242: Decision Diaries: How Decisiveness Changed Jennifer Holaday’s Business

Andrea Liebross: Welcome to the She Thinks Big podcast. I'm your host, Andrea Liebross, coach, speaker, life balance architect, and strategic thought partner for high-achieving women who want to think differently, lead confidently, and create success on their own terms.

As an entrepreneur myself and the bestselling author of She Thinks Big, here's what I know: You've been at this for a while, but somehow you can still feel stuck in the day-to-day. And running your business like a to-do list does not fulfill the vision.

So around here, we're not about more hustle, we're about smarter strategy, bolder thinking, and leading a business that fits your life. Each week, you'll hear the mindset shifts, real-world tools, and CEO-level conversations that help you reclaim your time, grow with intention, and elevate your leadership. Now, let's dive in.

Hey friends, welcome back to the She Thinks Big Podcast. Today's episode is for all of you who have been in business for a while, 5, maybe even 10 or 15 years, and you still feel like you haven't arrived or something's missing. I'm going to guess that you've probably built something really good, but you're wondering maybe why it doesn't feel great.

You're not new at your craft, but something is keeping you from taking that next-level leap. That is exactly what today's guest, Jennifer Holaday, experienced. She was running and still is running a solid business. She has clients, she has traction, she has a reputation. But under the surface, until a few short months ago, she felt capped. I think it's fair to say that sometimes she feels that way still.

But I invited her on today to share with you what helped her break through to that next level of thinking and showing up for her business. She and I have worked together for about, oh, I don't even know now, 18 months or so more. During that time, she's opened a showroom, even when she really didn't feel super ready. She's hired some people and she's learned why being decisive really can change everything. So Jen, welcome.

Jennifer Holaday: Thank you. Thank you for having me.

Andrea Liebross: I am happy you are here. I think your story really resonates with so many of the women I work with because you weren't stuck because you were failing, you were stuck because you were succeeding. So take us back to that moment when you realized you'd built something, but you really weren't growing the way you wanted to. I mean, you can tell everybody what your business is about too, and how you started and that kitchen table and all the things.

Jennifer Holaday: Yeah. Yeah. So my business is custom window treatments. For years, I worked in workrooms, sewing custom window treatments for interior designers throughout the Nashville area. I was doing this while the kids were in school. Eventually, I built a workroom out of my own house and started taking clients at my own home.

All of this was while raising kids and it was great and it worked perfectly. But as they got older, I was able to take on more and more clients. As I was taking on more and more clients, I was like, "I either need to really decide how I'm going to build this and what my next steps are professionally, or I'm going to have to start telling people no and turning business away." But it was like, well, how do I do that?

So I was like, "I guess the first thing I need to do is find a coach because I don't quite know how to get to that next level, but I know I wasn't ready to turn business away."

Andrea Liebross: Totally. That sounds like a lot of you listeners, I'm sure. So tell me a little bit about when you were doing everything from the kitchen table, you were following the mindset of being responsible and playing it safe, having all the ducks lined up in a row.

Jennifer Holaday: Right. I'm laughing because you know me well. Yeah. That's just been my personality all my life is being responsible means being cautious. That was what I've always thought, and that's just from where I made decisions. So I've always wanted to be responsible. I was one to get all my ducks in a row, like we say, and think through all the options and the possibilities and then make a solid decision based on all of that.

I quickly learned that that's actually not what you should do to be a good CEO. I learned quickly from you that that actually could be a hindrance. Being too cautious and too safe actually kept me from the business moving.

Andrea Liebross: I would say you were defaulting into, "I need to stay in control of all the things," versus stepping into possibilities.

Jennifer Holaday: Yes. Yeah, that's a good point. I wouldn't describe myself as someone who feels the need to control things.

Andrea Liebross: No, I would agree.

Jennifer Holaday: But I was feeling that that was the responsible thing to do. So I felt like I had to, which is, I've told you before, once this clicked, it was actually freeing for me because I didn't want to have to control everything. But I thought that if I was being responsible, I had to really be that way.

