My Jelly: Jenny Kaplan

Photos by Tommy Rizzoli, Words by Anamaria Glavan

Jenny Kaplan fell in love, traveled the world, got married, and started a business with her husband, Chris. They decided to make their business their baby for a year. “Looking back, it seems silly that I thought I could compartmentalize,” she reflects. A Maine native and co-founder of the design-forward Pieces Home, Jenny has spent over 20 years building an exciting life in New York. But her most rewarding chapter yet? Becoming a mom to her 5-month-old miracle son, Lenny.

After years of excruciating periods — and being told her pain could be chalked up to “hormones” — what began as a journey into motherhood turned into six years of a stage-three endometriosis diagnosis, a two-hour surgery that stretched to six, four IVF treatment rounds, five miscarriages, and surrogacy. From navigating the quasi-dating app world of surrogacy to the sheer panic of burping a newborn (been there), read on to discover Jenny’s inspiring story of love, loss, and the sweetness of embracing life with no expectations.

Patience is a virtue
I always knew that I wanted to be a mom but I wasn't in a rush to get pregnant. My husband Chris and I have been together for, gosh, 12 years. We traveled the world, started a business in May 2017, then got married 10 days later. We decided to make our business our baby for the first year. Looking back, it seems silly that I thought I could compartmentalize, start a business, wait one year, and then get pregnant. Ultimately, I found out that my body is not able to carry a pregnancy to full term. I've been pregnant over a handful of times but Lenny was born via surrogate. 

A tale as old as time—medical gaslighting
I’ve had a difficult period since I was a teenager. I was on birth control from high school through my late 20s due to cramps that were so horrible, I couldn’t get out of bed. I couldn't function. Yet when I would ask doctors what the root cause was, their answer would be, it's your hormones. It was a very lazy response. 

We were trying to get pregnant for seven months when my OB recommended I speak to an IVF specialist. He pointed out that I had a chocolate cyst (endometrioma) and that I would have to have laparoscopic surgery to remove this one cyst before starting the egg retrieval process. He was like, It's a really straightforward procedure and the recovery should be two weeks. Well, what was meant to be a quick two-hour procedure turned into a six-hour surgery. Turns out, I had stage three endometriosis. My fallopian tubes were stuck to my uterus and that’s why I wasn't getting pregnant. “It’s just your hormones.” Welp, okay.

The trials and tribulations of IVF
While I’m super privileged and grateful to have had access to IVF, the process was isolating. Chris couldn’t attend most appointments due to COVID restrictions, so I handled much of it alone. We went through four transfers over two years, all resulting in miscarriages at around six weeks. By the third transfer, we learned my case was more complicated than we realized—my doctor told me I was one in a hundred for women with three failed IVF transfers. After the fourth transfer in August 2022, which required a year of preparation with a new doctor and multiple procedures, we had to face the reality that it might not work. Chris and I spent that time openly discussing surrogacy if it didn’t. And, well, it didn’t.

Starting surrogacy is sort of like… Tinder?
Starting the surrogacy process felt like online dating (and I’m old school, I never online dated before). I received profiles, read through them, and waited for a mutual match. Our surrogate was in-state near the Canadian border which was the best case-scenario. It was crucial for Chris, me, our surrogate, and her husband to genuinely like and respect one another. This wasn’t just a transactional thing; they’ll be in Lenny’s life forever. We instantly clicked in our first Zoom meeting and that made this intimate process feel so much smoother. 

It’s overwhelming in the beginning because you have to discuss a lot of the stuff you don't want to discuss before you're even pregnant. What do you do if you get pregnant with twins? Triplets? What are your NICU preferences? There are some things that have to be left in the gray… there's just so many moving parts to pregnancy and labor that you can't totally plan for. We quickly found a comfortable rhythm though. We went to one in-person appointment (the anatomy scan) and FaceTime made it easy to virtually attend checkups and listen to the heartbeat. It was also important we respect that it was her body and her choice, so we listened to her needs and made her as comfortable as possible. For example, she wasn’t willing to waiver on being induced before 40 weeks, and we honored that in our contract.

