“Is it true that my life is a mess because I gained ten pounds?
Was my life better before I gained the weight or were my thighs just thinner?”
—Geneen Roth, This Messy Magnificent Life
📆 December 1, 2016
“What do you do for arms?”
People ask all kinds of career questions when they reach the front of a book signing line after a keynote, but this one was new. I blushed. Yoga and pilates, mostly. We were in the era of Michelle-Obama biceps.
The first thing you should know: If I gave a talk today, no one would ask me this.
The second: I live in stretchy clothes; a style aesthetic that my husband and I dubbed ComfCore, bordering sometimes on FrumpCore when I want to avoid attention walking through the city. I only depart from cozy fabrics when absolutely necessary.
On this day in December 2016, I was in a conference room just off Times Square, speaking in front of five hundred people. I delivered a Pivot breakout session for women in leadership at The Channel Company’s annual conference.
My second book launched three months prior, and I met Michael three months before that. I was still operating as my Single Solo Self, the one with all the time in the world, but with all of it tightly wound.
I wore black wide-legged linen pants that my much more fashionable friend helped me pick out from Reiss, a London-based boutique with a flagship on West Broadway. I tucked a black J-Crew t-shirt with dotted lace sleeves—a hand-me-down from another dear friend—into the just-barely-zippable high waist of the pants. I probably wore sky-high stilettos, as I would have from the stage in those days.
When I dug those pants out of my closet the other day, out of sheer (literal navel-gazing) curiosity—yes, for the sake of this post—I was appalled to discover that only one thigh could fit into the waist opening, with only a few inches of space remaining within their now-unimaginably tiny circumference.
How the hell did I ever get two legs in there?!
What I wanted at that time: a thriving business, and a body under tight control. Mostly single for the last ten years, I was convinced that gaining even ten pounds would render me unlovable.
What I needed: a little breathing room.
📆 January 30, 2020
I’m in Washington, D.C. interviewing a panel of leaders to kick-off the International Monetary Fund’s Shape Your Future career day.1 I had no idea it would be my last paid, in-person gig for more than two years. If I did, would I have savored it more?
My hair is in a bun near the top of my head, and I’m wearing another Reiss staple: an elegant pink silk top with graphic white and black lines dashing about abstractly, making me feel (and appear) fancier than I am. It buttoned high at the nape of the neck, with petal-shaped short sleeves.
Over it, I’m wearing a stretchy black blazer with the sleeves rolled up to my elbows, and black AG skinny jeans—my speaking staple at that time.
For shoes, I wore three-inch high chunky heels—a pair of buttery soft leather Baldinini boots that haven’t been taken out of the box since.2
Two weeks later, I attended Oprah’s 2020 Vision: Your Life in Focus Tour at the Barclays Center in Brooklyn. Michelle Obama was the headliner, in bestie belly-laughter conversation with Oprah about Becoming; about their before-and-afters.
The event was sponsored “presented” by Weight Watchers,3 who had just reduced their company moniker to a leaner “WW.” It was a thinly veiled attempt to fit in again with modern discourse, shifting the conversation from weight to inner and outer wellness—but who did they think they were fooling?
I look at us now as if from a SkyCam zooming across the seats: how hopeful we all were about our goals for this glimmering new year, scribbling into our WW-issued journals with a translucent white Oprah-branded click-top ballpoint pen under those bright stadium lights.4
May the record also state: Oprah is a major shareholder in WW International, holding ten percent of the company at one point. To the surprise of no one, WW has now pivoted back to WeightWatchers and thinness by investing in a subscription service for the newfangled rapid weight-loss drugs: “Ozempic-as-a-platform,” per one Reuters headline. Oprah recently set the internet ablaze by praising them publicly, giving credit for her newest “after.”5
What I wanted at that time: a thriving business, and a better handle on juggling the needs of our newly forming household.
What I needed: even more breathing room.
September 22, 2022
Two and a half years later, in a note-to-self that I titled “Closet Shock,” I attended a luncheon for a wedding that I would be officiating in Mexico soon for two of my dearest friends. Choosing what to wear fomented a full-blown crisis: