237: Why Successful Business Owners Still Struggle with Decisions After Years of Experience - Business Coach for Entrepreneurial Women | Sustainable Growth with Strategy & Ease
Why Successful Business Owners Still Struggle with Decisions After Years of Experience

237: Why Successful Business Owners Still Struggle with Decisions After Years of Experience

You survived the start-up phase, made money, and built a team. Now, several years later, you think you should have the ins and outs of running a business all figured out by now. Yet, even though everything looks great on the surface, it can feel exhausting, chaotic, even uninspiring on the inside…especially when you’re still wearing all the hats.

That’s where Andrea Liddane found herself with her 20+ year tutoring business. As the founder and CEO of Liddane Tutoring and Learning Services, she’s served hundreds of students and hired over 30 tutors. But after all this time, she realized she was emotionally and physically tired and felt uninspired by her passion. So she took a bold step and sought a guide who wouldn’t just hand her a map but take the journey with her.

In this episode of She Thinks Big, Andrea shares what it really looks like to be an experienced business owner who still needs support and why seeking coaching later in the game can sometimes be the most strategic move of all. As she and I have fun with revealing her story through forest analogies, you’ll see why knowing what you’re doing as an entrepreneur doesn’t mean you should have to do it alone.

What’s Covered in This Episode on Why Successful Business Owners Struggle with Decisions

4:36 – Introduction to Andrea Liddane, her business, and why she took the leap to hire a coach

9:02 – Why Andrea felt her business was stuck despite its success

12:00 – The need for an outside voice to get on the path to making the best business decisions 

17:02 – Examples of distractions (or “squirrels”) that kept threatening to push Andrea off track

21:07 – The turning point when Andrea “jumped across the stream” and made a big decision in her business

25:11 – How Andrea makes business decisions differently now and what keeps people stuck in indecision

28:47 – The power of having a sounding board to help you make quicker decisions and free up real estate in your brain

33:28 – Andrea’s advice if you think you should have it all figured out by now as an established entrepreneur

36:46 – How having a coach has helped Andrea reclaim inspiration for her work

38:07 – The return for Andrea on her investment in business coaching

41:14 – How Andrea feels about the future of her tutoring business 

Connect with Andrea Liddane

Andrea Liddane is the founder and CEO of Liddane Tutoring & Learning Services, a trusted educational support organization she launched in 2001. What began as her personal mission to combine meaningful relationships with creative, student-centered learning has grown into a team of experienced, empathetic tutors serving students from preschool through college—both in person and online.

With a background as a public school teacher and private tutor, Andrea brings deep experience to her leadership. She’s known for prioritizing personalized instruction, professional development, and collaborative problem-solving—ensuring that each student gets the thoughtful support they need to thrive.

Under Andrea’s direction, LTLS offers academic tutoring across all subjects, executive function coaching, study skills development, standardized test prep, and college application support. Her team also specializes in working with students with learning differences such as ADHD, autism, dyslexia, and more.

Behind the scenes, Andrea continues to consult with families, schools, and professionals—always centering trust, understanding, and holistic support. And in keeping with her lifelong commitment to educational equity, LTLS quietly offers support to a small number of students with financial need—reflecting her belief in access, dignity, and community care.

Liddane Tutoring | Facebook | Instagram | LinkedIn | TikTok

Mentioned In Why Successful Business Owners Still Struggle with Decisions After Years of Experience

She Thinks Big by Andrea Liebross

Andrea’s Links

Book a Call With Andrea

Quotes from the Episode

“We’re standing in front of this forest of life. There are so many different paths. As women, we have this notion that we can do everything and figure out the best path forward if we just look or try harder.” – Andrea Liddane

“As business owners, we can watch a million videos and listen to YouTube, podcasts, books, everything. But it’s not the same to almost have someone in your court.” – Andrea Liebross

“It wasn’t that long ago that I was taking client notes by hand, like on a napkin in the back of my minivan. I mean, that’s really how I started. And there’s certain parts of the business that aren’t that far from that.” – Andrea Liddane

“Now that we’re here on the other side, I feel like I have somebody who’s learning about my business, who’s understanding some of the sticking points, but also can make those decisions in the best interest of me as a human.” – Andrea Liddane

“I don’t want to spend the next 20 years trying to figure out what the next step should be and making all the mistakes. It’s really inefficient to do it without a coach sometimes.” – Andrea Liddane

Links to other episodes

152: How to Combat Decision Fatigue in Everyday Life

135: Where Do You Need More Freedom in Your Life or Business?

62: How to Make Decisions From a Place of Abundance Instead of Scarcity

60: How to Be Confident in Your Decisions

Andrea Liebross: Welcome to the She Thinks Big! Podcast. Get ready to level up your thinking and expand your horizons. I’m your host, Andrea Liebross, your guide on this journey of big ideas and bold moves. I am the best-selling author of She Thinks Big: The Entrepreneurial Woman's Guide to Moving Past the Messy Middle and Into the Extraordinary.

