We sat down recently with Hilary Rushford, personal stylist, mentor for fellow entrepreneurs, and founder of Dean Street Society. She told us all about her typical schedule and how she ended up with the amazing career she has today.
How do you describe your work?
Dean Street Society goes down two paths. One is personal styling where I help real people with real budgets make the best use of what they already own while filling in gaps in their closet with good investment pieces. The second piece of Dean Street is mentorship. I’ve been in business for two and a half years and became profitable at two years. Helping other aspiring entrepreneurs is a passion of mine. My main desire is to help out those who I’m just a year or two ahead of and help them see what’s feasible in a couple of years.
What was your journey to get here?
I was pretty focused on my path from day one. I spent a decade of my career in musical theater: I toured with a Broadway company and spent years with the Radio City Rockettes. I got paid to dance in high heels and vintage clothing, and I started wearing red lipstick at the age of five⎯my stylist roots were in there all along! I always got asked how I pulled off my style on a budget and my friends pointed out there was a business to be born. On February 1, 2011, things clicked into focus, and I knew that I wanted to be an entrepreneur. I found that a lot of the things that weren’t initially in my business plan came from listening to what people were asking for and what they were asking for help with.
How would you describe your work environment?
I just recently moved into a new studio, and I’ve tried to create a space that is aesthetically conducive to everyday. When you work from home, things like sunlight and fresh air are paramount—my current desk space is at a bay window with a nice flower box. I’ve loved the experience of creating an inspiring workspace to get things done in. For me, this is about the little things, like having a pretty coffee cup, putting on red lipstick and real pants, or lighting candles.
Could you walk us through a typical daily routine?
After throwing on a simple outfit and doing my hair and makeup, I’ll start the first part of my day working in one of the coffee shops in my neighborhood. Every day is different. I could be writing blog posts, writing newsletters, responding to emails, editing photos and videos, or conducting conference calls. After I finish at the coffee shop, I’ll take a quick walk and go home for another round of work from my desk. Something that I’ve come to realize is that, now and again, climbing into bed for a three-hour Scandal marathon is OK. When I’m working between 8 a.m. and 10 p.m. every day, I need to allow myself these kinds of breaks.
What’s the most unexpected thing that happened to you in business?
I already have the sense that I’m living the life I want to live, not just someday but now. I’ve become the woman I always wanted to be. There’s much more I want to accomplish, but I truly enjoy what I’m doing now and am able to support myself doing it, even in NYC.
What do you enjoy doing outside of work for fun or relaxation?
I love to travel whenever I can since I get so much joy and energy out of being in a new place. I also love to spend a lot of time with my friends in Brooklyn, whether getting a drink or chilling in the park and around the neighborhood. In general, I adore being outside, and I’ll often walk while I take a phone call.
Tell us about your proudest moment (in work or in life!).
My proudest moment was probably when I was twenty-two years old: opening night of my Broadway tour on 42nd Street. This exceeded all of my wildest dreams. There’s nothing harder than being a Broadway performer in NYC. It was a very real experience, and it changed everything for me.
What’s something you’d like to learn?
I need to learn how to say “no” more—that’s one of the biggest lessons for me. My ultimate desire is to build a thriving business that I love but not leave my life in a whirlwind in the process. Everyone I have ever admired was successful but often exhausted. I’m determined to be successful without being worn out. They don’t have to be one and the same, and I need to be levelheaded for myself, for my relationships, and for my team.
What are you looking forward to right now?
I’m looking forward to a new season for Dean Street. I told myself that I would be absolutely crazy for the first three years of having this business—it’s like being a single parent of triplets. In September, it will have been three years and I’m seeing the light at the end of the tunnel. My goals of taking this business to the next level is right around the corner.
What advice would you give to your twenty-five-year-old self?
The truth is, no matter what I would have said then, I don’t know that I would have believed it. My plans have changed a lot since then, but my main advice would be to be a planner, a dreamer, and a visionary in keeping goals alive. Also, figure out how to have really great bangs!