The Riskiest Decision of My Life
Even the smartest plan can feel terrifying in motion. Courage fills the gap between logic and leap.
The Riskiest Decision of My Life
Lesson: Betting Everything on the 5-Year Sprint
At 41, I made the boldest move of my life, a 5-year plan to build 20 cash-flow businesses. To even have a shot, I had to throw the kitchen sink at it: resources, time, focus, and energy. It’s been four years of chaos, risk, and relentless testing. With one year left, it’s easily the riskiest thing I’ve ever done, and somehow, the most exciting.
Insight: Big Risk, Bigger Alignment
Here’s what this journey has taught me:
- Volume Creates Opportunity: You can’t predict which bets will win, but by increasing your shots, you increase your odds.
- Calculated Risk Is Still Risk: Even the smartest plan can feel terrifying in motion. Courage fills the gap between logic and leap.
- Purpose Makes Risk Worth It: If your risk aligns with your purpose, fear becomes fuel. The goal stops being about safety, it becomes about fulfillment.
Action Item: Audit Your Risk Profile
This week, take 10 minutes to reflect:
- List Your Current Bets - Where are you investing your time, money, and energy?
- Assess the Alignment - Are those risks moving you toward your long-term purpose or just keeping you busy?
- Double Down on Purposeful Risk - Choose one area where you can lean in harder, even if it scares you.
If you like this content you can watch the video version of this.
Also, Young was featured as a guest on the podcast Farewell, Mr. Nice Guy, in the episode “My Journey with The Girl Dad Podcast Changed My Life as a Father.” Don’t miss it!
