A total do-over in mid-life, wipe the board clean and start again, not because that sounds like a great idea, but because that is what life called for at that time. Suddenly you find yourself counting the change in your pocket realizing that is all you have to eat on that day. We all are living in a time of tremendous upheaval, and also tremendous hope. Isabel knows a few things about both of these. What do you do when some of the pillars of stability in your life collapse upon each other? There are a few choices. The better ones involve taking stock and moving forward, never losing hope, and believing in her experience and capacity.
You had a bit of a life shock back in 2008 when you essentially started over. What happened?
In 2008, my then-husband and I and our two daughters were living in Southampton, New York in a wonderful 1920s farmhouse 4 blocks from the beach. We had just finished renovating it and were carrying a massive amount of mortgage and renovation debt, which we were chipping away at. And life was golden, all shiny, and relatively carefree like it was going to go on forever. Then I got a call from my then-husband, this would be around May 2008. His boss had told him that layoffs were imminent and to “Hope for the best, but prepare for the worst.” I remember being out in the garden, where everything was just starting to flower, having a look around, and realizing in a moment of searing clarity that this was all going to disappear. All of it. And it did.
“I remember being out in the garden and realizing in a moment of searing clarity that this was all going to disappear. All of it. And it did.”
We put the house on the market the same day Lehman Brothers crumbled and stayed ahead of the mortgage (just) until it finally sold in October 2009. I had gotten a freelance writing job at Vogue and was sleeping on a futon in a friend’s living room during the week, heading home to the family on the weekends. There was literally no money. I was eating $3 falafel for dinner and one day, had only the change in the bottom of my purse and found myself standing in front of the vending machine in the Condé Nast building calculating which was the most nutritionally dense thing I could get to keep me going till I got paid on Friday. So that was a laugh riot. We moved back into the city in December 2009, and I got a great job writing for Bergdorf Goodman, then got recruited to do brand messaging for La Mer, then moved on to spend nearly 7 years at Tiffany in charge of language for the entire company. Which is such a watered-down version of the emotional and financial extremes of those years, but there you have it.
“Mourning what was no longer just wasn’t an option”
How did you feel about being 44 and starting again?
It’s funny, because as scary, frustrating and frequently shitty as it was, I never lost my sense of self, or suffered any loss of hope. I never felt something that was due to me had been taken away. It was just like “Okay, here we are. No sense in resisting it. What can I do today to make things better, have a laugh, create some sense of continuity for my kids?” Mourning what was no longer just wasn’t an option. I was raised by two World War II refugees who literally lost everything, and I’m convinced there’s a hard steel thread of resilience woven into my DNA.
New husband too? Who is that handsome fellow?
Well, the stress of those years after the recession did take a serious toll on my marriage. We simply dealt with the calamity in very different ways, and my marriage ended in 2013. I met Rob Simonson, Mr. Platinum Fox, in 2015 on Facebook, of all places. Rob is a delightful human being, completely ridiculous, very tender-hearted, super helpful, very thoughtful and honest to the core. The fact that he was a big model in the ’80s and ’90s is really just icing, cause all the pretty in the world wouldn’t mean a thing if he weren’t also a stellar mensch.
“Courage is about focusing really hard on the two or three things right in front of you that you can actually affect, and then doing them. And they may be TINY. But you do them.”
Do you feel hope is connected to courage? What is the role of hope in your life?
So, in my mind, hope is sort of a passive concept, you know? Hope is like you sit in a chair, close your eyes, cross your fingers and “hope” that things are gonna work out. Courage is something altogether different. Courage, for me, is about not letting the 857 other shitty and uncontrollable things overwhelm you and dominate your thinking. Courage is about focusing really hard on the two or three things right in front of you that you can actually affect, and then doing them. And they may be TINY. But you do them. Like one day in about 2010 there still just wasn’t enough money coming in, and I took the change jar by the front door to the Coinstar machine at the supermarket. And then I had like $23.57 in my pocket and I felt GOOD! So hope isn’t really a thing in my life, except in the sense that I always have it. Momentum is. Keeping moving. Not giving in. Finding pleasure in even the smallest victories. And keeping humble. Humility and kindness have been huge touchstone concepts during this journey. And despite everything, I will always consider myself a hugely fortunate person.
