Mom With a Mic: Dorothy Cascerceri Simone on Infertility, Courage, and Reclaiming Her Voice
In this episode of Mom to MORE®, Sharon Macey welcomes media personality, podcast host, and storyteller Dorothy Cascerceri Simone, the voice behind That Greenwich Life. Dorothy has worn many professional hats including celebrity journalist, television host, producer, live event emcee, luxury travel writer, and now podcast host and auctioneer.
In this honest conversation, Dorothy shares how motherhood reshaped her ambition and led her to create an intentional hybrid mom life, designing her work around her children while still pursuing creative opportunities that energize her. She also opens up about her infertility journey, including multiple miscarriages and a late stage pregnancy loss.
Tune in for a candid conversation about resilience, reinvention, vulnerability, and redefining success in motherhood and career.
[00:00] Introduction
[02:14] Dorothy’s “intentional hybrid mom” approach to work and motherhood
[05:05] Why motherhood came at the perfect time in her career
[09:18] Finding her voice through podcasting
[14:35] Her infertility journey and late-stage pregnancy loss
[18:02] Breaking the silence around miscarriage and infertility
[22:23] Lessons learned from hardship and healing
[25:05] Launching That Greenwich Life and hosting live events
[29:13] Discovering an unexpected talent as a live auctioneer
[32:05] The mom skills that translate into career success
[35:10] Celebrity interviews, boundaries, and motherhood lessons
[37:46] Advice for women doubting their next chapter
[42:23] Dorothy’s vision for her “more”
Meet my guest, Dorothy Cascerceri Simone:
Website: https://www.dorothyontv.com
Instagram: https://www.instagram.com/dorothyontv
Podcast: That Greenwich Life
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Keep an eye out for episode #60 of the Mom to MORE® podcast where Sharon is joined by Samantha Yanks, Editor in Chief of Westport, Weston & Wilton magazine and cofounder of The Connecticut Edit. Coming soon - you won’t want to miss it ♥
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Dorothy (00:00)
for me, motherhood was interesting because it came at a time in my career where I was honestly so burnt out. I had done so much more than I had really ever dreamed of doing.
it was really the first time ever that this workaholic right here
said, you know what?
I'm gonna take a break from work and I'm gonna feel really good about it. And I'm going to dive in just as deep with my new job, which is raising this amazing human, my son.
Sharon (01:15)
Welcome back to a new episode of Mom2More. Hey, before we jump in, I've had so many of you ask about one-on-one mentorship calls. If you're at a crossroads and want that loving kick in the pants to go from dreaming about your next chapter to actually doing it, I've got you. Just head to mom2more.com forward slash mentorship for all the details. And if you're new here, welcome to the podcast that is shaping culture. And that is a bit of a shout out to the show's Signal Awards win. Please subscribe or follow the show.
so you always know when another Fabulous Mom episode is about to drop. Okay, today you are in for a real treat and you're going to love this next mama. Dorothy Kaskaseri-Simon is a true multi-hyphenated mom, podcast host, executive producer, emcee, live auctioneer, luxury travel writer and digital creator. Inhale. She is the voice behind the podcast, That Greenwich Life and a longtime media powerhouse.
who's interviewed celebrities, hosted primetime television, held positions at People Magazine, In Touch Weekly, and the National Enquirer and more. has partnered with major brands long before influencer was even a job. Named a powerhouse creator by MSN and one of Greenwich's women who lead, Dorothy blends authenticity and style in a way that truly resonates. She's also what I call an intentional hybrid mom.
thoughtfully building a dynamic career while raising two young kids, working in the in-between hours, and proving that ambition and motherhood don't have to be all or nothing. Dorothy is redefining what that can look like in the process. What I love about this mom is she is funny, vulnerable, brazenly real, and tells it like it is. Dorothy, welcome to Mom Tomorrow.
Dorothy (03:04)
Gosh, Sharon, that intro was insane. ⁓
Sharon (03:08)
you saying so?
Dorothy (03:10)
Thank That intro was so beautiful and I'm so flattered. also it gave me a minute to sit here and say, ⁓ my God, like that, that's
Sharon (03:21)
before we get into it, I want to set the scene with what I call my essential mom question. And that is how many kids you have and how old are they? OK.
Dorothy (03:29)
So my daughter, Gemma, is gonna be three in the next month or so. And ⁓ my son, Nicholas, is 10.
Sharon (03:38)
Nice, nice. Okay, so I want to talk, you know, I mentioned it in the intro about your intentional hybrid mom role because it is so different from what I experienced when my kids were younger, which was like in the last ice age. ⁓ I either had the option of working outside the home or working just as hard inside the home as a stay at home mom. So you are designing your work around your kids. And when kids are involved, we know nothing is ever sane.
