Six months on, Regan is walking 100 metres again, every day for 10 days, to raise money as part of Nedd Brockmann’s Uncomfortable Challenge. Inaugurated in 2024 with Brockmann’s brutal 1600-kilometre run – he “kind of died” out at Sydney Olympic Park over those 12.5 days, Brockmann says – proceeds from the event go towards Mobilise, a charity that offers direct funding for housing and essentials to people facing homelessness.

The rules of the challenge are to pick something that makes you uncomfortable, and stick with it for 10 days straight (it could be anything, says Mobilise founder and chief executive Noah Yang, who this year is meditating for 30 minutes and speaking to 10 strangers every day).

Last year, Brockmann raised at least $2.5 million for the cause. This time around looks a little different for Brockmann, and not just because he no longer has the nation’s most famous haircut; Brockmann isn’t physically participating in his “Uncomfortable Challenge” this year. Ironically, that’s something the 26-year-old electrician, who fractured his foot in June, told this masthead makes him uncomfortable.

“How on Earth can people listen to me if I’m not going to do something?” he asked. “If I don’t go to war with them, how on Earth are they going to do it for me?”

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Happily so, if you ask Regan, who has followed Brockmann since his mammoth 47-day run from Perth to Bondi Beach in 2022, and seen on social media what Brockmann has put himself through for “such a worthwhile cause”.

Brockmann has spent the challenge – which runs from October 20 to 29 – travelling around Australia to visit participants. On Saturday, Brockmann was at Gosling Creek Reserve in Orange, helping shift Regan’s frame as he walked 100m to cheers from almost 100 locals.

“Homelessness can happen to anyone,” says Regan, who is doing the challenge also to set a good example for his four-year-old son. “Even though this horrible thing has happened to me, I’ve been able to get through it because I’ve got a home, I’ve got the support of family and community, and people who are homeless don’t have that.”

No one knows this better than 24-year-old physiotherapy student Natalia Hogan, who took a break from her final year assessments to run, overnight on Saturday, from Sydney to Newcastle.

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Running makes Hogan feel strong, she says, and while 170 kilometres is by far the furthest she’s ever gone, for the 11-year-old Hogan who was couch-surfing with friends and felt like she had no control over her life, it’s worth it.

“I have such a big space in my heart to be able to help other young people who are going through similar situations,” Hogan says.

It took a while for Hogan, who grew up in and out of foster care, to feel comfortable enough to share her story. It wasn’t until she was 16, when she secured a studio apartment with Samaritans Student Accommodation, that she had a safe and stable place to live. Hogan didn’t want to be treated differently, or viewed as broken, when people found out.

“There’s a massive stigma around homelessness, that it’s their choice, or it’s something they’ve done … that’s so far from the truth, and I couldn’t imagine where I would be without those services,” says Hogan, who is raising money for Samaritans via Mobilise.

Hogan has spent the whole year preparing for her fundraising feat, practising her pacing and training with pretzels, mini blueberry muffins and noodles so her gut can get used to running with food in her stomach.

Her friends – who followed her on the highway in a campervan (with a toilet) or on foot with head torches – built her a playlist of “pump-up” songs to help her push past the moments of exhaustion, which is when doubt and injury creep in.

“It’s a really long, long process,” says Hogan, who crossed the finish line at Emu Park on Sunday afternoon. “But so worth it to make an impact.”