Ali wins Business Person of the year 2026 at the North Shore Local Business Awards

Last night I was honoured to be named 2026 Business Person of the Year at the North Shore Local Business Awards. Even writing those words feels surreal.

Going into the evening, I genuinely thought we had a great chance in the Fashion category, an award Philosophy Australia was privileged to win last year. We didn’t take home that title this time and, if I’m honest, I was disappointed. Not for myself, but for my team. I even texted them all to apologise, feeling like I'd let them down.

So, mentally, I’d already written the evening off. Then came the final award of the night. Business Person of the Year. As Tim James MP opened the envelope, smiled and said, “I’m so proud,” before reading my name, I was completely stunned. I don’t remember walking to the stage, just feeling incredibly overwhelmed. All the emotions were hitting me at once.  I’m not often lost for words, but I was.

Nobody Tells You What Business Ownership Really Feels Like

The evening began with a performance of 9 to 5, which made everyone laugh because every business owner in the room knew there is no such thing. It’s 24/7. It’s the 3am wake-up worrying about cash flow, answering customer messages across multiple platforms at any time of day or night. It’s having your best product idea halfway through a shower and writing blog posts on flights because inspiration doesn’t wait. 

It’s relentless, rewarding, exhausting and exhilarating, and always all at once.

Unless you’ve owned a business, it’s difficult to explain the weight of responsibility that comes with it. Responsibility for your staff, suppliers and contractors whose livelihoods depend on the work you create. Responsibility for your customers, to exceed their expectations, and to your own family to make it work. It is a privilege, but one I’ve never taken lightly, and now a way of life I couldn’t imagine changing. I’d never make it as an employee now.

Reflection Is Productive

Like so many business owners, I spend most days running from one item to the next, solving, creating, planning and firefighting.

Sometimes we need to step back long enough to ask ourselves whether we’re spending our energy on the things that move the business forward, rather than simply filling every available minute. That reflection is a reward in itself and why I enter awards, as I genuinely enjoy writing the application.

To every finalist across all categories in that room, everyone should feel like a winner.

Belief Is Contagious

I’m often asked what makes my business successful. I know it starts with belief.

Belief in our product. Belief in our people. Belief that what we’re bringing into the world genuinely matters. At Philosophy Australia, that belief has never belonged to just me, it’s a team thing. If you’ve watched Ted Lasso, you’ll know what I mean.

We all believe in the same mission. To create beautiful clothing that brings value. To manufacture locally, supporting Australian skills, women and their wardrobes. To prove that slow fashion still has an important place in a fast-moving world.

I also believe passion is contagious. Anyone who has met me probably knows I care, perhaps a little obsessively, about keeping Australian fashion manufacturing alive.

That passion becomes culture. Culture becomes purpose. Purpose becomes momentum and I’ll use every opportunity and platform I can, to get our message across.

Find a Win Every Day

My business coach, Michelle Broadbent from Accountability Alliance, gave me a piece of advice that has stayed with me. “Find one win or moment of joy every day. Write it down.” So, I have. For more than 800 days.

Not because every day is wonderful, usually it’s the opposite, as every day contains problems, setbacks and challenges. But if all we ever notice are the fires we’re putting out, we forget to celebrate the progress we’re making.

Those small wins become the evidence that we’re moving forward. They keep confidence alive, and confidence matters.

As business owners, our energy is contagious too. Our teams take their cues from us. That doesn’t mean pretending everything is perfect. It means acknowledging the difficult moments without allowing them to define the culture around us, but absolutely celebrating the wins when we can, as a team.

Confidence Wasn’t Always There

One of the biggest lessons I’ve learned over the past few years is that confidence can be built. Fake it, till you gain it, and then fake it some more.

In late 2023, John Elliott from Willoughby City Council invited Philosophy Australia to participate in the inaugural Shop Local campaign. I remember wondering… “How do they even know who we are?”

That single invitation became the beginning of something much bigger. It encouraged me to step outside my comfort zone. To apply for awards, say yes to interviews, speaking on panels, appearing on television, contributing to articles and podcasts; and to stop believing nobody outside our immediate circle would care about our story.

I’m not an entrepreneur; I’m a designer who loved a brand so much that she bought it. I therefore struggle to define myself as a business owner, and every day worry if I am “doing it right”.

As I mentioned in my acceptance speech “I feel like a fraud accepting this, as every day I worry what more can I be doing, and I never feel like I am doing enough” 

Our touchstone word for 2026 has been Emerge.

I said we didn’t want to be Australia’s best-kept fashion secret anymore. I knew we couldn’t be. In a tough economy, exposure is the key to our continued sustainability. Every opportunity we’ve embraced is a step in the right direction of welcoming more women into our community.

This Award Belongs to Many People

Although my name is engraved on the trophy, this recognition belongs to my incredible Philosophy family. You can’t be recognized without an exceptional business behind you.

To every team member, in house and contractor, who believes in what we’re building; every customer who has trusted us with their outfit, every boutique that represents us, every person who has liked a post, shared our story or recommended us to a friend; you are all part of Philosophy Australia story, so please share in this joy.

Mayor Tanya Taylor, thank you for your support, shout out and for wearing my designs for the night, that was a lovely touch.

To Every Business Owner…

If business feels hard right now, you’re not imagining it, and you are not alone. 2026 has been one of the most challenging years I’ve experienced, even more difficult in many ways than launching just months before COVID.

Some days business confidence comes easily. Other days you must choose to find it.

My advice would simply be this.

·        Believe deeply in what you do.

·        Let your passion be contagious.

·        Stay in your lane.

·        Control your controllables.

·        Celebrate the small wins and keep showing up.

Because sometimes, when you’re busy doing the work, you don’t realise just how far you’ve come. Last night’s award was a wonderful reminder to pause, look around, and be grateful for the journey, and for that, I truly am. (and still a little stunned!).

Ali x

Alison Lennard award win local business

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