Are We Creating a Lost Generation of Women in Our Workforce?

Throughout the past 16 years, I’ve seen many qualified women come through our doors who are simply passed over in the job market, judged on external factors rather than on their experience and capability. One of our clients, Sheba, came to us with an impressive resume and a long career working in non-profits and human resources. But in 2009 she was unexpectedly laid off from her job and has spent the last six years trying to navigate her way back into the workforce. Employed steadily since she was 17, Sheba’s now in her 50s and reaching her prime earning stages but subsequently receiving little interest from employers. Unfortunately, her story is not unique. Many women in their late 40s and early 50s are being pushed out of the workforce during what should be the height of their careers.

Since the recession in 2009 there are about one million fewer women ages 45-54 in the workforce. But these women are not leaving by choice. In fact, a recent study by Pew Research shows that middle-aged to older women value a high paying career as much as men while younger women value a career more than men.

Yet despite ambition women are still seemingly “retiring” earlier than men. According to the American Time Use Survey, only 55% of women ages 55-64 are still employed, compared to 64% of men the same age. And it’s not just women’s career aspirations that have changed; we also have the credentials to back it up, attending more schooling than men overall.  Women are still falling through cracks in the system every day, part of a lost generation who are too young to retire but seemingly too old to be marketable in the workforce.

Unfortunately, Sheba and many other hardworking women her age have little control over the structural and cultural factors that have left them out of work for years. Though some see it as antiquated, ageism is a real factor for many women I see, especially those who fall into the “middle-age” bracket and find themselves subject to stereotypes. In fact, at Dress for Success our largest demographic falls within this range.  Middle-aged women are being passed over in the job market, perceived as out of touch and even less productive than younger applicants. Rather than face years of struggle with unemployment or settle for below-living wages, many of them look to retirement so they can at least reap the benefits of their 401(k) or other security funding.

However, this path should not be their only option, and it’s not even a viable option for many, since women are generally still paid less than men.  We earn less over our lifetimes and are subsequently left with smaller pensions and assets. And with longer life expectancies than men, we are forced to live on less for longer, making us twice as likely to live below the poverty line after retirement.

But stereotypes are not the only hurdles these women encounter. As our health care improves, we are all living longer, but this shift has also positioned many women to sacrifice their prime earning years to serve as caregivers to sick and elderly parents. Others are stretched even thinner, caring for their own children, who are now living at home longer, as well as an elderly parent.  And with more and more women as single breadwinners, I’ve seen many struggle to take on the extra burden of finding an income large enough to support more than one household.

Despite the shifting attitudes and career progress for women, society still lacks the structure to support senior women in the workforce. Until we can create a system that will incentivize women to care for both their families and careers, we need to offer more services to give older women opportunities to utilize their experiences and skillsets in the workforce.

Shortly before she was laid off, Sheba was looking to move up in her career and came to Dress for Success to join our programs and improve her interviewing skills. She wasn’t receiving any feedback from employers, and, like many women we work with, she found it difficult to market herself. When she suddenly lost her job, Sheba’s lack of confidence was further complicated by gaps in her resume. After joining our Going Places Network by Walmart, Sheba participated in mock interviews and career counseling and learned to understand her resume as part of her own narrative.

As we age, we experience a change in perspective that causes some of us to readjust our career paths to find new means of fulfilment. Speaking with our career experts, Sheba decided to explore other options and go back to school. Attending college part-time, allowed her to still care for her elderly father. Now with a better idea of how to tell her story, Sheba is able to speak to her job experience as a part of “her brand” and is comfortable communicating her skillset to employers, even landing a work-study job while in school.

A recent graduate, she holds a degree in business administration and is currently enrolled in a certificate program for non-profit management. Like many of the women who come through our doors, Sheba lacked options but not ambition. With more services available to middle-age and mature generations, these women could regain the confidence and skillsets needed to overcome structural and cultural barriers that have left them prematurely displaced. Society as a whole would benefit from a new generation of untapped experience, bringing flexibility and productivity to the workforce.

