How to Make Big Decisions


When I was a kid, I had a hard time making decisions of any sort. It’s the stuff of family lore, and I am regularly reminded of how often I’d come to tears over having to choose between chocolate or vanilla ice cream. Fourteen years as an entrepreneur has sharpened my decision-making abilities, but that doesn’t mean every choice is easy peasy lemon squeezy.

We all face the tough choices from time to time. The ones with no easy answer and no certain outcome.

How do I handle my suddenly rebellious teenager?

Which job offer should I accept?

Is it possible to make ends meet if I stay home with the kids?

Which project should I tackle first?

How should I approach this uncomfortable situation with my supervisor?

Should we move or not?

Is homeschooling the best choice for our family?

Which college should I attend?

How should I invest this extra money?

Should I say yes…or no?

Sometimes, even after weighing every pro and con, the right choice can remain uncertain. However, it strikes me that one’s deathbed is the great clarifier. There, with no more “somedays,” “eventuallys,” and “maybe laters” at our disposal — and with regret breathing down our neck — suddenly the decision we should have made becomes obvious.

It appears that the best way to go about deciding anything is to make the choice you’ll wish you’d made on your life’s last day.

This technique rewards us with a regret-free outcome, whether we encounter success or failure. It also gives us immediate perspective on which things really matter and what things just…don’t.

Deciding whether or not to embark on that new and exciting (but scary and uncertain) adventure will make a big impact on how your story turns out.

Deciding between chocolate and vanilla…not so much.


  1. Alison says:

    If you look at every decision or every choice as leading you down a path, it’s pretty easy to look back and say, “Yeah, I like where I am. I don’t regret any of my choices, because each and every one of them has led me here.” When I look at life that way, I don’t look back with regret, because, hey, I like where I am. And if I didn’t? Well, then there are some more choices to be made.