This Side Hustle Made Me Braver: What I Learned Giving Food Tours in Toronto’s The Junction

On a tour with three guests in Spring 2025

When I started Toronto Food Adventures, I didn’t expect anyone to show up.

There was no pitch deck. No marketing strategy. Just me, a clipboard, and a walking tour I made up from scratch. I had lived in the west end of Toronto for years, and I loved the food and history of The Junction neighbourhood. So I put up a listing on TripAdvisor and waited.

At the time, I was managing a high-stress job, feeling stretched thin, and looking for something that brought joy without pressure. I didn’t launch a side hustle to build a business. I launched one because I needed a creative outlet that felt like mine.

What I didn’t expect was how much I’d learn from it. Or how much braver it would make me.

Why Side Hustles Are the Best Way to Build Risk Muscles

In The Uncertainty Advantage, I talk about “risk muscles”—the idea that your tolerance for uncertainty grows every time you take a small, manageable risk and see that the world doesn’t end.

Toronto Food Adventures gave me that in spades.

I wasn’t sure if people would sign up. I didn’t know if my stories would land. I definitely wasn’t prepared to tour former child stars and have the tour get interrupted by their fans. 

But I kept going. And every tour helped me build confidence not just in the tour, but in myself.

Walking the Junction Taught Me More Than I Expected

The tours were simple: Three hours of walking, storytelling, and sharing snacks from some of my favourite local spots.

I designed the script to weave together immigration history, neighbourhood change, and the ways food tells a bigger story about who we are. Some stops became crowd favourites—like Little Malta Bakeshop, where guests learned about the Canadian Maltese community through flaky, hand-folded pastizzi—or Taste Seduction, where food and culture collide in vibrant, unforgettable ways.

But the real magic? It wasn’t just the food.

It was the people. Guests from across the world bonding over shared meals. Locals rediscovering their own city. Solo travellers trading numbers after the final stop. 

This Is What Joy Looks Like

There’s a photo above from one of the tours where I’m smiling with three guests at one of my favourite restaurants, Taste Seduction. If you visit there, I highly recommend ordering their oxtail mac and cheese.

And the joy in that photo? It wasn’t a distraction from uncertainty. It was a way through it.

In a world that often tells us everything needs to be optimized or monetized, we forget that doing something just because it brings us joy is reason enough.

How You Can Build Your Own Risk Muscles

You don’t need to start a food tour. But you can build something playful, rooted in community, and full of creative stretch. Here’s how to start:

1. Host something small A walking tour, a coffee tasting, a backyard dinner. Start with what excites you.

2. Use what you know Your neighbourhood, your family’s stories, your weekend obsession with niche cheeses—that’s your material.

3. Build in public Post your progress. Share photos. Invite friends—small momentum matters.

4. Start before you’re ready My first tour script was a mess. People came anyway.

5. Follow the joy If it energizes you, keep going. If it drains you, change something.

   
   

You Don’t Need a Master Plan. You Just Need a Starting Point.

Toronto Food Adventures didn’t change my job title. It didn’t make me rich. But it gave me something more powerful: the confidence to create in uncertain conditions.

That’s what a side hustle can offer. Not just a second income—but another source of identity. A reminder that you’re someone who can build, connect, and grow.

If you’re ever in Toronto, walk the Junction with me. You’ll leave full of stories, snacks, and maybe even inspiration.

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