Life (and Business) After 50

Do’s and don’ts for older women entrepreneurs

The business of starting a business is fraught with challenges, some universal and some unique to your particular side of 50. Larchmont’s Felice Shapiro, executive coach and professor of entrepren-eurship at Tufts and, formerly, NYU, co-founded and publishes online magazine Better After 50 ( in 2011 to address the needs, both personal and professional, of women older than, yep, 50.

The site, which, according to Shapiro, receives 660,000 monthly page views, is a repository of ideas and stories about, for, and by women, with themes ranging from sex and relationships to personal finance. We asked Shapiro for the biggest pitfalls encountered by women over 50 looking to start a business. Hint: Coming up with a great idea might be the easiest part.

Pitfall #1: Motivation
Committing to a business requires an honest conversation with yourself, which means, says Shapiro, “realizing that you are going to invest time and energy. You need to be available, and you need to always be able to show up. I think for women over 50, if you’re in a more financially comfortable place, it becomes a bigger discipline issue.

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Pitfall #2: Picking the Right Partner
“An A team and a B idea are generally more successful than an A idea with a B team,” says Shapiro. When it comes to picking that A team (read: the perfect partner), it’s important to “really understand the motivation behind what your partner is looking for,” says Shapiro. “Try not to bring your own needs to the listening process; be objective in your listening. Talk about schedules, your availability, because that becomes a big issue. And, as with any relationship, you can’t force chemistry.


Pitfall #3: Cash Flow
The most common reason Shapiro sees businesses fail is cash flow. “Traditionally, women have not been comfortable talking about money says Shapiro, “but that’s changing. If you are entering into a partnership, it’s not just about how deep your pockets are, but how much are you willing to invest if the business requires an investment. Cash flow is something that you have to understand before you start.

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