My Greatest Regret Essay

Imagine you have a dream tonight in which you time travel into the future, to a point near the end of your life. In this future, you meet the older version of yourself, and soon find yourself asking this question: "So...If you could live your life all over again, what's the one thing you would do differently?"

Your older self considers this and looks off in the distance, thinking. Then, just as you're about to get your response, you wake up from the dream.

How do you think your future self would (will) answer this question? Could you benefit from knowing what your biggest regret might be?

In real life, the closest we can get to this kind of information is by asking someone else about their regrets—we love hearing revelations like these. Better yet, what if you could ask hundreds of people about their biggest life regret, to see which ones get mentioned most.

Some psychologists addressed this issue a few years ago by reviewing a number of earlier studies which all asked people to describe their biggest life regret. To simplify people's responses, each regret was categorized into one of the following domains: Career, Community, Education, Family, Friends, Finances, Health, Leisure, Parenting, Romance, Self, or Spirituality.

Starting with the most common domain, here's what they found:

1. Education. These regrets came in one of two forms. People regretted either: a) not getting enough education, or b) not applying themselves more in school. Many confessed that they didn't take school seriously enough, spending their time with friends who also didn't study much.

At first glance, it's surprising that regrets about education were more common than regrets about relationships, family, or health. But when you think about it, education improves a person's prospects in all these domains. More education generally means more money, and marriages tend to be stronger and family life more stable when people aren't burdened by financial worries. And in terms of physical health, many studies have shown that a person's education level is one of the best predictors of how long they'll live, even more important than income or type of occupation. So when people reflect on their life, many recognize that more education would have provided greater stability and more opportunities.

2. Career. As the second most common domain, people regretted that they didn't pursue the career they really loved. Instead, they chose a career path that was more practical, or one that would pay better. They knew early on what kind of work they felt passionate about, but it just seemed too risky to pursue.

3. Romance. These regrets took a variety of forms, such as marrying the "wrong" person, not putting more effort into their marriage, doing something to hurt their partner, or letting someone special slip away.

4. Parenting. One of two kinds here: For the first, some parents wished they had spent more time with their children while the children were young. These parents felt they had put too much time and energy into other pursuits, like work.

A second, very different kind of regret was that parents wished they'd postponed having their first child for just a few years longer—they regretted having children too early. This regret was more common among women, who have a shorter window of time in which to have children, and are more likely than men to make tradeoffs between having children vs. investing time in their education, career, and leisure activities. Many wished they had put off starting a family in order to build their career or get more life experiences.

Most of the life regrets fell into one of these four domains. Taken together, they do more than tell us what people consider their biggest mistakes; they also reveal what people come to value most in the long run.

But simply reading about these regrets doesn't guarantee that we'll avoid similar mistakes ourselves, when you consider that big mistakes don't usually result from conscious, one-time decisions (like choosing which school to go to, or whether to get divorced or not). Regrets that loom larger often grow out of a series of behaviors (or lack of behaviors) over a long period of time. For example, continually neglecting to call the brother you're holding a grudge against; or the hundreds of times you could have spent with your children but didn't; or the thousands of times you put off schoolwork to do something else.

Only later do we learn that lost opportunities have a way of sneaking up on us before we realize they're lost, before we realize the opportunities really meant something to us.

Every so often, then, it pays to slow down and re-assess what you're actually doing, to question whether your behavior isn't part of a larger pattern you'll someday regret. Do I really want to be the kind of father who misses his daughter's birthdays? How come I always start pushing someone away as soon as our relationship gets serious? How will I feel about myself if I spend the next 20 years in this dead-end job?

It's so easy to get wrapped up in comfortable rhythms of our routines that sometimes we need to confront unsettling questions like these, just to remind ourselves of the bigger picture.

Life moves pretty fast...If you don't stop and look around once in a while, you could miss it.

(This post was co-authored by Josh Foster.)


By Lisbeth Welsh

I’d never been hit before.  But then I’d never fallen in love with someone else’s husband before either.  I sat there and took it.  The screaming, the swearing, the cold hard sting as her hand connected with the left side of my face.   After all I deserved to have to sit and take it.  I had no leg to stand on.  I had done it.  Been in this affair.  I was the other woman that was blowing her life and marriage apart.  I deserved it.

Did I deserve for him to look the other way and allow her to hit me?  For him to not try to stop her?  For him to look away?  To stare down at his feet?

But what did I expect, he’d continually allowed her to hit him in arguments throughout their marriage.  Apparently.  He could ‘take a punch’.  Apparently.  If he had spent 33 years letting her hit him, why would he stop her hitting me?