The Success Diaries: Claire Mazur & Erica Cerulo

Dear Claire and Erica circa 2002,

You guys just met, at the dining hall! And, as much as you want to roll your eyes at the guy who introduced you—who thinks you’ll have so much in common because you’ve both dated college basketball players—acknowledge that he might be onto something. Definitely roll your eyes first, though, and then get down to it.

Eight years from now in 2010—when you’ll be an unfathomably old 26 and 27—you’ll start a business together. Can you even believe it? First, try to wrap your heads around the fact that you won’t be in college staying up all night, er, working on the chattiest floor of the library. Then picture yourselves in New York instead of Chicago with 1) less bronzer on your faces and 2) resumes that boast real, paying jobs. Then imagine you come up with an idea one cold day in January that you gets you so excited that you rally emails full of “what ifs” and “how ‘bouts” back and forth all night and decide that you have to meet for coffee the next day to workshop it some more.

What do you two know about starting this business you’ve dreamt up? Next to nothing. Neither of you has worked in fashion in a real way, you’ve only constructed a website via Tumblr, and you definitely don’t know the difference between an LLC and a corporation. But here’s the thing: That won’t hold you back. Below, the things to keep in mind, especially when banging your head against the wall or feeling the symptoms of imposter syndrome coming on.

1)   You’re going to have to get comfortable with risk.

The anxious, unsteady feeling that swirls around in your stomach when you’re not confident that something is a sure-thing—start embracing it. Don’t let it keep you up at night. Because, hey, guess what? Nothing is a sure-thing. The safe job you take could get downsized. The gig you think is your absolute dream could be totally obsolete in a decade. So set your sights, and get after it.

2)   Ask for advice—tons! and ignore a whole lot of it.

When you’ve never done something before, it seems like everyone who has even a teaspoon of experience must know better. Pick those people’s brains. Hear them out. Take it all in. But then use only what speaks to you, and don’t feel the tiniest bit of reluctance about choosing your own way. You might not know everything—or anything, really—but you know what feels right to you.

3)   Accept that some things will be so much harder than expected and that some things will be so much easier.

Today could be terrible, and tomorrow could bring an amazing surprise. This year could be mind-blowingly awesome, and next kind of the dumps. Don’t dwell on the bad or the good. Roll with it.

4)   Take care of yourselves.

And know what that means for YOU. Maybe it’s carving out time to work out every morning so you don’t lose your damn mind. Maybe it’s having a standing weekly date with your husband. Maybe it’s knitting or cooking or watching Nashville even though it’s gotten so bad. Just make it a priority, and don’t let it get stamped off your calendar by all of the emails and meetings and to-dos.

You’re gonna be great. We mean it.


Claire and Erica in 2015


Claire and Erica met at University of Chicago in 2002 when a mutual frenemy introduced them, suggesting they should be friends because they both, at some point during their college careers, dated (Division III) basketball players. They quickly realized they had other things in common, an appreciation of fashion and a Tracy Flick-like approach to their extracurriculars among them. Both girls moved to New York post-graduation, and often found themselves talking about peers who had started businesses and their mutual admiration for those who had taken the plunge. When they conceptualized Of a Kind—over the course of 25 frantic emails in 12 hours—they knew they had to pursue it. Of a Kind aims to support and promote on-the-rise fashion and home designers by giving you access to their unique products and personal stories. For more about Of a Kind, visit or follow them on Twitter, Instagram or Facebook.

Ted Gibson’s Guide to Job-Landing Locks!

Guest post by celebrity hair stylist, Ted Gibson

We all know that you need to “Dress for Success” for your interview to land the perfect job. Your appearance is super important, however, many women forget about one of the most important aspects of your look: HAIR!! One of my mantras is “Hair Changes Everything.” It really does! How your hair is styled for your interview can affect the interviewer’s perception of you. Here are my favorite hairstyles sure to make an excellent impression on any future boss!

