6th April 2015

From Tap Shoes to Girl Boss

From tap shoes to Girl Boss, you can’t visit her site, attend a course or watch one of her videos and leave without a smile planted on your face. Her bubbly personality and positive spirit is contagious. What makes that combo lethal is her passion for people and motivation to see others accomplish their dreams. She’s a virtual cheerleader to those she’s never even met, and she’s building her successful empire one strategic decision + dance break at a time.

We’re overjoyed to have the CEO of Dean Street Society, Hilary Rushford, gracing our pages today and sharing secrets as an entrepreneur, author, personal stylist and brand mentor. Oh, and of course, she couldn’t be the boss of Dean Street Society without sharing a few fashion tips to keep us looking our best!

There’s no easy way to make a long story that changed your life short, but the incomplete answer is that I read a blog post one day and had a lightbulb moment that I wanted her life: what I now know as a creative entrepreneur. Of course there were seeds that led up to that, but it was in one moment that it all came together that my passions could all exist in this one thing. I think I had the name of my business within a few days and literally never looked back. I am very driven!

Every fear I can think of, I didn’t really entertain: I might not make it, this might not work, I might not make enough money, I really have no idea what I’m doing — I think I just didn’t even let myself go there because failure was just not an option. As I said, I’m driven! But not just about anything. It was THIS thing, I just knew, it was so clearly what I was supposed to do with my life. It was like falling in love at first sight. It’s scary, but you basically have no control. Your heart is in it and you just run to keep up.

You need education and empathy. Learn from someone. There are so many people who’ve gone before you and made lots of mistakes. Don’t try to do it on your own. Take a comprehensive class, get a coach, do small group coaching. And you absolutely need peers who are doing what you’re doing. Your real friends won’t get it. It’s like being a new mom with a bunch of single girlfriends. You need other moms who know it’s normal to be awake at 3am and why you’re exhausted and how you’re so in love but so overwhelmed all at the same time.

A team and a project management app. At this point I must have help. Not just because there’s more to do, but really because after 3.5 years my brain just isn’t as strong as it was. I could sprint for a while, but now I have to have life be more manageable. So it has to be written down, and there has to be someone to hold me accountable, dive in to help get it started when I’m behind, take and finish it so I can move onto the next thing. But when we rush and skip the part of writing everything down, even a team can’t help. Everyone’s brain will fail them, so if you can’t afford a team yet or have a big one, writing every single little thing down is still the trick.

It pops up everywhere for me. I can be watching football or politics or sitting in church and I’m thinking about some takeaway about business or style. And Instagram is where I go for downtime, so I’m always seeking out new profiles there. I also love smart people, so whether they’re fellow entrepreneurs or fashion folks or not, a lot of my friends spark ideas and insights so I feel like drinks at the bar with my crew should always be a work write-off. {wink}

There really is no typical day, as it depends upon the season, whether I’m traveling, if we’re in a launch. But overall it’s a pretty typical 10-6 type of work day. When I sit down at the computer I am {not to overuse this word} focused! I get comments from writers all the time about it because I get into such a zone when I’m working. So while I love that I can be at home in bare feet, at a cute cafe, looking out my window at my charming street — oh and that I don’t have to spend time commuting or even putting on makeup most days — my work life is pretty typical.

In the mornings, I love listening to a podcast or book on tape when I’m getting ready. Sometimes they’re on business, or faith, or a biography of someone inspiring in fashion or politics.

And at night, that’s when my brain really shuts down. I tend to hit a wall when I just know it’s time to move onto dinner, go meet friends, or let my brain totally relax in front of the television.

Doesn’t my life sound glamorous? Ha. Don’t answer that. But the truth is that my work is my passion, so doing it all day feels much less like work than for the average person and I know that makes me crazy blessed.

Buy everyday clothes that feel chic. If you feel like you only wear mom clothes … stop buying mom clothes. If you have 12 sequin dresses you never get to wear, buy a sequin sweater instead you can wear with skinny jeans sitting at your desk.

It just takes one thing to be remarkable, worthy of remarking upon. That could be a great necklace, bold lipstick, professional purse — it lets you get away with much more easy breezy style. Plus you can wear those things almost every day, they fit at any size, and can often work from day to night.

How do you want to feel? Your clothes are one of the most empowering elements of your emotions every day. Do you want to feel sexy, feminine, powerful, effortless, artistic, mysterious? Does that happen with high heels or shoes you can walk all day in, with tight pencil skirts or flowing maxis? And remember you can change it up. Some days working in my pajamas feels powerful and other days I have to wear heels at my desk to get anything accomplished.

Morocco? Abu Dhabi? I have visions that there are these very exotic colorful cultures I’ve never explored that I really dream about visiting soon.

Also let’s be honest, anywhere with a hammock and a view of the ocean. That’s pretty much my daily dream spot.

What I dream about the most these days is white space. That’s where I can create, get creative, feel creative. The first 3-4 years of my business, as I said, have been about sprinting. It needed to happen, and I made it happen. But I know my best work is yet to come because it’s what happens when I don’t have a to do list and can write or create anything I want next.