Accepting no expectations
Chris and I could barely talk about our surrogate being pregnant with one another. We experienced so much loss and starts and stops that our mentality was, Okay, we got a good scan today. Let’s keep it moving. And she ended up having the easiest pregnancy. Nothing happened. Surrogacy is also wildly expensive and so varied. It's like a sliding scale. This puts added pressure because it might not work and, if it doesn’t, you just spent a lot of money. That’s the thing with IVF—it's an amazing tool but it's not a guarantee. You have to be okay knowing that you might walk away unsuccessfully. And I had to learn to let go of expectations. If you are pursuing surrogacy and you can find someone you like that has insurance, that’s going to help a lot with overall spend. Between freezing the embryos, the IVF prep for your surrogate, the agency fee, and the surrogate fee, I would say it’s a minimum of 150 grand. I chose to be transparent about the costs of surrogacy because there’s so much conflicting information online. For us, this made starting the process incredibly intimidating, especially since I didn’t have a friend at the time who could be honest with me and share insights to help us financially understand the true costs involved.

Son, meet surrogate
Conceiving was a heavy and dark thing for us for many years, but our surrogate and her husband came into our lives and—I don't know—they were like a breath of fresh air. They have a very lighthearted and fun energy, and they’ll be in our lives indefinitely. I send her photos of the baby all the time. I mean, she carried our son for nearly 10 months. We’re always going to be connected somehow. I want to introduce Lenny to how he was born as soon as possible, and I think it'll be really cool to see his relationship with our surrogate develop. I don't want it to be a thing that we don't talk about. It’s a part of our story and he wouldn't be here without her. I don't know. I'm still in awe that she gave birth to Lenny everyday.

Two things can be true at the same time
The beginning of the surrogacy process was really daunting.. I'm not going to lie. I had a lot of insecurities around it. But I made peace with the fact that me having a full-term pregnancy in this lifetime is slim to none. I'm not actively trying to get pregnant and, as time has gone by, I’ve changed my “maybe I can” mentality. Why would I rock the boat and put myself through something that could be potentially dangerous for myself and a future baby? It took a lot of therapy and time and facing things head on to be in a place where I was mentally strong enough to start the surrogacy process. There’s definitely moments where it feels weird that you're not carrying your own child. That you're not connecting with your baby in your belly. But two things can be true at the same time: I was endlessly grateful to our surrogate for carrying my baby, but she was definitely more connected to him during the pregnancy than I was. And that's a lot to wrap your head around sometimes.

“This is not about you, it’s about him.”
Lenny ended up in the NICU for a week because his umbilical cord was wrapped around his neck and he aspirated on fluids. He essentially pooped on his way out. I've learned it's a very common thing. But the first time the nurse asked if I wanted to burp and feed him, I freaked out because I felt like I was going to break him. Chris stopped me dead in my tracks and said, This is not about you, it’s about him, and this is all going to get sorted out. You're going to feel comfortable burping and feeding him in a day. He was right. I became more comfortable and confident every week. 

We had a five-hour drive home and Lenny slept the whole way. He was so little. Those days are a blur. Little sleep, many diapers, many bottles, but also probably the happiest we've ever been in our lives. We still feel that way. Every time we're alone or we sit down for dinner once he goes to bed, we still can’t believe we finally have our little family. It was overwhelming at first because I felt like I had no idea what I was doing but my sister-in-law always reminds me that everyone else is in the same position.

It’s okay to feel disconnected
I loved Lenny as soon as I saw him, but the bonding takes time. And I’ve been told that this is a very regular thing whether you were pregnant on your own or delivered via surrogate. I found myself wondering if I would be more connected if I gave birth to him? Thankfully my self-doubt around that has faded. It did take a couple months for me to let that go.

I wish I had found a glimpse of someone's infertility journey on Instagram—that would have given me hope that I could grasp onto for proof that I wasn’t alone. That’s why I want to do my due diligence and share as much as I can now with others who are struggling. It’s isolating, it’s scary, it’s emotional. I also understand that I’m in a place of privilege where we were able to do surrogacy, and I know it's not accessible to everyone. That's another piece that I'm trying to navigate around.

I will say this: All hardships and the roller coaster of fertility will eventually fade, and you don't want to look back and realize you lost six years of your life being miserable. I remember going home and talking to Chris about that. It sounds kind of cheesy, but we made a pact that while this was going to be a rocky road, we would try to live our lives to the fullest. And it was hard, but we did it.