My Journey to Motherhood

Jessy Grossman is a long time entrepreneur in the digital media space. She's passionate about supporting women in business and being at the forefront of innovation. She’s been quoted in Forbes and was awarded a spot in the “Influencer Top 50” by Talking Influence. In less than two years she created one of the fastest growing talent agencies in the country. Amidst unprecedented growth, she sold the multi-six-figure agency and pivoted to focus on her long-time passion project: Women in Influencer Marketing (better known as WIIM). Founded in 2017, today WIIM is the premiere professional organization for those who work with influencers. The community offers networking and new business opportunities, career services, continuous education and more. Jessy also does consulting, advising and influencer marketing recruiting with her company Tribe Monday. You can find inspiring stories and more about Jessy on the WIIM Podcast. Check out iamwiim.com and tribemonday.com for more information.



Jessy: So this is going to be a pretty personal episode. I did a quick poll on my Instagram, a personal Instagram, not WIIM’s, to ask if anyone would be interested in having me share my personal experience about being a stepmom. And fertility and wanting to have my own kids. I have been really struggling with this lately.

Like, I don’t know how much personal stuff to share on this podcast versus having it be straight-up interviews with really interesting people that you guys are very accustomed to hearing. I came to the conclusion that even if all of the handful of people said on my Instagram stories that they would be curious to hear the story on the podcast even if I could just reach those people and the rest of you guys are like, you’re not so interested, I’ll tune in next week, that’s okay. 

Because the sign behind me, if you’re watching this episode on YouTube, it says Women In Influencer Marketing. It doesn’t say people in influencer marketing and it doesn’t just say like we’re all business all the time in influencer marketing. I would love to talk more about this stuff and I would love to get more personal with you guys.

I just don’t know if there’s an appetite for it. So I’m taking a little risk. And if this isn’t your cup of tea, it’s all good. You don’t have to keep listening. Hopefully, you tune in next week though. But this week I am going to be talking about what it is to be a stepmom. What it is to also be, a mom in general, like a parent, the stresses, the great, wonderful parts, and also a little bit about what it is to be 36 years old and trying to have a kid. So, yeah, stick around guys, this one’s going to be pretty good

Jessy: All right guys, so I’m going to be as real and open and candid as I can be. This is something that I’m working on transparently, it’s not so easy for me to open up to anybody, honestly, like there’s like a tiny tiny handful of people in my life that I consider like my people that I can be super transparent, open with, but it’s a challenge for me on this podcast.

Even in my own office, I’m sitting here by myself and if I just, forget the fact that people are listening, maybe that’ll help. It’s probably a fear of being judged, I’m sure. But yeah, I’m gonna try to be really open and honest with you guys about my experience with parenthood. 

So, I became a stepmother, back in about like 2018 when I met my boyfriend, Paul. And I knew that he had a daughter, he was going through a divorce at the time and we survived that insanity. I don’t know if any of you guys have been through a divorce, whether it’s like your divorce or someone else’s, but it is quite the endeavor. 

We happened to be going through it during COVID, which had additional challenges as well because the court system closed and it was a pretty contentious divorce. I knew he had a kid and actually loved that.

So I think it is a great place to level set and explain why I loved it. I’m really not just saying that it’s because I’m a product of divorce. I had four parents growing up. I had my biological parents and my step-parents, both a stepmom and a stepdad, from the time that I was three which is like very serendipitous. Is that the word? Circuitous probably is a better word because Zoe’s parents split when she was three. 

And so that’s when I came into her life. I was excited to hopefully right the wrongs of my parents. I feel like, when you become a parent, that’s the goal always anyway, usually. Very few of us are fortunate to have like fantastic childhoods and parents to look up to. I certainly do not.

I really felt like it was my destiny. I know it sounds so over the top, but I really honestly felt like it was my destiny to be a stepmom and to do this thing right. And I was excited. Oh my god, I was nervous. You guys, when I first met Zoe, we were actually just talking about it this morning. 

We were talking about it this morning. I was taking her to camp and she was like, what’s the first thing I said to you when we met each other? And of course, I don’t remember the first thing she said to me, but what I told her is slightly different from when I first met her. 

