Chief Change Officer
#294 Jodi Silverman: Parenting, Purpose & the Dare to Begin Again — Part One
Sat, 12 Apr 2025
Jodi Silverman didn’t set out to lead a movement—she just wanted to figure out what came next. In Part 1, she opens up about career shifts, midlife transitions, and how becoming an empty nester sent her on a completely different path. Spoiler: it involved leaving behind a successful print business, embracing a “dare,” and launching a community that now supports thousands of women through their own identity resets.Whether you’re a parent or not, this is a story about transition, reinvention, and giving yourself permission to be more than one thing.Key Highlights of Our Interview:From Sales Rep to Accidental Entrepreneur“I didn’t know the word ‘entrepreneur’ back then. I just knew I didn’t want a boss—or a babysitter.”The Quiet That Changed Everything“Suddenly, I had free time… and I didn’t want to sell print anymore.” What happens when the kids leave and purpose takes a nap.A Guilty No, and a New Yes“Admitting I was unfulfilled felt selfish—but it was the start of everything.”Finding the Word That Fit“I was already doing it. I just didn’t know it was called daring.”How Moms Who Dare Was BornFrom a Facebook group to a full-blown movement, one post at a time._______________________Connect with us:Host: Vince Chan | Guest: Jodi Silverman --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: What inspired Jodi Silverman to start her new journey?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world. Today's guest is Jodi Silverman, founder of the Moms Who Dare community and someone who knows what it's like to face a totally quiet house and wonder what comes next.
She built a print business, raised a family, and then realized it was time to find something that lit her up again. In this two-part series, we talk about letting go of old roles, parenting when you are no longer the fixer, and why your next chapter doesn't have to look like your last one. Jody's story is honest, warm, and refreshingly real. Let's get into it.
Good morning, Jody. Welcome to Chief Change Officer. Welcome to my show. Good morning to you, Tuvitz. I'm so happy to be here on your show. Thank you. This is a special episode for me for a couple of reasons.
First, I'm stepping out of my comfort zone and doing this show on video for the very first time. So yes, I dressed up for the occasion. And second, I'm joined by someone who's also part of this little leap into something new. Jodi, thank you so much for being here and for jumping into this journey with me.
Of course, and I am so honored to be here as you step out of your comfort zone and dare to create video. And that's my platform. That's what I inspire others to do. And I'm always inspired when somebody like yourself, Vince, will step out of their comfort zone. Yay for you. I'm excited to be here. I can't wait for your listeners to hear what we're going to talk about today.
Sure, Jodi is the founder of a community called Moms Who Dare. We'll talk more about that, especially the word dare and why it matters for mothers. But first things first, Jodi, what is your story? I know you're a mom, obviously, but what about your career journey, job history, your family?
Let's start there and then we'll get into parenting, moms, and the whole idea of the empty nest, which is our main theme today.
Absolutely. Yeah. So I'm Jodi Silverman and I started my career before I was anybody's wife or mom. I started my career in sales. I sold direct mail marketing advertising. I found my way in sales. I loved it. I was with a national company, very successful for about 12 years. And during those 12 years, I met my husband, Sam, and we're now together 33 years.
And we've had two children, Ellie, who is now 29, and Daniel, who is now actually, Ellie at the time of this going live will be 30, and Daniel is 26. So during that transition of going from single to married to becoming a parent, my career transformed with me. It changed.
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Chapter 2: How did Jodi transition from a print business to a community leader?
And in order for me to still want to keep my toes and my mind sharp in the business world and yet be more present in my children's life, I dared. And I didn't know it at the time that it was daring. That came later. I dared to step away from this job, my career, and start my own business. I also didn't know there was something called entrepreneurship, Vince, but apparently that's what it was.
And so I started my own print sales company that allowed me to still work, make some income, but yet be more present. Pick up from preschool for my kids, go to their games and whatever school activities they had. And that was like the first step. Looking back in hindsight, I wasn't aware of it at the time. That was the first dare. And then, fast forward, my kids are in high school.
