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 firstname.lastname@example.org. I’d love to hear from you.