It's often wise to play it safe: Buckle your seat belt; toss expired milk; look both ways before you cross the street. But now and then you have to take a leap of faith. This month, readers celebrate the bold moves that brought them big rewards.

Illustration of two women climbing a mountain
Credit: Christopher Silas Neal

Five years ago, I decided to search for my birth family. With just one phone call to the adoption agency that handled my case, I found them—my biological mother, father, and five half siblings—all scattered in various parts of a town just eight miles from where I grew up. Now I not only know people who look like me but also understand why I always wear my sunglasses on top of my head and dip my bread in pasta sauce.

Leigh A. Reposa

Narragansett, Rhode Island

At age 58, I joined my adult daughter on an 18-day, 100-mile trek through the Himalayan Mountains. It was the toughest, most wonderful experience I have ever had. The greatest moment: when we reached the summit of Thorong-La Pass, at over 17,700 feet, and my daughter turned to me with pride and said, “Mom, you are such a badass!”

Mary Wesley

Statesville, North Carolina

Young and naive, my husband and I married at age 20, became parents at 21, and were divorced by the time we were 30. The best gamble I ever took: remarrying him at age 35, when we realized we still loved each other. That was eight years ago, and we haven’t looked back since.

Carrie Mihalko

McKeesport, Pennsylvania

In 1998 I watched a movie called Dance With Me and was immediately seized with the desire to learn ballroom dancing. Unfortunately, my husband refused to accompany me to lessons. I cringed at the idea of attending by myself, but I did it anyway. For the next decade, I danced competitively—making new friends and losing weight in the process.

Denae Monroe

Bonney Lake, Washington

I was the victim of a violent crime last summer, and as a result I became fearful. However, because of my job as a social worker, the opportunity arose to teach a parenting class to fathers in prison. I was terrified at first, but with the support of my friends and family, I summoned the courage to teach the class. My students helped me heal without even knowing it. Watching them change for the better gave me hope that I could change, too.

Kat Steiner

Drums, Pennsylvania

In 2009 I opened a bakery, even though the economy was bad and I was only 21. Why? Our town had no bakery, and I wanted to show people just how delicious homemade goodies could be. Three years later, I have a small staff, am working toward paying off my loans, and, best of all, can treat myself to a cookie whenever I want one.

Alixe Ingoglia

Columbia, Pennsylvania

While studying Czech at a foreign-language school for members of the U.S. military back in 1987, I met a fellow soldier who was learning Polish. After dating for only 2 1⁄2 months, we got married on one of our lunch hours. (I wore army fatigues to the ceremony.) Afterward we both went back to class. Everyone thought we were nuts! But the two of us will celebrate our 25th wedding anniversary later this year.

Jackie Hart Meeker

Lander, Wyoming

At 42, I finally faced my fears and learned how to drive. I had lived my whole life in Philadelphia, somehow managing to get around on public transportation, via bicycle, and by hitching rides with friends. But as my partner prepared to give birth to our first child, I realized just how much I had limited my life by not being able to go where I wanted when I wanted. I got my license one week before the birth of our son—just in time to drive my partner to the hospital.

Denine R. Gorniak

Collingswood, New Jersey

In the mid-1980s, I signed up for college classes to earn my teaching degree, all while raising three kids as a single mother and squeezing my full-time job into 30 hours a week. The schedule was grueling but worth it in the end. I more than doubled my income, and I have a satisfying career.

Eleanor Krimmel

Lawton, Oklahoma

It was difficult when my husband and I decided to move from Manchester, England, to Atlanta, Georgia, for his job seven years ago. We had to leave our kids, ages 23 and 21, behind. But it ended up being great for everyone. Our children learned to take care of themselves, and my husband and I got to have new experiences in the United States. We have made wonderful friends and have taken up tennis. (It was too rainy to play back in England.)

Lesley Kenny

Atlanta, Georgia

When my son, Ryan, was two, he was diagnosed with cancer. After he failed to respond to traditional treatment, I enrolled him in a clinical trial at a faraway hospital, leaving my husband to care for our other three kids at home. The trial was risky: It might not have helped Ryan and could even have hurt him. But I am thankful we did it. The trial gave us an extra 18 months with him—precious time we wouldn’t have had otherwise.

Kimberly Madrid

Euless, Texas