Lifestyle
At 53 I turned my creative hobby into a thriving business
NSW-based artist Pamela Woods, 64, discovered her creative power in her 50s, and she’s living proof that it’s never too late to begin again.
By Elli Jacobs
In my 50s, I relocated from the UK to Sydney to support my mother, who was suffering from dementia. I wasn’t her full-time carer, but I became the family support she relied on. After living in England for nearly twenty years, returning home was a jarring and abrupt transition.
At the time, I had two young children still in school - aged 10 and 12, and we were essentially rebuilding our lives from scratch, with the added challenge of my partner facing serious health issues.
Finding work in your 50s
Trying to find work at 53 was a real eye-opener. My background was in drama and media, and I had built a creative, fulfilling career. In the UK, age had never felt like a barrier- I was still teaching acting and performance at institutions like Middlesex University and the Drama Centre in London, mentoring the next generation of talent and working in television right up until I left.
But in Australia, suddenly, none of it seemed to matter. I’d walk into interviews and feel the shift in energy. I could almost hear the unspoken thought: “Oh… she’s a bit old.”
Age-proofing a resume and finding work in my 50s proved quite the challenge.
I scoured the internet for opportunities, cold-called organisations, and I reached out to people whose work I admired. I even messaged someone I’d read about in the Sydney Morning Herald who was running creative classes in cafés at night. I thought, Why not ask if I can teach too?
That’s when things began to shift. I stopped trying to fit into something and focused on creating space for myself. From there, opportunities snowballed: councils, shopping centres, private venues. I was teaching arts and crafts wherever I could. It was a patchwork hustle, but it was mine and it was growing.
Eventually, I landed a part-time university role, which felt like a win - until the course folded. After that, I applied for anything I could: secret shopping, Airtasker gigs, casual teaching. It was all hustle, and I kept reminding myself - any money is good money.
Creativity through adversity
In 2017, I took the plunge into entrepreneurship and launched ClassBunny, my own little universe of creative classes and artistic offerings.
I’d run businesses before, years ago, so I wasn’t entirely new to the game. But this was different. This was a from scratch and kitchen-table startup - born out of necessity, run on a shoestring, fuelled by passion, and built around a DIY website that tested my patience at every turn. Setting it up, learning the tech from scratch, and adding each piece was an act of sheer determination. ClassBunny wasn’t just a name, it became a banner under which I poured all my creativity, resilience, and resourcefulness.
Then I threw myself into teaching painting with watercolours at first, but soon expanded into terrariums, and seasonal crafts - whatever was trending, and people were loving. I hustled, posting classes wherever I could: libraries, councils, event companies, even on platforms like ClassBento - an online marketplace for creative courses, to reach more people.
I started small, with no big expectations - if one person showed up, I ran the class. Some sessions had just one or two people, but I never cancelled. I taught with joy, built trust, and let word of mouth do its quiet work. With no budget for venues, I partnered with councils and charities, moving through pop-up spaces to keep the momentum alive.
I never gave up and slowly, the momentum began to build. I started landing bigger bookings: workshops in bustling shopping centres, sometimes with up to 80 participants in a single day. It felt like all those quiet efforts, those near-empty classes and pop-up partnerships, were finally paying off.
Covid prompted a business pivot
But just as things were taking off, the world came to a halt. The lockdowns hit, and overnight, every workshop was cancelled. Suddenly, everything I’d poured myself into seemed to unravel. I really thought that was the end - that the fragile foundation I’d so carefully laid had given way.
But as the saying goes, when one door closes, another opens wide.
I quickly pivoted to Zoom, and just like that, my classroom expanded far beyond Sydney. Suddenly, I was leading creative workshops for large groups around the world.
The online format brought unexpected gifts. Students could see close-ups more clearly, feel less self-conscious behind their screens, and for the first time, people who were housebound or immunocompromised could fully take part.