So I first met her, I’ll tell you both. I first met her, after my boyfriend’s grandfather passed away. He had people over his apartment. After the funeral and his daughter didn’t go to the funeral. She was super young, but she came, to the house after I think her mom must have dropped her off and everybody, family, and stuff was over. That was the first time I was going to be meeting her.

You guys. I don’t think, honestly, I’m like nervous right now recounting the story. I have never been so nervous in my entire life. You guys, I have been on stages. I’ve pitched businesses. I’ve been in really high-stakes situations to this day. I don’t think I was ever as nervous as the day that I met Zoe.

You guys she was three and a half. But I think we knew each other for about probably almost a year at least before, I met his daughter. So I had heard about her for a year and like all this anticipation and just I know how troubling my childhood was and like what I wanted to be for her, who I wanted to be for her was it was like a fairy tale character like I wanted to be something that was like near non-human for her. So the expectations from my mind were huge and I was just so nervous. 

And so that’s when I technically met her for the first time, although when she asked me just this morning what did I first say to you, I remember I met her again the second time and she was like asking me to, play dress up.

She wanted to play dress up with her cousins, like dresses for when she was a kid and she had some like princess dresses and stuff. And then we ended up on the balcony of my boyfriend at the time, his apartment. We ended up on the balcony and she was like riding her bike like back and forth on this teeny tiny balcony. What a New York moment, right?

And that was the first time that I met Zoe. I may just be like the luckiest person on earth when it comes to her, but like I’m obsessed with her. She’s the voice at the end of this podcast, I don’t know if everyone’s aware of that, but at the end of every podcast, we have her like four-year-old little voice that says tune in next week.

That’s Zoe. I’m lucky you guys, cause she is like the best kid ever. And I feel like it’s like selfishly, it’s like healing some wounds from my own childhood and my stepparents that I just didn’t get along with and my parents that I no longer have a relationship with. But also, she’s just the best.

She’s so funny. I am looking at a picture of her right now on my desk. She’s so funny. She’s so empathetic. She’s just the biggest joy. I also think it’s I wonder if this age is just so magical. I met her when she was a little close to four, but she was three and she’s almost eight now. And these past few years have just been incredible. She’s my pal like she’s wonderful.

So with all that being said though, you know, I love meeting stepmoms because I don’t know very many at all whatsoever, and so when I meet one usually they’re a little bit older but not always.

And it’s just people don’t understand at all what it is to be a stepmom until you’ve walked in our shoes. It’s like definitely one of the most thankless jobs because parenting in general is a fairly thankless job, but you always have to be like backseat second fiddle to the parents, like her real mom and I’m using air quotes when I say that.

it’s a constant mind fuck, to be honest with you. And again, as I come into this having quite a bit of experience, firsthand experience as the child, of course, but like having had step-parents, it’s such a mind fuck.

The relationship, between our family and her mother has like definitely improved over time, which is great. But she has issues with me being in her life and I never quite know my place. I wish I felt like I had more of a place in our family that was more defined. 

And Paul does everything to support me like being her parent, like a huge person in her life. But I am her parent and, he does everything to make me feel a part of this family unit, but it’s a bizarre family unit to be a part of.

And I think that I also, I get in my own head and I question things. I get nervous. You guys, like I have invested so much like love and just been so vulnerable and like falling head over heels in love with Zoe. And I get nervous that one day she’s just gonna turn on me or other circumstances will basically like have her turn her back on me and be like who are you to me? You’re just my stepmom. You’re just my dad’s girlfriend. We’re not even married. 

Oh, that’s a really tough pill to swallow and for any of you guys who are also step-parents, I know you can relate. I’m privy to there are other stepmoms out there who follow this philosophy called nacho.

Like I’m nacho mom. I’m not your dad. Like I think it’s ridiculous personally like I try not to judge people but like I just don’t understand how you can do that and I feel very strongly about it because I grew up with stepparents who I don’t think my parents took into consideration who they married as they’re like second marriages, in reference to me. I don’t think that they were like, would this person be a great parent or step-parent to my kid?

