The Hidden Danger of Playing It Safe (and 7 Ways to Fix It)

Small downside. Big upside. That is the sweet spot. That's a asymmetric risk.

And when you have asymmetric risk, it pays to be bold.

Look for bets where a miss costs little, but a hit changes everything.

Take the swing when the worst case is recoverable.

Even when it doesn’t work, you gain pride, skills, and memories.

The “safe” path can be expensive, because regret can last a lifetime.

You don’t want to spend your years wondering what would have happened if you just tried.

Youth multiplies upside and cushions downside. That’s because when you’re young, you have time to learn, pivot, and try again.

Give yourself a few focused years to chase your dream. If it flops, you can return to stable work or retrain.

First, write down the worst case scenario.

Next, list the safety nets you already have: income options, insurance, help from family, marketable skills, etc.

You will likely find the nightmare is smaller than the one in your head.

Boldness changes form with age.

It can mean walking away from a role that no longer fits, and using your hard-earned money to buy time and fulfillment.

Most people fear running out of money more than wasting their life. Don’t be one of those people.

Do not let the hassle of moving or the fear of leaving home keep you stuck.

Where you live (or travel to) can have a massive impact on your life, whether for career opportunities or general life experience.

What’s easy should not decide your life.

Your choices reveal your priorities, so make them on purpose.

How much risk you take is up to you. Just be honest about the trade.

Read the next chapter here.