Three years later I still feel that sting.  I still live on anti depressants and anti anxiety medications.  I still don’t sleep properly.  I still walk under the cloud.  I still haven’t forgiven myself.

He was my boss.  And so was she.  Her name was the one that sold the brand.  She was probably the one that had to sign my pay check every week.  And every week she signed that check for me to hang out with her husband and for us to fall deeper and deeper in love.

I suspect she knew long before she confronted it.  In fact no, I believe she willed us into being.  I walked into working with a couple who were falling apart.  Whose family was falling apart.  Whose grown children were a mess and plagued with self destructive diseases and addictions.

“I hate him.” She would throw those words around every day.  She would constantly stop, roll her eyes and mutter how hard it was to deal with him.  “I’ve told him, he either gets medication or divorce papers.”  The comments were endless.  He never said one bad thing about her to me.  He didn’t need to.  She would say it all to me for him. 

I could see how she treated him.  How she broke him.  People around were only too glad to share their observations with me. “Why does he stay?  She talks to him so badly. What does he get out of the relationship that keeps him there?”  Endless comments from others, unsolicited from me as I stood and watched the man I loved being broken by another woman

The man who I had become a friend and confidant to had fallen in love with me and I’d fallen straight in after him.  We didn’t even know until it was too late.  I had gone away for the holidays and that being apart was unbearable for us both.  But he was my boss.  I mistakenly believed we were protected by his marriage and our employer / employee relationship.  We had a boundary naturally imposed.  But we had woven a complicated emotional web as friends.  We had developed a deep bond.  Eventually he crossed the line.  I remember the feel of his arms around me.  His lips on my neck and I knew that there was no turning back.  I was scared for us both.  I was scared for my future.  I knew the day it started that it had to stop.  He was careless.  In public and in private.  We were like 14 year olds.  Excited to wake up in the morning.  Every day was full of life and laughter.  Every minute was an adventure.  The future was a wide, open, thrilling ride into the unknown.

I tried to make him be my best friend.  He couldn’t do it.  He wouldn’t do it.  He wouldn’t talk about it.  He KNEW that this was how everything would end for them.  He didn’t know how but he KNEW that I was gonna be his girl.  He knew everything.  And I believed him.  Because I wanted to?  Maybe.  Because I thought I knew it too? Maybe.

But three years later.  I knew nothing.  My biggest love is my biggest regret.  I cannot forgive myself.  Or him.  Or her.  The 3 of us are bound together by love, hatred & regret.  He would only leave if she allowed it.  Her threats of talking to newspapers and chat shows and taking all the money.  Threats of his children hating him and their sickness’ spiraling out of control.  The guilt that the unraveling of his children would all be his fault.  His ego that kept him there.  That kept the family together.  The ego that still calls and tells me how important it was to keep the family that way.  How hard it still is for him.  But she’s trying.  She’s working on her anger issues.  But that ego that still tries to keep me hanging on and tells me ‘that it could all change tomorrow’.

Three long years later.  I nearly destroyed myself.  I nearly destroyed my career.  I still live under a shadow of darkness.  Of regret.  Of lost love.  The black dog of depression and anxiety my closest friend.

Three years later, the sting still as cold on the skin of my left cheek as it was that day.  The day he called me and warned me she knew.  That he had told her.  At least, had told her a version that made me out to be some awful little whore.  She ultimately read the emails.  Changed his password to his account without telling him so that she, with sole access could go through and find what was there.  She knew the truth.  She would never let me know she knew the truth.  She acknowledged to him that he’d ruined my life.  And she was right.  And sometimes I want to say sorry to her.  Other times I want to scream that she doesn’t deserve him.  She pushed and got her wish and then changed her mind.  Because she loves him? Maybe. Because she’s a control freak?  Maybe.  Because she could not bear the public humiliation that the brand people have believed her whole career is a lie? Maybe.

Three years later, I’m still the ‘silly little bitch’ that fell for someone else’s husband.  That believed a spineless, weak man.  That crossed the line.  But had seen the hurt in him and healed it for a moment.

Three years later, I still can’t fully let him go.  I still answer the phone when it rings. I’m scared of never finding love like that again.  I’m still hurting.  Still angry.  Still broken.  Still full of regret.  Regret for what I did.  Regret for ever meeting him.  Regret for everything I know we’ll never have.

Three years later, I feel that sting on my cheek like it happened seconds ago.

Lisbeth Welsh is a writer who is taking life one day at a time.

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