I think in my situation like it was all selfish reasons about why they remarried these people, which is fine, you would like to think that there was some sort of consideration to say is this person going to be. A good parent to my child, like there’s some sort of prioritization there that like I brought a child into this world and I want to make sure that this person who is in their life is going to add to it, not detract from it.

And that was just not my experience. I don’t think my mom or my stepmom I don’t think they liked children. I don’t think they liked children. And it’s like a whole separate conversation, of course, but, I think that, with Zoe, I’m very lucky and I don’t understand the philosophy that I was explaining before, which is I’m not your parent because if I’m going to be your parent, like I’m your parent.

I don’t take lightly my responsibility with this young, impressionable girl, like this young, impressionable child who is like so reliant upon me and the rest of her parents and looks up to me for guidance. And I don’t take that job lightly. 

There are stepmoms and stepdads who they’re like, it’s not my kid. And like washing my hands of it. And I’m around sometimes and, or maybe they’re just like a fricking taxi driver driving them to and from places. I don’t really understand it, but there are people who are happier operating that way.

I think the reason real, realistically is like what I was saying before they don’t want to get hurt. They don’t want to invest so much only to get really hurt. There are relationships between former spouses can be really complicated and like, how you fit into that can be very challenging.

I’ve experienced it firsthand, but I think that I care so much less about the adults and I care so much more about the kids in this situation. So my philosophy is I give a big fuck. I give a fuck and I give a huge fuck. Sometimes I give maybe arguably too much of a fuck. 

But I love her so deeply that I couldn’t imagine having things be any different. But yeah, real talk, I get scared. I get nervous. If something God forbid happened to her, I can’t make a decision for her in a hospital I can’t make, I have influence, and there is something to, having things be official.

And even, once Paul and I do ultimately get married, I’m still quote just a stepmom. And even that vocabulary, like even that verbiage, it’s like really messes with a person. And it can be really confusing. You say I just believe that words are really powerful and saying things like that have an effect on a person, have an effect on me.

All that being said, step parenthood is right for me. I know that. like I said earlier, I think I’m healing from a lot of my like childhood garbage because I’m able to experience it from the other side of things and just do it better than my parents did it. I think that it’s the best fricking way to know if your partner is a good parent because you get to test it on like their kid from another relationship, which perfectly segues into that, yeah,

 we’re trying to have our own kid right now.

and the reason, there are lots of reasons, why I want to, one of the reasons I’m so confident in wanting to with Paul is because am in a very unique situation where I get to see firsthand how he is as a parent and he is the best dad ever. I love who he is as a dad.

It is such a turn-on to see how he is as a father and, I’ve not always wanted kids. That’s probably something worth mentioning. In fact, I made like a proclamation, like my mid-twenties I don’t think I’m the kid type. I was the youngest. I had step-siblings. So I didn’t really ever have kids around me that were younger. I was always the youngest.

I just like never really found myself around kids as a young person. And as I got older, I like got really into my career and it’s just it was not a desire of mine. It certainly wasn’t a burning desire that I was, one of those people that was like, oh, I can’t wait until I can finally have babies. That just was not my thing. 

To probably like my early thirties you hear this a lot and I’m certainly not the only one to experience this, but it certainly was what I experienced early thirties things just changed for me, but also I would say things really changed for me once I met Paul.

And once like I found the person that I wanted to be a parent with, it made a huge huge difference for me personally. So, we had to just get this giant divorce behind us, settle into life a little bit, like post-pandemic, as we live together during the pandemic and life has just been crazy.

And now I’m 36 and wanting to have a kid at 36 has its challenges. I’ll be so personal with you guys. For years have had this unfounded belief that I wouldn’t be able to have kids or that I would really struggle at the very least in having kids. So having Zoe, I felt like I was like, oh, I like tricked the universe.

What a cool way around this, because even if I’m not able to have my own, I can still experience parenthood. I could still scratch that itch of wanting to be a mom through her. But in the past year and a half or so, I’ve really decided that I want to have also a biological child if I can. I at least want to try.

So here I am at 36 trying. We’ve been trying naturally for close to a year, probably at this point, and there’s so much that I’ve learned, but there’s, oh my gosh, so much that I am continuing to learn. I should probably stop here and just say, I am absolutely no expert in trying to get pregnant at all whatsoever.