They're about three years apart in high school. So my daughter was getting ready. It was a year she was getting ready to graduate. She was going to go off to college. I'm in the States. She was going to go off to a university. And I found myself sitting in this really quiet space. I had the print business for months. Gosh, about since Daniel was two, so about 10 years.
And I was in a very quiet space and we tend to go in our heads and start to think about things when we're in a quiet space. And I realized in that moment, I was sitting there wondering, what was I going to do with all the free time that was about to open up? As my daughter left and my son was in high school, free time was opening up. Is this what I really wanted to do?
Is selling commercial printing really what I wanted to do? And I was like, ew, no, I really didn't want to do it. And it was a hard answer to swallow and accept because here I was, fortunate and privileged enough to have my own business, schedule my own time, and yet here I was feeling unfulfilled and I didn't want to do it anymore.
All the guilt of feeling like I'm ungrateful for the gifts and the privilege that I have started to surface and it was also in that quiet space. So I was in this quiet space for a couple hours. Oh, I asked the question, I answered it. I felt a little uncomfortable with my answer and guilty. And at the same time, I realized my feeling unfulfilled had nothing to do with
me as a partner and a wife with my husband had nothing to do with me being unmonitored, everything to do with what did I want for myself. And I know, Vince, that a lot of your listeners out there, no matter where they are in the world, wherever you are in the world, we all are more alike than we're different. And we've all experienced, most of us have experienced that moment in our lives.
I know you. with all the change and shifts and daring you've done, get that feeling like there's something different, something bigger for me. And I didn't know what it was. But just by sitting in that space, asking the question and allowing the answer to be, no, this is not what I want, opened up my mind to be receptive when an opportunity showed itself for me.
I have to confess, I'm not a parent. I made the decision pretty early on that I wouldn't have children. So that was my choice. That means there are certain things about parenting I may never fully understand. So bear with me if I ask questions that might seem a bit off. Now, you mentioned that at some point you became an entrepreneur. You dared, you took the leap, but you also made sacrifices.
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Chapter 3: What challenges did Jodi face as an empty nester?
Yeah, it's a good term to use. So for me personally, I knew that I would miss my daughter terribly. I have a daughter. I have a son. There's things my daughter would do with me that my son wouldn't. My son really didn't feel like he wanted to weigh in on my outfits. Is this a good outfit to wear? My daughter was my fashion consultant. She would go and get manicures and pedicures with me.
Chapter 4: How does Jodi define the word 'dare' in her journey?
My son had no interest in getting his nails done. I tried, but he had no interest. So I I there are all there's a range of different emotions that all parents, moms and dads alike. And I would even dare to say, Vince, if you were not a mom in the traditional sense of the word, but you're an aunt.
or you're an uncle and you have children in your life that you're very close to it can affect them as well but the range could go from what you said a complete loss of feeling like you're no purpose what is my purpose if i'm not a full-time mom anymore that was not really what hit me but i know that is how it affected a lot of people i know a lot of my close friends for me
I was both excited for my daughter, and I'll talk about her because she was the first to leave, because she needed to go to college. She was ready for college. I was excited for her. I was sad that her personality would be missing from our home. It changes the dynamic of a home when one child leaves school. and whether it's an only child or you have other children at home.
So the dynamics of the home was going to change. And with that being said, I was also excited because now I had some focused time with my son at home. To get back to your original question, for me, it was a combination of, it was a bittersweet moment. I was so happy for her, and yet I was going to miss her on a day-to-day basis.
The biggest feeling of disconnection that I hear most parents tell me about is not knowing what they're doing every day. We go from 100% full-time parenthood. We know who their friends are. We know where they are. They come home at night. We know where they're going on a Friday night or a Saturday night. We know what they're doing after school. We don't know what they're doing when they're away.
They're navigating their life on their own terms. They're meeting new people. So that is where the feeling of disconnectedness comes from. And it's a very hard, difficult, uncomfortable emotion and feeling to deal with as a parent, to feel disconnected from your child after 18, 20 plus years being 100% connected. It's a hard one. So it does hit... parents at different phases of emptiness.