Brooklyn to Oakland and a Pandemic
You recently left Brooklyn for Oakland. What was that like?
I had been at Tiffany nearly 7 years and both of my kids were off to college, so when the opportunity to move to California for a new job came up, I decided I was down for the adventure. I was going back and forth between Brooklyn and San Francisco from November 2019 until February 2020, and then moved full-time to Oakland right before the pandemic really got cranking. And it was glorious. I rented a house with a big fig tree in the backyard, I had a car and a washer/dryer like a BIG GIRL for the first time in years. And then I lost my shiny new job in June. Wheeeee! So here we are, starting the next cycle of small victories. But you know what? Best thing ever. I never would have had the guts to quit corporate if it hadn’t been forced on me, but wow did it feel good to get off the meeting/managing/politics hamster wheel for a minute and sit with myself. I’ve been freelancing and kinda job searching, but also taking a moment to think about what I might really want to do now. Maybe landscape design? Interior design? Dunno yet!
Did your daughter come with you?
My older daughter was in her last year at Savannah College of Art and Design, and my younger one had just started studying graphic design at Chapman University in Southern California. Her school shut down and I had to scoop her up and bring her back to Oakland, where, instead of making all the gloriously questionable choices you do when you finally get to college, she was doing Zoom school. With me in the next room. If anyone got robbed this year, it was her!
“I have a garden now for the first time in 11 years and it’s as exciting as a trip to Paris!”
You seem to have a passion for flowers. Any favorites?
How much time do you have? I have a garden now for the first time in 11 years and it’s as exciting as a trip to Paris! Just taking coffee outside every morning to see what’s changed, what’s unfurling, what’s blooming, is magic to me. I have so many favorites but a few are variegated solomon seal, bleeding heart (white, not pink!) and ostrich ferns. But I could go on and on. I’m also weirdly good with orchids. At Tiffany, my friends called me the “orchid whisperer” because I could bring even the raggediest, most abused orchid back to bloom. It’s really not that hard but shhhhhh. And there’s all this crazy SHIT just casually growing by the side of the road here in California, like really weird space flowers. I saw an Agave the other day while walking the dog that was the size of a house. I kid you not.
Being “Responsibly Immature”
Tell us about being responsibly immature. What does that look like?
“Responsibly immature” is actually a phrase coined by Rob, which I love. Basically, it means you do all the (yawn) adult stuff, like pay your bills on time, go to all your check ups, floss your teeth (sporadically), etc. But you still have a healthy appreciation for the absurd, for doing dumb stuff and laughing at stupid things and just finding the humor in life, even if it’s sometimes DARK. David Sedaris said this wonderful thing in his Masterclass on writing, something like even if something really bad happens, you know one day you’ll be able to laugh at it, and then you can write about it. God knows this year has provided plenty of material.
Giving Brands Their “Voice”
What sort of work do you do? I see some fancy names on that resume of yours.
Yeah, that’s just a cavalcade of fancy on the old CV, right? And I suppose it was, but sometimes you’re too young (or just too dumb) to appreciate the incredible experiences you’re having. In the simplest terms, I’m a writer. And what I have been doing is taking strategic, kinda bloodless brand thinking, and translating it into language that human beings actually respond to emotionally and intellectually. Mainly, I’ve been doing that in a marketing capacity, giving brands their “voice.” But I really love speechwriting, sitting with a smart, thoughtful person, and helping them polish their thoughts and ideas into a powerful narrative that’s articulate and moving. I wrote speeches and book forewords for Calvin Klein and a number of other notable people over the years and it was so satisfying. Kinda like being a midwife, but not as messy. Maybe the next chapter is “overpaid speechwriter?” Who knows. Although, I’d love that. As a freelancer, I’ve been working on a re-branding project for a jewelry company, writing copy for a start-up makeup brand being created with a major musician (NDA on that, so no details. Sorry.), working on naming and writing positioning for a new baby and children’s brand and creating marketing messaging for a non-profit that supports sexual assault victims. So, all really diverse and really exciting.