So what does that really look like on a daily basis?
Dorothy (04:08)
It looks like complete insanity. I don't have a full-time nanny or even a part-time nanny or ⁓ live in au pair or anything like that. And for people who are listening and thinking, you know, well, lots of people don't have that in Greenwich, I'm kind of more... Exactly. I'm more in the minority. And I intentionally don't have that kind of help.
Sharon (04:24)
An anomaly.
Dorothy (04:31)
because I'm a masochist now because I, I want to be with my kids, you know, and I, I haven't quite figured it all out. my, as you know, when you're working for yourself, your schedule really kind of changes day to day and week to week. And it used to be that there were like really, really busy periods and then kind of lulls. yet in the last year or so, the abundance that has been coming in.
I feel like there is just no lull. And so I'm trying to figure that out. So it's a lot of late nights. It's a lot of being on my laptop after the kids go to sleep. ⁓ And it's a lot of squeezing it in during nap time. And it's a lot of sacrificing other things that I need to do. I mean, you don't want to see my toenails right now.
Sharon (05:23)
Okay, she's wearing boots, so I can't see them.
Dorothy (05:27)
Through all of that, I've been able to kind of make it work, but I have to do a better job this year of figuring it out so that it's a little bit more sane.
I feel like someone's had their foot on my neck for quite some time now. And I don't want to feel that way when I'm with my kids. When I'm with my kids, I want to be with them. I don't want to think about all the deadlines.
Sharon (05:48)
to be all there. Yeah. I get that. And even just today, I'll point out that you are a little late because your daughter is sick. you know, mom to mom, been there, done that. Yes. Right. There's nothing you can't tell me about anything that's going on with your kids that I haven't already experienced. That's right. I get that. Yes. I do know. So talking about your intentional hybrid mom role, was there a moment when you realized that motherhood didn't replace your ambition?
Dorothy (06:03)
you now.
Sharon (06:15)
but rather redefined and refocused it.
Dorothy (06:20)
Yeah, so I think for me, motherhood was interesting because it came at a time in my career where I was honestly so burnt out. I had done so much more than I had really ever dreamed of doing. Of course, there were still things that I hadn't done that I wanted to do, but I really had gotten to that point where...
I accepted my accomplishments and I was able to give myself a real pat on the back and not just be, okay, that was great, but what's the next thing? And so when I became a mom, I had a hard time connecting with a lot of other moms in the sense of them talking about how they really missed working and they really missed doing something just for them and building something and creating something.
For me at that stage of my life, it was really the first time ever that this workaholic right here kind of said, you know what? I'm gonna take a break from work and I'm gonna feel really good about it. And I'm going to dive in just as deep with my new job, which is raising this amazing human, my son. So I never really set out to work.
⁓ Again, I think I was always going to work again, but I didn't really set out to do it. It just kind of called me.
Sharon (07:44)
But
you really then started as the stay at home mom. And I think there's something beautiful in dialing back what we did. We all had careers and then we had kids. You just happen to be at a crossroads where you're like, I am so ready for this. I really want to dial it back versus our decision to say, OK, I'm going to put my writing career on my background was advertising. I'm going to put that on pause for a while and lean into family life and be there. So interesting how you sort of are like, I am so ready to have kids.
Dorothy (08:13)
Yeah, actually, it's funny because I actually don't even think that I was so ready. I think it was a big transition. Oh, huge. Huge transition to kind of be that like not single because my husband and I were married, but you know, like no children living in Manhattan, going out all the time, work. I could work all the time, right? Like I could work as many hours a day as I wanted to work. And I did because I executive produced and hosted a TV show, a weekly TV show. And
That was great. I had a lot to do during that time, but I had the hours to do it. I had the office hours to do it. I think now my biggest struggle is that I just don't have the office hours. And it's a problem of my own making, because I could have them. But then if I had them, then that would mean that I wouldn't be able to take Gemma to gymnastics. Right.
Sharon (09:03)
Right, you wouldn't have the time with your kids.
And they're only young once, and it goes so fast.
Dorothy (09:07)
Yes, and this is my last baby. Yeah. 100%. And I struggled to have her. I struggled for five years. I went through tremendous loss. Yeah. And so I think also that perspective, I see mothering her even a little bit differently than I did see it when I was the mom to my son when he was this age. Because it's every single moment is just...
Sharon (09:15)
And we're going to talk about that.
Interesting.
Dorothy (09:36)
something that I know I can't get back. I didn't have that perspective necessarily with my first one.
