Cindy Eckert, 44
Thinking pink is a way of life for Cindy Whitehead. The spirited pharma-tech entrepreneur, known for her liberal use of the color pink and for the $1B sale of her female sexual health company, is laser-focused on helping female entrepreneurs flourish. In 2016, she founded The Pink Ceiling, an innovative incubator which looks to build female-lead brands into success stories. “For those who thought I couldn’t do it,” says Whitehead, “I’d say the same thing to them today that I said then….watch me.”
1. What made you choose this career path? What has been your greatest achievement?
Maybe entrepreneurship chose me? I most certainly didn’t fit in conventional corporate environments and was exasperated with the homogeneity and unwritten rules of how things get done. I recognized that ownership was my path to freedom; freedom to do things on my own terms, freedom to surround myself with other misfits who wanted to change how things get done and financial freedom.
"After building and selling two businesses, my greatest accomplishment is the ripple effect of ownership. I love watching the power that ownership has given to my employees to do their best work, to follow their passions and to pay it forward."
After building and selling two businesses, my greatest accomplishment is the ripple effect of ownership. I love watching the power that ownership has given to my employees to do their best work, to follow their passions and to pay it forward. That is the very basis of what I do today at The Pink Ceiling/Pinkubator--propel power through ownership. I’m going to help other female-focused businesses to have outcomes like mine and delight in watching each of their ripple effects.
2. What’s the biggest criticism/stereotype/judgement you’ve faced in your career?
I was told I was too Pink to be Boss. Now I have lipstick in that custom shade.
"I was told I was too Pink to be Boss. Now I have lipstick in that custom shade."
3. What was the hardest part of overcoming this negativity? Do you have an anecdote you can share?
If you were to introduce an audience to a pharmaceutical CEO who has built and sold two businesses, the last for $1B, do you think they’d ever expect me to walk onto stage? Never. Now picture that for every major career milestone of my life! Bottom line, I am unexpected; I am pink in a sea of gray and blue suits. The fact that I don’t fit ensures that I will be underestimated, and the fun is letting that reality fuel me. I learned a long time ago to not allow underestimation to fill me with self doubt, but rather to harness it for the element of surprise when I show up and kill with competence.
4. How did you #SWAAYthenarrative? What was the reaction by those who told you you “couldn’t” do it?
I went right toward it.
With stereotypes you have two choices; you can rail against them to prove they are incorrect or you can go directly toward them since it’s obviously the conversation we need to be having. I show up in blazing hot pink. Always. I like pink and no one is going to take that away from me. When people called my medication the “little pink pill” the only thing missing was the dismissive pat on the shoulder.
So, I went to FDA meetings in hot pink since it was the dismissiveness of women’s sexual health that needed discussing. Pink to me is about owning it as a woman - and all you uniquely have to offer. For those who thought I couldn’t do it, I’d say the same thing to them today that I said then….watch me.
5. What’s your number one piece of advice to women discouraged by preconceived notions and society’s limitations?
I feel strongly that society is full of “unwritten rules” that hold women back. If a ‘rule' exists for absolutely no good reason at all, break it. Let the injustice ignite you.
"There are no good men out there," yet another woman my age declared. At 50, I was freshly divorced after two decades of marriage and motherhood. My unhappy marriage had shattered my faith in men and romantic relationships. Based on my ex-husband's opinion of my sexual appeal, I was afraid my naked body would cause future lovers to run screaming from the room. Rather gleefully, I announced to my girlfriends that I was done with men, and sex, forever.
For the first year, I got tangled in my sheets alone every night, overjoyed to have the bed and my body to myself. I felt liberated by divorce—free to be me, skip showering, and make dinner for one. But it bothered me when women decried the scarcity of men, because I'd known so many good ones—college boyfriends, my brother, my best friend from business school, etc. The first of many naked truths gradually crept up on me: I was not going to find my juju again through self-help and yoga. The feminist in me didn't want to admit it, but going for too long without men was akin to starvation.
