When Life Doesn’t Go As Planned and Something Better Shows Up

When I was 22 and fresh out of college, I had a clear picture of how my life would go: I’d land a career I loved and climb the corporate ladder. I’d marry someone creative and artistic, and together we’d live in a trendy New York City apartment before starting a family. We’d have two kids—a boy first, then a girl—and eventually move to the country to renovate a charming old farmhouse (all while juggling our thriving careers, of course). Then, once I retired, I’d spend my days dabbling in art or writing.

Let’s all take a moment to remember the dreamy, naive girl that I was. 

Okay, are we back?

Here we are, almost 40 years later, and guess how many of those things came true? One. Just one. I’m kind of a writer - and not the glamorous, bestselling kind - the I’m sort of journaling online and sharing it kind.

As for the rest? I married a blue-collar guy who isn’t the least bit artsy but can build me anything I dream up. We stayed put in the small town five miles from where we grew up, had one wonderful son, but after a rough pregnancy, I knew I wasn’t going through that again. And the corporate career? It turns out that corporate America was not my vibe.

There were other disappointments, too. I had hoped to marry into a big, happy family. Instead, I found myself navigating complicated dynamics that often left me feeling drained. And I still scold myself for walking away from the career I trained for many years, without giving it a real shot.

But alongside the hard stuff, there’s been so much unexpected joy. My son has given us a beautiful grandchild, with another on the way. My husband, now in retirement age, has a side gig he loves, and I’ve been slowly learning how to be a writer. Moving to Florida brought us close to my son and his family. And I’ve found an incredible circle of friends here who inspire me, support me, and remind me daily of what really matters.

It’s a great life. And yet, sometimes I still grieve the life I once imagined. 

I don’t mean that to sound ungrateful, but sometimes I feel sad and surprised at all the ways my life veered off course. But, with the help of an excellent therapist, here’s what I learned: Midlife is about holding opposing truths at the same timest, things like being invisible but freer, being more comfortable in your own skin, yet aware of every wrinkle; having both strength and vulnerability; appreciating both your freedoms and your responsibilities and - most importantly - having the courage to let go of old dreams and daring to make new ones. 

In our 20s, life is all about the future, with things like careers, dating, marriage, and children, but midlife is different. It’s standing in the middle, holding the past in one hand and the future in the other, and learning what to cherish…and what to release.

Midlife is where we reconcile the life we planned with the life we’re living. And the truth is—there’s no bypassing that tension.

It’s not easy. But there’s comfort in knowing that standing in this in-between space means we get to hold both gratitude and hope, thankful for where we’ve been, and still excited about what’s ahead.