TIL: One Question To Ask for Grey Area Decisions

Some of life's decisions are sketched in black and white. What's good for you is easily discernible from what's not profitable viz:
-Should I start smoking?
-Do I need to start exercising?
-Should I vote?

Side note: That would be No, Yes and Yes in that order.

The grey area questions are a little harder because the pros and cons jostle for prominence. Each path looks promising and without a crystal ball, it's hard to determine which path will deliver on its promises. Most decisions are grey because the benefits/adverse effects are not all easily quantifiable.  For me, the grey decisions of life today are
-Should I get a tattoo?
-Should we get a dog?
-Should I go back to school for a postgraduate degree?

For these decisions, both sides have a hold on my heart. The one question that helps me pull the trigger finally?

Will I ever regret this choice?

One of my life policies is to make the best decisions I can today so that I will have no regrets tomorrow. I don't want to ever look back and bite my finger in regret. Case in point is the argument for Getting a tattoo or not.  I can get one at any time or any age so my desire for one (or more) can easily be fixed. Could I feel regret about a tattoo I get today? Quite easily. And there will be an expensive and possibly painful price to pay for remediation in the form of tattoo removal. Suddenly, CLARITY! 

With this one question, I am able to make my grey-area decisions with a bit more conviction both now and in the future when I know I will second-guess myself.

Do you have any guiding principles for making the not-so-black-and-white decisions?

Side note 2: No, No and Yes

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