Knowing when to let go with Cyndie Spiegel | ep 116
How do you know when something is no longer for you? What do you do when it’s time to move on from the career, the dream, or the passion you always wanted?
In the first of my Courageous Conversations series, I’m interviewing one of my favorite human beings, Cyndie Spiegel, who truly embodies what trusting your intuition and following your compass looks like when it’s time to shift and pivot in life.
So, I first heard of Cyndie through a colleague and, at the time, she was a business coach helping women create their own businesses, break out of their fear, and do their own thing in her amazing community — The Collective of Us. When I heard this, I knew I needed to join this. And let me tell you, doing this with Cyndie was the ignition to everything that Wholehearted Coaching has become.
I literally attribute so much of my success to Cyndie Spiegel because she gave me the permission to do the things I really wanted to do. And since then, Cyndie and I have been in touch and now I know her on a more personal level and can call her friend.
A quick bio about Cyndie Spiegel
Cyndie Spiegel is a born storyteller and former fashion industry exec turned writer. She’s an aspirational voice and igniter of powerful conversations. Cyndie declared she’d never have a job ever again and instead would live her life getting paid for what she loves.
You can find her spreading hard earned truth and wisdom while also showing up as an inspiring and provocative keynote speaker and founder of Dear Grown Ass Women, a diverse and highly relatable social community for women 35 and older (that you should absolutely join!).
Tell me about little Cyndie. Her life, what she saw, what she believed was possible for her and her future.
Cyndie Spiegel:
Oh, you just went right into the childhood. So, when I was little, I grew up very poor. I saw a lot of drugs around me. I lived through the AIDS epidemic. I watched a lot of people die in the 80s that were very close to my family, many of them in my family.
Even saying that, I had a lovely childhood. I had a mom who loved me in addition to her addiction. I had siblings who loved me as much as older brothers could. And somehow, through everything, I always knew that more was possible.
When you grow up in poverty, you know it only in comparison to other people. So by yourself, you have no idea you’re living in poverty. You're just living your life and this is the way things are. But you don't know that you are any different until you meet other people who are different.
And so I had the opportunity even as a child to meet lots of people in lots of different situations and so I knew that there was more available to me and I mean that not in a scale of where I was being less, but I knew that there was a big wide world out there and that I could choose where and who I wanted to be in that world.
I also grew up with a mother who told me I could be anything and do anything.
I'm really grateful that I believed her. At that point, I was just a little mixed kid trying to figure out who I was in the world. I was made fun of a lot as a kid. I had freckles, which was not a normal thing where I grew up. I had a birthmark on my face, which is not a normal thing where I grew up, but I always knew at home that I can do anything I wanted and that outside of what anybody else told me I can do and be anything. And so I held to that and I believed it.
You really do embody that to me. One of the things we do, especially in our late teens and early twenties, is we create “The Plan.” Like, this is what my future is going to be.
For you, what was “The Plan?” What was Cyndie Spiegel going to do?
Cyndie Spiegel:
Cyndie was going to do exactly what Cyndie did and I actually don’t consider that the naïveté of being young. I think it’s a part of who we are. We are really challenged in our culture because we think that there’s only one way to be in the world. You graduate and somehow we’ve given kids, literal children, the responsibility to have to dictate what they want to do with the rest of their lives at the age of 18 or 19 years old.
So, when I think about it, I did exactly what I knew I was going to do when I was 20 and made that decision which was to spend a career int he fashion industry.
I always worked as many jobs as I could so that I could buy fabulous clothing. I worked at the Gap and I went to my community college for two years. Then I transferred to FIT for my bachelor's degree. I always knew that I wanted to go to FIT, but I also knew that I was poor, so I should start at my community college. So shout out to community colleges everywhere.
I did my internship abroad in London, working for a fashion forecasting company. I came back to New York and I interned for DKNY and Liz Claiborne. I went on to have a long career at Coach working in product development. I traveled the world and I left it all when I was 35.
So from the time I was 20 to 35 or 36-ish, I did exactly what I thought I was going to do. But I think what was different was that I knew when I was done and I knew that “done” didn't mean when my career was over. It just meant that I was done with that chapter.