Sleek Bun

Whether parted to the side, in the middle or with no part at all this classic style is perfect for your next job interview. It’s neat, clean and screams sophistication!

The Bob

First impressions are super important. You want your potential new boss to take you seriously and know that you are capable of taking on the job you are interviewing for. The bob is so versatile and there is a version for everyone! Whether cut just below the chin or a “lob” (long bob) grazing the shoulders, a bob says “I’m stylish, I care about my appearance and I mean business!”

Fresh Blowout

There’s nothing like a fresh blow-out! It’s such a clean and refreshing look – you absolutely cannot go wrong! I think it’s a great idea to get a fresh blowout before any job interview. Whether your hair is short or long, super curly or straight, a blowout can do wonders for your look! Here’s how to do a Gibson girl blowout at home!

  1.  First, you will need a good blow drying hair spray. You want to look  for sprays that say they will  add volume and shine and have a heat and UV protection. Spray this throughout your hair while wet.
  2. Next, the secret to the perfect blowout is to start with your fingers. Pull your fingers through your hair starting at the roots and shoot the heat at the roots while holding the hair taut. Get your hair about 75% drying using this method. Then, part your hair in your desired part.
  3. One of the biggest mistakes women make with their at-home blow dries is that their sections are too large, resulting in flat hair. When blow drying, you want to take 1 – 1 ½ inch sections.
  4. In the salon, most stylists blow dry hair using a  boar bristle and nylon round brush, however this requires practice and skill. If you are not comfortable using round brush, use a boar bristle and nylon paddle brush. The boar bristle in the brush gives hair great body and shine.  You never want to use a metal brush when blow drying your hair  – the metal heats up too fast and can burn and break your hair off. Take one section of hair, hold your dryer by the handle about 3 inches away from your head and blow dry while brushing with the paddle brush.
  5. Once your section is dry, curl the hair up in a Velcro roller. Do this to your entire head. Once you’re finished and the hair is cool, take out the rollers and lightly rake through your hair with your fingers. Turn your head upside down, shake it out a bit, and spray with a light, flexible holding spray. Flip your head up and you’ll find you’ve given yourself a salon quality blowout at home!

Ted Gibson is one of the most sought-after editorial, runway, and celebrity hair stylists in the business.  His work has appeared in publications such as VogueHarper’s BazaarElleMarie ClaireVanity FairPeople StyleWatchW, and Allure and backstage at runway shows such as Chanel, Prada, Dolce & Gabbana.  He is also a huge influence and presence at both Fall and Spring New York Fashion Week styling some of the top American fashion designer labels including Pamella Roland, Carmen Marc Valvo and Lela Rose.  Ted is perhaps most known for toiling over the tresses of top celebrities including Anne Hathaway, Jessica Chastain, Debra Messing, Angelina Jolie, Ashley Greene, Lupita Nyong’o, Gabrielle Union and many more.

Soledad O’Brien: Navigating the Not-So-Linear Career Path

At one point in her career a typical day would start at 3 A.M. and wrap up around 3 P.M. And that was just the work day. Then it was home to her four kids, who were all under four years-old at the time that she was also hosting her own morning show. Award-winning journalist and self-proclaimed optimist, Soledad O’Brien has always been short on time, but never on passion.

Known for telling the stories that are often left out of mainstream media, she has navigated one of the most rapidly changing industries and still came out on top.  Most recently, she started her own production company, Starfish Media Group, all while still balancing freelance journalism and running a foundation to aid young women, as well as being a wife and a mother to her four children.

But if you ask about her biggest challenge so far, she’ll tell you it’s not unique: “I think it’s hard being a working mother. “

After 12 hour days, “I still left work with a million things to do. I think it’s a typical story for a lot of people. How do you manage to do the things you want to get done, the important things, and they’re all important things? It’s really hard,” says Soledad.

