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How Breastfeeding Inspired Jessy’s Business

In honor of Breastfeeding Awareness Month, Bonsie joined in conversation with Jessy, the founder and creator of Titty City Design. Motherhood inspired Jessy to create a business to normalize and celebrate breastfeeding. Titty City Design is also a platform to educate and empower mothers about breastfeeding, breast health, and to promote body positivity. We admire Jessy’s passion and advocacy and are excited to share her story with you.


Jessy, founder and owner of Titty City Designs.
Jessy, founder and owner of Titty City Designs.

Before delivering her baby, Jessy thought that breastfeeding would feel instinctual. She had no idea of the difficulties and wonders that awaited her.


“For me, breastfeeding was something I wasn’t very familiar with. Sure, I understood the concept, but I never heard anyone that I know talking about it. When I was touring hospitals while pregnant with my son in 2019, I learned about a breastfeeding class that was offered. Naturally, I signed up for the class in preparation for postpartum. There was a lot of information (some resonated, but most did not), and yet, to me, I felt like breastfeeding would just come naturally, because I hadn’t heard any differently from others, including my closest friends and family.


"Woah! Not the case exactly. I had planned for a vaginal birth with an epidural. However, my son’s birth did not go as planned. After over 28 hours of labor and three failed epidurals, circumstances required an emergency C-section.”


Like so many moms, Jessy’s delivery did not go as planned, and her breastfeeding adventure began as both wonderful and challenging.


Jessy and her son practicing skin-to-skin contact.
Jessy and her son practicing skin-to-skin contact.

“It was not the birth experience I expected, planned for, or wanted, but there we were. Right after surgery, my baby was examined and then given to me. I went over to the recovery room while they did a few more checks on my baby. When he was cleared, the nurse brought him to me to begin bonding and breastfeeding.


"My son found the boob right away – Yay! And our breastfeeding journey was actually off to a really good start. Although after four days in the hospital and being completely exhausted, we returned home and that’s when all the realities started to set in.”


C-section recovery, engorgement, and cracked nipples were Jessy’s first major postpartum hurdles.


“After having major surgery, it was really hard to move around and to even hold my baby. This is also when the engorgement started. Engorgement is when your breasts start to feel a lot of pain as they are producing milk. They feel huge, swollen, and rock-hard as they are producing milk for baby. Engorgement occurs until the milk gets removed from the breasts, so they can continue to make more milk.


“This was the first real breastfeeding struggle I encountered.


"I have to say, breastfeeding can be freaking hard!

"The pain I experienced during my breastfeeding journey was equal to, if not greater than, pregnancy and birth at times.


“Engorgement was just the first of my breastfeeding struggles. I had cracked nipples while I was adjusting to breastfeeding and I remember standing in the shower crying over the pain. We then moved into the cluster feeding stage where I felt like I was constantly feeding all hours of the day and night. This was exhausting! I also had one of my breasts that seemed to be producing most of my breast milk, so naturally, my son favored that breast and it would become engorged more frequently – ouch!”


By day 10 postpartum, Jessy developed an infection from her C-section and had to go to the emergency room.


“To paint the scene, this was about 2 weeks before the pandemic was officially announced in 2020. The hospital looked like a scene out of a disaster movie. People were everywhere, in chairs, on the floor, standing wherever there was space! My son was not allowed in because they were unsure of the dangers for newborns.


“This was the first time I was going to be away from my son, and I was so worried about how I was going to feed him. Luckily, I had collected maybe 8 oz of milk from a breastmilk collector that was in my freezer. My husband was able to bottle-feed my breastmilk to him while I was away. Thank goodness he took the bottle!


“I had never even pumped before, but I was at the hospital for nearly 12 hours being treated and I had to remove the milk from my breasts somehow. My first pumping experience was in the emergency room on a medical-grade breast pump in my treatment room. Well, “treatment room” is a bit of a stretch. I was in a closet because the hospital was likely over capacity. Luckily, I had a nurse show me how to do it, because I had no clue how to work the foreign machine.


“I survived my first pump and was so thrilled to see my baby when I was discharged from the hospital.”


The physical challenges of breastfeeding are only one piece of Jessy’s postpartum puzzle.


Jessy and her son at the beach.
Jessy and her son at the beach.

“My breastfeeding challenges had really only begun. Don’t even get me started on the clogged ducts! Seriously, this happened at least three separate times that I recall, and it was awful. And seven months into my breastfeeding journey, I got mastitis – or as I called it, the boob flu.


“I want to point out that all of these challenges I mention were only physical. There were also emotional struggles due to hormones and challenges from juggling my corporate job (at the time), a baby, sleep, and all the things. Breastfeeding is hard work.”


Despite these difficulties, breastfeeding was and continues to be important to Jessy, and as she looks back on the two years she spent nursing her son, she feels proud of her determination and achievement.


“There were honestly so many challenges throughout my breastfeeding journey. My son and I overcame them together and persevered. There were so many times where I could have given up, or thrown in the towel, but I just wasn’t ready to be done.

“For the most part, breastfeeding worked for us, and we kept going. It takes an incredible amount of time, effort, and commitment to breastfeed. To this day, I feel so much pride and empowerment from my breastfeeding journey.