Sharon (09:41)
Interesting. I like that though. I mean, there's that realization. I remember when our son was born, my father said to me, tomorrow he'll be in kindergarten. it's like, what do they say? The years go fast, but the days go slow. Yeah.
Dorothy (09:54)
Yeah,
I say that all the time. I even with my son, when I used to look at him on his changing table in our apartment in New York City, I would look into his eyes and think to myself, it's going to be tomorrow and I'm going be dancing with him at his wedding, which you just.
Sharon (10:07)
Which I just
It does go fast. It really does go fast. So I want to go back to what you've done in the past, because it's so interesting. And when I did a little research on you, you were like all over TV, which was really incredible. You have lived so many professional lives, media insider, producer, on-camera talent, podcaster. Was there a version of Dorothy that surprised you the most when she showed up?
Dorothy (10:33)
I love that question. What a great question, Sharon.
You know, I think one of the most vulnerable things that I've done, which surprised me the most, would be starting my podcast, That Grown Itch Life. I've never been a person that's been very, very private. My nursery school teacher always used to say to my mother when,
they were going through like a terrible divorce, my mom and dad, know, Dorothy's gonna be just fine because the world is her therapist. And that rang true throughout my life. Yes, it is. It is my DNA. is. ⁓ I've always been, I feel like I came out of the womb with a microphone in my hand, but I think the podcast is definitely something that's, that version of me surprised me the most because
Sharon (11:06)
DNA.
The awesome DNA that you have.
Dorothy (11:26)
I had a very small baby at home when I was offered the opportunity to start my podcast and I was sponsored by a studio that opened in Greenwich. And I leaned in and I said yes, even though I had no idea how I was going to manage the workload and the mother load with the workload. But then I ended up being really, really honest and really just one-
100 % myself in a way that I think I've always been myself throughout my life, but I think it wasn't until I went through all of the trauma and the loss that I went through trying to have my daughter that I really stepped into a completely different version of myself. Someone who is a little bit calmer, which I've always am so reluctant to say that word because people are like, wait, this is a calm version of you? What were you before?
Like, what were you prior to this calm version, quote unquote? But I think with That Greenwich Life, with the podcast, I think it really was a place where I talked really honestly about the hardest time of my life. And even just recently, I did a whole episode on Family Estrangement, because that's a thread that has been going on for me. And it really just kind of has surprised me
I have been able to feel and to be with some of the really, really hard things that I went through.
Sharon (12:55)
And I'm sure that family estrangement is, I mean, that is so common, right? That we don't realize how common it is.
Dorothy (12:59)
I
cannot believe the feedback from this episode. I mean, I can because I think we are talking more about it, but yes, it helped so many people and that was my motivation for doing it. But I think it's that version of somebody who is just a little bit more at peace within herself. Not perfect, but just able to talk about things in a way that I can speak with kindness and with honesty.
Sharon (13:27)
that resonates and people get it. And there is no perfection in this world. People need to realize that. Yes. Especially us moms. Yes. We try to make everything perfect and we can't. And it doesn't matter. True. Yeah, that's so true. Hey, Dorothy, we're going to take a quick break. And when we come back, we are going to talk about your very public journey of infertility and a surprising way that you found yet another voice. Don't go away.
Dorothy (13:38)
That is so true.
Sharon (15:19)
Dorothy, you are very intentionable.
That is not even a word, it? I'm having a hard time today. Very intentional. There we go. Okay. About how you design your work and your family life now. But there's another part of your story where intention and planning didn't protect you the way you had hoped. And that is your infertility journey. And I want to ask you about that next because you've been so open about it. And I know that one of the reasons you started
Dorothy (15:26)
and make.
Sharon (15:50)
that Greenwich life was
because this is so common in this world and you wanted to give voice to that experience. And you went through a late stage pregnancy loss at 21 weeks, I think it was, which is devastating. How did those experiences and deciding to share that through the podcast help you, change you? Talk to me about that.
Dorothy (16:16)
So when I was in the depths of all of it, I was dead silent. I took a break from Instagram. I had no voice. For several years, I really lost my voice in a way to the point that I didn't know if I was ever going to get it back. I didn't know if I was ever going to create anything, much less a new life.
because I went through so many miscarriages and failed IVF cycles and like the very devastating TFMR at 21 weeks, which was just like, you can never ever think about being in that situation and living. Yeah, it was absolutely horrific. And so when I started that Greenwich Life, you I knew that I didn't want it to be a podcast just about infertility and loss.
Sharon (16:58)
five months.
