As founder of Habituelle, Jessi Sheridan helps women slow down, get honest about what they want and build lives and leadership that actually feel good.
Discover Jessi's tips for reconnecting with yourself and balancing it all (plus get inspired by her fierce style) in this interview with our newest Real Woman of REALM.
It didn't take long for me to realize that Jessi Sheridan is a gem! In just one hour during our first meeting over coffee, we instantly connected and discovered that we had much in common. Our purpose and passion are rooted in uplifting and supporting women through meaningful conversation and connection.
As the founder of Habituelle, “A Space for Ambitious Women,” and a Leadership Coach, Jessi has created a community where heart-led, go-getter women come together to pause and reflect. She reminds us of the importance of cultivating the space we need to thrive and how to take the time to reconnect with ourselves.
Jessi possesses a gentle, yet undeniable strength and is as beautiful on the inside as she is on the outside. Her presence is an invitation—to slow down, lean in, and reconnect with what truly matters. Her story is one of intention, depth, and quiet power. Settle in and join us as we explore the heart behind Habituelle and the woman who so beautifully leads with purpose: our new Real Woman of REALM, Jessi Sheridan.
Ann King Lagos
Founder + Designer
REALM Fine + Fashion Jewelry
ABOVE: Ann King Lagos and Jessi Sheridan wear jewelry from REALM's CZ Blanc and CZ Azure collections.
BANNER: Jessi wears jewelry from the Everyday Chains + Pearls and Corset Cuff collections.
Q+A with Jessi Sheridan
What do you do for work?
I'm a leadership and performance coach and founder of Habituelle, a leadership coaching practice and community for ambitious women. Habituelle was born from my own experience of being successful yet deeply tired at the same time. Now I coach ambitious women to slow down, get honest about what they want, and build lives and leadership that actually feel good.
for play?
Spend time with my daughter Elle (the namesake of Habituelle) and husband, Connor. We're true city dwellers—on the go, shopping, dining, exploring all the city has to offer. I also teach power yoga, love to cheer on Philly sports teams, and enjoy a great historical fiction.
for others?
I believe deeply in gender pay equity and am drawn to organizations that help women and children feel empowered in their finances. Currently, I volunteer with Junior Achievement of Southeastern PA, which helps children and youth strengthen their financial literacy.
GET JESSI's LOOK
You have extensive experience working in the corporate world. What made you switch to be an entrepreneur and what skills carried over?
I spent nearly two decades working in various industries. I learned how to lead, build strategic relationships, and to navigate complex systems. At a certain point, I realized I had achieved my goal of making it to the C-Suite yet felt so depleted.
Choosing to be an entrepreneur was a personal decision to listen to myself and consider how I wanted to feel at the end of a day or week. I wanted to work in a way that honored both my career ambition and my personal life. The skills that carried over most were strategic thinking, emotional intelligence, and the ability to hold space for others. Those are the same skills I use now whether I'm growing my business, coaching women, or creating community.
Jessi with her husband Connor and their daughter, Elle,
the namesake of Habituelle.
How did you come up with the name Habituelle and what is the meaning behind it?
I have always been a very consistent person. I do what I say I'm going to do, I enjoy a semblance of balance, and I thrive in systems and processes (which made me a great Chief Operating Officer). I believe that leadership is a habit. When we habitually show up for ourselves and for others, there is a profound ripple effect on our families, communities, and economy.
Being able to have my daughter's name in the title was important to me because she was my wakeup call and remains a daily reminder that what we are building with Habituelle is a path for women and girls everywhere.
What sets Habituelle apart from other networking groups?
Our focus on true connection over transactions. Rather than centering everything around events and calendars, we've built something rooted in a way of living. We believe a woman's career is deeply connected to the life supporting it, which is why we intentionally weave together wellness, meaningful conversation, learning opportunities, and economic growth. When we move beyond the standard “What do you do?” conversation, vulnerable trust forms naturally and from that trust, real connection and advocacy follow.
At its core, Habituelle is grounded in sustainable ambition. In a culture that glorifies burnout, we offer an alternative—one that values clarity, presence, and the power of being in community with other generous and supportive women. We bring together executives, entrepreneurs, and creatives because we know the most interesting ideas emerge at the intersection of different worlds. Habituelle isn't just another commitment on your calendar. It's a place to exhale, to think expansively, and to experience real belonging.
