When you have an important decision to make, ask yourself, “Will I come to regret this later?”

It could be about your career, business, finances, relationships … whatever. It cuts across pretty much everything.

As long as you’re honest with yourself, answering that question can help you make the right choice instead of the easy one. It can help you face your fears and break outside your comfort zone. It’s a pretty effective litmus test for determining if you’re making a good decision or one that might come back to haunt you later.

While I can think of a few things that are worse than remorse – cancer, strokes, heart attacks, hemorrhoids – regret may very well be the most preventable cause of misery and depression that seems to plague so many later in life. I’ve seen it eat away at people. It’s pretty sad.

Granted, we can’t control everything and we all make bad choices, so we all have regrets. But if you know you made the best call you could make at the time – or at least learned a valuable lesson from making a bad call – then it’s not likely to plague you down the road.

Jazz great Miles Davis said, “When you hit a wrong note, it’s the next note that makes it good or bad.” The problem is, we sometimes realize we’ve hit a wrong note long after the concert and we can no longer play the saxophone. That’s when regret takes hold.

I used to think that I have few regrets because I’ve been alive long enough to see that bad choices can indeed be turned around, to Miles Davis’s point. Perhaps that’s true, but it’s also important to be self-aware enough to ask yourself that fateful question and try your best to stay true to the answer.

Long ago, a friend told me, “You can go crazy thinking back and wondering, ‘What if?’” Obviously that resonated with me, since I still remember it after all these years. It’s like the popular saying, “Live life, no regrets.” But it’s not always so easy to do that, especially when it comes to life-changing decisions.

Sometimes, you can’t stop yourself from asking, “What if?” And when you do, knowing that you took your best shot when you had the chance can make all the difference between peace and regret.

Image credit .bravelittlebird Flickr