Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.
Kate Christy
I go back and forth about this all the time. Would it have been easier if I started my business sooner, before I had kids? Watching other folks on the internet doing cool things, sans kids, as a business owner kept that question quietly nagging in the back of my mind for years. Read More>>
Colleen Lindberg
I started my business back in May of 2010 …. wild to think it’s been that long. Looking back, it was one of those now or never moments. I didn’t overanalyze it, I just felt the pull and trusted myself enough to leap. Read More>>
Sandy Murad
I started my business in 2020 during COVID, at a time when my life looked completely different. I was working two emotionally heavy roles as a CYW with the TDSB supporting special-needs youth, and at 360° Kids through the Hope Program. My entire career was rooted in compassion and service, and that part of me never changed. Read More>>
Holly Ryan
If I could go back in time, I think every part of me would want to say I wish I had started my business sooner. I began my floral preservation and memorial keepsake business at 22, at a stage where I was still figuring out who I was, what I wanted, and what kind of artist I was meant to be. Read More>>
Chris Kelly
I wish that I had started sooner, or rather, I wish I had taken more time to consider all of my options and what I possibly could’ve done to help propel my creative career earlier. Read More>>
McCall Bliss
My bandmate and partner Mike and I took an unexpected route to our creative career – both of us met our final year of school after studying computer science and started out working 9-5 for most of our 20s. The two of us did music in the background as a hobby but never went all in so we struggled to progress. Read More>>
Richard (Ric) Westman
I didn’t really get into photography until I was in my late fifties. I had the good fortune to do a lot of traveling around the world and was lucky enough to see a lot of beautiful sights and people, but it never dawned on me to record my travels thru photography. Read More>>