“We all have only one life to live.
How we choose to live that life matters.
My hope is that more women give themselves permission
to slow down, get honest about what they want,
and build lives that feel as good on the inside
as they look on the outside.
Living in alignment isn’t a luxury.
It’s a responsibility to ourselves
and to the people we lead and love.”
— Jessi Sheridan
You speak a lot about the importance of reconnecting with yourself. What advice can you offer our community?
Life became so much clearer (and more exciting) when I began an inner practice—journaling, meditation, mindfulness, and yoga. There is so much noise all around us at all times. When you take time out to get quiet and really reflect on how you feel, what you want, and how you want to impact others, you start making decisions from a place of alignment rather than obligation.
My advice is to start small and stay curious. Reconnecting with yourself doesn't require a dramatic life overhaul. It begins with a few intentional moments of honesty. Ask yourself simple but powerful questions: What feels heavy right now? What feels energizing? What am I holding onto that no longer serves me? Over time, those answers create clarity, confidence, and a deeper sense of trust in yourself. When you're connected to who you are, everything from your work to your relationships starts to feel more intentional, grounded, and fulfilling.
We love your style! At REALM, we talk about our jewelry and Empresses having a “Classic, Romantic or Rock Star” vibe (sometimes all three). How would you describe your personal style?
My personal style lives at the intersection of classic and romantic, with just enough edge to keep it interesting. I'm drawn to timeless pieces that feel grounded and feminine, but I love when there's a subtle boldness. I appreciate when something unexpected reminds me that I don't have to fit neatly into one category.
Your favorite pieces of REALM jewelry? Favorite REALM collection?
This is a really hard question to answer because each piece and collection has intentional depth and meaning. But if I had to narrow it down, I really love the DOMAIN collection, specifically the playfulness of the Dual Tassel Earrings, the elegance of the Duet Marquise Cuff, and the boldness of the Majesty Chain Bracelet.
JESSI's TOP 3 FAVORITE REALM JEWELRY STYLES
Why do you love REALM Fine + Fashion Jewelry?
I love REALM because it's rooted in meaning, not just aesthetics. The brand honors women as complex, powerful, and multifaceted which is much like the work I do with women every day. REALM isn't about decoration; it's about expression, identity, and wearing pieces that feel like a reflection of who you are becoming.
How did you and Ann meet? What kind of connection did you have then/now?
I met Ann through a mutual connection, another Real Woman of REALM. Ann and I had an immediate connection—both of us with big hearts and a passion for uplifting women. Over our first coffee, we laughed, we cried, we held hands, and we planned for how we would support each other. It was kismet. Now, our friendship has solidified and I'm certain we will continue to support one another through business and life's ups and downs.
WHAT DOES IT MEAN TO:
#BeYourBestSelf
Being your best self isn't about constant self-improvement or perfection. It's about self-honesty. It means listening to what you need in this season, honoring your limits, and choosing alignment every time. Your best self is the version of you that feels clear, present, and rooted, not stretched thin trying to be everything to everyone.
#BeYourOwnEmpress
To be your own Empress is to lead from within. It's claiming your authority without waiting for permission and trusting your inner voice. An Empress knows her worth, sets and holds boundaries with confidence, and allows both ambition and rest to coexist. Power doesn't have to be loud to be real.
#ReignThoughtfully
Reigning thoughtfully means being intentional with your energy, time, and influence. It's understanding that how you lead matters. Thoughtful leadership is rooted in clarity, compassion, and long-term impact, not urgency or ego. It's choosing presence over performance and building a life that reflects your values.
Jessi addresses the crowd at Habituelle's Anniversary Party, held each September, to honor the women across the city of Philadelphia.
Anything else you would like to add…
We all have only one life to live. How we choose to live that life matters. My hope is that more women give themselves permission to slow down, get honest about what they want, and build lives that feel as good on the inside as they look on the outside. Living in alignment isn't a luxury. It's a responsibility to ourselves and to the people we lead and love.
CONNECT WITH JESSI
Social:
@_habituelle_
@jessisheridanspeaks
Website: habituelleleadership.com
Hashtags:
#habituelle
#womensupportingwomen
