By Esther Mann

Dear Esther,

Not long ago, I attended my 30-year high-school reunion. Somehow, we skipped the 10- and 20-year marks, but some women decided it was long overdue and arranged it. I was excited to go and hoped to have a wonderful time.

There was much to enjoy. It was great seeing women I haven’t seen in years, catching up, reminiscing over good times and meaningful moments. All good. But, unfortunately, I found that once I got home and thought about the myriad of emotions that were flooding my head, I couldn’t seem to shake off some negative feelings.

Basically, the story is that when I was in high school, I was a terrific student. I wasn’t brilliant or anything like that, but I worked hard in order to get high grades, and I achieved my goals of academic success. I was proud of my standing in the grade and, though it’s hard to admit, I occasionally looked down on some of my peers who did not take school seriously and did not do well at all. I probably felt a bit superior and for that I am ashamed.

Ironically, catching up with some of the women at the reunion, I was astounded to learn that some of the least-likely-to-succeed girls are quite successful. A few of them have businesses of their own. Some have gone on to higher education and are lawyers, partners in accounting firms and even doctors.

If that wasn’t enough for me to deal with, I noticed that many of them looked absolutely great — stylish, well-dressed, and youthful. I’ve always been practical and never fussed over my looks. I rarely take time in the morning to put on makeup, I wear comfortable (though no doubt unattractive) shoes, and I wear clothing that is functional and comfortable. The stark difference between me and so many others at the reunion is still reverberating in my brain.

Though I was a great student through college, I got married straight out of college, began my family immediately, and never pursued a career. Through the years, I’ve been very busy with my children and now a few grandchildren. I have no regrets over being a dedicated mother and wife, but I’m suddenly realizing that my potential was ignored and that I never really did anything with my abilities besides being a good homemaker, etc. Not to put that down in the least — I do believe it is an honorable and important way to invest one’s time. But I can’t help but feel as though I peaked in high school, when many of my peers were first getting warmed up!

I’m having a hard time dealing with this new epiphany that I’ve managed to ignore this realization all these years. The reunion was a wakeup call, highlighting all that I am not. I find myself feeling so sad and filled with regrets. If these other women were able to do it all, why couldn’t I? Why didn’t it even occur to me to do it all? I was living in my little family bubble and didn’t realize that the rest of the world was passing me by.

I am proud of my family and my dedication to them. But how do I get past my feelings of missing the boat and failing to see the bigger picture? I almost feel like I’ve been in a coma over the past 30 years.

Any hope for me?


Dear Regretful,

No one likes to have regrets—and yet we all have them! Like taxes, they seem impossible to avoid. Show me one person who can look back on his or her life without any regrets whatsoever, and I’ll show you someone who is in denial or maybe not the most honest person in the world.

Obviously, you acknowledge that your past 30 years were not wasted in the least. You raised a wonderful family, devoted yourself to their well-being, and clearly are enjoying nachas from your devotion to them. Perhaps there were women at your reunion who spent the same 30 years totally focused on their careers and now regret not putting the same amount of time and dedication into their family. Who knows? It’s possible. The point is that we never get it absolutely right. There is no perfectly lived life.

The important thing at this point is to listen to the whispers that are presently swirling around in your mind, making you feel uncomfortable and unhappy. They are telling you something important, and you need to listen carefully. Be grateful that this wakeup call happened at your 30-year reunion, rather than your 50-year reunion. You returned home from your reunion feeling like there is some unfinished business in your life, and possibly that’s true. But you need to understand that it’s never too late to reinvent yourself. Perhaps your “peaking” is yet to come! You acknowledge that you know how to apply yourself toward a goal, work hard, and achieve success. That’s great. Now it’s time to figure out what those goals might look like today.

Frankly, you are still young, so don’t convince yourself that it’s too late. If you need help figuring things out, there is always help available. If you need to speak to a career counselor, by all means do so. It sounds like you have the ability to devote time to this now, so go for it!

Regarding your image, that’s easy enough. If it bothers you that your contemporaries are enjoying the benefits of paying more attention to their looks, and that maybe you’re feeling a bit frumpy in comparison, there are plenty of people out there who can lead you in the right direction of recreating your image. But only take that step if it’s important to you and affecting your self-esteem.

When life holds up a mirror to us and we don’t like what we see, we have a choice. We can feel downtrodden and depressed, filling our hearts with regret and sadness, or we can get busy changing things up and making things happen. In the spirit of the New Year, I wish you the energy and tenacity to turn around the parts of your life that are feeling disappointing right now, creating a new reality that will energize your life and enable you to show up at your 40th reunion feeling like a true winner!


Esther Mann, LCSW, is a psychotherapist in Hewlett. Esther works with individuals and couples. Together with Jennifer Mann, she also runs the “Navidaters.” She can be reached at or 516-314-2295.


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