Ep 39. The Power of Giving Back w/ Craig Hollywood

What if the only thing standing between you and something meaningful… is starting?

In this episode of the Reconnect to Self Podcast, we sit down with Craig Hollywood, founder of the charity Short Back & Sidewalks, to talk about how one small idea turned into a movement helping tens of thousands of people across Australia.

Craig didn’t have a plan.

He wasn’t a social worker.

He wasn’t in the charity sector.

He was simply someone who cared — and decided to do something about it.

What began as one free haircut in a Northbridge car park has now grown into a nationwide initiative restoring dignity and connection to people experiencing homelessness and hardship.

But this episode isn’t just about charity.

It’s about the courage to start something meaningful, even when you have no idea what you’re doing.

Craig shares the story behind Short Back & Sidewalks, the challenges of building a movement from scratch, and the lessons he learned along the way — from facing rejection, to getting comfortable being uncomfortable, to nearly running out of money and wondering if it would all survive.

If you’ve ever had an idea in the back of your mind — something you’ve thought about doing for years but felt too uncertain to begin — this conversation might be the push you need.

Because as Craig proves in this episode… You don’t need a perfect plan to make a difference. Sometimes all it takes is one small step.

In This Episode We Cover:

• How Craig started a charity with no experience and no plan

• Why haircuts restore dignity, not just appearance

• The moment the first haircut changed someone’s life

• How to start something meaningful with baby steps

• Why you’ll hear “no” far more than “yes” — and why that’s okay

• The importance of surrounding yourself with people who know more than you

• Getting comfortable being uncomfortable

• And why anyone can make a difference if they simply begin

Connect with Craig / Short Back & Sidewalks

Website: ⁠www.shortbackandsidewalks.com⁠

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Disclaimer: This podcast is for information only and isn’t a substitute for personalised therapy.