When was the last time you did something so bold it made you laugh out loud? In this episode, I sit down with TEDx speaker and coach Gregory Russell Benedikt, who tested a wild hypothesis: What if the universe really does reward bold action? From quitting his “dream” finance job to a 100-day rejection challenge, Gregory shares how courage, messy cannonballs, and playful asks transformed his life, work, and relationships — and how you can start taking bold action in your own life, no matter what chapter you’re in.
Guest: Gregory Russell Benedikt – TEDx speaker, coach, and host of The Dare to Dream Podcast (if you want to include his show)
In this powerful (and fun!) conversation, I am joined by coach and TEDx speaker Gregory Russell Benedikt, who is on a mission to live a story worth telling — and help others do the same.
Gregory shares how he walked away from his “dream job” in finance, realized his ladder was up against the wrong wall, and decided to reinvent his life around meaning, joy, and bold action.
You’ll hear the behind-the-scenes story of his 100-day boldness challenge, why he believes the universe truly rewards courageous action, and how becoming “the boldness guy” helped him build a life that feels aligned, alive, and deeply fulfilling.
Growing up as the “numbers guy” and landing the dream finance job — only to feel completely empty on the inside
The research on the top regrets of the dying, and how the #1 regret (“I wish I’d had the courage to live a life true to myself…”) shook Gregory awake
What it really feels like when your ladder is on the wrong wall — and the moment he chose to climb back down and change
Quitting his job with no clear next step, trusting the unknown, and starting a nonprofit with a stranger from the internet
How a book (Rejection Proof by Jia Jiang) sparked Gregory’s 100-day boldness challenge
The cannonball that went viral: asking a stranger to use his backyard pool and getting 350,000+ views overnight
The power of community and “commitment devices” — why telling people about your scary goal makes it harder to quit
What rejection actually means (and why most “no’s” have nothing to do with you)
Bold action vs. bold action on purpose — and why aligning your brave moves with your values and dreams matters
How taking bold action led to exponential progress, unexpected opportunities…and even meeting his girlfriend
Confidence as a byproduct of doing the thing scared, not waiting to feel ready
What Gregory would tell his 12-year-old self — and what his 12-year-old self would say back to him now
“One of the saddest things is getting to the top of the ladder and realizing it was against the wrong wall the entire time.” – Gregory
“If you don’t ask, you’ll never know. The worst thing that can happen is you’re in the exact same place you’re in right now.” – Gregory
“Confidence doesn’t come from knowing. It comes from doing.” – Michelle
To connect with Gregory. Life & Leadership Coach - helps people take BOLD action and live a story worth telling
https://gregoryrussellbenedikt.com/
Gregory's Tedx Watch my TEDx Talk.
Host of The Dare to Dream Podcast
Connect with Gregory on LinkedIn
xo