My Empty Nest Came in 2 Different Acts

One at 26 and the other 30 years later!

By

Jennifer Cannon

 
Published May 21, 2026
Rose Wong

I was 26 the first time my nest emptied. I stood frozen, my heart seizing in my chest, as a blur of airport activity swirled around my precious 8-year-old son. I can still see his sad eyes — and me. This was the part where I needed to formulate a goodbye as he was about to board a plane from California to Florida to live with his dad.

That day in the early 90s feels like another lifetime, and it was.

At 56, my nest emptied for the second time, moving my youngest daughter across the country to college in August 2023. It was also a final reminder of the hundreds of moments missed with my son. The reflection in the aftermath is blinding.

In the mid-90s, my ex-husband moved his family across the country for work. I had a decent secretarial job, but I knew in the deepest recesses of my unprepared-for-motherhood-at-18 soul that letting him leave at this time was the best option for him.

I met his father in high school in June 1984. I was sitting with friends on the football field on the last day of my junior year, signing yearbooks, when he ran up and asked me to sign his. I did and included my phone number. I’d finally turned pretty the summer before, but didn’t truly feel it. (And I loved the streaming show The Summer I Turned Pretty.)

He was my first serious boyfriend and I was that girl who was desperate for someone to love her. I was five months pregnant the day I walked with my class at high school graduation in June. It was also my 18th birthday.

I married him that July, our son was born in November and we were divorced by the time he was two.

My son’s father re-married, and together with his new wife, they were a “real family,” a mom and a dad with college educations and steady jobs. While I was working my way up in the corporate world, I was still a secretary.

That awful day my son was moving across the country, I hugged him tightly and promised to fly back to bring him to me for spring breaks and summers. I didn’t want to further upset him, but I couldn’t hold back my tears as he looked at me with his big blue, questioning eyes.

I waited and watched, sobbing and waving, until the plane pushed back from the gate, a pre-9/11 luxury to get up close to departing loved ones. Driving away, I was overwhelmed with shame, guilt and something I couldn’t acknowledge at the time — relief.

In a messy, half-baked life, I was not equipped to be a part-time parent.

After many hard years of ups and downs and fighting with my ex and his wife, today I’m grateful to call my son’s stepmom one of my dearest friends. We’ve healed together, and grown up together.

We freaked out together when our son announced he planned to take a gap year after high school because his band had an opportunity to go on tour opening for a bigger-name band — which never happened. We agonized over what to do as our bright, beautiful boy spiraled into the depths of heroin addiction, and rejoiced as he fought his way miraculously back.

We beamed with pride as he graduated college magna cum laude with a degree in electrical engineering after his life had taken a decade-long detour. Then came the joy of us celebrating together at his wedding and the birth of sweet grandbabies.

I’ve been fortunate to build a stronger relationship with my son through open communication and the ability to take accountability for our past mistakes. I’m thankful for the love and grace he’s shown me.

While Act 1 of parenthood was less than ideal, Act 2, 18 years later, has proven to be rewarding beyond measure. Still, it’s inexorably intertwined with guilt about the first.

At the time, I had no desire for more children, and I certainly didn’t think I’d find the love of my life on Match.com, but that’s what happened. We met in January of 2001 and married in November — a big, happy whirlwind that changed my life overnight. The idea of motherhood a second time around was at first terrifying. When we really talked it through, I decided I wanted another chance.

Our first daughter was born when I was 36, the second, at 38. At this stage of life, I was financially and emotionally equipped to stay home to change every diaper, make every meal, and meet their bus after school.

In Act 2, I was present for every milestone, made birthday cakes, kissed away boo-boos, read bedtime stories, prepared family dinners every night. I was a dedicated chauffeur to sporting events and the cheering mom in the stands for competitions in lacrosse, equestrian, archery and fencing.

As I’ve watched my daughters grow into fiercely independent young women, the regret of having missed so many of these moments with my son is often overwhelming.

On the somber trip home from dropping our youngest daughter off at college, my head was filled with cliché phrases, like this favorite one: “The days are long, the years are short.”

Yesterday, my daughters were washing their pink battery-powered Jeeps in the driveway, and I was awash with memories. Weren’t they just in kindergarten, insisting their dad take the training wheels off their bikes?

These two starkly different phases of parenthood have brought realizations about the power of forgiveness — not only from my son and others, but from myself. I’ve learned to find more joy than sadness in the bittersweet losses we experience as parents.

My nest might be technically empty, but I feel myself continually evolving as a mother — now grandmother. My heart is full and ready to embrace the next act, which will include more writing and spoiling my grandkids rotten.

Jennifer Cannon is a New Jersey-based freelancer who’s written for Vanity Fair, The New York Times, Town & Country Magazine, TODAY, Business Insider and more. A mom of three, spanning two generations with two grandkids. She's empty nesting with her husband and two rescue pups. Connect with Jennifer on: https://linktr.ee/jjcannon