I've been on over a dozen multigenerational family vacations. We book separate accommodations and talk about money before leaving.

Tech Insider : Travel, Travel, Business
Multigenerational family crossing a bridge over water on a hike.
The author (not pictured) has been on multiple multigenerational family vacations over the years.

Fly View Productions/Getty Images

My ex dumped me by sending a voice note. It was painful and confusing.

Tech Insider : Business
a woman listening to a message on her phone
The author (not pictured) received a voice note from her ex.

Westend61/Getty Images/Westend61

I committed a white-collar crime while bipolar manic. Years later, I'm still facing the consequences.

Tech Insider : Business
side by side of David Funes during a manic episode next to him happy and smiling
The author has bipolar disorder and experienced manic episodes.

Courtesy of David Funes

I accidentally threw out my kids' Christmas crafts. A teacher surprised me with some just in time for the holiday.

Tech Insider : Business
Close up of a Christmas tree decoration that has been handmade by a child.
The author accidentally threw out all of her kids handmade ornaments

Peter Lourenco/Getty Images

I always thought we'd retire in Europe. We spend our time in Mexico and California instead.

Tech Insider : Travel, Business, Economy
A woman sitting in her camper van with a cuddly toy in one hand and a book in the other. The back doors of the van are open, and a beach can be seen next to it.
The author often travels with her husband in a camper van.

Courtesy of Louisa Rogers

I thought I didn't want kids. My father's sudden death changed my mind.

Tech Insider : Business, Sports
A woman and a man lounge under a green umbrella on a beach.
Here, my dad and I are enjoying a sunny day in Porto de Galinhas, Brazil. Unexpectedly losing him after a heart attack made me realize that having kids was something I might want to do after all.

D.C. Macedo

I was in the best shape of my life when I got hit by a car. The debilitating pain during recovery left me emotionally shredded.

Tech Insider : Business
Winston Chiang wearing a hooded poncho and glasses and sitting on a concrete structure.
The author was in a bike accident in his 20s that left him physically injured and depressed.

Courtesy of Winston Chiang

I'm a manager, and I had a new employee quit after just a few weeks. It made me rethink my management style with new hires.

Tech Insider : Business, Environment, Sports
a woman shaking a manager's hand
The author (not pictured) is a manager who had to rethink his management style.

Nathaphat/Getty Images/iStockphoto

I waited until 40 to have kids. Now I realize I may never meet my grandchildren.

Tech Insider : Business
Sweet asian happiness new parent couple Asia cheerful pregnant woman getting ready for her new born baby preparing baby cloth and baby room with her husband
The author (not pictured) had her son when she was 40.

travelism/Getty Images

I went back to college at 42 to finish my degree. My daughter is my classmate, and it's only brought us closer.

Tech Insider : Business
The author and her daughter Siri standing outside on a sidewalk and smiling with trees and leaves in the background.
The author goes to the same college as her daughter, Siri.

Photo credit: Paige Mast

Subscribe to Essay