I think sometimes we think “I want to shift careers” and we see it as this sense of failure or we think “Oh, I invested all of this time and effort into this.”
When it was time for that pivot to happen, how did you know you were done?
Cyndie Spiegel:
The first thing I want to acknowledge is growing up the way I did and then working my way into this life that I did, which was a life of privilege — you just have to call it what it is — I never took it for granted.
Those business class flights around the world, being in the spaces that I was in — I never took it for granted in ways that I think some of my colleagues did. I always knew that this reality wasn't necessarily one that most people will ever see, so I think that was a really important part of me being able to walk away because I never took it for granted. I always understood how special it was and it was glamorous in a lot of ways. I mean, where else do you get to fly across the world business class and eat these beautiful dinners that cost more than rent on a New York City apartment?
So I think in order to walk away, I had to understand that first.
At the time I was 35, I was a director at Narciso Rodriguez, doing their accessories, flying to Italy, and doing all of these cool things. And I just knew.
It was Spring 2013 Fashion Week and we were at the show in New York City, in the tents with all the glamour of fashion models running back and forth and I remember looking around and going, “Wow. This is it. This is the thing. This is what this culminated in. How lucky for me. And I’m done.”
I knew I was done. I didn't have a plan. I didn't know what “after” was going to look like, but I remember a girlfriend meeting me at the show and we went out to eat Thai food. I remember even now looking back on that being exhausted and looking exhausted. I was probably 120 pounds. I was just exhausted. I knew that my heart no longer aligned with the work that I was doing.
And there was no other way. I was done. I didn't fight being done.
I also trusted — and again, I'll go back to what my mom always said, “I can do anything,” — I trusted that I was smart enough, savvy enough, and connected enough to figure out another one.
Now, I won't say it always seemed so easy, but I trusted my own instincts that said the only way I'm going to figure out what's next is if I do this hard thing which is to walk away from this. I can't be in this while trying to figure out what's next. I need to separate myself from this. And so I did.
And, up until 2020, that was by far the hardest year of my life: the year between knowing what I was doing to not knowing what I was doing and it was hard.
When we see people shifting in their careers, we might think, “Oh they must have had something set up and I have to have a very concrete plan or exit strategy.”
Can you describe that time of your transition? What would you say was hard about that?
Cyndie Spiegel:
I didn't have a family to lean back on that would pay my bills when I didn't have any money. I didn't have a partner at the time to lean on, there was no one. If I didn't have a job, I didn't have money to pay my bills. There was no backup. In fact, I was the one sending money home to continue to help my mom. My dad had already passed away and I wanted to help in any way I could.
I had been saving money since I was 16 years old. I had a 401k plan and I actively chose to use my savings to live. My rent in New York City at the time was like $2,600 a month and I knew that I wasn't willing to give up my apartment. My apartment was the one thing that grounded me. So the “right thing” to do would have probably been to get a cheaper apartment. I wasn't going to do that because it was the only thing that would ground me and if I uprooted my life, my career, and everything I once thought was true and then moved, I don't know how I would've gotten out of it.
So I chose the alternative which was to work through my savings and eventually my 401k which I didn't work through, but I certainly used it in faith believing that I would be okay and I would be able to add that money back.
At some point I knew it was a privilege to even have that money to access. At 35, I was not really thinking about what I was going to do at 70, but I remember being very conscious about my choice and saying, “This money is available to you right now. Use it.”
I would make money however I could. I was teaching yoga and meditation classes at my apartment once a week and it certainly wasn't paying the bills that I had, but it was allowing me to feel into my purpose and to find different ways of being right.
That was really the start of public speaking, getting comfortable not being an expert but doing it anyway, building community. It was this very small thing that at the time was like $75 and that'll get you four classes in my apartment. There were probably six to eight women that would pour in, take off their coats, go to my living room and have to find space on the floor. These women were helping me move my sofa to find a space to do yoga.
It was the start of so much of who I am today and it was because I took those risks and I didn't have a backup plan. What I knew to be true about myself is that without a backup plan, I would figure it out. There was no other option. I would figure it out. I didn't spend all that money on my education, I didn't know all the people I knew, I didn't move to New York City to not figure it out. I knew I would figure it out. I just didn't know how or when.
