‘Aha’ moments of my reunion weekend

It is reunion season for many of us.  Including me.  What’s been interesting to witness is how the earlier enthusiasm I felt, fueled by text chains and pre-reunion dinners, turned into anxiety, comparison-itis and dread in the days before mine.

“Do I really want to go?”   

What is it about school reunions and large gatherings with past friends that brings out our innermost insecurity?

Last month, I coached many GSB alumni around their own spring reunion.  Session after session, we worked through reunion-sparked themes that I didn’t identify with in the same way until my own reunion approached: 

Themes like: 

I am not as successful as I thought I would be.  

Did I live up to my potential?

Others appear to have their lives figured out. 

I thought I would be (happier, wealthier, more settled, etc.) by now.

I still don’t know what I want to do with my life. 


These anniversaries can be triggering because we can come to squarely face our youthful ambition, complex expectations of self/society and our best laid plains. All were sprung from our upbringings and translated into career and personal goals in our early decades of life. Our ‘jobs’ since have been to execute these plans. We had invested decades into dreams for ourselves where we had believed that the harder we work, the more we achieve…and the more life would yield.

Reunions are also natural measuring stick by which we compare how others may have navigated life differently than us. It is understandably triggering to reconnect with classmates who are running companies or seem at the top of their game, no matter how different your wants. We held the same potential in many ways and same education. Yet, sitting next to a CEO in our former classroom does make me reflect upon my life choices. Doubly so if that person appears to have a happy marriage, too.

But that’s a mirage.   

Curveballs for all

In late night conversations with friends and vulnerability-sparking classroom experiences, what I learned over the weekend is that life delivered us all the unexpected since graduating:  career endings, relationship curveballs, children with struggles, health issues, financial wins/losses, geography moves and more.  Some share these more openly than others.  Success and hard work did not shield anyone from the natural swings of life.

Some of us downshifted careers, got fired or gave up on start-up dreams. Curveballs came to us all, forcing both wonderful and difficult pivots. Through these, we discovered ourselves more in closed chapters, career pivots and life choices made more in alignment with our values.   Someone shared, “I learned more in my failures than I ever did in my wins.”

In these moments, we confronted our humanness on another level.  No degree, title or bonus amount could insulate us from the universal struggles of life. We also drew closer to what mattered to us.

Confronting old dreams

In returning to this formative place in my life, I also reunited with that version of myself from 20 years prior.  I collided with glimpses of the life she envisioned in retreading her footsteps in the halls of Spangler. As I passed by couches where I collaborated with classmates on projects or cozied up with my then-boyfriend, feelings of loss, grief and questioning welled up my eyes. 

Could she have understood the why behind the choices she would make? Did she possess the maturity and capacity to understand the inevitability of life these days, from the larger dress size she wears (despite best attempts) to having a career optimized for balance not pay or prestige and being single now? I know she was expecting that her hard work and that HBS degree would have created a different trajectory – a more perfect one.

Would could I have done differently? The many choices floated through my mind as I meandered through the halls of campus.  After indulging in that space of ‘what ifs’ and lost dreams, I decided to stop myself.  

Enough, Shibani. Everything is exactly as it should be. In fact, many things are WAY better in many regards.

Wisdom of today

What I was reminded of again this weekend was the futility of staring into the rearview mirror of life for too long. It is helpful in some capacity – but spending too much time in the past distracts us from the journey we are on.  In looking back for too long, I saw a hidden assumption that if I had made different choices, my life would have been better, happier or different.  Sure, I made mistakes. What I learned is to live differently now because of these. These ‘mistakes’ are the human process for growth.  

Today, my life is exceptionally meaningful and rich. And just as it should be, I know in my heart.

That 20-something aged woman I was couldn’t have understood the complexities of life without experiencing them first.  In this realization, I can more easily drop her ideals and projections of life.

And this was the topic of conversation with so many of my friends over the weekend. That, in our youth, we idolized external success, for we believed it was the formula for happiness. Yet, we know now that our careers are only half the story.

Success doesn’t smooth out all parts of life and provide meaning alone.  Our life’s challenges do this.  In facing them we cultivate strength, success and inner knowing.And the development of our inner virtues aren’t on display on our name tags, aren’t printed in the class notes or mentioned in the cocktail conversation. 

What I was reminded of, ironically, on the quad of the ultimate symbol of stature, career and capitalism, is that the essence of who we are has little to do with our job title, our bank accounts or our team size.  Our personal relationships with ourselves, our innate harmony and our congruence with how we live life determines our peace. Isn’t this true success in life?

With this redefinition, I can more easily let rest the hopes of that 20-something old woman who I once was and live more fully as the 40-something old I am today, with more confidence and hope and an inner bank rich with knowing that all went exactly as it was supposed to.

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