Dorothy (17:11)
But I knew that that was such a huge theme in my life. And I think in talking about it, it was scary at first. Even just talking about my initial loss of our angel son, Dean, that's very scary to kind of be very open and very public about that because it's such a vulnerable thing and it's such a personal family thing. And I also realized that
there was, for several years, think there was a lot of shame around it. And I think I judged myself and what was wrong with me and why couldn't I have a healthy baby and just all of these horrible things that we talk to ourselves in a way that we would never speak to anybody else. Like I would never.
Sharon (18:00)
So come.
blaming
ourselves for that when it's not us who's making that happen.
Dorothy (18:12)
So I think I had to go through a lot of healing and do a lot of work on my own before I was ready to then talk about it on my show. By the time that the show, the opportunity for the show was offered to me, I think the timing of that was, it was right. Because I think if it was a year prior or even two years prior, definitely three years prior, no way. I never would have done it. And if I would have done it, I would have done it all wrong.
and I wouldn't have been able to help anybody because everything was just so raw. And so I think being able to talk about all of this on my show, it really allowed me to help so many other people. And I didn't, I actually did it, I think, more selfishly. I didn't do it like, okay, now I'm gonna talk about everything that was hard for me and that's gonna really impact other people's lives. And it's gonna be great and that's why I'm gonna do it.
I don't know why, but that's just not the way that it registered in my mind. But that's what ended up happening.
Sharon (19:15)
And it also comes out as vulnerability.
Dorothy (19:17)
Right, right. And like the amount of messages that I got from people, that I still get from people, day in and day out on Instagram mainly, and even just like some people who are going through really hard struggles with trying to get to their second child or have their third child or whatever it might be, you know, I've even given them like my phone number if they want to text me because my heart breaks, you know, and my heart breaks for anyone that's in that situation because I was there.
So I think really just it's allowed me to just really help so many women and really, really have a huge impact on their mindset and their mental health throughout their journey.
Sharon (19:58)
because that is so important when you're going through it. And I want to share something here too, because researching your story helped me reframe mine. I've had four miscarriages, I had one, and then I had two live births, and then I had three in a row, three miscarriages in a row. And I didn't quite realize until then that two miscarriages, two subsequent miscarriages, is considered infertility.
And so when I finally got pregnant with our third daughter, with our youngest, our daughter, ⁓ I was high risk. I didn't quite realize until I did this research, I didn't quite realize that all of these miscarriages are actually considered my own version of infertility. So everything you just said about blaming ourselves, why can't I carry a child to term, what is wrong with me? It's not that,
And I discovered other things that were going on in my body that I had to deal with so I could have a healthy child. So that was a really interesting journey.
Dorothy (21:01)
I'm really sorry that that happened. imagine even especially at that point, a lot of people weren't talking about it. was like a little bit. at all. Yeah, it was a much more private situation and a private thing. you know, now it's so there's such a huge community of women to support one another. So I just wanted to say that real quick.
Sharon (21:22)
Thank you, thank you. So to the women who are listening to this, who have experienced a miscarriage or two or more, and from where you sit now, what advice would you give to them? Because I know, as we just said, you feel alone, you feel invisible.
Dorothy (21:37)
So I really don't like when people say everything happens for a reason. I don't like that. So there's something about that phrase that feels dismissive. So what I'm going to say is every hardship that you endure and every painful experience that you experience, you have to just keep in the back of your mind and trust.
that as painful as it is and as disappointing as it is, it is happening for you.
Sharon (22:11)
Hmm.
Dorothy (22:12)
Nothing is happening ever to us. We're only victims of this life and of other people and of circumstances if we have that in our mind.
like if I was able to go back, and of course hindsight's 20-20, but if I was able to go back and if I was able to say to myself, okay, this is now, because I had three miscarriages in a row as well, and it's
Sharon (22:38)
Sister
Dorothy (22:39)
It's debilitating
situation to be in. Because it's you're like, it's like Groundhog Day of the worst sort. And if I was able to go back and say to myself, okay, this is horrible, it is horrible, cry, be upset, scream, be angry, have every single emotion, but just keep your eye on the fact that you're not gonna be in this situation forever.
It is leading you somewhere. You don't know where and you don't know when. But these horrible things that happen, they are leading all of us somewhere. And I guarantee you, without the shadow of a doubt, they're all leading us somewhere that's better than we could have ever dreamed. Now, that's easy for me to say, right? Because I have my daughter, I have literally the girl of my absolute dreams.
So I feel like people are like, well, it's easy for you to say it because you got your daughter in the end. And I got my daughter, by the way, not through five rounds of IVF, not through getting pregnant even naturally, because then I had another miscarriage doing that. But then after all of that, getting pregnant when I wasn't even trying and didn't even give it up.
