I first encountered Margaret Heffernan in 2005. She had just published The Naked Truth: A Working Woman’s Manifesto on Business and What Really Matters, her research into the issues women face when trying to climb the traditional career ladder. I was interviewing her for my own piece, “Building a New Ladder to the Top.”  We spoke by phone and her contributions to the article were invaluable. She was wise, on point, and a dream to quote.

For her next book, How She Does It: How Women Entrepreneurs Are Changing the Rules of Business Success, she interviewed hundreds of women entrepreneurs, including over-40 fashion guru Eileen Fisher, to find out why privately held, women-owned businesses grew at three times the rate of all American privately held firms between 1997 and 2007.

Heffernan is not just a published author. She has been CEO of five different businesses in the U.S. and the U.K. A lot has changed since our initial conversation, and I was curious about what advice she would have for those of us over 40 who are struggling to find a perch in today’s precarious work environment.

I connected with Heffernan in December, when she graciously offered to call me from the U.K., where she was spending the week. Born in Texas, raised in Holland, and educated at Cambridge, she has a British accent; it flowed confidently down the wire as she answered my questions.

What is your advice for a woman over 40 who has lost her job during this ongoing recession and is trying to get back in the game?  

The first thing I’d say is, Don’t take it personally. Don’t take it as a judgment on your capacity or ability. One thing we know is that it isn’t just you. There are an awful lot of completely brilliant, totally competent people being laid off. It’s really important not to let it dent your confidence and make you think, “I’ve made this happen, or it’s just me, or if I’d been somehow more…intelligent, clever, creative, well-connected, or whatever, this wouldn’t have happened.” The reason I’m emphasizing that is because women tend to blame themselves for a great deal.

And don’t look for the past job, the old job, the old company. Be willing to understand what’s happened to your profession or discipline and how to do it the way it’s being done now. One of the hardest things around this,  I’ve noticed with a lot of my former employees and friends, is that when they get stuck, it’s because they are looking for things to be the way they used to be.

If anything, this new world requires us to be more strategic and to think about what skills, talents, and interests I have, and how I fit those to the companies, clients, and customers that are out there. How do I focus my efforts relentlessly to fit them? Just because things aren’t the way they used to be doesn’t mean that your whole discipline goes out the window. In fact, it becomes more important then ever.

What steps should we take when changing careers?

Photo: CNN

First, have a story about why you are going from A to B. This is extremely useful to the outside world for two reasons: first, people like a coherent narrative,  and second, otherwise they may infer that you failed at the first thing.

For example, when I moved from television to software, my argument was that television is an old technology, I’ve gone a very long way in it, and I want to move from the old thing to a new thing. So I was making the leap for people. To this day, they don’t see that connection unless I draw it for them. Then they see that what looks like a huge leap actually isn’t.

Then, think hard about who in your network knows people in the world you are hoping to move into, and reach out to them. What are the formal networks in that new industry or discipline that you could join? Do endless amounts of research, and understand who the key players are and how this new industry or discipline works. Ask yourself, what do I need to get into it—either in the way of formal qualifications or experience—and what do I already have that’s relevant?

Meet with anybody who appears relevant. When I moved from television into software, I met lots of people, many of whom were not immediately instrumental in helping me, but it made me much better informed and look much more knowledgeable.

A lot of us have trouble asking for help. Can you suggest a baby step for getting started?

It’s important to understand that almost everyone takes [being asked] as a compliment. Asking someone to help you shows that they have something that you respect. It’s a sign of trust.

When asking for help, be clear about what it is that you need. Most people will want to help if they know what you need. But if you simply come to them with a problem, that’s a lot more challenging. So if instead you say, “This is my problem, and this is how I think you could help,” now you’ve made it easy for me to say, “Yes I can help you like that”—or, “I can’t help you like that, but I can help you like this.” But simply articulating a problem and saying “help” is unproductive.

What tips do you have for the older woman trying to find a job working for someone else?

A lot of women are getting bent out of shape because things either aren’t what they used to be or aren’t the way they want them to be. Being realistic and adaptable is fundamental.

Talk to your children! Especially if they are grown up and in the workforce. They are the rock face. Find out what they are seeing. What do they see go wrong? What are the gaps they see in organizations? Learning in families is a two-way street. Our kids have a lot to tell us. Not everything they know or say is right, but they are a source of information and insight.

Heffernan's newest book, 'Wilful Blindness.'

What have you learned from your kids?

I look at the way they way they use technology. I’m really interested in the questions they have. Especially if you are thinking about starting your own business. Successful businesses solve problems. Listen to the problems that the people around you are having. What is it that doesn’t work? Your kids will tell you that. And chances are, if they think there’s something out there that doesn’t work, it’s probably a growing market.

I recently had a conversation with my teenage daughter about how everybody’s backpacks are too heavy and weighing them down. Well, one reason they are too heavy and so uncomfortable is that they don’t fit your back very well. So why couldn’t you make backpacks out of that material that’s used in memory foam, so that it actually molds itself to your back? That’s a beautiful idea for a business.

So much has changed since you wrote your book on women entrepreneurs. What are some of the characteristics you identified as common to them that individual women can use in starting their own business? 

Women are great at noticing what doesn’t work. If you can take something that doesn’t work and find a way to make it work, that’s a business. Of the hundreds of successful female entrepreneurs that I’ve interviewed, the vast majority of them do that.

Women often hugely underestimate how much market insight they have. They have that market insight because they are the market. Women are still responsible for about 85% of purchases. They have this knowledge whether they want it or not. So they have a huge opportunity to take that knowledge and apply it to thinking about “what kind of business would I like to start,” or “what are the businesses out there that are solving this problem that I could contribute to.”

A lot of women get stuck because their idea for a company is a product that needs to be manufactured but they don’t know how to do it. One of the most interesting developments is a company called TechShop. TechShop is to prototyping what Kinko’s is to printing. It provides the machines that you need to produce something, and the people who know how to use them.

That means that prototyping from an idea is now easier and cheaper than it has ever been. And the barriers to entry, both financial and intellectual, are lower than ever. You don’t need an engineering degree anymore. If your idea is a product, look around for an organization like TechShop. Or your local university may have evening classes in these kinds of things. There are ways to do it so that you can at least get to the point where you have something to show people. It’s the most exciting thing I’ve seen for maybe a decade.

What types of professionals should we consult with when changing careers?

It depends on the kind of business. There has been a real rise in peer-mentoring groups. When entrepreneurs get together to help each other, this is fantastically powerful. The reason they are so important and so successful is that as an entrepreneur, you often have problems you can’t share with your employees. You get honest feedback from people who understand what it’s like. In the early days of your business it’s a source of moral support and good, practical tips, and it will help you maintain your momentum. Find one of those locally, and go for it. It’s very, very effective.

Margaret Heffernan blogs at BNET and The Huffington Post. For even more wisdom, see her other books:

Willful Blindness: Why We Ignore the Obvious at Our Peril (2011, Walker & Company)

Women on Top: How Women Entrepreneurs Are Changing the Rules of Business Success (2007, Penguin)

The Naked Truth: A Working Woman’s Manifesto on Business and What Really Matters (Jossey-Bass, 2004)


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  • b. elliott January 9, 2012 at 2:13 pm

    Such incredibly valuable insight and information. Thank you so much.