Andrea Liebross: Yeah. Like a responsible business owner. Also, if you think about parenting, I mean, we want to make sure all the ducks are lined up in a row and our kids are doing exactly what they should be doing. So that's a natural way of looking at everything.

But here's another thing I think you noticed, that even though things were working in your business, it wasn't exciting. By staying in that control thing, you were missing out on some exciting possibilities, I guess.

Jennifer Holaday: Right. Right. It almost prevented me from thinking too much about possibilities because I was like, "I don't have room for that."

Andrea Liebross: Yep. Yep. All right. So you said, you told me once that coaching really felt like learning a whole new language and that there wasn't a textbook, we couldn't read about it, but you did more of like a language immersion program.

Jennifer Holaday: Yes. Yeah, that is how I've described it. You could learn how to speak Italian in a classroom for years, but until you actually go over to Italy and spend three months immersed in the culture and having to get around on public transit and order and all of the things, then you suddenly are speaking the language and understanding the nuances. It just becomes a part of you to naturally speak that way. I definitely think that that is what coaching is.

Not just the coaching, but being part of the mastermind and being around other business owners, women. Because it's like after months and months of this language, you don't even know you've learned it until you hear yourself talking and you're going, "Oh, who is this person? Because this is not who I was six months ago." But it fits. But six months before or a year before, you couldn't have even understood that language.

Andrea Liebross: Yep, I think that's a great point. Another thing that I think is like the vocabulary piece of the puzzle. You weren't even using words to describe yourself as a CEO, or as a leader, or becoming more decisive. I mean, those words are all in your vocabulary, but they weren't at the tip of your tongue.

Jennifer Holaday: Yeah, yeah.

Andrea Liebross: When I learned how to speak Italian in college, which I don't know if you knew that. Did you know I didn't speak Italian?

Jennifer Holaday: No, I didn't.

Andrea Liebross: Yeah, so we learned through this thing. It was called the Rassias Method and you had to go to, they called it drill. So every morning you would go at like 8:00 AM to a classroom and there would be like a drill master.

Jennifer Holaday: That doesn't sound very good.

Andrea Liebross: It wasn't fun. It wasn't fun. But what it was, it was like learning through repetition. I think that's another thing. In the time we've been working together, you've had things that have happened repeatedly, we'll call it. But I think each time, you've gotten clearer faster.

Jennifer Holaday: Yes. I like how you described that, clearer, faster. Because yeah, sometimes you got to keep learning the lessons, but you're going to recognize them more quickly. I've learned to pivot more quickly. That goes back to being decisive. Part of that being decisive as a business owner, I describe that as freeing because I learned if I make a mistake or I realize it's no longer working for me, I can change my mind.

We can pivot. I think I was feeling this pressure that once I make the decision with whatever direction it is, that's it. I've made it, and I've got to live with it. So that's why it felt so heavy and so responsible. But the minute it's like, nope, make the decision with the information you have, move forward.

Then if you need to change or pivot later, go for it. But there's no real time for a CEO to be dwelling over all the decisions. You make a decision quickly with what you've got and you move on.

Andrea Liebross: Yeah, CEOs don't wait. They decide, they move, they pivot, they adjust. So true. So true. So what are some big decisions you've made? Let's get specific. Let's share. What have you decided? What do you think?

Jennifer Holaday: Well, as you know, when we started, I was renting a small office with an interior designer friend of mine, and she had some extra space. So I had rented a little corner from her for a little while because I was like, "It's time to get out of the house and have a space to meet with clients." But quickly, I was like, "I need more space."

It was quickly decided I needed to hire help. So I started looking for office space to move into for just me and my next hire. One of the things that I had thought I would want to do down the road, and I had this dream, but it was also, I really focused on it and it really came into clarity when we did our Vision to Action workshop.

