Dealing with What Might Have Been

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Image by Elena Medvedeva/Getty Images

Regret

Regret usually comes in one of two basic forms. For one, it may emerge as a sense of remorse, sadness and, often, guilt over things that happened but shouldn’t have. Deeply offending or betraying a friend would be an example. But in the other version, the focus is on what didn’t happen but should have. Like deciding against a potentially life-changing adventure and living to regret it. Both feed into a sense of “what might have been,” but clearly wasn’t.

Connie was into regret big time. Like the rest of us, she perpetrated her share of misdeeds and offenses over the years, but she made peace with herself and others over these transgressions (what shouldn’t have happened but did). These no longer vexed her, but something else did.

“I can’t stop thinking about what might have been,” she told me, a weariness in her tone.

Psychic Hostage

The “might have been” that took Connie’s psyche hostage had to do with two aspects of her life — intimacy and career. 

“I walked away from the love of my life,” she confessed. “I chose the safer guy, the one that seemed secure and risk free. Now, it feels like I took a bigger risk by not following my heart.”

Similarly, in her vocation she had passed up an opportunity to be an artist, with all the uncertainties that entails, in deference to becoming an attorney, where, understandably, prestige and security seemed more probable. 

“I’ve made a success of my career, but sometimes that’s all I feel like I’ve made,” she sighed.

Missing Our Prime?

Nearing 60, Connie pushed back against some of her regret by reigniting the artistic bent she smothered four decades ago, but she worried that, like an athlete who started too late, she missed her prime. And while doing her best to make up for lost time in the creative arena, the lost relationship was another matter altogether.

“How do you make peace with choosing the king of diamonds over the queen of hearts?” she pondered eloquently, referencing the financial security of her spouse over the potential emotional fulfillment.

“If you had opted for your soul mate, there’s still a chance it would have turned out poorly,” I reminded her.

“I can’t argue with that. But with him there was at least a chance at happiness, and I didn’t take it,” she replied.

Limits to Regret

There’s a limit to what one can do to salve this kind of regret. If one’s remorse is over some pursuit left undone, such as Connie’s artistic aspirations, then, often, one can still give it a go, at least in some fashion. Perhaps not with the same vigor or success as earlier in one’s life, but still sufficiently to enjoy the experience. But when one’s “it might have been” is about a love lost, there’s more work to do in finding peace with one’s past choices. Sure, staying focused on the here-and-now and finding satisfying ways to remain engaged with life usually proves helpful, but only to a point. 

“The sense of it won’t go away,” Connie mused. “Even when I’m not thinking about it, I can still feel it in the background. In no small way, it defines my life, and not for the good.”

Each type of regret takes its own unique toll. While there clearly are exceptions, the most difficult form of regret to reconcile is not over deeds done, but deeds left undone. Perhaps this is because, within reason, we can treat our transgressions or failures (deeds done) as learning experiences. They usually leave us with something to work on, salvage, atone for or otherwise resolve. We can often make amends with those we’ve let down or hurt. And even if that proves impossible, we can “pay it forward” by bringing some offsetting goodness or support to others.

But many of the things in our lives left undone offer little to work with, challenging us to reconcile with ourselves more than others. Sometimes, that’s a steep hill.

As author Jonathan Safran Foer wrote, “The mistakes I’ve made are dead to me, but I can’t take back the things I never did.”

For more, visit philipchard.com.