How to Change Your Mindset to Become an Entrepreneur

May 25, 2017

Have you ever had an idea for a startup but questioned your abilities to carry it out, so your company never got off the ground? If so, you’re not alone. Helena Cawley faced the same problem—that is, until she changed her outlook and founded not one but two successful companies.

Formerly a corporate lawyer, Helena Cawley left her legal job to follow her entrepreneurial dreams, cofounding Uplift Studios in 2012. After years of running the NYC fitness studio, she started a subscription-based activewear service called SweatStyle, which provides personalized “athleisure”—fashionable fitness clothing—to customers according to their style preferences.

Recently, we spoke with Cawley about her new company, decision to leave her legal job, and journey as an entrepreneur. The following is an excerpt from that conversation.

VAULT: Can you tell us how you got started with SweatStyle? What was your motivation behind the company?

CAWLEY: I started SweatStyle to help women find the right fitness clothes to suit their workouts, lifestyles, and preferences. With the fundamental shift over the last few years to women leading healthier lives and wearing athleisure both in and out of the gym, there was a great demand for new, fun clothes to wear for workouts and beyond. Designers were taking notice, too; amazing new brands were launching with hi-tech fabrics, fantastic colors and prints, and a range of options for women across all sizes and workout preferences. Yet a big disconnect remained between the brands producing these wonderful new clothes and the women who wanted to buy them. Many brands were very young companies themselves, which made them hard to find. This left them wondering where the customers were, and the customers wondering where they could find new styles. Enter SweatStyle.

VAULT: Did you always aspire to found your own company?

CAWLEY: Yes and no. Most of us have had at least one or two ideas before about a business or product that would make our lives easier but doesn’t exist yet. “How has no one thought of that before?” is a very common question in my mind! But taking the leap from daydreaming about it to actually creating it is a big one, and it required me to get over a huge mental hurdle. I spent too much time at first thinking of all the reasons I couldn’t be the person to do it. “I’m not special,” I thought on a daily basis. “I don’t know how,” was another common one. I think it’s very easy for women to question themselves and their abilities, sometimes even after they’ve achieved great success. It’s that nasty imposter syndrome that can frustrate and hold back so many of us.

So, instead of giving into that feeling, I slowly but surely started to retrain my thoughts, and my new motto, instead of “Why me?” became “Why NOT me?” I saw a need in the market for SweatStyle, and I wanted to go after it. I didn’t have answers yet to all my internal questions and fears, but I had the confidence in myself to know I would figure them out. Then once the ball started rolling, I found that it’s easy and exhilarating to gain momentum and really make things happen.

VAULT: You worked in a corporate job prior to starting SweatStyle. How did you find the transition moving from a corporation to a startup?

CAWLEY: Going from being a corporate lawyer to a fitness entrepreneur is quite a change. All of a sudden you go from having a dozen bosses to being your own boss. There is no one else to tell you what to do, which can be thrilling and can be frightening. There are times when having someone to guide you is reassuring, but ultimately it’s about becoming more and more confident in your own ability to follow your vision and pare down all the things you need to do to get there. Being a lawyer first gave me an incredibly strong work ethic, and that has served me very well.

VAULT: Do you have any advice for someone who’s thinking about leaving a corporate job for a pursuit they’re more passionate about?

CAWLEY: Taking a business from idea to reality requires a good deal of tenacity, patience, and good old-fashioned elbow grease, and growing it from a seedling to a viable business is no different. Once I brought SweatStyle to market, my work was just getting started. Making changes to benefit the growth and longevity of your business can be difficult and painful, but it's necessary. You need to be able to part with things that just aren’t serving the business’ bottom line (including people), and make room for the new. So much of being an entrepreneur is finding ways through brick walls. After you make it through that first brick wall onto the other side, you know that you will be able to do it over and over again. And really that’s half the battle.

VAULT: What tips do you have for those who aspire to start their own business one day?

CAWLEY: Talk to as many people as you possibly can about your business idea. At the worst, you’ll perfect your own pitch when presenting your business. At the best, you’ll get valuable feedback, meet potential partners, and come up with new ideas. Your passion and energy is going to be what gets the business from an idea to a reality, so you need to share that with people and start making it feel real. Also, if it's a business that could never work (there are many), you’ll realize that quickly when you start to talk it out!

by Isabel Sperry

© 2017 Vault.com Inc.

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  • “After taking a brief hiatus from the practice of law, I was looking for a position which would enable me to enjoy a better balance between work and my personal life. I turned to Gary D’Alessio not only for his assistance in exploring opportunities for me, but to provide me with the counseling and guidance I needed. Gary’s personal experiences, familiarity with the Chicago legal market and timely knowledge of various opportunities ultimately led me to a part-time position at which I have never been happier.”

    Michelle K. Episcope, Associate

    Burke Warren Mackay & Serritella PC