But I was thinking three years down the road, maybe I'll have a showroom, which would include all my fabric and wallpaper samples, all my hardware, a place where people can come and really be able to shop and meet with clients, and have designers come in and be able to meet with their clients. But my full idea was that's down the road. Right now, I just need an office space.

I started looking, and nothing was quite right. There was this one space in downtown Franklin, this cute old building. I had my husband with me that day. We just went to get coffee on a Saturday. I'm like, "Well, it's probably not going to work, but let's just go check it out." The realtor said she'll show it to us.

So we walk in, and it's a huge space, huge. I told her, "There's no way." Because it was like the back of the building, front of the building. I was like, "I love the space, but I can't do it." She's like, "Well, we've thought about splitting it in half, front of the space, back of space." Once she said that, I was like, "Oh, wait a minute here. This was not in my plan."

But it has a great balcony. So my husband and I walked outside and taking this leap to do something like this, I wanted to make sure I had my best friend on board with me. So I looked at him and I'm like, "I think I want to do this." I just wanted to get his thoughts, his opinion.

He looked at me, he goes, "You'd be crazy not to do this." I was like, "Done." So between my husband's encouragement and knowing I had the backing of you and the ladies in the mastermind, I was like, "I can do this." But I would say that was very quick decision. I made that decision that day, had not planned on saying yes to anything that day. And it was basically go time.

Andrea Liebross: Did it make you feel more grounded, or did it make you feel reckless, or what did you feel?

Jennifer Holaday: Oh, that's a good question. I would not use either one of those. I didn't feel reckless. I did feel nervous. Of course, it was a little scary because I've never done anything like that, but I wouldn't say reckless.

Andrea Liebross: What about focused? Because now you were like, "Okay, I'm in this, let's go."

Jennifer Holaday: Yeah. Once I knew I had all the support, I was like, "All right, I'm in, I'm focused. Let's do this." I called one of my designer friends, and I said, "I'm going to need your help with your design expertise to help me get this place going. Do you think we could do it in eight weeks?" Which any designer knows that's crazy.

I had to get all my samples in. I had to paint. Well, I had to do everything to get ready. It may have been a little more than eight weeks, maybe closer to three months. But still, the timeline was incredibly tight.

Andrea Liebross: You did it.

Jennifer Holaday: Yeah. We did it 30 minutes before the grand opening.

Andrea Liebross: I was there. I can attest to this.

Jennifer Holaday: It's crazy. Yeah, we had everything good except this whole row of shelving. It was supposed to be delivered a month before. They kept saying, "Oh, it's in Nashville. It'll be delivered." Each day, each week was passing. It's supposed to be delivered. We couldn't find it. They couldn't find it.

So the night before, we're literally running around figuring out plan B. Then somebody called and said, "We found it. We can deliver it tomorrow morning." I'm like, "Well, tomorrow morning is my grand opening. We've got a big event. Designers are going to be here. I have a speaker coming, all the things." They're like, "We can be there at 9:00." We're like, "We start at 9:30. Can you be here at 8:30?" They said, "We'll try."

So we crossed our fingers. Sure enough, we have photos of what it looked like at 8:30 AM, 9:00 AM, and then 9:30. It was all hands on deck. I had some great support, lots of help. We got it done. Everybody walked in and had no idea that we were scurrying 20 minutes before.

Andrea Liebross: Who knew? But that's actually an example of you trusting. Trusting yourself, trusting that things are going to work out in some way. I think taking that leap and investing in that space became that next-level business. By becoming that next-level business, do you think it's fair to say that you're now attracting the next-level client?

Jennifer Holaday: Yes. I do think that was some of the conversation that was seeping into my brain of if you're waiting for the right client, you have to be the right business to attract that right client. So I'd already had several clients that I had worked with that I knew I wanted more of that type of client. Then I wanted to add more. So it did help to just decide I'm going to build it if I want that client.

Andrea Liebross: You have to act like the kind of business that your ideal client would hire.

