Skip to content

The Best Investment I Ever Made!

For some, it’s a winning stock pick; for others, it’s a gutsy bet on themselves

  • Star Jones
    Gregg DeGuire/Getty Images

    Bar Review Course

    Star Jones, former cohost, ABC’s The View; president, National Association of Professional Women, New York. When Jones, now 53, graduated from law school, she spent her graduation money on an expensive review course to help pass the bar exam. It worked, launching her career as a successful prosecutor, TV talking head and, ultimately, cohost of The View. Bottom line: Know your needs and invest in yourself.  

    1 of 10
  • Best investment Apple stock Desireé Owen, Duck-farm owner, Barlow, Kentucky
    Courtesy Desireé Owen

    Apple Stock

    Desireé Owen, duck farm owner, Barlow, Kentucky. When Owen was in the middle of a career that has included stints as a lobbyist, campaign manager and news anchor, she noticed a computer company that looked as if it had potential: Apple. In 1998, she bought shares. She was drawn to the company because she had an Apple computer and liked it. The stock is now worth over 100 times what she paid for it. Partly as a result of that early investment, Owen has purchased a 156-acre farm that she is turning into a duck hunting club, trading office life for rural paradise. Bottom line: With stocks, select what you know — and like.

    2 of 10
  • Robbie Montgomery’ restaurant Sweetie Pie
    OWN: Oprah Winfrey Network

    Her Restaurant Business

    Robbie Montgomery, star of OWN’s Welcome to Sweetie Pie’s, St. Louis. Montgomery, whose reality TV show documents her challenges and joys as the owner of a family restaurant, says her best investment was when she started her business in 1997. A former backup singer for Ike and Tina Turner, she was working as a dialysis technician when one of her patients offered her a loan of $10,000 to help her realize her dream of opening Sweetie Pie’s soul food restaurant. “I was frightened to death,” she reveals. “Every penny I made, I reinvested in the business.” Today she has not only a restaurant business but a TV show and a new cookbook, Sweetie Pie’s Cookbook: Soulful Southern Recipes, From My Family to Yours. “I’m 75 and having one of the better times in my life,” she notes. Bottom line: Following a dream can lead to a lifelong payoff.

    3 of 10
  • Antique table,  dealer Carolyn Bryner
    Getty Images


    Carolyn Bryner, retired nurse, Hendersonville, Tennessee. After Bryner, 63, retired, she needed more income. With an eye for decor, she started traveling to buy antiques, then sold them online. She soon began making $500 a week. Bottom line: Invest sweat as well as money.

    4 of 10
  • Jim Gash, Farmer, Owenton, Kentucky
    Courtesy Jim Gash

    Biotech Stocks

    Jim Gash, farmer, Owenton, Kentucky. With a brother who works in medical research, Gash became intrigued with biotechnology. In 2002, he started investing in biotech stocks, which can be very volatile. But Gash has managed to time those swings to come out ahead — way ahead. He knows investing in such a volatile sector isn’t for everyone. “I’ve made my living as a farmer, and that probably makes me a little more risk tolerant,” says Gash, 65. His gains have allowed him to build up funds so he won’t have to give up the farming lifestyle as he ages. Bottom line: Know your risk tolerance.

    5 of 10
  • Grow nest egg
    Photo by Getty Images

    AARP Offer: Protect your money, grow your nest egg

    Take advantage of great information and tools. Subscribe to AARP's Money Newsletter to help build your financial future and prevent money from going down the drain. Join AARP and start saving for your dreams today.

    6 of 10
  • Catherine Collinson, President, Transamerica Center for Retirement Studies
    Courtesy Catherine Collinson

    A Creative-Nonfiction Writing Class

    Catherine Collinson, president, Transamerica Center for Retirement Studies, Los Angeles.
    Five years ago, Collinson, 53, enrolled in a $415 creative-writing course through the UCLA Extension program. “It was time to learn something new,” she says. Today, Collinson continues practicing the lessons she learned in the class — with a writers group of former classmates — and she’s writing her grandmother’s life story. Bottom line: Learning a new skill is important and satisfying as we age.

    7 of 10
  • Yoga certification - Wendy Bonvechio, Retired hotel-industry executive, Ojai, California
    Courtesy Wendy Bonvechio

    Yoga Certification

    Wendy Bonvechio, retired hotel-industry executive, Ojai, California. After practicing yoga for a long time, Bonvechio, 63, decided to invest in a 200-hour teacher training course for around $2,500. That was three years ago. Today the former Marriott International executive teaches classes to cancer survivors and military veterans. Bottom line: Pursuing targeted education can change your life.

    8 of 10
  • Donna and Ray Moon do charitable work
    Courtesy the Moons

    Charitable Work in Haiti

    Donna and Ray Moon, retired nurse and retired FedEx operations manager, Hales Corners, Wisconsin. For more than 10 years, the Moons, both in their early 60s, have been volunteering each year in Haiti, even though it has taken a bite out of their retirement savings. They even helped an American doctor build a new clinic. “We feel we’ve been really blessed,” says Donna. “It was time to give back.” Bottom line: Investing in others can be rewarding.

    9 of 10
  • Money Channel Slide Show end slide
    10 of 10