The crippling clutches of ‘what if’

Imagine a life lived without regret. What exactly would that look like?

As a writer and journalist, I often find myself asking people what they regret about their life. Very few offer much in detail. Far more than most say something akin to “no regrets. Sure there are small things here or there, but it’s all worked out.”

On the surface level, I can understand what they mean. Our lives, for better or worse, have a certain linear development to them. If you begin to strip away some aspects, you lose others. Soon the whole thing unravels. Every movie about time machines are based on this basic notion. Think Pleasantville or Back to the Future just for a couple of good ones.

But if I drill down to specifics, many say they would do a lot of things differently. As I talk to people who have some tread on the tires, far fewer are truly happy and content, say, compared to the hope that spills over at every commencement ceremony ever held.

A large swath of us in America enter adulthood teeming with optimism and faith and confidence that our lives will turn out well. But far too often they don’t–at least not as well as we think we deserved or hoped we would achieve. In light of the result of our lives, wouldn’t we all have some regrets?

Of course, we would. Who doesn’t regret decisions at 19 we made when we thought we were the smartest people in the world or the decisions we made at 40 when we knew we weren’t and still didn’t know how to get the help we need? Who wouldn’t like a small redo at life?

The harsh truth of this life is it is lived without Mulligans. It all counts. Pick up any newspaper in the country, flip through a few stories and somewhere in there a life will be lost because of a bad decision, a seemingly random illness, a tragic circumstance, an act of hate, a terrible addiction, an injustice or an intentional act of evil. You read the headline and for those people whose number has come up on the Wheel of Misfortune, nothing but regret remains.

Somehow we ignore this obvious clash between our sense of entitlement and the reality of life.

I have come to believe that few questions scare the living bejesus out of a great many of us more than “what if?” What if I __________?

We pause and think of a small thing, a twist in the road, a fork chosen and wonder how much better things might have been. If only I had known, we think. Or: If only life was fair. Or: if only cancer had a cure. Or if only … and the regret seizes us with a Spock-like grip bringing us to our knees.

That is how we ignore it. The pain is too great. We brush away the notion of regret and convince ourselves we are fine, all the while our nagging inner voice that fills our head with so many unspoken, gripping, terrifying words, grows louder and louder, demanding an answer to “what if?”

If live can be lived without regret, I have no idea how to do it. But life can be lived with insight gained from all those what if moments.

If addicts learn one thing it is not how to have a life without regret but to live fully despite them.


We have a lot of words for this so feel free to pick the one you like best. In AA we call it “amends.” The media likes to talk about “second chances.” Politically we talk about “reparations.” Spiritually we talk about “forgiveness” and “atonement.” Psychologically we talk about “acceptance.” All of them are a part of living with the what if’s in truth rather than fear. Pick a word, any word and grab tight to it. Live it fully.

I choose grace. The God I love offers grace not because I’ve jumped through enough hoops to please Her, but because She made me and loved me and knew I’d screw up countless times but resolved to keep at it with me until I figured this out. And She’d provide ample grace–forgiveness that is not even warranted but freely given out of love–as the fuel to propel me past my regrets toward my best self. It’s an ongoing process that never finishes, but in the process of growing, learning, making amends, finding truth, making better choices, living more honestly, and becoming a decent me, I find the strength to keep at it despite regrets of all that I missed, all I have hurt, all I have failed and all I could have done so much better than I did.

What if? Yeah, it could have been great. But what is, is still pretty good, and I remain wildly optimistic about all that lies ahead.

Author Jane Hamilton, in her novel The Book of Ruth, wrote, “Sometimes I feel that I’m only just ready to start my life. I know what I need to live it a hundred times better. As far as I can see, no one is out there waiting for me with a ticket that says, ‘try it again.’ I’ll probably really figure out exactly how to be alive right when I’m gasping my last breath.”

Recognizing that is the key to a life lived free from the clutches of “What if?”


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