Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Judy Hoberman, Founder of Selling In A Skirt, located in Southlake, TX, USA.

What's your business, and who are your customers?

Are you an Executive Woman in Sales? You are my people! My goal is to empower professional women and give them the tools they need/want/deserve to be successful.  Stop being ok with doing ok... I specialize in working with Executive Women In Sales who want to Get ahead, stay ahead and move ahead Faster!

My company, Selling In A Skirt, empowers Executive Women In Sales, giving them the tools to elevate their personal brand and amplify their voices so that they lead with confidence, negotiate with authority and grow the next generation of leaders.

Tell us about yourself

I came through the ranks of financial services, and I was the only woman when I first started out. And as I got to be more successful, I was able to recruit more women into the business. When I decided to go out on my own and become a business owner, I asked myself what I would want if I were starting over and what I would have wanted was someone that looked like me… not physically, a female mentor who would help me navigate business and how to create harmony in my life, not do the work for me, but hold me accountable and celebrate my win, so I became that woman.

We've all heard about the leaders that lead through intimidation and think there is only room for one person at the top. I hear that ambition is often a dirty word or a taboo subject. When you combine ambition with women, the result is generally seen as negative. You don't have to rise through the ranks by stepping on or over someone else. You don't have to be THAT woman.

When you lead with serving, you will grow and bring others with you. I had to figure that out for myself. I watched as others were out for themselves and didn't worry about the mess they left behind. That is not how I lead, and it isn't who I want to be surrounded by. My mission is to help one woman a day, and my tagline is "Women Want To Be Treated Equally...Not Identically" ® because that's where I come from, and that's who I am…

What's your biggest accomplishment as a business owner?

As you go through the timeline of your business, many things stand out and make you excited about what you do. One of the biggest accomplishments recently was coming through the pandemic successfully, after seeing two-thirds of my business vanish in minutes. I was devastated, and the thought of losing my company was very difficult. I gave myself permission to cry and grieve the loss, and 20 minutes later, I gave myself permission to get up and decide what would be my next move. At that moment, I created virtual events and programs that would become some of my best programs. I also provided panels of exceptional women where women would have a safe space to talk about change, shifting, connection, and staying focused. We kept it open at no cost for 12 weeks. It was originally a one-time event, but the response was so tremendous that I knew it was exactly what was needed. Women came from all over the globe. My speakers from 10 different countries donated their time and brilliance, which is still a topic of conversation. It was a connection that we all needed. During the pandemic, I was also named as one of 14 Sales Pros building trust from LinkedIn as well as Coach of the Year from Powerful Professionals. What started out as a year in tears became one of my proudest and happiest year of accomplishments.

What's one of the hardest things that come with being a business owner?

One of the hardest things that come with being a business owner is staying focused. You can think of it as keeping your eye on the prize or whatever visual works, but it is difficult on so many levels. When I decided to start my own company, I asked myself several questions to help me define my focus.

  • What do I know the best?
  • What could I do that would help people?
  • What unique insights do I have to offer?
  • What makes me an expert?
  • What do I really care about?

The last question is the most critical. You may be great at something and have your unique insight to offer, but if you are not passionate about what you are doing and don't keep your focus on that, then the business may be destined to fail. Your passion for what you do motivates you to get started every day when no one is holding you accountable and provides the energy that keeps you going through the ups and downs. You spend hundreds of hours trying to get noticed, and when you finally start to gain traction in your business, life turns into an episode of Project Runway. One day you're in, and the next day you're out. Throughout all the ups and downs, you have to keep your eye on the prize. Go back and review your initial goals and objectives. Have they changed? Have you added to them? Is the business still your passion? No matter what, things change, and it's how you ride this roller coaster of business, is what counts. It's a mindset thing. Be clear and stay focused. You can't be everything to everyone. I always remember a saying I saw in someone's office -

Almost every successful person begins with two beliefs: the future can be better than the present, and I have the power to make it so.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Know Your Why - Unless you have a compelling "why," it will be very difficult to stay focused and stick with your business plan when you hit some of the speed bumps. Is this something you would do, even if you didn't get paid?
  2. Know Your People - What makes them do what they do and, more importantly, why they do what they do? Know about their life outside of work. What motivates them? If you don't know that, how do you take them on the journey you are asking them to follow?
  3. Know Yourself - A good part of that is to be intentional with the market you serve, how you stand out, how you communicate to and with them, how you define success and how you use your time. No matter where you go, what you do, and why you do it, it's time to be intentional.

Is there anything else you'd like to share?

There are so many things that I love about what I do, but I truly love the fact that women are able to ask for and get the support that they need without really having to ask for it. We all know that women often have difficulty asking for help… So, what I do is, create an environment where they feel safe, and they feel heard. I'll answer their questions, and they know that if they have a question I can't answer, I have the resources for someone who can. I love to watch them be successful and go from level to level to level. My mission is to help one woman a day. And when I do that, a woman always raises her hand and asks, "Can I be your woman today?" It's the most humbling thing I've ever done.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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