LOVE this quote from James Clear. It's exactly what we are doing here...
The best type of risks to take are ones where (1) the worst outcome is manageable and (2) the best outcome is life-changing.
Think: Asking someone on a date. Or, investing an amount of money you can afford to lose into a business with high upside.
Look for opportunities where it won't kill you if it goes poorly, but you'd be blown away if it goes well.
James Clear - Author, Atomic Habits