Marla Wynne: A Playbook for Women Over 50


Women over 50 are well-positioned to make a career comeback in today’s volatile economy, mitigating the wage losses and ageism of the past. But the secret is to take the initiative and to take charge. Fashion entrepreneur Marla Wynne exemplifies this trend.

Women over 50 are the largest age and gender workforce category in the U.S. economy and are growing, according to the Bureau of Labor Statistics. Almost 4 million women over 50 will become a part of the U.S. workforce by 2026, while male workforce participation in the same category will actually decline by around 3 percent.

Don’t Back Down, Double Down!

When your first-act career runs out of steam, you have two choices. You can call it quits and resign yourself to struggling through your remaining years. Or you can dig deep, find your usefulness and your passion, and build a next-level, second-act career.

Marla Wynne Ginsberg had never sewn a stitch when she bought her first sewing machine in 2009 and embarked on a risky career reinvention that wound up challenging every ounce of her resilience. She emerged in one piece, made her new fashion business an enduring success, and learned many lessons in the process.

Marla had been a successful TV executive in LA. She and I were contemporaries in the business and had interacted and socialized for years. While entertainment sounds to many people like a glamorous business, what you see on TV is the tip of the iceberg. Down in the depths, the business is volatile and unforgiving. Traditionally, it has been very unforgiving to women, and to older women especially – a reality sadly reflected in the broader economy as well.

Her story has been reported extensively over the past decade. We reconnected and I interviewed her about her business about six years into the venture. My goal in this piece is not to retell her story but to deconstruct it and analyze it so that you can use her lessons for your benefit.

Use this strategic toolkit to frame your own second-act career transformation.

Go With What You’ve Got

Would-be entrepreneurs, including women over 50, aching to start their own ventures, often lament their lack of resources or viable ideas.

“If only I could figure out my own business, I would leave corporate and build something on my own!”

They want clarity and certainty. But that’s not the way entrepreneurship works.

If Marla Wynne had stayed stuck waiting for certainty in her career reinvention, she would still be struggling to produce TV series.

Instead, when her career took a left turn, she looked at who she was, what was available to her, and what inspired her. She knew that she didn’t have the time to learn a new set of skills or go back to school. She had a family, financial pressures, and had to move fast.

Don’t Be Afraid to Take a Different Path

Marla Wynne returned to Los Angeles following a productive and successful thirteen years working on TV series productions in Paris. Among the challenges of re-settling her career, her life, and her family, she saw that the fashion choices for American women over 50 were, to put it mildly, lacking.

When she had left, she had been barely forty. Now she was in her early fifties and accustomed to working and shopping in a city that breathed fashion for women of any and every age.

When the 2008 recession hit on the heels of an industry-wide writers strike, she lost her high-profile job with a big TV studio. When other job possibilities evaporated, she was forced to downsize, short-sell her house and radically reassess her career.

Although she was able to pull in some consulting work, maintaining momentum in her TV business career was becoming more and more difficult. Many of the underlying production/distribution framework that she had worked under for so many years was changing. She knew that ageism and sexism were going to be insurmountable obstacles for her and for the other women over 50 she knew in the business.

Desperate to pin her hopes on something solid, she pivoted to another industry that she had known and loved – if only from afar as a consumer and a fan: the fashion business.

“At the time, the prospects of finding a job were about as likely as finding a natural blonde in Beverly Hills.  So I decided to reinvent myself by combining my creativity and passion for fashion.”Marla Wynne

Even though she had no formal fashion background, she felt strongly that she had something to contribute. She believed that her vision and her drive would help her succeed.

She also had a plan.

Women Over 50

You Are the Market

Her dissatisfaction with the wardrobe choices available to her was the key insight.

She reasoned that she wasn’t the only woman feeling this way and that many more women over 50 would welcome a clothing line designed “by a boomer woman for boomer women.”

This single-minded mantra rang in her head as she sat in her garage by herself with her new sewing machine and designed and sewed her first collection.

She had no idea whether her line would be successful. But she knew that she was the customer – a boomer woman over 50 with a certain sense of style.

Still, were there enough women over 50 who felt the same way? Would they think that her designs were good? Would they buy them?

Betting on an idea you think is commercial, or betting on your own taste can be risky. Thousands if not tens of thousands of small businesses and business ideas fail every year because people haven’t done their homework. Your idea has to be truly useful if it’s going to work.

If you are starting a business, you have to research it and figure out whether your customer exists. You have to learn whether they actually need what you’re offering, and how much they’re willing to pay.

But you do have to start with yourself. You have to be the first and best customer for what you are selling.

If you can’t pass this litmus test, then you will forever be adrift and second-guessing every decision or challenge in your business.

Don’t Quit Your Day Job

Marla Wynne committed herself to her venture, but she also made a smart transition from the business she knew. While she still had her entertainment business consulting clients to fall back on, she began designing and sewing her first collection.

Many entrepreneurs and business launchers dual-track their new ideas as an insurance policy against something going wrong. Every new idea has kinks that will need to be worked out. This was especially true in Marla Wynne’s case, given that she had no formal background in fashion.

We talk a lot today about “side gigs,” and indeed the digital economy makes it easier than ever to start a business. Sites like Kickstarter and Indiegogo are a great way to not only launch a new product but to build a fan and consumer community around your product and business.

Prototype & Iterate

Marla Wynne used this period when she was dual-tracking her business. It gave her the space she needed to clarify her design approach, and make mistakes.

Starting a business will always be fraught with unexpected changes and unpredictable challenges. This is why it is so important to spend time in the beginning to develop and test your ideas. This could involve building prototypes of your product and seeing how people respond. It can involve testing your service on a small group of prospective customers.