One of the most meaningful projects I took on during that time was running online classes for children living with cancer through Camp Quality. Connecting with those kids - bringing even a little colour, joy, and creativity into their days, was incredibly humbling. That experience has stayed with me, helping others has that effect.
While lockdown was devastating for many, it quietly opened doors for those who had long lived in isolation. For some, it wasn’t a disruption at all - but a long-overdue invitation to participate, connect, and create.
ClassBunny is still thriving today
Today, ClassBunny continues to flourish in ways I could only dream of when I started. I now run workshops for major councils and teach over 2,000 children each year at the City of Sydney’s Christmas Carol Concerts - an annual highlight filled with glitter, laughter, and wide-eyed wonder.
To bring these large-scale events to life, I’ve even built a small team of talented young artists who help make the magic happen. It’s deeply rewarding to support emerging creatives while expanding what ClassBunny can offer.
Despite the growth, I still run things on a lean, grassroots budget and my priorities haven’t changed. I choose projects that are fun, meaningful, and creatively fulfilling, where community and joy come first.
It’s a far cry from those early days of scraping by and teaching in borrowed spaces. But looking back, every step, no matter how scrappy or uncertain, was part of building something I’m truly proud of.
Then came Art Battle
I first saw a call-out for something called Art Battle, online. I hesitated as, I’m a woman in my 60s, and it looked like a competition dominated by graffiti artists and hip twenty-somethings. But then I thought, why not? I filled out the form and forgot all about it.
A few months later, to my surprise, I was invited to compete. I hadn’t painted in acrylics on canvas for decades, and the nerves hit me hard. Full of self-doubt, I began to practice, timing myself carefully, because in Art Battle, you only get 20 minutes to paint a full piece, live, in front of hundreds of people standing around you. DJs blare music so loud the canvas practically vibrates. The adrenaline was real; my hands were shaking, my body was sweating, and my heart racing. But I loved it.
I entered just for the experience, but to my astonishment and despite being one of the oldest competitors, I won my first ever competition in August 2023. That win lit a fire in me.
I competed four more times, but after a serious car accident I paused my journey, I came back strong and won the national grand final in November 2024. Now, I'm the Australian Art Battle Champion.
That win changed things. It gave me confidence, visibility, and got me painting again - really painting, not just teaching. I have sold all my Art Battle paintings in a silent auction at each battle. This has led to an exhibition, and I started selling my work on Blue Thumb, an artists’ marketplace online, and became a featured artist. That wouldn’t have happened without Art Battle.
So, what’s the biggest lesson I’ve learned?
Don’t be afraid to try. It’s okay to feel silly, unsure, or like you don’t belong. I’ve learned to walk hand-in-hand with those feelings rather than let them lead. I’m not afraid of failing anymore - especially not at this stage in life. If something sparks curiosity or excitement in me, that’s my green light. I follow it.
Another big shift? I no longer feel I have to do everything alone. There’s wisdom in partnering with existing platforms, in standing on the shoulders of others. Piggybacking on someone else’s momentum isn’t cheating, it’s strategy. There’s no need to reinvent the wheel when you can learn from what’s already rolling.
To any woman in midlife wondering if she’s missed her chance to be creative, I want to say this clearly: You’re not too old. You were never too old.
I remember feeling like I was already “late” at 22! I was to believe the clock is ticking, that doors close, that ships sail. But guess what? There’s not just one ship and the ocean is vast. There’s still time, space, and possibility for you.
Yes, starting something new takes courage and grit. But we’ve grown into that grit. We procrastinate less, worry less, and we know ourselves far better. That self-knowing? That’s not just confidence, it's our superpower.
This chapter of my life? It’s rich and expansive. I’m creating from the heart, connecting with people who inspire me, and finally giving myself permission to thrive. And the best part? I’m doing it on my own terms. No apologies, no shrinking.
Midlife isn’t a closing act, it’s a creative renaissance.
Feature image: Pamela Woods
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