Jessica Feld didn’t set out simply to start a business. She set out to build a life that felt meaningful. After more than a decade in corporate finance, she took a leap in 2023 to launch Generation Dragon, a modern country club apparel brand designed for today’s woman. Along the way, she has been navigating the same questions many women face: how to grow something ambitious while staying present for family, protecting your wellbeing, and trusting your own path. In this conversation, Jessica reflects on building a brand from the ground up, the role community has played in her journey, and the lessons she has learned about balance, confidence, and creating a life that feels truly her own.
Building Something That Doesn’t Cost Everything Else
What’s your dream life, and are you living that dream life?
This question is very relevant to what I’m trying to figure out right now: what I want that life to look like. Over the past year and a half, I put so much pressure on myself to hit milestones with my business and I forgot my why, my dream, and why I am doing this.
My dream life is creating a business with longevity, something I am proud of and that my family is proud of, while still being present for my daughter and the one on the way. I also do not want to lose the spark with my husband. Both of us are building things right now and it is easy to get caught up in our business worlds and forget about each other and what we need.
I want to find balance between business, family, and myself. I want to realize that not everything needs to happen overnight, that I do not need to put so much pressure on myself, and that I can do things my way, not the way someone else says or the way other retail businesses grow. I also want to focus on becoming the best version of myself and prioritize my health and mental health because that can slip easily, especially when you are building a business, raising a young family, and trying to manage everything. It is hard to pour from an empty cup. There have been times over the past year and a half when I felt that way. I need to keep my cup as full as possible for myself and for the people around me. I cannot be the mom, wife, or business owner I want to be if I am dwindling inside.
Filling Your Cup So You Can Keep Showing Up
How do you keep your cup full?
I focus on taking care of myself when I need to. I try to be better at asking for help from my husband or family, like having someone watch my daughter so I can go to a workout class. It is the little things. Sometimes I can just shut off my phone and go for a walk or a workout to clear my head. That really grounds me. It may sound simple, but it works.
Spending time with my friends is also important. I have a group of high school friends I’ve been close with since high school. When I am with them, we do not talk about work or business. Turning that off helps me stay grounded. That said, they have all been so supportive, and I would not have this business without my community. But sometimes it is nice to just be with them and recharge, especially when I haven’t seen them for a couple of weeks.
The People Who Helped Bring the Vision to Life
How has community been a part of your journey to today?
Community is everything in entrepreneurship, especially in retail. It is hard to get your name out there. I am very grateful for my friends and family who support me, whether it is sharing something on social media, buying products, or connecting me with contacts. Every little thing helps.
Local support in Philadelphia and New Jersey has been amazing. It is not easy to get into club stores because they receive hundreds of emails every day. I feel fortunate for the support I have.
I am trying to create a community of women in golf and at country clubs. I did not grow up in that world; my dad and brother did, but I did not. It was intimidating at first. I did not know what to wear or how to act. I love seeing country clubs become more relaxed, whether in dress codes or general culture. I want women to feel more comfortable and I am working on growing this community through clinics and events. Women often have a harder time finding lessons or connecting with others who golf. Men can jump in a group more easily. I want to help women feel confident and supported.
Early Mornings, Clear Priorities, and Headspace Walks
What habits have allowed you to get to where you are?
I am big on waking up early. I need at least an hour and a half before my daughter wakes up for some me time. I either work out first thing in the morning or make my list of priorities. Without that, my day is off.
I get up around 5:30 and set my goals for the day. If my husband does not have to leave early, I might take a workout class or go for a walk. Walking is my sanity. When I feel overwhelmed, it clears my head. Sometimes I walk in silence, sometimes with a podcast, or I write emails while I walk. It keeps me grounded.
I make a lot of lists and live by checking things off. Staying organized is critical with a business, a daughter, and a husband. I need to know when he will be home. These are the big things that keep me focused.
The Confidence Gap That Keeps Dreams on Pause
What keeps women from taking bold action?
I see it with friends and have experienced it myself. Women often have a hard time trusting themselves. I did not trust my gut for a while. Many of us feel we are not good enough, and starting something new can feel overwhelming. Confidence is a big factor.
Women can get stuck in jobs or paths they are content with because it feels safer. I want to empower women to take that leap and guide them. I want them to see their strengths and realize they can pursue something bigger without giving everything else up. You can still be a mom, friend, wife, or partner while chasing something that makes you happy. There is space for everyone, and women should lift each other up along the way.
Learning to Trust Her Gut the Hard Way
What is a hard lesson you have learned over the past few years?
One of the hardest lessons I learned is to trust my gut. Early on, especially with manufacturers, I had hiccups because I did not stand my ground or trust my instincts. I have learned a lot about asking the right questions and finding my voice. Jumping the gun and bringing certain people in created challenges, but those experiences taught me lessons and led me to a better place with the people I work with now.
Letting Go of Pressure and Leading With Grace
What advice would you give your younger self?
Do not be so hard on yourself. I have always been competitive with myself and feel like I should be doing more. My advice is to give yourself grace. It is going to be okay. Be easy on yourself. My husband always reminds me not to get lost in the chaos of life.
About Jessica Feld
Jessica Feld — wife, mom of one (with another on the way), and founder of Generation Dragon —made a bold career pivot in 2023 that changed her life. After more than 10 years in corporate finance, she took a leap of faith to build Generation Dragon, a modern country club apparel brand designed for today’s woman, with select men’s pieces and kids styles coming soon.
Introduced to golf through her husband, former Drexel Golf head coach, Jess quickly saw a gap in the women’s apparel space and set out to create pieces that are stylish, functional, and versatile. Today, she’s building the brand from the ground up while balancing motherhood and growing her family — redefining modern country club style along the way.