Your willingness to iterate and make changes at the beginning will save you time down the road. It will also let you make mistakes (and learn from them) while it is still possible to make corrections. Being a good listener is also very important at this stage. Don’t let your single-mindedness prevent you from hearing good advice that may go against your assumptions or your wishes.

Marla Wynne explored a number of different business and distribution models for her line. She also learned a lot about production and cash flow issues that can be mission-critical in the fashion world.

It’s Who You Know

Networking and business relationships are key. They are also a double-edged sword. People you know might want to think of you only in the context of how they already know you. They may not want to believe that you are going to be capable of succeeding in a different kind of business.

Strategize accordingly. Build networking momentum with people who are more broad-minded and more imaginative. They will be the ones to connect the dots and understand how you and your idea can be successful. Spend time with these more visionary connections to craft your sales pitch and value proposition. They will understand how to help you communicate your venture to others who may be more skeptical.

Understand Your “Ask”

Many times, would-be entrepreneurs connect out to their network without a clear message.

Each of your connections is a unique individual. Your outreach should be custom-targeted to each person based on who they are, who they know, and how your idea or business could benefit them. Think this through and be crystal clear about what you need from them.

Early in Marla Wynne’s journey, she realized that one of the most important ways she could reach her target market of women over 50 was through home shopping channels.

All she had was the first rack of designs she had thrown together in her garage with her new sewing machine.

Nonetheless, she marched into the offices of Creative Artists Agency in Beverly Hills, the Hollywood powerhouse organization that had represented her career as a producer.  Plowing through their skepticism, she wowed them with her vision. So they agreed to introduce her to their contacts at HSN.

Partner Wisely

It’s hard to do this alone. Even if you are confident in your idea or you’ve built a great prototype product, your expertise only goes so far. You can’t be an expert in all areas. It is indeed important in many cases to find a partner who complements your skill set. Find someone who can be the “yin” to your “yang” and vice versa.

Use extreme caution in drawing up a partnership with someone else. You may have known this person for a long time in a different context. Perhaps they are a personal friend, someone you know through your family or a social circle. Maybe it is someone you’ve worked with at the same company.

Working together on a new business is an entirely different proposition. It will test you and your partner in significant ways. For a partnership to work well, you must establish it based on shared values, ideals, ethics, and priorities.

Spend time together before agreeing to work together to explore these questions. Do your best to ensure that if things go south, you and your partner will be able to stand shoulder to shoulder in mutual support.

Unfortunately, Marla Wynne found out the hard way that partnership can be tricky. At the very beginning of the business, she partnered with a seasoned fashion industry executive. He had what appeared to be a viable process for manufacturing her line. But when the 2008 downturn hit, he pulled out and left her with a stack of orders that she would not be able to fulfill. Even though she was able to find a backup, the sting of this betrayal cost her a lot.

Don’t Be a Martyr

Follow the old adage to “first take care of yourself so you can help take care of others.”

Your business will not be served by you burning yourself out. Don’t turn down help and support because you don’t want to take “handouts” or “be a burden” on your friends.

People want you to succeed. When appropriate and when needed, allow others to help you out.

It is easy to lose perspective and become so narrowly focused on short term deadlines and other goals. While they are important, remember that you may be too close to your own problems. The input and support of others can go a long way to helping you smooth out seemingly unsolvable problems.

Marla Wynne experienced burnout as her business went into its second big phase. She was living in Montreal with her kids, but commuting regularly to New York. She was willing to soldier through it because she couldn’t afford to move to the Big Apple. After six months, friends insisted on helping her. The move let her actually focus on her business instead of on juggling travel and family.

The Universe Rewards the Bold Move

We have to dig deep to find our passion, and to find our courage. Like Marla Wynne, we must in ourselves against all odds to make it real. “I no longer look back to see who I was,” she says, “but forward to what I am yet to become.”

This is an attitude that is helpful for all of us to adopt. It doesn’t matter what situation or business we are in.

Marla Wynne’s commitment to herself, and her adaptability to changing conditions are valuable lessons for women over 50. Today, her line, Marla Wynne ( is a global brand and a top HSN mainstay in the U.S.

We all need to pay attention and look for opportunities to be more entrepreneurial. This is especially true as we navigate the new, more uncertain pathways beyond midlife. The world is moving too fast for us to look backward.

What is Your Bold Move?

Whether you are employed, self-employed, or looking for work, what is a business idea you just can’t get out of your head? Indulge yourself and spend some time developing that idea. Write an executive summary. Dare to think that it could be successful.

Maybe it will light a spark for you. Maybe it will lead to another, even better idea. Maybe it will get you into a conversation with someone who will be impressed by your vision. That person could introduce you to yet another person. And that person could change your life.

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John Tarnoff is an executive and career transition coach, speaker, and author who supports mid and late-career professionals in defining, planning, and achieving more meaningful and sustainable careers.

Fired 39% during his 35 years as a film producer, studio executive and tech entrepreneur, he learned how to turn setbacks into successes in a volatile business. He reinvented his own career at 50, earning a master’s degree in counseling psychology to share his career lessons with others going through similar challenges.

Since leaving entertainment in 2010, John has coached individuals, groups, and led career workshops for university alumni, including for UCLA’s Anderson School of Management. Corporate coaching clients have included Bank of America, Bridgewater Assoc., Levi-Strauss, Softbank, TD Ameritrade, and Thrive Global.

He is the author of the best-selling Boomer Reinvention: How to Create your Dream Career Over 50 and has been named a Top Influencer in Aging by PBS/NextAvenue.


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