I actually feel like I learned nothing as a child. And very little as an adult. I am very much on the journey right now to figure this all out for myself. I swear to God, I feel like I barely even knew my own biology and I’m not even exaggerating with you guys. I learned nothing.

Do you know what I learned? That if you look at a boy wrong, you’ll get pregnant. That’s what I learned. I don’t know about you guys. Did anyone else learn that way too? Cause that’s how I grew up. And now that I’m trying to get pregnant, I am doing much more than looking at a guy and I am not getting pregnant. So I was going to like my OBGYN.

Finding one that I liked was tough and I also switched to insurance recently. So I finally found that office that I liked a lot. They decided to put me on what’s called Clomid, I’m not an expert. So I’m honestly gonna even struggle to like to recap what I’m currently experiencing.

Don’t shoot the messenger if I am screwing this up a little bit. But basically, I think Clomid basically makes your follicles pop. Like not literally, but like they make them more mature so that, they can be fertilized easier. And you can get pregnant. 

So I’ve been on Clomid now for was it two or three months? They like increased the dosage last month. They doubled the dosage last month. And nothing was happening. And I don’t know exactly who it was, who suggested to this probably at least two or three people, but some people in my life are basically saying, you should probably look to finding an infertility doctor, like someone who specializes in that stuff sooner than later.

Don’t just go to an OBGYN, like it doesn’t hurt to have someone good queued up and like just go and see. Take an appointment and see what they think about the situation. And I’m actually so glad that I did. So if that’s any advice that I can give anyone listening who’s going through the same thing, it’s that.

There’s no reason to wait if you’re 36 and older. So, 36 for some of you guys who don’t know. From a doctor’s perspective, like a medical perspective, that’s like the line, which I hate saying that this even exists. Cause we all have seen Kourtney Kardashian fricking get pregnant at 44.

So she’s giving us all hope here. there was who’s Naomi Campbell. Was it her? My God. She just conceived her own baby, like in her 50s. I might be misquoting that but like basically there have been lots of more mature women who are getting pregnant and there’s a lot that is like medically possible however 36 whoever decided that I don’t know is this like Line where you were considered a quote geriatric pregnancy.

Okay, I fucking hate the person who coined it because wow, I’m 36 I feel fine. I feel a little older than I was in my 20s. But do we feel geriatric? No, is that messing with me? Because now I’m thinking like I’m not gonna be able to conceive because I’m too old hell. Yes, that is messing with me. So when you are 36 or above, technically speaking, if you have been trying for at least six months and are not able to conceive naturally, then you are technically considered infertile and you can go and see an infertility specialist.

If you are under 36, it’s a year that. You are able to make that determination and that determination, is also, I think for insurance purposes. So just to like level set here. Okay. So it’s been at least a year that we’ve been trying. I would say actively trying for at least six months. So we went to go see this doctor. I like our initial intake appointment, which consists of them asking a ton of questions.

And then over the course of this first month, they’re doing like a lot of testing. And then next week we go back in and we actually speak with the doctor. We haven’t seen the doctor yet. And they basically look at all the results of the tests and we’ll see what happens. And hopefully, they make good recommendations.

I will say this a lot of people in like communities that I’ve joined to learn about fertility and infertility and how to get pregnant and all that, what is it? TTC trying to conceive. I’m like learning the jargon. A lot of people point to stress as being a major contributing factor to not getting pregnant.

So people will say things like, definitely use acupuncture, get massages, like try to alleviate the stress in your life. But I’m like, So, I was also simultaneously told to get off of my anti-anxiety medication because theoretically, you don’t want to have medication in your system while you’re trying to conceive because you don’t want anything to affect the baby.

So my anxiety levels have been a little extra elevated in the past year that I’ve gotten off of my medication that I’d have been on for years prior. And yet, I’m just supposed to relax. You guys, it has just been a giant mindfuck. I do want to explore acupuncture. I’m all for massages.

