July 2007
Becoming your own boss in retirement
Illustration by Bob Eckstein
But when we spoke with him, he was seven years into a successful second career as a travel agent, specializing in cruises, tours, and military reunions in his home port of Charleston, S.C.
While Pickett took a decidedly informal approach to starting a retirement business, his story says a lot about the right way to go about it. For one, he built on what he knew and enjoyed, including world travel, cruises, and the interests of veterans like himself. Second, he took the time to learn before he launched, apprenticing for six months with a friend who was already booking cruises for a living.
What’s more, he knew that being the captain of his own entrepreneurial ship was the way he wanted to go. “I didn’t want a corporate environment,” he says. “That was just not for me at this point of life.”
Many retirees are coming to the same conclusion. A recent Merrill Lynch survey of baby boomers age 40 to 58 found that 13 percent considered running their own business the ideal work arrangement for their retirement years. If you agree, here’s some advice that can help you get started:
- Do what you love. Paul Edwards, co-author of “The Best Home Businesses for People 50+” (Penguin, 2004), suggests looking at your existing interests
before you start exploring totally unfamiliar fields. “A lot of people are interested in hobby-related businesses,” he says.
“Basket weaving and chair caning will never be highly paid, but they’ll be around for a while.” If you enjoy working with
tools, he says, consider becoming a handyman/woman. If you love animals, look into pet grooming or dog training.
- Think small. Sure, Colonel Sanders built an international fast-food empire beginning at age 65, but even he started small, working out
of his car while surviving on his $105-a-month Social Security check. Today’s entrepreneurs have two advantages that may be
nearly as valuable as the colonel’s secret blend of herbs and spices. One is the boom in home-based businesses, which has
made working out of one’s house not only perfectly respectable but, in some ways, enviable. (Excuse me for a second. My dog,
Bob, wants to go out.)
Second is technology, which allows many entrepreneurs to do business no matter where they are. “All you need in my business is a cell phone, a laptop, and your knowledge,” Pickett notes. “I’ve booked cruises from the deck of a cruise ship.”
Where to get help - SCORE, the nonprofit Service Corps of Retired Executives, offers a lifetime’s worth of business advice at its Web site (www.www.score.org), as well as in-person help through local branches across the U.S.
- IRS Publication 334, “Tax Guide for Small Business,” is available online at www.irs.gov or by calling 800-829-3676. It explains tax forms and filings for small-business owners.
- Your local Social Security office or the SSA Web site (www.ssa.gov/r&m5.htm) shows how earned income affects your retirement benefits.
- The Small Business Administration Web site at www.sba.gov offers tons of information for would-be entrepreneurs, including
online courses and a guide to creating a business plan.
- SCORE, the nonprofit Service Corps of Retired Executives, offers a lifetime’s worth of business advice at its Web site (www.www.score.org), as well as in-person help through local branches across the U.S.
- Have a plan. You may, like Pickett, be able to apprentice yourself to someone who is already established. Otherwise you should at least
chat up people in the field to get an insider’s perspective of what the work is really like. Either way, drafting a written
business plan is well worth the weekend or two it will require. A business plan is essential if you’re looking to borrow money.
But even if no one but you will ever read your plan, sitting down and writing it can help focus your thoughts and advance
your business from daydream to day job. A useful tutorial on the subject is yours for the browsing at the Small Business Administration
Web site, www.sba.gov.
- Be prepared for some grunt work. Former senior executives may find the transition to sole proprietorship rocky at first, notes Nella Barkley, president of
the career-counseling firm Crystal-Barkley Corp. “They’re used to large organizations, where they had a lot of support. It’s
difficult if you’re opening an antiques business and have to sweep the sidewalk every morning. These jobs don’t come with
corporate perks.”
- Consider your mate. “A lot of spouses want to work together,” Barkley notes. “This is enormously complex. They need a shared vision, and they
need to look at how their talents mesh. In some cases it works very well. In others they’ll decide they each need to do their
own thing.” Any partner you consider should bring skills you don’t possess to the enterprise.
With any luck, you’ll be as satisfied in your retirement business as Pickett seems to be in his. While he’s quick to admit that selling cruises and vacation packages isn’t a first-class ticket to Big Bucksville, it does offer some rewards he considers more important. Says Pickett, “It feels good to sell a product that makes people happy.”
