On Turning 50: Regrets, Dreams and Possibilities

By Guest Blogger Dana Kobernick

As I slide into my fiftieth birthday with all the grace and composure of a train half off the rails, I can’t help but go through the typical machinations of a woman approaching – or past – middle age. Until now, I have led a fulfilled life. I recognize my fortune that manifests primarily through my rich relationships with family members and friends. I have had a productive career, indulged my passion for travel and been active in community initiatives.

Still, there are regrets.

I have not (yet) married and I don’t have kids. Over the years, there have been brief moments of reflection, during which I questioned whether this was something I truly wanted or if I was buying into the social expectation that I get married and have a family. Those ruminations produced the clarity I needed to affirm my true desire to be a wife and mother. But due to circumstance, timing or other such explanations as to why this did not happen, today I do not fulfill either of these roles.

When so many claim their children as their greatest achievement, their legacy, it becomes that much more challenging to define your own measures of success. Notwithstanding what I have already acknowledged, I still find myself searching for some sort of validation, for something to show for the fifty years that I have spent on this planet.

photo credit: great-happy-birthday-ideas.com
photo credit: great-happy-birthday-ideas.com

Many of my friends, also heading toward this milestone birthday, are thinking about similar issues. Interestingly, one of them, who is in a happy marriage and has three thriving children, lamented the fact that she did not have a career. Another friend is now having to weather the fallout of a broken marriage. And another admitted to me that she regrets not having pursued her dream of becoming a travel photographer.

None of this is particularly surprising. That everyone has regrets is as much a cliché as my mid-life crisis, and no great revelation. But it made me rethink how I view and value my own accomplishments.

I have spent much of my professional life in communications and writing has always been an integral part of my career. But I have also used writing as my creative outlet to voice opinions, share experiences and explore thoughts. I can trace my love for writing back to my high school days, when I reveled in my ability to create a graphic description of a brutal shark attack. My writing is no longer quite so morbid but my passion for this form of creative expression, for producing a story where only a blank page existed previously, has persisted since that time.

For me it was just a matter of time until I would tackle a novel. And once I found my muse, I grabbed hold and didn’t let go until I gave birth to a 220-page manuscript. It’s my baby, one that I have nurtured and watched evolve over the course of five years. It has been joyful and exhilarating and also frustrating, daunting and overwhelming. But it is a great source of pride.

photo credit: elephantjournal.com

To be clear, I am not literally comparing a book to a baby. Nor am I suggesting that this endeavour can fill the void of not having children. Nothing can. But it is something that I can claim as my own creation, as something that I have produced because of an unyielding desire to chase the dream.

When I first started writing, I knew that if I wanted to publish my book through the traditional channels, I would be opening myself up to a boatload of rejection. Completing the novel, on the other hand, was fully in my control. And I realized that failure to publish would only occur when I stopped trying. As author Elizabeth Gilbert says, “Becoming a published writer is sort of like trying to find a cheap apartment in New York City: it’s impossible. And yet…every single day, somebody manages to find a cheap apartment in New York City.”

photo credit: ronernbphilly.files.wordpress.com
photo credit: ronernbphilly.files.wordpress.com

So the dream stays alive. And I can proudly say that I am going after it, however long it takes. But whatever happens, I feel like I have accomplished something already.

Yes, there are pangs of regrets. There are voids that cannot be filled. And I wish there were do-overs. But to the extent that do-overs are not possible, I know that I am better off recognizing what is and what can be, instead of what isn’t or what will never be. At least for me, I’m hoping that I will not only accept my fiftieth birthday, but embrace it as well.

After all, some people don’t make it to fifty. I’m one of the lucky ones.


Dana 2

Dana Kobernick is a communications consultant and writer living in Montreal. 

Read her blog post on The Hardest Part of Writing a Novel.  

Dana was my sleepaway camp counselor when I was eight years old. Please share your thoughts with Dana, she will be reading. I’d also love to know, do YOU have any regrets? Do you have stones still unturned?

Happy Monday.