Please, I freaking love a massage. So, oh my god, go relax. But just telling me that, I’m supposed to just like, basically, don’t be stressed. Stop being stressed, Jess, and then you’ll get pregnant. It’s just it’s a big mindfuck. I think the ep the title of this episode should just be, trying to conceive, what a fucking mindfuck.

So I’m going to try those things, look into it. I’m curious to see, of course, what this doctor will say, basically to get even more specific with you guys, because the whole reason I’m having this conversation on this podcast in this forum is that I’m hoping that this will help people who are going to maybe go through this in the future or presently going through this.

Preliminarily, my doctors think what’s going on is that my follicles just aren’t getting large enough to be fertilized. Basically, like I have a lot of them, which is really good. If I have to end up going the IVF route, a freak ton of money. And I’m just trying to see if I think that this law in each state varies.

So I think New York might cover some, but I have to see if I have the right insurance to get it covered, like the whole thing. I don’t know. But basically, it’s good that I have a lot of eggs. I have a lot of follicles. It possibly could be because I have PCOS, which has actually never been diagnosed, but that’s possible.

And someone just the other day was saying like, having a lot of eggs could, like I said, be helpful if you end up going through IVF, but the issue with, trying to do this naturally is that my eggs aren’t getting big enough or something. I don’t know. My body’s not working for me.

So with all that being said… That’s where I’m at. It’s been a year plus of this, but I only feel like I just started and there are days that I feel pretty defeated and I feel like I haven’t even started. I’ve heard that it’s like, it can be a very challenging road. I’m literally looking at it on my desk right now.

There’s this thing, it’s like a prenatal vitamin that. I have on my calendar that I’m supposed to be taking every morning and I’m just not doing it. It’s like stupid things that I should just be doing. I’m like, if this is difficult like being a parent is going to be of an infant is going to be way more difficult.

I feel good about the parenting thing. I never went through the baby phase and I know how challenging that could be. I just visited with my best friend and she’s a three-month-old and the overnights and all the thing, it’s quite a lot, but I’m like, it’s we got to I test my urine every morning to see if I’m ovulating and I don’t know.

There’s just lifestyle changes and It’s a lot. It’s just a lot. So this is obviously a very personal story that I’m sharing with you guys. I know people listening are going through it or have been through it. So if you have any words of wisdom, if you have any recommendations, suggestions, don’t pretend to be a doctor, but if you’ve gone through it yourself and there’s any advice that you want to give someone who’s like just getting started at it by all means message me on Instagram I’m very open to recommendations.

I think my next step after this doctor’s appointment is going to be looking into acupuncture because so many people have talked about how helpful that’s been and hopefully my body will cooperate my geriatric 36-year-old body, hopefully, that will cooperate.

Anyways, you guys, I appreciate you listening and I know this is a little bit of a non-traditional episode. but I’d like to bring you guys less traditional episodes because it’s my fucking podcast and I can do whatever I want. So there, again if you want to reach out and you either have questions.

I have limited experience, but I’m more than happy to share what I’m going through or if you have advice or recommendations, or whatever. My personal Instagram is at Jessy Grossman. And of course, that’s Jesse with a Y Grossman. I’m excited to have more intimate conversations with you guys on the podcast.

I hope you guys listened to the episode from last week. It was really good and I hope you guys tune in next week as well. All right, guys, until then, see you soon.


Founder of Women in Influencer Marketing and CEO of Tribe Monday

Jessy Grossman is a long time entrepreneur in the digital media space. She’s passionate about supporting women in business and being at the forefront of innovation. She’s been quoted in Forbes and was awarded a spot in the “Influencer Top 50” by Talking Influence. In less than two years she created one of the fastest growing talent agencies in the country. Amidst unprecedented growth, she sold the multi-six-figure agency and pivoted to focus on her long-time passion project: Women in Influencer Marketing (better known as WIIM). Founded in 2017, today WIIM is the premiere professional organization for those who work with influencers. The community offers networking and new business opportunities, career services, continuous education and more. Jessy also does consulting, advising and influencer marketing recruiting with her company Tribe Monday. You can find inspiring stories and more about Jessy on the WIIM Podcast. Check out iamwiim.com and tribemonday.com for more information.

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