Any plans on writing a book?
For sure, if I weren’t so LAZY!! What is it with writing that no matter how good you are at it, you just put it off for as long as you humanly can? Or is that just me? I’ve been kicking around an idea for a decade now about resilience. Possible title “A Legacy of Loss.” Sounds like fun, right? Maybe that’s why I haven’t gotten down to it. I mentioned my parents were both WWII refugees and their stories are insane. There’s actually a little synopsis of my dad’s history somewhere on my Instagram feed. I know that fortitude and putting your ego aside and striving for rebalancing life when it’s off kilter is a learned skill. I’ve seen it in myself over these past few years. But I haven’t yet figured out how to make the book darkly funny and not preachy and self-helpish, so hence the delay. And then there’s the series of essays on the ironies of growing older a la Nora Ephron’s I Feel Bad About My Neck or I Remember Nothing that I’ve been noodling on this summer, all playing out in the shadow of Covid, BLM and the elections. What an insane, fruitful f’in year for material this has been, man!
Reading, Watching, Listening
What are you reading, watching, listening to these days?
I usually have at least three books going at once. Recently completed are And the Mountains Echoed by Khaled Hosseini (The Kite Runner author), Nothing to See Here by Kevin Wilson (dark and insanely funny story about a woman who’s looking after a set of twins who spontaneously combust when they get upset. Seriously.) and I re-read Late Bloomers by Brendan Gill of The New Yorker, which is a series of one-page essays about people whose greatest achievements really didn’t happen until much later in life, everyone from Coco Chanel to Julia Child and Edward Hopper to Mother Teresa.
I’ve been listening to a podcast called “The Dropout” about Elizabeth Holmes and the Theranos debacle. Music: a SoCal band called Slightly Stoopid that my younger daughter turned me on to. Not sure about the name but the music is beautiful. Fave songs are “Closer to the Sun” and “Wiseman.” And on opposite ends of the spectrum, have been watching “The Durrells in Corfu” on Prime Video for escapism and “Sex Education” on Netflix to scratch that “responsibly immature” itch.
Do you have a hero/role model?
Can I choose a role model who’s not necessarily famous? If so, I’d have to say my old boss and mentor at Tiffany, Caroline Naggiar, has been a source of wisdom and inspiration. Caroline, who was the Chief Marketing Officer, is one of the most gracious, thoughtful and articulate people I’ve ever met. Even in the toughest situations, she maintains her composure and is a lady to her core. She also has an unparalleled knack for taking a delighted interest in people, always curious to hear your thoughts and learn about what’s happening in your life, which is just the biggest and most generous gift you can give someone. She gives great advice and is one of those people who make you want to sit up a little taller when you’re with her and choose your words a little more carefully. Plus, she’s hilarious!
“Losing my job during a pandemic at age 55 was actually a wonderful chance to push pause for second and reconsider EVERYTHING!”
Any wise words for people whose lives have been disrupted by our current situation?
Not sure if they’re wise, but what was true for me was that losing my job during a pandemic at age 55 was actually a wonderful chance to push pause for a second and reconsider EVERYTHING! Which is something we never really give ourselves permission to do. Plus, in a year where absolutely nothing is normal, all the rules about what success and happiness look like have changed. Remember you’re never alone and that the people who love and care about you also want to help and support you, so ask them. And laugh! ‘Cause if you can’t find the humor in the depravity and kerfuffle of this year, then what’s the point?
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