A Midhurst resident is taking on a 10-mile challenge to raise money for Chichester-based homelessness charity Stonepillow.

Jenny Jackson, head of income generation at Stonepillow, will take part in the Great South Run on October 18, putting herself through a challenge she hopes will highlight the charity’s work supporting people experiencing homelessness across Chichester and Arun.

The 10-mile race takes participants through Portsmouth and its historic dockyard. Although Jenny does not consider herself a natural runner, it is not her first major running challenge. Twenty-three years ago, she completed the Great North Run while working for another charity.

“Twenty-three years ago, which is really scary that it’s gone that quickly, I did the Great North Run for the charity I was working for at the time,” she said.

A Midhurst resident is taking on a 10-mile challenge to raise money for Chichester-based homelessness charity Stonepillow. Photo: Jenny Jackson.

placeholder image — A Midhurst resident is taking on a 10-mile challenge to raise money for Chichester-based homelessness charity Stonepillow. Photo: Jenny Jackson.

“I’m not a natural runner, it was just something we were asking people to do - we thought we should get someone working for the charity to do it.”

More than two decades later, Jenny decided it was time to set herself another challenge.

“I suppose there are a few reasons why I wanted to do it,” she said. “My family is from Portsmouth, so it’s an area I always went to as a child. I thought it would be really nice to run back through the areas my grandparents used to take me.”

Jenny, who works in Chichester, is currently balancing training with family and work commitments.

Although Jenny does not consider herself a natural runner, it is not her first major running challenge. Photo: Jenny Jackson.

“I’m training - so that’s running and then doing other exercises just to build the strength for it. I’m trying desperately to stick to a training plan around family and work commitments,” she said.

She plans to run the event alone, although friends and family will be there to support her.

A passion for tackling homelessness

Jenny’s commitment to Stonepillow’s work comes from years of work in the charity sector, including at youth homelessness charity Step by Step.

The charity offers a range of challenge events for people who want to raise money. Photo: Stonepillow.

She said the experience gave her a deeper understanding of the complex reasons people become homeless.

“I guess that’s where my passion about ending homelessness came from,” she said. “When I worked for them, that was when I really got insight into the many, varied reasons that people become homeless.

“The things that happen to people by the time they’re 16, 17, 18 shouldn’t happen to people in a whole lifetime, let alone when they’re that young.”

Jenny explained that homelessness can be the result of a series of traumatic experiences and circumstances that build up over time.

“It’s trauma after trauma that accumulates into adulthood,” she said. “And when you see the reasons behind homelessness, it really opens your eyes and makes you think that it could be any of us. It’s a few mortgage payments away, it’s being in a non-positive relationship.”

She also wants to challenge perceptions that homelessness is not an issue in relatively affluent areas such as Chichester.

“People see Chichester as a really affluent area, and so they think it doesn’t need the support because surely there can’t be a homelessness problem there, but there is,” she said.

“Our teams go out and do outreach, and they find people who have tried to hide themselves away.”

Jenny said the same misconceptions can apply to rural areas such as Midhurst and Petworth, where homelessness is less visible but is still present.

She also highlighted the number of people experiencing hidden homelessness, including those who are sofa-surfing rather than sleeping rough.

Extreme weather adds to the challenges

Stonepillow has seen the impact of extreme weather conditions on people experiencing homelessness.

Jenny spoke about the harsh winter of 2025-26, when the charity operated a Severe Weather Emergency Protocol (SWEP) which allowed them to open an overnight shelter.

She also warned that hot weather can present serious dangers for people without a home.

“I think sometimes people don’t think of a heatwave as being devastating for people who are homeless, but if you’ve got nowhere to get water, no shelter, no suncream, the real basics, then it can be equally as deadly,” she said.

Supporting Stonepillow

Jenny said Stonepillow is supported by “very generous and loyal” people across the local community, but that the level of support has fallen.

The charity offers a range of challenge events for people who want to raise money, and currently has partnered tickets available for the Chichester Half Marathon. Its retail spaces also need volunteers.

Jenny hopes her Great South Run will help raise both money and awareness for Stonepillow’s work across the area. For her, the challenge is about more than completing 10 miles.

“I believe passionately about ending homelessness and also that you should lead by example,” she said.