Jennifer Holaday: Yeah, you said that much better than I did.

Andrea Liebross: No, but if you want to attract an ideal luxury client, then you need to be an ideal luxury business.

Jennifer Holaday: Yeah. You and I talked about this. Within a month of opening, I got a call from, I would say, she's probably my favorite client, my favorite designer I work with. She is who I was thinking of when I was, not her particularly, but everything about her was in that realm of ideal client.

She did not come to my grand opening, but she contacted me several weeks later and just said, "Hey, I saw that you were doing the grand opening. I saw that you have a showroom and I've got several projects." She started describing the projects. She said, "I was looking at you specifically because I want a showroom. I don't want to just go to a workroom. I want to go in and I want somebody to help me select all the fabrics and just take care of it all for me so that I'm not dealing with a thousand different vendors." I was like, "Great." We did some really fun projects right after that. She's still one of my favorite designers I work with.

Andrea Liebross: So it's like build it before they come, like build it, they will come. We get to build it before they come. That's exactly what happened.

So I think we can't guarantee, as business owners too, we want to try to guarantee that you're going to get a return on investment. But there are no guarantees. So you've got to really believe that you will get that return. I would say 9.9 times out of 10, it happens.

Because making that move really changed how others perceived you and how you saw yourself. That's a great example. That woman saying, "I see what you're doing. That's what I want." That leap really set the stage for growth that wasn't happening before.

That kind of growth, that kind of client.

Jennifer Holaday: Yeah. Or the ability to grow because again, I was getting some clients, I was getting the calls, but I didn't have the structure in place to be able to adequately take care of more and more clients in the way I wanted to. So I had to make some big leaps in order to be able to say yes to more of the type of clients I wanted to work with.

Andrea Liebross: So, do you think if you had waited to feel a hundred percent ready, do you think any of that would have happened?

Jennifer Holaday: No. Uh-uh. No. Of course not.

Andrea Liebross: It's like the real growth comes after the investment, not before. But our brain wants to offer up we need to grow, and then I'll be able to invest. Isn't that interesting?

Jennifer Holaday: Yeah. Just as we're talking, it's like having kids. They put stuff out all the time. You know, kids cost you this much.

By the time you've raised children, it will cost you this much. There are some people out there that I know are like, "Well, we need to plan and save for children." But, at least when it's come to me, I've been like, "We'll figure it out." You can't plan for children in the sense of all the financials or all the details about having kids, because you don't have a clue until you're in it.

Andrea Liebross: So you can read all the parenting books you want. You can read all the parenting books, but you're not going to get confidence in being a parent until you're actually doing it. It's like learning that confidence is the byproduct of the courage of taking the leap of investing in a showroom or saying, "Yes, let's go for kids right now." You don't get that until after you take the leap. I think it's so interesting.

Jennifer Holaday: Yeah.

Andrea Liebross: So if you remember, things were comfortable, but they were also constraining. Nothing had gone wrong. It was all fine and comfy, but it was constraining you.

Jennifer Holaday: Yeah. I just had to make the decision if I was going to be fine with where I was at. That's what was not comfortable. I was fine with where I was at. I was doing well, I was able to help support my family, I had time, but my kids are older now. I'm ready for more. I wanted more. So it was time.

Andrea Liebross: Do you think, I guess I'll say like this, what happened or what you've done in the past 18 months, it wasn't really a start over. It was just to think different. If someone's listening out there and you've been in business for five or 10 years and you feel like you're waiting for clarity or readiness or revenue or the right time, what would you tell her? What do you think you'd say?

Jennifer Holaday: I'd say get a coach and get into a mastermind or surround yourself—I would, because surround yourself with other people who are successful and doing similar things. I think I was the only one in our group that did exactly what I do, but we were all able to learn from one another.

