How I Force My Hand to Create Things

I was full of doubt.

When I decided in August that I was going to do an event on October 19th, all I had was a date and a desire to bring together creative and curious people who do work with meaning.

That's it.

I had no name, no theme, and no idea what the programming would be. And while I was in talks with a few venues, I didn't have a space confirmed. I had my eye on one place with a stunning view, but I was hesitant.

The little doubter in my head was talking smack: What makes you think you can host an event THIS big? Who the heck are YOU to do something in a space like this? What if it flops?

But...

I also knew that if I wanted folks with busy lives to attend, especially people from out of town, that I needed to announce it asap. For the event to actually happen, I had to start taking action in spite of the uncertainty and doubt. So I quickly threw together a poster in Canva and shared it with my community.

It simply said "Are you coming?"

The background was an image of Toronto. It had the date, the Growth Habit logo, plus a few pictures from one of our previous events. That's it.

It didn't necessarily look bad, but I didn't like it.

I shipped it anyway to get things started. Once the event was announced, it created a forcing function for me to figure out the details. I now had no choice.

While I knew deep down which venue I ultimately wanted, my inner critic kept me searching in hopes that I'd find something "almost as good". It was exhausting. Thankfully, we had a family cottage vacation booked mid-August.

I spent most of that week unplugged.

That meant lots of time walking along the beach, laughing loudly, and quietly admiring sunsets. It was soul food. I was talking through ideas with my fiancé when it hit me:

It's not just a theme in my community, it's written on the orange Growth Habit socks + stickers our clients receive. And it's what I had to do. I had to commit to the bold leap of booking this incredible venue and then we could shape the entire event around this theme of doing bold sh!t.

I locked myself up in the bedroom and the words poured out of me.

All the copy for the landing page flowed in one sitting. I knew exactly how I wanted the event to feel. And I had ideas for activities + speakers.

But I was still stuck on visuals.

And was tight for time. The event page needed an image before my newsletter went out the following day. So I created something quickly that at least had the event title on it.

Did I love it?

Nope. But I still published it because I had to keep things moving. I also knew that publishing something subpar would push me to figure it out it, asap.

That's the beauty of building a business in the digital age. You're rarely pouring concrete + everything is relatively easy to update. So take action + iterate.

Because if I had waited until things were "perfect", until I knew the theme, or until I felt no uncertainty or doubt, the event wouldn't have happened. Or it would've been a fraction of its size. And there's no way we would've had a dozen people fly in to be there with us.

I doubt it would've ended with me being called out to make it an annual thing.

And guess what?

I did the same thing again for next year. I needed an image for the limited 2025 early bird tickets being offered. So I took the final image from last week's event and slapped a "2025" across it to simply get it out.

I'll see you next Saturday.

-Robb

It's now officially a two-day event and DO BOLD SH!T 2025 will be held on Saturday October 18th & Sunday October 19th, 2025 in Toronto. You have a chance to lock-in your spot for a special early bird price.

• Full price for the two-day event: $697 CAD (about $501 USD)

• The special early bird price for the two day experience: Only $497 CAD (about $357 USD)

•  There's only 20 of these available and 6 of them have already been scooped up.

Lock in your early bird price here.

How to get your special rate:

1. Click on the arrow beside "Have a coupon code"

2. Enter your coupon code: DBS2025EARLYBIRD

3. Click the "apply" button so that the price changes