He Lost Three Businesses. Here's How He Started Over.
Things worth taking away
- Career shocks are the norm, not the exception. Herminia Ibarra's research frames reinvention as trying on possible selves and learning from what you find.
- Start moving before the path is clear: taking action gives you clarity faster than endless planning.
- After a business fails, own your part, refuse to treat the setback as permanent, then narrow hundreds of ideas down to the few that fit your strengths.
- A decision invites second-guessing; a choice means stepping forward and finding out as you go.
- Resilience is a daily choice, made easier by people you can call at any hour and proof, borrowed from others' comebacks, that it can be done.
About this episode
Career changes rarely go as planned. Simon Levin lost three businesses, started over every time, and at 62 is running a successful coaching practice.
In this episode of The Connection Experiment, Simon tells Nathalie what he learned building a garment business from scratch, how he handled major setbacks, and why those early failures forced him to change the way he listens and communicates. They get into taking action when you feel stuck — why moving forward brings clarity faster than endless planning — what it actually takes to rebuild a career after losing a business, and how learning to truly listen reshapes both business and life. Along the way, Simon draws a sharp line between making a decision, which invites second-guessing, and making a choice, which means stepping forward and finding out as you go.
This week’s connection experiment: at bedtime, name one thing you’re grateful for, so it’s the last thought on your mind; in the morning, speak one positive thought about the day ahead.
Book mentioned: The Goal by Eliyahu Goldratt. Simon built his new coaching practice through Coach Academy’s ICF-accredited program. Connect with Simon Levin on LinkedIn and Nathalie Blais on LinkedIn. Learn more at Canada Coach Academy.