8 Regrets From Real People Reflecting on Their Twenties


There is a book in stores titled 30 Lessons for Living. Compiled by a Cornell professor Karl Pillemer, the book is a collection of life reflections provided by a group of people that Pillemer refers to as “the experts” – aka over 1,000 older Americans who were asked to share lessons learned after decades of life. When New York Times writer Jane Brody reflected on the book, she summarized their advice for living a regret-free-life as, quite simply, “always be honest.”

In your 20’s, when making what feel like life-changing decisions on a daily basis, it is difficult for honesty to take top billing. In fact, it often feels like we have altered the relationship between honesty and regret by making the fear of regret the most powerful motivator. If I take a new job, will I regret leaving my old one? Will I regret not having traveled or having traveled too much? Will I regret breaking up with this guy? By the same coin, we use regret as a constant threat. “I just don’t want you to regret this later,” or “she’ll be the one to ultimately regret it.”

I’ve wondered if this use of regret is a millennial trait, and thought about why “regret” is a word – and a feeling – that for our generation seems to hold so much weight. Perhaps we are at an age where self-honesty is tough, or perhaps it’s merely symptomatic of the fact that we still haven’t lived enough to put things in perspective. Or maybe, what we are labeling as “regrets” should actually be called “choices.”

In thinking about regret, I spoke to people about their own experience with the subject. I never really understood before what a personal feeling regret could be. In asking someone about their regrets, you are essentially asking them to admit to something that makes them vulnerable; you are asking them to reflect on their life in a manner that is not hopeful but, instead, sad. After speaking with people older, and wiser, than me I decided to share some of their regrets in the hopes of refocusing the millennial definition of the word. 

On Tuesday, the New York Times published an article in which they said that regret is a good thing for young adults, as holding onto regret is a necessary motivator to try harder. While this perspective is thought-provoking, it only manages to view regret in the terms of competition; it doesn't allow for regret to be a point of self reflection. Regret shouldn’t be a threat, or a worry, or a motivator for our decision-making. It should, however, be a reminder to remain honest to what we feel and what we want. Hearing other people’s regrets is, of course, sad but it also provides a window through which to identify our own priorities, and identify the things that matter most as we move through our own lives.

So I leave it to the experts, friends and family who have lived a few years longer than I have, to tell you about regret. Hopefully, their thoughts will give you the space to slow down, to reflect, and to appreciate the things in life that matter to you the most.

8. “I have some regret about living most of my life in a big city, when the country (not the suburbs) and the beauty of nature give me such pleasure.” – Bill, 59

7. “I regret taking a job that I knew I would hate.” – Lili, 40

6. “When I was completing my master’s degree, I was encouraged by my faculty advisor to stay one more year to get my Ph.D. But, I was in love and couldn’t imagine having a long distance relationship for another year. Realizing as I do now how quickly time passes, I regret not getting that degree.” – Shelley, 59

5. “I deeply regret the loss of my son. I try very hard to hold on to the fact that I had him for 29 years and that that was a blessing and I cherish the memories. His loss is the regret I mourn the most.” – Rhea, 70

4. “I think my biggest regret is that my father died so young, something I had no control over. I was 18, we were always close, and our relationship was just evolving into an adult relationship. Plus he never knew my wife and daughter, who he would have loved. But then again, in my memory he will always be a relatively young man.” – My Dad, 59

3. “I regret not slowing down the pace of my life when my children were young, and appreciating and enjoying moments with them. Little did I know that time would move so fast. If I could rewind the clock I would concentrate harder on their lives as children and share and enjoy that period of time more.” – Fred, 59

2. “I regret not talking to my father more.” – Armando, 40

1. “I’m sure I’ve made bad decisions, but I don’t think I can call them regrets. I thought them through, made a decision, and knew I would have to live with it. Therefore, I can have no regrets.” – Maggie, 59

What do you regret?