design your life: hilary of dean street society

Hi guys! First of all, I’m sorry for being tardy for the party with this post today. Did anyone else think today was Tuesday? No? Anyway, I am so very excited to share this weeks DYL interview, for a multitude of reasons. First of all, I knew I’d love Hilary when she sent her first email to me and signed off “With Grace and Gumption, Hilary.” How much more adorable can you get? Hearing about her personal styling business made me all the more certain that she would be a perfect person to share her intentions with Jess Lively readers this week. Hilary’s business, Dean Street Society, began a year ago, when she set the intention to help “real people with real budgets” look and feel like the best version of themselves. I love that her passion doesn’t necessarily lie with fashion or trends (as she put it) but rather with seeing someone glow with confidence for that first date they’ve been dreaming about, or that big job interview they have coming up. I’ll let her take it from here, so read on for more about Hilary’s intentions with her life and business. See you guys next week! –Caitlin

DESIGN YOUR LIFE: Hilary of Dean Street Society

My new year’s resolution for 2012 was to “make things happen + love people well”. As a solo-preneur I am, honestly, overwhelmed on a daily basis with how much there is to do for Dean Street Society. Deciding to “make things happen” is about taking action today, right now, in this hour. It’s about taking the first step in a long project, just sending the tough email, not letting myself get immobilized by the overwhelm. I have a vision for my business that is bold + I think the #1 baddie that can get in my way is myself if I lose my big vision + confidence that I can make it happy little by little each day.

There’s a book called “The 5 Love Languages”. I haven’t read it. But the basic premise is there are 5 ways people give + receive love. So often what makes me feel loved, is not what makes you feel loved. NYC is a busy, bustling place filled with people with fast-paced lives. I can’t love everyone + I’ve had to accept that I have far less social play time since I started a business. But I try to focus when I’m with people on asking about them, making eye contact, remembering details, sensing whether or not they want to share a struggle or be distracted with silliness. I’m not perfect at it, but I desire to cherish the people in my life + love them uniquely in the ways that really fill their hearts.

A few summers ago I worked in a tiny no-stop-light town on a lake upstate. At first my best gay friend + I were losing our minds with the long stretches of day with nothing to do. After a few weeks, the rhythm of my soul began to slow, change, embrace. As a girl who often thrives on the adrenaline of NYC, I now also crave quiet, simple, rest like water. There was a season in which I was only a power-walking city girl. And glowed. Now I need both. And carving out that space in my life was a huge motivator in starting my own business.

It’s been fascinating as a stylist to realize how much fear people have. Fear of color, fear of pattern, fear of being seen, noticed, too much, not enough, wrong, uncool, unflattering. It breaks my heart how many people leave the house hoping not to be seen, just blend in. When I wear a saturated peacock blue dress or a fun pair of polka dot pants, people compliment me + they smile. It’s like having fresh flowers in a room. It brings light + joy. It makes the picture prettier for everyone else, while also making you look confident in your own skin, which is always a delight to be around.

In her book “The Fire Starter Sessions” author Danielle LaPorte asks you to distill what it is you want to feel in life. For me these three words sum up everything. I want to be in control of my life, of my days, with the ability to create, help, teach. I want to be around joyful people, doing lovely things. I want to use my talented + gifts to the fullest. When I’m working with a one-on-one client, on set for a photo shoot, filming a style segment on-camera or talking business with a fellow entrepreneur friend over coffee — I feel all three of those things + am affirmed that I’m absolutely doing what I’m meant to do in life.

Check out past DESIGN YOUR LIFE interviews.

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  1. Anna

    Hilary, I actually love you with all my heart. I love the way you’ve written this and find it really inspiring. Thank you for sharing! Anna x

  2. rita

    i love these! thanks hilary for sharing! also, i’ve been working my way through the fire starter sessions and it’s amazing… thank you for inspiring me to pick the book up again!

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