Should You Be Bolder or More Cautious?

Should you live more riskily or more cautiously? A 13-item self-assessment.

Posted Aug 02, 2020

 cnener/Creative Commons 2.0
Source: cnener/Creative Commons 2.0

Some evidence suggests a genetic predisposition to risk-taking. Notwithstanding that, and philosophical determinists from Kant to Sam Harris, I like to think we retain a measure of free will. With that as an assumption, here’s a self-assessment inventory that could help you decide whether you want to direct your free will in a new direction. For each of these 13 items, mark where you’d fall on the continuum.

Work

Tell your boss s/he’s wrong.

Wouldn’t <-------------------------------------------->  Would

Suggest a major new direction for your work group.

Wouldn’t <-------------------------------------------->  Would

Quit a bad job even though you haven’t landed a new one.

Wouldn’t <-------------------------------------------->  Would

Start a business.

Wouldn’t <-------------------------------------------->  Would

Relationships

Admit a serious liability about yourself on the first or second date.

Wouldn’t <-------------------------------------------->  Would

Ask someone to marry or live with you when it’s only 50/50 s/he’d say yes.

Wouldn’t <-------------------------------------------->  Would

Break up with a so-so romantic partner.

Wouldn’t <-------------------------------------------->  Would

Money

Buy a house when you can barely afford its mortgage and expenses.

Wouldn’t <-------------------------------------------->  Would

Put all your long-term savings in stocks or an all-stock mutual fund.

Wouldn’t <-------------------------------------------->  Would

Lend a significant chunk of money to a friend.

Wouldn’t <-------------------------------------------->  Would

Recreation

Go on a weekend backpacking trip where there isn’t cell phone coverage.

Wouldn’t <-------------------------------------------->  Would

Have unprotected sex with someone you weren’t sure was safe.

Wouldn’t <-------------------------------------------->  Would

Accept the risks of using tobacco or marijuana.

Wouldn’t <-------------------------------------------->  Would

Try LSD.

Wouldn’t <-------------------------------------------->  Would

The takeaway

Now review your answers. In general, or with regard to one or more of the items, do you want to be bolder or more cautious?

I read this aloud on YouTube.

The previous posts in this series are Should You Be More Adventurous or Less? and Should You Be More Suspicious or Less?