This Her View piece is the first of a series of personal essays from guest editors on a wide range of topics. I am including these on TFI, because I feel as women, if we can’t engage in open and honest conversations, we can’t move forward. I have known Cindy Weber Cleary for years—she was a fashion director at InStyle for over 15. Recently she launched a fashion site called Apprécier that quietly targeted older women, a weirdly overlooked demographic considering we (because I am now one) spend the most $$$. (Luxury advertisers should be swooning over us, not ignoring us, but I digress.) Cindy reached out to me after I wrote about Owning Your Age. I didn’t realize that her site had shuttered and was frankly shocked and saddened. While failure is part of being an entrepreneur, it still smarts and can leave you wondering what’s next. Cindy didn’t choose a career reboot, but she now finds herself at the crossroads. Here, her thoughts on what that means.
I always took it as a complement when friends and colleagues described me as Type A. High energy? Check. Ambitious? Check. Detail-oriented? Check. In fact, writing checklists seems to be part of my DNA. My mother’s to-do lists are the stuff of legend.
My goal-oriented, deadline-driven personality served me well in the three decades I spent as a fashion magazine editor. I loved the ever-changing cycle of fashion, the challenge of coming up with a new way to spin a story I’d told 30 times before, the camaraderie of a team, the travel, the parties, the hoopla. I prided myself on helping to produce a very large, successful magazine, InStyle, on time and on budget, month after month. Looking back, I see that this high-wire act gave me a literal “high.”
My obsessive traits didn’t always translate well to my personal life. My husband likes to tell the story of the first time we held a garage sale. Our kids, a boy and a girl (check) had outgrown all of their baby gear. I purged the attic of beat-up suitcases, ancient sports equipment, and unloved wedding presents. The night before, I set the alarm for 6:00, but found myself wide awake at 2:30 a.m., worrying about how much to price the high chair and about whether to sell our old record albums individually or as a lot. I turned on the lights and started writing a list of everything. My husband began to stir. “What the hell are you doing?” he muttered, half-asleep. When I told him I was taking inventory of our junk, he looked at me as if I had lost my mind.
When the print-magazine world started to wobble on its axis a few years back due to the digital revolution, I began writing a pro/con list of other career options. The one that made the most sense to me was to embrace the shift in consumer behavior: I decided to launch an online blog, content and shopping site. Shortly thereafter, I was downsized from full-time to part-time, at my magazine job. In a weird way, the timing seemed perfect. I had already found a business partner for my project and I knew how to connect with a specific audience and motivate them to shop. How hard could this be?
Pretty darn hard. I didn’t realize how few start-ups founded by women actually get funded. A recent article on Bloomberg.com stated that just 7% of the 2,005 founders on their list are women. I spent two years working 24/7 on my project with no pay, only to have the business run out of money in January. We had grown a small deeply-engaged following, but, these days, if you can’t deliver a million unique views per month, it’s unlikely that you will even get a chance to pitch your concept to investors… I have no regrets. I had a blast producing the content, honed my digital skills, and met some fabulous women along the way. Their support meant the world to me—and who knows where it may lead?
My husband and I have decided it’s time to sell our spacious suburban house. The property taxes are nuts. Our kids are (semi-) launched. It’s a seller’s market. Over the last few months, we have arranged weekly donations of furniture, clothing, and housewares to the Vietnam vets and it felt great to get rid of stuff. Today, the movers came to put some of our most treasured possessions in storage— and I didn’t even make a list. We don’t know where we are going, because I don’t currently have a job. Oh, and I’m turning 60 in May… Once, I would have panicked. My younger self would have had an army of realtors and headhunters on speed-dial. Now, I feel more curious than anxious, even slightly excited.
I am in constant contact with three friends I met in the early 80s when we were all fashion assistants at Vogue. We liked to describe the experience as the “camaraderie of the trenches”. We worked long hours for little pay, endured verbal abuse for such serious transgressions—as not having all the hangers on a clothing rack facing in the same direction, or for describing a fabric as “organza” when it was actually “mousseline.” Nevertheless, we loved every minute of serving those eccentric, iconic editors. We got an amazing education and got to laugh our asses off over cocktails many evenings at Un, Deux, Trois, the bistro around the corner from the office. The four of us have recently started a “fantasy file” of places we might move together in a few years. Maybe we’ll buy an old campground in the Catskills and build “tiny houses”? Maybe we’ll find a sun-filled stucco compound in Portugal? Maybe a group of palapas with a central kitchen/living area in Mexico? Who knows?
One thing’s for sure, none of us wants to retire to a golf community in Florida and live in individual “units” with our husbands. As much as we adore them, we know that female friendships are almost equally important. None of our kids are married or nearly “settled,” so we can’t build our future around them. Hell! We can’t even convince them to take our lovely furniture and belongings. They’re nomads who don’t care about material possessions the way we did at a similar age. This about-face has the luxury and retail businesses in a tizzy. Truth be told, even I no longer care about this season’s “it bag,” although I still love to look at beautiful things.