I say it's all different. It can happen during high school. I say the first phase of emptiness, when they get their driver's license here in the US, so 16 years old, that's independence. They don't need you to drive them anywhere. It's the first moment of the, they don't need me anymore mindset.
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Chapter 5: What emotions do parents experience during the empty nest phase?
It actually starts earlier, around age 10 or even 11, when they begin pulling away from Suddenly, they got their own friends, their own life. And you hear things like, leave me alone. You know they will eventually leave home. That part is certain. But even when you see it coming, it still hits hard when it happens.
We all know our goal. What is our goal as parents? To raise confident decision-making children to become confident decision-making young adults to adulthood to go out on their own, bring new experiences and meet new people and discover who they get to be. We know that's our role. We know that's our goal. And when it happens, most of the time we're really not prepared for the separation.
And Kim, Vince, what I'll say is I believe a common mistake in some listeners, some moms out there might not like what I'm about to say, Vince, they might not like it. A common mistake is viewing your relationship with your child as a friendship. I hear a lot of moms, a lot of moms, because I do deal mainly with moms, but I hear a lot of moms say, they're my best friend.
Our children are not our best friends. You can like your children. You can like them. In addition to loving them, you can like them. And yet, they can't be your friend. You have to have other... They're not your friends. Think about... What you share with a friend. That should not be what you share with your children. You can feel the emptiness.
But if we can change that shift in, you're not losing a best friend. You're not even losing your child. You are gaining this amazing young adult to watch them blossom. And now you get to gain a more adult-like relationship with your children.
which once you move through the emotions, the sadness, the disconnectedness, and you can understand those feelings and move through them, the adult relationship is fabulous with your children. It can be. It can be.
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Chapter 6: How does disconnection affect parents when children leave home?
Earlier, I used the term identity crisis. And clearly, you moved past it. In fact, you went on to create this amazing community, Moms Who Dare. What sparked that? What made you decide to start something like this in the very first place?
Yes, and the identity crisis is a good description of events. It's really well said because even for me, somebody who always worked outside of the home, The majority of my time was spent being a mom, was spent parenting. And those moms that decide to become full-time moms, it's even harder. It's even harder because they don't have it. They put away their career.
They put away their interests and their hobbies to be a full-time mom, which is no joke. It's no joke. It's a serious job. It's a career. So what happened for me is when I was in that moment and I decided I wanted something different, An opportunity for a new business venture was presented to me in the multi-level marketing, direct sales industry.
And for anybody out there who has ever been part of a direct sales, multi-level market, network marketing, whatever, it's called direct sales, multi-level marketing, network marketing. They're all the words. You'll know that it opens up the doors to the world of personal professional development.
And what I mean by that, Vince, is it opens up the doors to the thought leaders who have written amazing books over a lifetime, like Think and Grow Rich from Napoleon Hill. Everybody knows that. So many, Brene Brown is a universal name that most people know. It opens the doors for that. And that's what happened for me. It opened up the door.
It surrounded me with people who were all on the same journey of rediscovering who they were and were looking for something else that they were meant to be doing. And I attended one of the dares I did before I knew what daring was my word. I said yes to attending a local women empowerment conference. So I walked into this room with 300 other women, small business owners. I was a life coach.
I became a life coach at the time. I knew I wanted to support other women, specifically moms, because up until this point, I was stepping out of my comfort zone. I started a new business. I was meeting new people. I was scared. I was doing it scared. I had doubt, but I was enjoying. I was excited again. Even my husband, Sam, said, you're reborn. There's this excitement about you.
It was fresh and new. So I'm sitting in that room, and the keynote speaker was a woman named Luann Kahn. She's an eight-time Emmy Award-winning journalist from my town, Philadelphia, Pennsylvania. And she gave us each a copy of her book that she was on stage talking about. And it was called I Dare Me, how she did something new every day for a year to get unstuck.
And I sat in that room, Vincent, in that moment, I felt like Luann was only talking to me. Like everything went quiet. I'm like, oh my gosh. Because she was talking about daring, stepping out of your comfort zone, trying new things. All is the same word. And I thought, oh my gosh, I've been daring. And it was such a playful word for me and everything about me. I like play.
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