  1. Great post Dana.
    We all have things we haven’t accomplished in our lives that sting from time to time.
    For me it’s a career that never amounted to much. Yes we are all lucky to be alive and healthy at 50
    Can’t wait to read your book. I’m sure it’ll be awesome!

    1. Thank you! As you read, I understand that “sting”. I think that we can feel it, all the while appreciating what we have.

  2. Great read. And I understand the idea of the creation of something from start to end. Something like a child where people are always making some kind of edits. And at times, even though I have a child, I didn’t have to push through labor as I had a C section and feel like I didn’t work enough to have the kid. But that is neither here nor there. I work hard every day raising him.
    I just turned 40 and will not say I have regrets. However things could’ve been different and i’d be okay with that. Take this time to accomplish anything you want. It’s your time. Your life. Just go do it!!!!

    1. Thanks for taking the time to read my post and comment, Heather. Happy 40th! I agree with you: we can accomplish anything we want (and at any time).

  3. Dana,

    Beautifully written.

    We have some things in common:

    I just turned 46. I’m single, no kids – by circumstance.

    I’m from Montreal originally, although in NYC 21 years, in the [relatively] “cheap” apartment I found years ago.

    I’m a writer too – author of two books (the first, Savvy Auntie, Elizabeth Gilbert blurbed and supported)
    The second is: Otherhood: Modern Women Finding a New Kind of Happiness (Penguin Canada). Erica was at a book talk I gave in Montreal last April. It’s a reported memoir about our generation of well-educated, financially independent, fantastic women who haven’t found the love we expected to lead to marriage and motherhood.

    You’re right; a book is not a baby. But writing a book that others read and are touched by is giving birth to ideas. Women of the Otherhood are not waiting for life to happen to us; we choose to keep moving forward.

    Cheers to you and your novel! And I can vouch for you – and for Liz Gilbert – that the most unexpected things happen every single day.

    Regret is behind us; love is ahead.

    Melanie Notkin @SavvyAuntie

  4. Beautiful piece, Dana. Thank you! Having taken the plunge, (and as a proud member of the Otherhood), I can share that it is liberating to look back and see all that has been accomplished, break away form the model we were raised to follow, and realize, “Hey, I’m doing just fine, better than fine, despite what society dictates.” Having the freedom, and courage, to write that book, create that newspaper, organize a fundraiser musical, etc…is all important, fulfilling stuff that makes the world go round, and a better place. I can’t wait to see what comes next for you!

    1. Thanks for your comments, Wendy, and I agree with you on all counts. Since you took the plunge first, I will be looking to you to guide me through.

  5. Dana,
    You write with incredible depth and grace and it makes your work highly relatable. Good luck publishing your book! I am sure it’s a wonderful read.

    1. Thank you so much. You have no idea how encouraging your words are to me. It is my hope that my book will resonate with many people in the same way.

  6. as Anais Nin commented when asked what it meant to be a writer She explained it was like BREATHING Maybe that’s how it is for you! Keep on doing what you Love !

  7. It is not easy to summarize a life lived for the last fifty years in a short blog. Your experience is a true testament to the choices and chances we make and take in our lives..Living with attributes of grace, compassion and kindness is a shining example of how we should all aspire to live. Although I still have a few more years before I hit the big, 5-0, these milestone birthdays are opportunities to keep our moral compasses in check. Thanks for sharing Dana..VERY proud of you!

  8. Dana… another huge baby was the Segal Centre fundraiser. Had you not approached me 6 years ago and mentioned that you wanted to volunteer and create something special,., this wonderful annual event would never have been born! Think of all the people whose lives this annual event has touched.. The monies raised, the friendships created… That event is still alive and kicking and thriving because if you! Now.. WHEN CAN I READ THAT BOOK??? I have been waiting for a very long time!!

    Next time I see you I’ll buy you a kahlua and milk! on Ice.. 🙂


    1. Sorry for the delay, Shari, I am just seeing this comment now. Thank you so much for the recognition. I am proud to be a part of the Segal Centre family.

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