I stayed home while my family traveled because I needed a break. I loved my alone time.

Tech Insider : Travel, Business, Style
Woman eating dinner
The author chose to spend the holidays alone and really enjoyed it.

Courtesy of the author

I'm 52 and thought I'd be financially secure by now. But I'm still facing debt and long-term unemployment.

Tech Insider : Business
Chantrise Holliman headshot
The author is still financially struggling in her 50s.

Courtesy of Dana Lee Jones

My grandmother is 97. She's taught me to lean into what makes you happy, and that quality is better than quantity.

Tech Insider : Business
The author's grandmother enjoying a cocktail.
The author's grandmother is now 97.

Courtesy of Nicole Findlay

My family lives nearly 2,000 miles away from my mom, but my kids are still close to their grandma

Tech Insider : Business
The author's daughters reading with their grandmother on the Readeo app.
The author's family lives almost 2,000 miles from his mother, but his daughters stay close with her through regular FaceTime calls and reading together through the Readeo app.

Courtesy of Brendan Knapp

I left a mom group over parenting decisions. I don't regret it.

Tech Insider : Business, Style
Split image of a little girl facing a pond and her mother on the right

Courtesy of the author

When my family of 4 moved to a small town, we downsized. We now spend more time together and less money.

Tech Insider : Business
Family looking out the window at snow.
The author's family (not pictured) spends more time together after their move.

AleksandarNakic/Getty Images

I used to be afraid to dine alone. Now I love it.

Tech Insider : Business, Travel
Man eating alone
The author used to be afraid of dining alone in public.

Courtesy of the author

I recently learned my 12-year-old son is dating. I'm worried I waited too long to have the sex talk.

Tech Insider : Business
a father and son sitting on a couch talking
The author put off the sex talk with his son.

ridvan_celik/Getty Images

I regret not practicing gentle parenting with my oldest kids. I'm making up for lost time now.

Tech Insider : Business, Style
A mother and child walk in a park.
The author (not pictured) said she mostly stuck to "old-school" parenting techniques as a new mother.

Oscar Wong/Getty Images

My grandfather helped me open an investment account for my 21st birthday. He didn't just give me money — he gave me financial literacy.

Tech Insider : Business
The author with her grandfather sitting in a car.
The author is grateful for the gift her grandfather gave her when she turned 21.

Courtesy of Alice Draper

Subscribe to Essay