Regrets and the Road Not Taken

by Lisa Rothstein on 07/19/2011

Regrets for things we never got around to, or “the road not taken” is probably the greatest pain a creative person can have. For someone with multiple talents, regrets are a virtual guarantee. Because even for the most deft and multi-disciplinary DaVinci among us, there’s no way we can possibly follow all our dreams in one lifetime.

Of course, this isn’t a problem for people who are really successful, right? After all, they obviously made the right choices in life.

My friend Ken told me a true story after I shanghaied him into attending an impromptu pity party I threw for myself on a recent phone call last week. The story takes place a while back in a men’s room (probably why I never heard it before). It seems my friend found himself at the urinal next to a very prominent New York elected official. (No, not prominent THAT way. Or at least that’s not part of the story.)

Anyway, my friend took the opportunity to ask this important man about working in politics, as he was in a related field and had always felt he’d missed his calling. Were there any jobs for someone like him?

This man — a lion of public life, not only in New York but on the national stage, a great orator, part of a whole American political dynasty, with a spotless career and reputation and legacy, turned wistful. He told Ken how back in the day, he’d been playing triple A baseball and was up for the position of second base with the New York Yankees. But Willie Randolph had been on the same minor league squad, and beat him out for the spot. This man is convinced that had Randolph not been there, he would have been the second baseman.

All these years and all that success later, he still sighs when he thinks about it.

“Even after everything he’s done?!” I cried. “Even after being so famous, and doing all that good work, and helping all those people, and even having a son who is following in his footsteps and carrying on his name in New York politics — he still has regrets?!”

I’m not sure why this story made me feel so much better. It wasn’t schadenfreude — I’m not happy that this man still carries these pangs, except that it helps me understand my own.

When you’re so talented that you could do anything, but you can’t do everything, there are going to be regrets. That comes with the territory. The trick to not having regret being the main dish instead of just a garnish on the plate that is your life is to do what you ARE doing the very best you can. This man did (at least I think so).

So here’s what I’m doing from now on to handle my regrets. I invite you to do the same.

    1. I’m going to grow up. I’m not 25 anymore and all doors are not still open. Even back then, I could never have walked through them all — it only seemed that way. It hurts to accept that you’re probably never going to be all the things — or even several — you wanted to be when you grew up, but resistance equals pain. Time to lay that burden down.


    1. I’m going to celebrate. I’ve done a lot of great things so far. The unique life I’ve had, and have now, would have been impossible had I taken any other road. I wouldn’t have my friends,  my husband and a lot of other things I would never want to trade for anything. I’ve got some nice laurels to rest on, if I wanted to.


    1. I’m going to do better. With whatever time I have left, I’m going to live a life that will lead to pride and satisfaction instead of regrets. That means making different choices with how I spend my time. That means focusing on what’s important when my brain wants to be scattered among multiple distractions. That means doing what scares me if it’s part of my path.


    1. I’m going to do it NOW. Regrets are the most common side effect of procrastination. The things I regret most, I never actually said “no” to. I just said “not now” … until the opportunity wasn’t there anymore. So I’m going to get clear on what matters, keep it in front of me at all times and do something towards those goals every day. Now. Today. Not next month. Not “as soon as (fill in the blank)”.


  1. I’m going to make mistakes… and like it. The surest path to regret is paralysis due to the fear of doing the wrong thing so that you end up doing nothing. (Or doing something safe and boring.) So I’m going to take action and revise later. I’m going to expect mistakes. Get ready for some doozies.

Activity: Make four lists: your greatest regrets; your greatest accomplishments; the important things, people and experiences in your life that you wouldn’t have if you had gone any other way; and your most important goals right now. Now, go do something towards one of the things on list #4.


getoverit flat cover sm

For more on this topic, check out Liisa Kyle’s book “GET OVER It:   Overcome Regret, Disappointment and Past Mistakes”.  Available here:



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{ 2 comments… read them below or add one }

Nisha Jackson July 19, 2011 at 1:51 pm

I identify with #4 and #5. While my children were younger, I played it safe in part due to the fear of not being there to give the very best of me to them. In turn this led to regret and procrastination in doing the things my heart longed for.

Lisa Rothstein July 19, 2011 at 2:59 pm

But now you’ve got a chance to do what you want to do right now. Resistance will always find a reason. Make your reasons for doing something bigger than your reasons for NOT doing it, and you will. If you can’t, maybe it isn’t something you want badly enough. Find something you do!

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