the Roundabout system share their personal stories and experiences with secondary school pupils. This programme helps students better understand the realities of youth homelessness and its root causes.

> Upstream, a newly launched schools-based early intervention project supported by the Royal Foundation’s Homewards programme. This initiative is designed to reach young people well before they are at risk of homelessness, offering education and support in a familiar environment.

> Rapid Rehousing, a specialist team made up of dedicated workers who go out into the community to identify homeless young people who need intensive support. They help young people access safe accommodation and develop the life skills they need for long-term independence.

We are also seeing a growing number of young refugees fleeing war and conflict arriving in South Yorkshire. Many are now being referred to Roundabout. Our policy is clear: any young person in danger of homelessness qualifies for our support, no matter their backstory.

Peer Educators delivering a workshop during a recent visit to Sheffield from HRH The Prince of Wales. Photo credit: The Royal Foundation.

A Changing Landscape

“Part of the sadness of my career is that things have got worse,” Ben admits.

“When I started here in 2005 there was no rough sleeping at all in Sheffield. There was investment from government in homelessness which got it to a minimum.”

“For whatever reason, there isn’t that investment in all sorts of services, which means all sorts of people now need our services and Roundabout supports more people than ever before.”

From the cost of living crisis to the legacy of the pandemic, a rise in domestic abuse, and housing shortages, the reasons behind youth homelessness are growing and becoming more complex. But Roundabout is determined to meet the need, every single day.

Looking Ahead: Consolidation and Community Support

With services expanding rapidly, Roundabout is now focusing on strengthening from within.

“We have grown so much and so quickly over the last few years,” Ben says.

“We have expanded in Rotherham and the number we are supporting has doubled in the last three or four years and now we need to catch up internally.”

Ben is also working closely with national focus groups, helping to advise the government on a new homelessness strategy expected to be published later this year.

“We need to focus on prevention because if we can solve the issues that lead to young people being homeless, we can save lives and money,” he points out.

Ben taking part in Roundabout’s annual Sleep Out.

Why Your Support Matters

None of our work would be possible without the incredible support of our community – from local businesses and schools to individual donors and event participants.

From events like the annual Sleep Out to the popular Night at the Musicals, every fundraiser helps us continue delivering the frontline services young people depend on.

“We have massive shortfalls in funding so without donations we couldn’t do what we do,” Ben admits.

“It is those donations and support that helps us stop young people sleeping rough.”

Here’s to two decades of compassion, innovation, and lasting impact.

Join Us in Preventing Youth Homelessness

At Roundabout, we believe that no young person should ever have to sleep rough, and with the right support, every young person can achieve a brighter, independent future.

You can learn more about our work here.

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