I didn't want another husband. But I needed men, a lot of them.
The universe signaled its approval by sending Mr. Blue Eyes to me at an airport. He was 29 and perhaps the sexiest man I'd ever kissed. Being with him convinced me, pretty decisively, that men were going to heal me, even though men had destroyed me many times before. I became the female incarnation of a divorced, clichéd older man: I bought a sports car, revamped my wardrobe, and took younger lovers. "I want five boyfriends," I told my best friend KC after that first tryst ended. "Sweet, cute, smart, nice. Enough that I won't get too attached to one." My message from the frontlines of divorce at 50 is that to restore your confidence as a woman, especially in the wake of a crushing breakup, try dating outside your comfort zone, expanding your dating pool to include partners you might never have considered before. It may not be the recipe for a lasting union, but in terms of rebuilding your self-esteem, it can work wonders.
The first thing I noticed—and liked—about dating younger men is that they didn't want to marry me or make babies with me. And I didn't want that either. Frankly, I didn't even want them to spend the night. Since I'd been 11, I'd been taught to seek out and value men who wanted commitment. To my surprise, I found it refreshing, even more authentic, to be valued not for my potential as a mate, but instead for my body, intelligence, life-experience and sexuality.
And the sex! I quickly realized that—warning, blanket stereotype coming—men under 40 are more straightforward and adventurous than older men, maybe since they were raised with the Internet. You hear so often about the scourge of crude, sexist online pornography; and I agree that the depersonalization of women as sexual playthings is deeply destructive to all genders. However, from sexting to foreplay, I found younger men uniquely enthusiastic about getting naked and enjoying sex. Every younger man found my most erotic zones faster than any man my age ever had, with a lack of hesitation men over 50 seemed unable to fathom.
Also, about my big fear of getting naked in front of a younger man? Completely unfounded. I started to shake when Airport Boy took off my sundress in our hotel room. Had he ever seen a woman my age nude? How could I stand to be skin-to-skin with a body far more perfect than mine? I had given birth to eight-pound, full-fucking-term babies. I'd nursed them, too, and at times by breasts looked (from my view at least) like wet paper towels. "You have a spectacular body," he told me instead, running his hand over the cellulite on my stomach that I despised. That night I learned that younger men who seek older women accept our physical flaws—they don't expect perfection in someone 20 years their senior. These men taught me to see my body through a positive, decidedly male lens, to focus on the pretty parts (and we all have them) rather than the flaws that we all have too, whether you're 19, 29 or 59.
I even found the pillow talk lighter, easier and more intellectually stimulating, because a younger man's world view differs so vastly from the pressures of my 20-something kids, annual colonoscopies, 401K balance and mortgage payments. They have simple financial problems, like "Can I borrow a few quarters for the parking meter outside?" or "Do you have any advice on consolidating my student loans?"
Everything feels simpler with younger men. Men under 40 seem less threatened by assertive women; they grew up with them. They like cheap beer instead of expensive wine. They don't snore (as much). Leftovers a 55-year-old would scoff at look good to them. Their erections NEVER last more than four hours. Their hard-ons end the old-fashioned way and 45 minutes later they are ready for more.
But what I enjoy most about younger men is not the sex, or the cliché that they make me feel young again—because they don't. Younger men make me feel old, and to my delight, I like that. I feel valuable around younger men, precisely because I am wiser and more experienced in life, love and between the sheets.
I know I'll never end up with one for good. The naked truth is we don't have enough in common to last. One recently put it exactly right when he told me, "I love this, but there's always gonna be a glass ceiling between us." That lack of permanence, the improbability of commitment and "forever," doesn't mean I can't pick up a tip or two about self-esteem, and enjoy the magic of human connection with younger men. And vice versa. The experience can enrich us both, making us better partners for people our own ages down the road.
*My viewpoint is from the perspective of a heterosexual woman, because I am one. But change the gender identification and/or sexual orientation to whatever works for you and let me know if the same advice holds true. Thank you.