Sharon (23:53)
heard that happens,
right?
they end up adopting, and then they get pregnant. Yeah. Because your body just is like, okay, we're good.
Dorothy (23:57)
It's wild.
Who knows? Who knows how or why or when? I think for me, I think I had to go through all of that because I needed to learn the lessons. I needed to learn. I needed to adjust. I needed to change a lot of things about myself and heal deep, deep rooted things that were not connected necessarily to the present IVF cycle or the present miscarriage. It's like way, way, way back. And I just try to tell people now,
Like, honey, I know, I know that you're having another miscarriage. I know it's another month and it's a negative pregnancy test, but I promise you, you will not be here forever. That I know.
Sharon (24:41)
Yeah.
That's true. And you know what this reminds me of? It parallels this whole mom reinvention journey. Oftentimes women will try something and they'll think their perception of failure, but you realize that you're not failing. You are learning something. You're learning something about yourself. You're learning something about your capabilities. Even in the miscarriage situation, I had never thought of it that way, but thank you for that. You're learning. It's happening for us. Yes. Not to us. And I think that's brilliant. So thank you for that.
It's.
Dorothy (25:12)
because in the situation, like, you you're in a terrible situation and you're depressed and you're anxious and you're hopeless. And so you don't really want to be optimistic. Like, well, this is all happening for me. It's very, very difficult to say that. It's hard to see it that way. But if you can just a tiny, tiny bit trust, have just blind faith that the universe has your back and that it's all working for you.
Sharon (25:29)
to see it that way.
Dorothy (25:40)
It's really unbelievable what kind of miracles can happen.
Sharon (25:43)
I love that. Well said. Thank you. All right. Switching gears. That Greenwich Life. OK. You are clearly having such a blast doing it. I was at the season two kickoff party that you threw. Another phenomenal mom skill. Right. You know how to throw a good party.
Dorothy (26:00)
You really did. Thank you. Thank you. It was awesome. It was a really awesome night.
Sharon (26:04)
of
fantastic night and you had your husband and your kids there until it was bedtime and then he had to escort them out. So what has surprised you the most about running the show?
Dorothy (26:13)
So the event, what surprised me the most? I I think when women step back from their career and they take a break from what they've always done best, I think, and then they come back to it, there tends to be a little bit of doubt, more so than ever in the past. Like, can I still do this? Do I still have it? Am I still like...
My brain kind of feels a little bit more scrambled these days.
Sharon (26:41)
That's
the same thing with the whole idea of reinvention and next chapter. Right. I've lost my skill set. I don't belong here. Nobody wants to hear what I have to say. Right. 100%.
Dorothy (26:51)
Right,
I knew that everything that I did throughout my career set me up perfectly to be able to throw that Greenwich Life live and then, you know, the party was the easy part, by the way. Like looking, you know, all dressed up and wearing some fun sparkly shoes and taking pictures of everyone. You and I took a picture together on the step and repeat and, you know, having like a...
Sharon (27:15)
your pal.
Dorothy (27:15)
Sip of the champagne, having the DJ, that was all the easy part. But then moving everybody, 150 women, into the quote unquote recording studio and coming in with a seated audience and a full run of show that needed to have a very tight timeline with a lot of different audio visual components and this video needed to play at this time, which of course I wasn't doing, right? I had my AV people.
Sharon (27:44)
It was really well orchestrated.
Dorothy (27:45)
Thank
you. like producing that part of it, that's the part where I was like, can I do this? Can I do this? And I was like, wait a second. I've like hosted live TV. I know how to be a traffic cop. had a timer. I had a clock right there on the floor. And I kept time and I did it. And I did it well. And I did it just as well as I always have my entire career. And it reminded me that even though some things about our lives may change and that we might change, those
Sharon (28:14)
Thanks
Dorothy (28:14)
things
that we were born to do and those things that we just are so good at and that we know how to do and we can do in our sleep. They be there. And women have to remember that. Yes. Because even if we take a break, they're always going to be there.
Sharon (28:21)
Be there.
Exactly.
And I think that's a really good lesson for moms is no matter what you did before, whatever you're doing now, leaning into family life, hybrid mom, whatever you're doing, who you were before, you are still that person, right? I was still a writer, a copywriter in advertising. I was still an award winning copywriter in advertising, even though I wasn't doing that for the time being. So I think that's a really good point for women to realize.
