It's as if these experts—a financial planner, a Pulitzer Prize–winning writer, a veteran parenting guru—have come back from the future to put your hand-wringing at ease. Ready to stop sweating the small stuff—for real?

By Rebecca Webber
Updated August 20, 2015
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Woman with convertible reading map on remote road
Credit: Colin Anderson/Getty Images

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Woman with convertible reading map on remote road
Credit: Colin Anderson/Getty Images

1 The impractical splurge.

I tried on a wedding dress 25 years ago, an ivory silk floor-length gown with short sleeves that fit like a glove. I absolutely loved it, but it was $1,500. I'm a practical person, so I ended up getting a $700 dress—bright white with long sleeves that were puffy at the top. (The Princess Diana look was popular then.) I cringe a little when I look at the pictures today. We had an inexpensive wedding, and we had done everything to keep it low-budget, so I really should have splurged on that dress and made that memory for myself. Don't regret spending on things that are tied to memories, like a vacation or a special piece of jewelry for an anniversary. As a financial planner, I can tell you—the real problem is impulse buying or constantly saying, "I've got to have that outfit." It's not the infrequent purchase decisions that hurt you—trust me. —Laura Scharrbykowsky, certified financial planner and principal at Ascend Financial Planning. She lives in Columbia, South Carolina.

2 Your teenager's purple hair.

Kids go through phases. You don't need to worry about most of them or what they'll mean for the future. I spent years despairing over my son's limited diet. Now he's a gourmet cook. When my daughter was 19 or 20, I didn't know where she was for weeks. Turns out, she was in Mexico. She had met an artist! I was furious. Well, you know what? She married the artist, and now he's a science teacher. They are parents to my amazing grandchildren. Life, and growing up, is hard work. The best thing you can do for your kids is be someone they can talk to who helps them find clarity. —Adele Faber, mother of three and a coauthor of How to Talk So Kids Will Listen & Listen So Kids Will Talk. She lives on Long Island.

3 Problems of privilege.

We fret so much about which smartphone to get or that we weren't invited to a party. I've wasted time being annoyed because I had to buy a cross-country flight after the price went up. We take that disappointment, and we multiply that times a thousand. Lots of people across the world will never have enough money to celebrate a birthday or take a flight. It's obvious, but we all need to constantly repeat, "It's not the end of the world." The little things can cause stress and crowd the big picture. You may miss a real opportunity to solve a problem or make a difference in the world. —Sheryl Wudunn, Pulitzer Prize–winning writer and a coauthor, with husband Nicholas Kristof, of A Path Appears: Transforming Lives, Creating Opportunity. She lives in New York.

4 Your career path.

I spent much of my career at FedEx, starting as a driver and working my way into human resources. Then I left to work at an investment bank. I thought investment bankers would be so much smarter and so much better than truck drivers, which they aren't. It was the worst work year I ever had. It was a mistake. But mistakes aren't a big deal. Women especially are under pressure to be perfect. Some of the most interesting things happen as a result of OMG-what-am-I-doing? And really, in 20 years, unless you were the CEO of Facebook, few people will care what your job title was. —Beth Portolese, human-resources director and the founder of the blog FiftylstheNewFifty. She lives in New York City.

5 Having a ton of friends (or Twitter followers).

Concentrate on a small group of good friends, not a ton of cyber ones. In the five years I spent visiting parts of the world where people live unusually long and healthy lives, I found that those with the highest levels of well-being focused on face-to-face relationships. Research shows that the happiest people don't spend a ton of time on social media. You need a few friends you can call on a bad day and whom you genuinely like for who they are, not what they bring to the table. Also, I found people who have a drink or two a day live longer than non-drinkers, so have a glass of wine together. —Dan Buettner, author of Blue Zones Solution: Eating and Living Like the World's Healthiest People. He lives in Minneapolis.