In this reflective conversation, Casey Dworkin—brand strategist, creative advisor, and former founder of sustainable footwear brand Sylven New York—shares how intentional living, community, and conscious renewal have shaped her evolving path. With deep roots in values-driven design and a passion for guiding next-gen brands, Casey invites us into the honest, in-progress journey of building a life and career that aligns with purpose, creativity, and personal growth.
When you think about leading a life you love, what does that look like for you, Casey?
Slowness is the thing I’m really challenging myself to practice in order to lead a life I love. Having access to nature is a big part of that, too. Coming from New York, where everything feels so reactive, my goal in life is to ask: how do I move as slowly as possible? How do I move with intention? How do I make space for a 15-minute walking break? Just to get out and look at the sky instead of the computer screen in front of me. Slowness is something I’m really trying to lean into. It’s not always easy.
How do you balance your ambition with that slowness?
A big part of finding the balance between ambition and slowness is budgeting the time. If you have eight hours dedicated to work in a day, not all eight of those hours are going to be concentrated, heads-down time. It’s a lot of constant reminders that the best way to sit heads-down is to take an hour and be heads-up.
What role has community played in helping you get to living that life that you love?
The role community played in building the life I love is massive. There are so many people I’m privileged to call friends. It’s always this reciprocal exchange, taking an interest in what people are doing and who people are because roles change. We are definitely not defined by what we do, even though we spend so much time doing those things.
It’s always been great to be surrounded by great people. Maybe that’s the scrappiness that comes with being a founder, where you’re like, who do I know? Which friend of mine can I call who’s in photography? I always think about time as being the greatest thing I can donate to people. It’s a precious resource. But there are lots of ways to give and take.
My network also evolves with me. There’s this blurred line between friend and professional, but it’s about how you communicate in that space—bringing things to your friends, working on projects that are just for fun. If you want to call in favors, you also have to give out favors.
There have been tons of times where I’ve been on set at a photo shoot and helped with wardrobe styling or prop styling because someone was hired for a creative project with a small budget. How do we uplift our friends and keep money in the hands of the people we like? How do we test things out and try creative things?
Sometimes gigs are paid, sometimes they’re experimental, and sometimes they overlap. There’s also the importance of being someone people like to talk to—asking questions, seeing who you know in common, and keeping people in your circle who are doing the same.
What are some of the habits that have allowed you to get to where you are both in your professional and personal journey?
The first habit I want to talk about is sobriety. Taking alcohol out of my day-to-day life has been massive for my mental health and productivity. That was one of the first major pillars for me in getting a really focused brain, keeping my blinders on, and making sure I was as healthy as I could be.
Secondly, spiritual practice. I’ve gotten really into tarot, and I love to take the time to build my own rituals. I’ve been exploring candle magic and creating small practices focused on intention and calling in certain things. I’m trying to merge creativity, spirituality, and play.
Also, I’ve got a tarot mentor, and I’ve been working on studying because I want to be fluent in card reading—which takes time and practice. The ritual has been fun, and I’ve seen the ripple effects on other parts of my life. Also, being able to read for my friends is just a form of introspection you get to share.
What do you believe is the key to helping more women step into their power and lead with confidence?
Confidence is something that almost needs to be practiced. I’m a big believer in “fake it till you make it” because we don’t always feel confident and that’s okay.
For me, it’s always about: how can I do things that I enjoy? In terms of leadership, I’ve always had a very entrepreneurial, scrappy mindset. If I want to be in a room with certain people, how do I plan that event?
How do you leverage yourself as a leader? How do you find people you admire and bring them together? You see how you can help and connect people. I think it’s about finding what excites us individually and leaning into what we’re already good at.
If you could write the rules for women, what’s something you’d change?
I don’t fully believe in rules. I believe in understanding the rules so that you can figure out what works for you. I’ve always believed that when you do what works best for you, there’s no blueprint.
Things are harder now than ever. Resources are strapped. Financial systems are in flux. A lot of what used to work doesn’t anymore.
If you’re starting your own thing or working alongside others, figure out how you want to do it. That doesn’t mean you shouldn’t research. You absolutely should know what your competitors are doing but don’t feel like you have to follow how it’s been done. It probably barely worked for them anyway.
It’s tough, and it takes a little leap of faith, confidence, and maybe even some naïveté. There’s something beautiful about not knowing how things are “supposed” to be done because then you have to do it your own way.
Leadership isn’t just one thing. I think good leaders empower the people around them to make good choices and to do things in a way that works best for them.
What is the legacy that you leave?
I ran a sustainable footwear brand, and I really wanted to be the innovator that changed the footwear landscape. Now that I’m no longer working with that company, I’ve realized my impact isn’t tied to a brand.
I want my impact to be that when I’m not in a room, the people who know me can still connect others through me. Legacy is much more interpersonal. It’s about how you impact the people around you and not just about financial or growth goals.
I love a growth mindset, but I’ve become more focused on how I move through life. If that inspires people, that matters more than making a pair of shoes.It was very cool to make shoes people wore on important days—I accomplished that. That’s part of my legacy. But even more than that, I want people to say they enjoyed working with me, and that I created a positive environment for those around me.
Anything else you want to share—something else you want the world to know?
After running a business for so long and then fielding the question of what’s next, something I’ve tried to do (and hope I’m still doing), is not just jumping into the next thing or believing that the next pivot has to feel permanent.
Nothing has to be forever. Do things as long as they serve you. After running one company, people kept asking, “What are you founding next?” Once an entrepreneur, always an entrepreneur but I needed to remind myself (and others) that it’s okay not to have it all figured out.
I had all these avenues in front of me and didn’t know which path to choose. So I said: If I don’t know what I want to do next, I just don’t have enough information yet. That created space for exploration. You don’t have to make a decision. You don’t have to choose just one thing.
Who knows where I’ll be a year from now? Right now, I’m taking a few paths at the same time. I’m trying things out. I’m experimenting. I feel like I’m back in college, figuring out what works for me.
I wish I’d heard more “how I built it” stories, how people fundraised, bootstrapped, and navigated messy paths. My journey has had a lot of ebb and flow. I’m on a different path now, and I’m just enjoying the ride.
It’s not easy but I’m like a little fish in the current, just moving with it.
Casey Dworkin is a brand strategist, creative advisor, and former founder of sustainable footwear brand Sylven New York. She works with fashion, lifestyle, and next-generation material brands to build intentional identities and growth strategies rooted in values and design. In addition to her client work, she also teaches accessory design and creative process as an adjunct professor. Casey’s work is fueled by a belief in conscious renewal, both in business and in self.