Dorothy (28:52)
And one other thing that I want to say too is that the fact that I'm able to sit here and say how great it went and how great of a job I did, that is something different. That's something different. An older version of me, if I were to do that whole event, if in my 20s, before I had kids, before I grew up, before I went through all the trauma that I did and I grew so much as a woman and as a person, that person would be like,
Yeah, it was awesome. It was great. But you know, like this happened and this didn't go the right way and I could have done this better and I did. And you know, I don't feel that way. I feel like I was able to walk away from that event and be like, yo girl, you killed it. Like you killed it, mom.
Sharon (29:42)
And you know what? That goes to the whole perfection thing, right? Let's be happy with what we can create when we create it. And no one notices if something went wrong. That's right. It was beautifully orchestrated. The timing was great. And it all happened in sequence. And that's what you want. So you did it. You did it. right.
this is sort of you finding your new voice. You were telling me about that you had stepped into this auctioneer world. Yes. And that you have been compared.
To Lydia Finett, I I'm saying it
Dorothy (30:12)
It might be a self-comparison, but yes.
Sharon (30:14)
But that is serious praise because she's extraordinary.
Dorothy (30:17)
It actually, yeah, no, I'm sorry. You're right. It's not a self-comparison because there were several. because I told you this. Several people came up to me over several years after I did the auction, the live auction for my son's school and mentioned this woman's name to me.
Sharon (30:29)
which is, you're like, at first, she's like,
I don't know who this is. She's amazing. She's amazing. She gets like $10 million gift. Yeah, she's so how did you stumble upon that skill? And is it something that you want to grow into even more?
Dorothy (30:40)
So yes, I do want to grow into it even more. ⁓ It's so much fun. And I have lot of fun with it when I'm up on stage because it's unscripted. And so I get to really kind of bring my own personality into it and engage the audience in a lot of different creative ways. And I stumbled into it because my son's school did a parents' fundraiser every single year. And they had a live auction as a component of it.
and they auctioned off things like principal for the day and a reserved parking spot and things like that. And so they,
Sharon (31:14)
important things. exactly.
Dorothy (31:18)
asked me to do it and because they knew my background and I said yes, because I don't know what like there's gotta be like nothing really to it, right? Like you just kind of get up there and get the crowd excited and you talk about the things and I don't know. I try to as much money as you can and so
Sharon (31:34)
I didn't, as much money as you can.
Dorothy (31:38)
I don't know, I had a couple guidelines, like the starting bid and how they were gonna be increased, but I just kind of got up there and it was an Alice in Wonderland themed event and so I was the queen of hearts. So I was up there screaming off with their heads and bidding people up on all of these different prizes and it's not a really formal event, it's not like a gala and so it's a standing room only and it's loud and the acoustics are bad and everyone's talking and socializing and.
It was really a trial by fire and I did it and I don't know, I just knew how to do it. There's no other way to really put
Sharon (32:16)
So we see more of that in your future.
Dorothy (32:18)
For sure, because
I since have been asked to do it for other events. mean, I literally yelled sold to Aaron Judge from the Yankees last fall at a gala for the Carlos Rodan Foundation. So, yeah, I'm doing it now like with like celebrities in the audience. I mean, it's wild. So Lydia is my mentor. She's just incredible. I love her. I went to one of the retreats that she did. I'm in close touch with her and she's
really become like a mentor of mine, you know, to kind of move forward in this industry.
Sharon (32:50)
I love that. That's so nice.
switching a little more into
what part of your career do you think would have been impossible without motherhood? And what part of motherhood would have been harder without your career?
Dorothy (33:02)
what part of my career would have been impossible without motherhood? I'm going to go ahead and say, I keep coming back to it, but it's just the truth. mean, I think my podcast. just don't think that I could talk about the things that I talk about in the way that I talk about them without being a mom and having that perspective on life and on the community and.
my listeners and things like that. And then the part of motherhood that would have been impossible without my career, I think it's probably the organization. Now, I don't claim to be organized because I'm not. I can fake it. And I think my career and working for myself, because I started my own production company when I was 28 years old.
Sharon (33:48)
But you
Dorothy (33:59)
And I think running that company,
it made me like figure out how to be organized, right? And how to kind of pace each day and each schedule. Like working for yourself when you're working from home well before COVID and everybody was working from home. When you're 28 years old, that's a different kind of experience than almost all of my peers were having at that time.
Sharon (34:21)
Or at that point I was working in an office. All right. So that sort of is a beautiful segue into mom skills. What are the ones in addition to organization that that you rely on on a daily basis?
Dorothy (34:23)
And everybody was.
Mom skills. Well, mean, listen, I have to say the number one thing that I rely on is patience.
Sharon (34:36)
and call them life skills too.
⁓ huge.