Although she’s a pro, it’s not her multitasking, but genuine character that makes her so relatable and successful across the board.  Soledad has made a career out of giving a voice to those who aren’t often afforded the chance to use their own. In doing this, she has found her voice, which she owns with fortitude and merit, effortlessly gaining public respect.

As her formal name suggests, Maria de la Soledad Teresa O’Brien has quite a mixed heritage. Her father was Irish and Scottish, but hailed from Australia, and her mother is Cuban with a blend of both black and Latina roots. Growing up in a predominately white neighborhood in St. James, New York, Soledad did not fit the cookie cutter mold of the Northeast. But with a supportive family behind her and a relentless drive, she learned not just to embrace her differences but capitalize on them.

“When I was 13 years-old, I felt like an outsider, but as I got older, and as a journalist, it was a great thing because being an outsider as you try to figure out other people’s experiences is a plus,” she explains.

Even after marrying her husband, Brad Raymond, Soledad kept her full name, seeing it as a moniker for her veritable personality.  She began her career as a journalist with a goal to fill in the gaps of mainstream media and report on the issues and people who are too often left out of the conversation. In doing this, she learned her unique culture and appearance could be a tool for understanding, helping her to transcend the emotional walls that block the truth and allow her to relate to a diverse population.

Although she now views her background as a platform to create change with her stories, Soledad knows not everyone is afforded the same luxuries of support and guidance growing up as a minority. Which is why in 2006 she started the Starfish Foundation to help young girls in need afford an education and reach their highest potential.

True to her character, whether speaking at women’s conferences or one-on-one with the girls at her foundation, Soledad is always real, often shrugging off her impressive resume and explaining it as a highlight reel.

“There’s a lot of bad and challenging things that have happened, and yeah I’d love to forget some of that stuff, but it really helps people to realize that it is not magic. I had a lot of great opportunities, some things I completely fumbled and here’s what I learned from it—I think that kind of honesty is really critical,” she explains.

While for NBC News as a producer, Soledad learned this early in her career.  On her day off, she was cleaning her office when a story broke, and she was forced to jump on a plane to cover a press conference in jeans and cowboy boots. Laughing as she defends that it was really good outfit for cleaning, she admits, not so much for a young professional producing a news story.

Despite the cowboy boots incident of ’91, Soledad has set herself up and achieved success, graduating from Harvard University and working her way up from a local news station in Boston to become one of the most respected correspondents for several prestigious, national media outlets. But even after taking all the right steps to land her dream job, the real challenge has lied in navigating her career as the industry rapidly changes.  Throughout the years, Soledad has been able to remain so effective as a journalist by maintaining a macro view on her career, allowing her to look at every job as an opportunity to grow her skillset.

“When you think of your career that way, all the little things that can be frustrating become small because you have bigger mission and goal; it’s not necessarily about the job you’re doing right now.”

When Soledad made a bold jump from the widely popular NBC News to a less glamorous role on cable television for CNN, she had a lot of people questioning her decision. Today, she will tell you that move allowed her more flexibility and the opportunity for growth that led her to become the founder and CEO of her own company and, more importantly, maintain her original goal to really create change with her stories.

Crediting her mom’s age old advice that “most people are idiots” in their opinions of what you’re doing, Soledad has been able to navigate her ever-changing career by staying true to herself.  Much like the stories she breaks, there are no bows that neatly tie up her career and label it a success, it’s constantly evolving with no clear edges or lines to divide a story that she knows will never be read as black and white.

Although Soledad’s authentic sense of self and honesty is half the reason she has made it so far in her career, she faces her fair share of judgment as a minority woman in the media. And as a television reporter, she’s well aware of the power of appearance and the influence it can have, especially on a media career.

“I think everybody is judged in the first minute if meeting somebody, so my theory is don’t give people ammunition to judge you poorly,” she says.