So, for the first time I can remember, I’m going to see where life takes me, instead of trying to wrestle it to the ground. I’d like to keep working, but I no longer need the adrenaline-fueled pace and I definitely don’t miss the daily commute. I have learned to enjoy working on a variety of projects. Simultaneously, I have discovered how much I love to write. What I value most now is time. Time with my family and friends. Time to be outdoors as much as possible. Time to read and write.
After a lifetime of “checks,” I’m looking for balance… and serendipity! Who knows what tomorrow may bring?
Think you have a topic for Her View? Send me an email jennifer@theflairindex.com. I’d love to hear from you.
Wonderful article Cindy, enjoy your adventure!
Thank you, dear friend!
Bravo for letting your checklist self go. It took a three year illness to force me to do that. After my break, I’m not trying to forge a second act as a “novel” writer of true stories. Guess we’ll both see how it goes!
Thank you for sharing! Be brace! And let’s support each other
I love Cindy! So happy to read her story, to know she’s enjoying not having a list, a deadline, or a long commute. it sounds fantastic. She is one of the chicest women to have ever worked in fashion, and generous and kind too!
Robbie, thank you so much for your kind words. They mean so much to me! And the feeling is mutual!
xxC
Fantastically said by my best friend!!! She has shown courage and grace in her new journey. J’adore!!
Looking forward to our next chapter of communal living!!
Voguettes and women creating the lives we want to live!!
P.S. I want to raise sheep and farm the land!!
Exciting things to come!!
Well, you know how much I love you! There is nothing more to say
Thank you, dearest friend! Just catching up on these comments! Would love to see you or, at least be in touch! xxC
Oh my god I love this piece! My Type A DNA still has me beholden to my to-do list but I love this glimmer of my more carefree future self. Best of luck to Cindy. Keep these features coming!
Thank you, Katie! It’s not all pretty and perfect, but doing my best to find an authentic life!
Cindy your talent for crystallizing the winds of change – whether in fashion or in life- is appreciated by many. I’m right behind you in this journey. Thanks for shining light on the path.
So touched, Dee! I never imagined so much turmoil at this stage, but I am finding so many wonderful surprises every day! I will never forget our fun time at The Point! Magic!
xxC
Dee! Please forgive me for not responding to this. Life got in the way! But I will always treasure meeting you at The Point! What a memorable experience! Let’s stay in touch as we all try to figure out how to live the way we want to!
xxC
Beautiful and timely article. One thing I know about strong, independent, and confident women… we land on our feet!
Dearest Deb,
Please forgive me for not responding earlier. Life got in the way! But I’m feeling really good, as we move forward. Let’s make a plan to see each other soon!
xxC
I, and so many, are going through this right now, Cindy! It’s so profound and so liberating. The only fear I have is that I am experiencing *no fear*. How can that be?! Shouldn’t I be losing it? Instead I’m off to Portugal (for reals). I’ll let you know of an ace compounds we come across. x
So much to relate to in this forthcoming “share”. Thank you!
Keep riding the waves. Being knocked under comes as a shock but get your head back above the surf ready for the next thrilling ride.
xx
Casey (once a Jersey girl, ever a Jersey girl…)
Cindy’s writing is a special gift. Her authenticity, candor, intelligence and insight are always enlightening and inspiring, especially for women! We need to hear more from you Cindy!
Spot on, Cindy. I am going through precisely the same thing — downsized out of a print job that I loved after 30 years (with two kids in college and a mortgage, and also soon approaching that milestone birthday). Strong women survive. Thanks for relating that it’s not the end of the world, and the difference might be in embracing the journey as an adventure, rather than a defeat.
Here’s to sunny compounds ahead!
Dianne
As I read this I suddenly realized how few retirement parties Ive gone to to celebrate people who’ve retired on their own terms. It doesnt happen like that anymore. Among boomers, the new normal seems to find us broadsided and suddenly at 53, 57, 60 that alternative list of careers? It’s a lot more limited than one thought.
It takes some considerable time to work it through from ego, emotional and financial perspectives, but once sorted, relish this time. I have found comfort that the daydreams I had of the life I was working toward,–while sitting through relentless board room presentations that seemed to go from sunrise to sunset–is now very much here and ressembles fairly well what I had envisioned…just accelerated.
We need to recognize at an earlier age that things very likely WON’T go according to plan. So having a clear Plan B that can comfortably become Plan A is vital. It’s an important message to pass on to younger women who cant fathom a day when they might themselves the most oldest woman on staff at 51 and feeling a might but vulnerable in a changing world.
Though should I imagine colleagues this afternoon still wrapped up in the frenetic pace of it all or sitting in a boardroom, I’m not a wit nostalgic. Been there. Would prefer to pour myself another green tea….and look out over Paris.
Best of luck to you, Ms Cleary whose career I’ve watched. You can now turn all of your glorious talent on yourself.
Cindy, so well said, simultaneously insightful and inspiring. You’ve shined a light on how liberating it can feel to be a certain age, a light that’s a beacon for all of us who look forward to a life that must change to become a life that gets better. Be inspired by those classic words from Mary Oliver: “Tell me, what do you plan to do with your one wild & precious life?”. We were born to be wild, so let’s live these days with the new found freedom from what we’ve left behind.