What happens if this goes right? In business and life we’re quick to ask “What h
By Robbfraser · October 2, 2026 · Curated by George's Blog
What happens if this goes right?
In business and life we’re quick to ask “What happens if this goes wrong?”
We protect our downside. And that’s a good idea. But I don’t think it’s the most important question.
Asking “What happens if this goes right?” prompts you to prepare for success.
Because there’s a special kind of pain in having an opportunity you’ve dreamed of land in your hands and realizing you weren’t ready for it.
I know because I’ve been there. Not asking that question has caused me a lot of unnecessary pain.
This was one of six lessons I shared from my decade building OUTWAY into Canada’s #1 independent sock brand during my keynote at the Startup Canada Tour in Victoria, BC.
Getting on stage in front of 300+ people to share my journey was exciting and nerve racking. Memorizing and delivering a 30 minute talk was a new muscle to flex.
Huge thanks to the Startup Canada team for the opportunity, and to everyone who came out and shared such kind feedback.