"I remember some people telling me that it was okay to stop. Truthfully, that isn’t what I wanted to do or what I needed to hear. What I needed was support, the proper resources, and encouragement to keep going.

“I had no idea I would breastfeed for two years (technically 25 months), but that’s what happened. In fact, in the beginning, I didn’t think I would make it past one week! My son naturally started weaning himself around 18 months and by the time our breastfeeding journey came to an end, he had been feeding for a short amount of time every other morning. The end was bittersweet, and it took some time to adjust to as well.”


The postpartum period can be filled with transformation, uphill battles, and big emotions. Postpartum during a pandemic? That’s a whole different story.


“The postpartum journey tends to be incredibly isolating for so many. For me, becoming a first-time mom at the beginning of a global pandemic felt incredibly lonely.


“Going through quarantine while transitioning to motherhood was unlike anything I could ever imagine. There were no local mommy and me classes, no meeting up with friends or family, and no physical support outside of my home. The ‘new mom struggles’ were real.


“I didn’t realize how challenging postpartum, and breastfeeding would actually be prior to becoming a mom. On barely any sleep, I worked from home, with my baby always on the boob — for feeding or for comfort.


"After experiencing almost every breastfeeding struggle, I truly understood how incredible and strong mamas are.

All at once, we learn to breastfeed, care for a new human, and recover from giving birth with minimal sleep. It’s nuts! Not to mention, becoming a mother is a whole other identity that takes time to adjust to and can make you forget the person you were before.”


Jessy snuggles with her son.
Jessy snuggles with her son.

Not only did Jessy far surpass her breastfeeding goals amidst a pandemic, she also created her own company as a way to celebrate motherhood and the incredible strength of the female body.


“To get back in touch with my creative self, I channeled my awe for motherhood through art. I began to paint my ‘Titty City’ design on ceramics while my baby was asleep as a form of self-care. While painting, I thought of the other new moms out there experiencing this, too. I wanted to reach out, hug them, and let them know they weren’t alone.


“In November 2020, I was inspired to create Titty City Design — a brand that speaks to new moms — and build a community that empowers and encourages each other with love and positivity. I strive to shower new moms with praise and support while working to break down barriers and normalize talking about breasts and our experiences with them.


“At Titty City Design, I create products to help strike up conversations about our experiences with breastfeeding and to celebrate our bodies (because breastfeeding deserves to be celebrated).


“My body-positivity brand is intended to make people smile and feel seen and celebrated. Breasts are a part of our lives and they should not be ignored or shamed. In fact, they should be supported, like a good bra!


“I’m an advocate to my core and work tirelessly to build this community — in real life, on social media, and with my “Let’s Talk Titties” blog — that promotes body positivity, and celebrates new moms, and breastfeeding.

A graphic of Titty City Design — a brand that speaks to new moms — and build a community that empowers and encourages each other with love and positivity.

Normalizing breastfeeding, providing moms with more support and resources, and sharing our breastfeeding stories is crucial to the health and well-being of babies everywhere.


“Breastfeeding is something that is learned between mother and baby and creates a strong bond between the two. Breastfeeding has lifelong benefits for the mental and physical health of both mom and baby. In fact, according to the World Health Organization, increasing breastfeeding universally could save more than 800,000 lives a year, the majority being children under six months.


“Normalizing breastfeeding is very important. It is one of the most natural things in the world, but it does not always come naturally, which is one of the reasons it’s so important to talk about and normalize.


“Breastfeeding can be REALLY hard. You’re exhausted, uncomfortable, and recovering from giving birth. It’s easy to feel like a failure or give up when it doesn’t go as expected. The truth is, you’re doing great! It’s more than OK to feel worn out and in need of help. It’s a tough and demanding role and you deserve support and access to resources.


“By sharing our breastfeeding experiences openly and honestly, we can help educate and share resources on breastfeeding to make postpartum and the transition to motherhood feel less lonely. And we can encourage and cheer each other on.


“And that is why I started a social movement, #TheBoobment to normalize talking about breasts and our experiences with them. All the products I create at Titty City Design are meant to help strike up conversations about our experiences with our breasts. I believe that the more comfortably we share about breastfeeding, the more normal it will become. Come be part of ‘The Boobment’ with us!


“Whether you breastfeed your little one for days, weeks, months, or years… Know this: you are amazing and deserve to celebrate your breastfeeding journey!”

Choose the perfect gift from Jessy’s New Moms Collection to celebrate your incredible breastfeeding milestones, or get a gift for your "Milk Maker" bestie to show your love, encouragement, and support on their breastfeeding journey.


Shop her products and baby shower gifts for moms at tittycitydesign.com and join her on Instagram (@tittycitydesign) and TikTok (@tittycitydesign).


Bonsie is proud to be a part of the #BOOBMENT and eager to share resources to help new moms thrive, find community, and celebrate their breastfeeding journey.


More about Jessy:


Hi! I’m Jessy, the founder, and creator of Titty City Design. I grew up in the suburbs of Chicago and graduated from the University of Illinois with a BFA in graphic design. I learned that I feel happiest near the ocean, so I moved to southern California where I built my career as a creative director and met my soulmate. We now have a spider-man-loving toddler, a cuddly labradoodle, and live in the South Bay.


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