Dorothy (34:44)
Patience and I think probably I needed to have a lot of patience throughout my career because
my ambition was just always so huge and then it doesn't always Go at the pace that you want it to go right and I feel like it's similar with my kids. It's a little bit different but Patience is so important without it. I feel like I would just be a mess every single day
Sharon (35:10)
Yeah. Patience will save your sanity. Yes. Yeah.
Dorothy (35:13)
And save my children. Yes. For me, like lashing out.
Sharon (35:18)
I remember once I was in Chicago with my sister. We were in the car and the kids were in the back and they were like screaming and going crazy. And I was just being like really chill about it. My sister said, why are you so nonplussed about this? I said, what am going to do? Right. Right. I can just say something and they'll get even worse. I'm just going to ignore it. Yes, exactly. Good point. Patience, organization. Love that. OK, I have a couple of lightning round questions for you. Yes. You ready? Yes. OK, here we go. Work hours or mom hours?
Dorothy (35:47)
Mom hours.
Sharon (35:48)
figured you'd say that. A boundary you wished you had set sooner.
Dorothy (35:53)
Ooh, hiring a person that was not a good fit for the job, because that can cause a lot of unneeded stress.
Sharon (36:04)
Very true. Because you've talked to so many of them, do you have a favorite celeb that you interviewed?
Dorothy (36:11)
⁓ well, I didn't really officially interview him, but it's probably Bradley Cooper. I mean, I ran into him on the street and then we ended up walking like five blocks and chatting with each other because I told him, you know, I was a celebrity reporter and we're both from Jenkins Town and he's my hall pass. If he ever gave me a chance, my husband's just, he's done.
Sharon (36:33)
All right. How about just an interview, though? Maybe like an official interview with Bradley Cooper if you're listening.
Dorothy (36:33)
⁓ And he knows it.
Sorry,
an official interview, my favorite celebrity that I've ever actually sat down with and interviewed would have to be Dave Matthews. Because I'm just such a lifelong fan. they just announced that he's gonna be headlining the Greenwich Town Party this year and I was screaming when I found that out.
Sharon (36:58)
Yeah, yeah, I love that. Something motherhood gave you that no job ever could.
Dorothy (37:04)
think it would be like a softness. I think motherhood has softened me in the best of ways and no job that I ever worked in or industry for sure was ever going to be softening me. If anything, it was gonna have the opposite effect.
Sharon (37:06)
Hmm.
Interesting. I like that answer. Thank you for that. So for a mom listening who is sitting on an idea and she's waiting for something until she feels it's more legit or she feels that she's really ready or 100 % ready, which that never really happens. What advice would you give to her at this moment?
Dorothy (37:42)
Quiet the doubts. Say goodbye to the doubts. Like, let them be there, but just put them in the background. Because if you listen to the doubts, you're never gonna do anything. Would you talk to a friend and use the same language with your good friend who wants to start something as you're hearing in your head with your own doubts? You would never talk to a friend like that.
So why are you talking to yourself in that way?
Sharon (38:13)
think
women in general, also moms, we're so good at doubting ourselves. When you realize everything that we've been doing to raise the next generation of humans, we have such an enhanced skill set that we should be like, yeah, I can do any of that that you want me to do.
Dorothy (38:30)
Well, we're very good at being practical because it's our job to kind of keep everybody in the house, in line, keep things organized, have some kind of structure. And we have to be realistic about what the day is going to look like and how many activities we're signing our kids up for and things like that. So we have this practicality about us. And I think sometimes because we're so practical, it prevents us from taking steps to pursue the things that we dream about.
and the things that we're really good at. Because it's not going to make enough money to justify the cost of childcare, or it's going to be too inconvenient with the other things that you have to handle on a day-to-day basis. We're just so practical, because we try to, I mean, we're CEOs, right? We're running our own companies just within our own households.
Sharon (39:01)
Good point.
CEO, CFO, so many titles.
Dorothy (39:28)
Yeah, and so anything that
interferes with the system that we have in place and the well oiled machine that we've Kind of created I think it's easy for us to just shoot it down and come up with so many reasons why we shouldn't
Sharon (39:42)
Why not? You the other thing I'll add to that is, it's never really too early to start thinking about what you think your subsequent chapter could be. And so for a mom who's in that moment, she may not have to act on it yet, but even just having those ideas, writing them down, having a journal, just putting down those ideas and dreams and wishes of things that you want, that's still moving forward in that direction.
Dorothy (40:11)
That's right, because
you can even just do something so small, not even every day. I don't really subscribe to the idea of like, do something small for five or 10 minutes a day. Sometimes there's days I can't find five or 10 minutes. I hear you. I just can't, you know, like it just is what it is. So I don't subscribe to that, but what I do subscribe to is when you can.
