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Regret, Gratitude, and Middle Age: Learning to Receive the Life You’ve Been Given

No one ever told me that middle age would be marked by regret. I didn’t know the “choose your own adventure” of my upper-middle class existence would come to an end sometime in my early 30s. I didn’t understand that those decades in which I was invited to explore, in which the world was my oyster—whatever that means—in which I would certainly “fulfill my potential” through the endless possibilities available had an endpoint. I didn’t know a page would turn and suddenly the choices I made—most of which were not particularly adventurous at all, and some of which weren’t even choices—I didn’t know those choices would become inevitabilities. I didn’t know I would turn around to look at all the other adventures on offer and find that doorways that once had been open to me were now gated and sealed.

We moved to Connecticut in 2012, with a 6-, 4-, and 1-year-old in tow. We moved four times in the first year, so my ability to write blog posts and essays and books slid into crevices of my life, like Cheerios in the panels of the minivan, hard to retrieve, quickly forgotten. Soon, I was easily-identifiable as the mother of those three children, and as the wife of the newly-appointed Head of School, but not easily identifiable as me, the writer and thinker. I didn’t know that I was nudging the door shut on obtaining a PhD and on becoming a school chaplain. I didn’t know I was losing touch with the network of people who might become thought partners and connections to exciting work and generative creative opportunities.

I also didn’t know that the regret I started to feel about all these unintentionally closed doors would be paired with gratitude. On the one hand, I mourned the loss of identity, of hopes and dreams, of potential careers. And on the other, I received so many delightful days and experiences. I hiked in the woods and got to know the great blue heron my friend Anne named Greg. I bundled up when it snowed and hugged our kids and listened to them while we drove thousands and thousands of miles in circles around Litchfield County as they played soccer and danced ballet and went to the mall. Over time, I found new thought partners and renewed old relationships and found myself continually amazed by the people I met. And I still read books (I’ve saved years’ worth of favorites here) and wrote books and wrote essays and even started podcasting. I just did all of that more slowly, and with less fanfare, than I had once expected.

I started to believe what Psalm 16 says, that “the boundary lines have fallen for me in pleasant places.” That this life of constraints and missed opportunities is the life I have been given, is the life for which I am incredibly grateful. Maybe I needed to acknowledge and grieve the losses in order to be able to see and receive all that I have been given.

On the podcast this week, I get to talk with Dr. Curt Thompson about grief and hope. It’s really a conversation about facing the hardest aspects of our lives honestly, with the loving support of people around us, and beginning to recognize that when we face those hard things in community, we can emerge with hope. As I enter my 50th year, I’m grateful for this past decade of little losses and renewed hope. I hope the same might be true for you—that the hope outweighs the losses as you receive the life you have been given.


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