How did the clarity come to you for the next chapter?
Cyndie Spiegel:
I used what I had at the time which was a 15-16 year career in the fashion industry, multiple degrees, contacts throughout the world for production. I knew a lot of folks who wanted to start fashion brands, particularly women, and I would start to coach them.
When I first launched The Collective of Us, it was for women starting fashion businesses. After about two or three rounds, I realized that it didn't matter what kind of business you were starting, the process was the same no matter what. And that's when the collective became the collective.
What I think is so beautiful about when we go into the next thing is we realize how our previous experiences all came together. So, how was that a great addition to the work you were doing those years before?
Cyndie Spiegel:
I’ll answer a question you didn’t ask first. I want folks to really understand that there is no wasted career, there is no wasted experience. Yes, I was doing something different, but I could not have done what I was doing had I not had that career in corporate fashion where I learned leadership skills, where I worked my way up the ranks. I would not have built the confidence and the know-how to say at 35 or 36 years old, “I’m doing my own thing,” and “I don’t really know what this thing is, but I’m going to give it a whirl.”
It wasn’t about fashion, but I had taken all of my transferable skills and the fashion and style piece just became a part of who I was. Who you are is always there and it’s inherent in you. There are not separate parts of Cyndie, there are just evolutions.
There’s no drastic change between these evolutions because when you live into who you are, you’re simply evolving. There’s a very natural evolution and we get stuck when we feel like we are our titles and we are what we do in the world. The second we realize that we are not those things, we can just evolve very fluidly into the next thing. We don’t have to answer to anybody Why or How.
I think your superpower is knowing when you’re done with something. A lot of people will really drag and stomp their feet not facing that inevitable truth of “I’m done with this.”
Just listening to you, that’s such a great reminder for all of us that when intuition kicks in saying that you’re done, acknowledge it.
Cyndie Spiegel:
I don’t think it’s as clear for some of us as it is for others. I grew up with a foundation of impermanence. I never had a belief that anything was forever and that became much more apparent in 2020. But, in writing my next book, so much became clear to me how this foundation of impermanence taught me to grow up in a world where I understood that nothing is wholly mine. I am not wholly anyone’s. What I do is a part of me. It’s not who I am. There’s not a sense of clinging and permanence that I expect. When you don’t expect things to be forever, there’s a comfort in letting them go.
*Tune into episode 116 | Knowing when to let go with Cyndie Spiegel wherever you love listening to podcasts (or click here) to here the full interview and don’t forget to connect with Cyndie Spiegel at any of her amazing resources below.
Connect with Cyndie Spiegel:
Learn more about Cyndie Spiegel
Stay in the know about Cyndie’s second book: Microjoys: Finding Hope (Especially) When Life is Not Okay
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Have you ever wondered how to listen to your intuition? Or how to understand and strengthen your intuition? This week’s episode is a crash course in intuition that teaches you the basics of how to listen to your intuition and distinguish between the voice of Ego and Impulse.
A quote to take with you:
“When you know that something isn’t for you anymore, stop.
Listen to your gut. Listen to yourself.”
Did you know that each episode comes with free guided journal prompts?
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About your host, Shirin Eskandani
Hi, love! I’m Shirin.
Coach, speaker, writer, and life alchemist.
I teach you how to listen to your intuition again, tune out all the BS, and let your heart lead the way.
Because once you strengthen your inner GPS, decisions become easier, boundaries become clearer, and belly laughs become a daily thing.
A LITTLE BIT ABOUT ME:
I’m a certified life coach (accredited through the International Coach Federation)
My husband and I met on Instagram and we live in Brooklyn, NY with our plant babies
I have a masters degree in Music and was a professional opera singer for twelve years. I worked all over the world singing on stage at Carnegie Hall and the Metropolitan Opera (more on that later…).
I believe in the woo just as much as I do the work (internal and external). No amount of crystals and affirmations will make up for a lack of a healthy mindset and aligned action.
I love all the Real Housewives franchises. Don’t make me choose one… seriously, don’t.