Do something small to further that. If you're thinking about maybe starting some kind of a needlepoint group, I don't know. I don't know why I gave that as an idea because I would never do that. I'm not interested in that, but I know it's a big trend right now. But if you're interested in doing something like that, then maybe like five minutes before you go to bed at night, maybe you can hop on your phone, even though they say, don't look at your phone before bed, hop on your phone and look at some Instagram accounts, some needlepoint.
Instagram accounts. Maybe you're thinking about going back to school to become a therapist. I don't know, I use that as an example because that's something I've always thought about doing. And if you wanna do that, maybe you find a book that's interesting to you. Baby steps. And maybe you read the book, maybe you read a chapter of the book at night before bed.
You know, it's really just like, how are you using your free time? Because chances are you don't have a lot of free time. If you're like me and you have even one child who's not in school full time, you don't have a lot of free time. So you have to use that free time really, really carefully.
Sharon (41:37)
Right. And those baby steps help you, you know, build into whatever your next chapter might be. Right. Okay. So speaking about next chapters, I have a question that I ask all the amazing women such as yourself that I get to interview. Since this is the Momtimore podcast, and we are all about reinvention and next chapters, when you look ahead, going beyond everything that you have created already, what feels like your next more?
Dorothy (42:05)
I love this question because I feel like throughout my entire life, I've always wanted more and I've always had something more in the distance that I'm working toward. And I certainly do, but I don't need it. I don't need it in the way that I once did. I want to...
Continue.
doing the podcast, I'll be doing a third season down the road after I've taken a sufficient break from that workload. I wanna continue traveling and writing about travel and going to incredible places. I have this year ⁓ couple amazing trips coming up. I'm working with a tour company and potentially going to Africa with my son on a press stay safari. Are you?
Sharon (43:03)
We're going there in August.
We are. It's so exciting. Finally. Safari.
Dorothy (43:08)
I need to hear more about that. That's amazing.
Going to Lake Como with two friends for their 50th. I have a lot of things coming up and I'm going to be writing about it all and I love doing that. I want to continue spreading my name throughout the nonprofit sector so that I can continue emceeing and doing live auction for galas and events. I want to do another really fun, big event for women like I did for That Greenwich Life Live for season two.
I would say my more is probably just more of everything. It's not like something huger and greater, something that I'm not already doing. Probably down the road there's a book, but it's really far down the road. It's gotta be at a time where my brain has way, way, way more space because right now I just don't. Yeah, so it's gotta be like when my
Sharon (43:59)
a little.
Dorothy (44:04)
know, when Gemma, my daughter, is in school full time. And I don't even mean kindergarten. You know, the book is like way down the road. ⁓ But I think it's just more of what I've been doing because I really enjoy it. You know, I love what I do. And I just, my biggest more is just like that it will continue.
Sharon (44:25)
Okay, Dorothy, so please tell our listeners where they can connect with you online. And folks, everything is gonna be in the show notes.
Dorothy (44:31)
So I'm on Instagram at Dorothy on TV. That's all the behind the scenes, the personal, the professional, and the breakdowns, all the in between. And then my website, dartheyontv.com, revamped it this past summer. It's everything there is to know about me, everything that I do, everything that I have done. And you can also listen to That Greenwich Life on Apple Podcasts, Spotify, and wherever you enjoy your show.
Sharon (44:53)
Dorothy, my friend, this has been such a lovely conversation. What's so interesting for me is I've gotten to know you on a different level from this super honest conversation. So I appreciate your time. I love everything that you have going. I love your more of just more of what you're doing. Your show is fantastic. Your energy is undeniable. you. And just...
wakes everybody up when you walk into the room. So I just want to say thank you for your time today. It's been a wonderful.
Dorothy (45:21)
I to tell you also, Sharon, for the fact that I've been doing this since the early 2000s, I am so impressed by you.
You're an incredible interviewer. And it was nice to be the one kind of in the hot seat for a second.
You had a lot of really creative and thoughtful questions.
And I think that's really admirable.
Sharon (45:41)
Well, thank you for that. And I think it's a perfect place to end. Really appreciate your time today, Thank you so much for being here, Dorothy. I'd like to read another five star review with a shout out to Mia NKC. And Mia wrote, there's a reason this podcast is winning awards and climbing the charts. Great host, great topics, great guests. It is the podcast trifecta. Well, thank you, Mia and listeners. If you keep writing those five star reviews, I'll keep reading them.
Dorothy (45:46)
Thank you for having me.