You can only go so far by yourself. If you're feeling that itch of "I know there's more out there. I know I want to do more. I know I want to take my business to the next level, but I don't quite know what to do," just step out and be part of some coaching mastermind, something. It just shifts your whole mindset. You end up speaking a completely different language, and then you start seeing the possibilities. Once you start seeing it all, then you can decide which step you want to take next.

Andrea Liebross: That's a great point. You have to become the person who can handle that next level by stepping into it. You've got to surround yourself with people who are speaking that same language of growth that you are. I always find it's not that you need another course or another download. You need a mindset environment. That's the key, I think.

Jennifer Holaday: Yeah. Because there might be somebody out there that just knows exactly where they want their business here, here, and here. They have that plan so tightly figured out, I did not. But I had all these ideas. I had this feeling of, I know there's more, I have ideas, but I just didn't know how to get myself into that mindset to know what was next or how to make the next steps.

Andrea Liebross: Well, all the things you've done are amazing. All right. So, tell us as we wrap up, who is an ideal client? Who needs to come find you?

Jennifer Holaday: Well, I work with both designers and homeowners, but the majority of my business is the luxury interior designer. I am like an extension of the designer's team. It's crazy the things designers have to do. They're picking out tile, flooring, doing furniture layouts, doing everything. The amount of detail is astonishing.

But window treatments are their own bird. There are so many details with window treatments. When you're doing whole-house jobs in this luxury market, you cannot afford to make one tiny mistake because that's thousands and thousands of dollars down the tube. So I say, let me be that extension of your team. I will come in, I will help you start to finish, and take care of all your custom soft furnishing needs.

Andrea Liebross: Love it. What if someone doesn't live in the Nashville area? Can they still work with you?

Jennifer Holaday: Yes, actually, yes. I have been starting to work with some designers from a distance and it's a little bit different. I'm not able to do quite the extent that I can with some of my local designers. But one-on-one, we jump on some Zoom, I give very detailed instructions on what I need from them.

I can then often do the rest from here and have everything shipped to them and give them directions on installation and ensure that they have a seamless process.

Andrea Liebross: All right. So it doesn't matter where these people are.

Jennifer Holaday: No, it doesn't. It doesn't.

Andrea Liebross: Okay. Where can they find you? If someone is not following you on Instagram, they need to do that right away, first of all.

Jennifer Holaday: Yes, please. Just Brave Maggie Designs. You might be wondering who's Maggie if I'm Jennifer. Everybody asks me that. Maggie is my grandmother. She is the one that taught me how to sew and is the whole reason I started this business. So that is where Maggie comes from. But you can find me at Brave Maggie Designs, or my website is just bravemaggiedesigns.com.

Andrea Liebross: We will have all of that in the show notes, of course. Thank you for sharing the real and raw version of what growth really looks like after you've already made it, and why that mindset and decisiveness and community matter more than ever at that stage, after you've made it.

So if you're listening and this hits home and you've been in business for years and you're wondering why it still feels stuck or doesn't have momentum, or you're just in the comfort zone, this is your moment, people. Let's talk about you shifting into that CEO mode, new vocabulary, and what it could look like for you. So feel free to go to andreaslinks.com and book a call. I mean, that's what Jen did. You can do it too. All right, Jen, thanks for being here.

Jennifer Holaday: Thank you.

Andrea Liebross: Bye, friends. I will see you on the next episode of She Thinks Big. Thanks for listening to She Thinks Big. I know you’re committed to yourself and your businesses because you listened all the way to the end of this episode. But this isn’t really the end. It could be the beginning of your next power move.

If today’s episode gave you clarity, courage, or just a much-needed breath of fresh air, take that as your sign to take the next steps. So do it. Visit andreaslinks.com to take my Silent Saboteur Quiz and to discover our next steps in getting you to take action and achieve the success and freedom you crave.

You can also keep your momentum going by hitting subscribe right there on your screen so you don’t miss the next episode. Don’t forget to grab a copy of my book. She Thinks Big can be found on Amazon or at your favorite bookstore. Until next time, keep thinking big.