I support women like you with the insights and mindset you need to think bigger and the strategies and systems you need to turn that thinking into action and make it all a reality. Are you ready to stop thinking small and start thinking big? Let’s dive in.

Hello, my friends, and welcome back to the She Thinks Big podcast. How are you? Where are you listening from? On a walk? In the kitchen? Driving around?

I'm serious about this. I want to take a little survey and find out where people are listening from. So message me.

Today, here's what I want to talk about. There's this belief that floats around in the entrepreneurial world—especially, I think, the entrepreneurial world for women—that once you've been in business for, let's say, five or more years, you should have it all figured out.

You've survived the startup phase. You've made money. You've probably got a bit of a team going on. You've probably had a few "I can't believe I'm doing this" moments along the way. You're like, "Huh, I should be able to figure this out."

But here is the truth. Even when the outside looks successful, the inside can feel, well, messy. The inside can feel uninspiring. It can feel exhausting, especially when you're still the one holding all the decisions and carrying the weight of what you've built.

I know a lot of times we feel like that. If you're a mom, you feel like you're holding all the pieces together in your family. Maybe you really are. But you also might be feeling this way in your business, and you're carrying that mental load.

That is where today’s guest found herself. So I am joined today by Andrea Liddane. Yes, another Andrea. We’re not the same person, though you would be amazed by how many email threads and calendar invites and voice messages might say otherwise. Let’s just say it’s a good thing we don’t both work with the same clients or there’d really be an identity crisis happening.

So Andrea Liddane is the founder and CEO of Liddane Tutoring and Learning Services. She's got a business that she’s built for over two decades. So that’s like four times five years. She’s served hundreds of students, probably even thousands. She’s got a team of 30+ tutors and staff.

After all that time and success, she realized something. She was tired. She realized she was tired, not just physically, but emotionally. Her passion to help students had turned into pressure. She couldn’t really see that next step forward.

So she did something bold. She stopped trying to figure it out alone and decided to trust someone else to help guide her through this forest. We do talk about forests in this episode of decisions.

Someone who wouldn’t just hand her the map, but actually walk along the trail with her. So in this conversation, Andrea is going to share what it really looks like to be an experienced business owner who still needs support, and why getting coaching later in the game is sometimes, I would say, the most strategic move of all.

So if you’ve ever thought, “I’ve been doing this long enough, I should know what I’m doing by now,” I want you to hear this episode. Because knowing what you’re doing doesn’t mean you should have to do it alone.

All right, sit down, buckle up, and let’s get into it.

Share with me a bit about Liddane Tutoring and who you serve and how the business has evolved since 2001. That is a long, long time ago. Tell me.

Andrea Liddane: Yes, and I was a teacher before that. So, I mean, it depends on where you want to put the start button.

So, I'm Andrea Liddane, and I'm the founder and CEO of Liddane Tutoring and Learning Services, and we are based in Seattle, Washington. I began this journey a long time ago when I was raising my own children.

I stepped away from teaching to be home more with my kids and started tutoring on the side. Then a friend of mine had said, "Why don’t you try tutoring?" because I had missed teaching. Then I hired people because my students needed more than just me.

So then in 2014, I opened my first office, and now we have two locations in Seattle, and we work online as well. I have a staff of around 30-plus people at any given time. Currently, we're serving about 200 students plus, and that's always rotating.

So yeah, we're doing a lot. For me, the business started where I—so I'm going to reference camping and hiking a lot because I love to camp.

Andrea Liebross: I love that.

Andrea Liddane: I think you gave me that analogy at one point—or somebody did—about, so we're standing in front of this forest of life. There are so many different paths. There are an endless number of paths to get through the forest.

I think one of the things that I've recognized, especially because I'm no spring chicken, is that we now—and maybe especially as women—but we have this notion that we can do everything and we can figure out the best path forward if we just look or try harder.

So I was one of those. I pulled myself up by my bootstraps, and I created this business with no formal business background.

Andrea Liebross: Like most business owners, actually, to be honest.

Andrea Liddane: Yes. I'll bet that's true. Right. Also carried the notion, I mean, a podcast wasn’t a word before I started this business, and jumped on that bandwagon. I've listened to so many podcasts. I've listened to so many books on business. I’ve learned so many things in that route. I thought about, "Oh, should I go back to school to study business?"

My business now, before I started working with you, Andrea, I had been doing this for a long time. We survived the pandemic. We did the thing. Like all of these things. But the problem, when you get to a certain point, if you don't have the knowledge or experience, whom are you going to ask?

Andrea Liebross: Your friends are your friends, and we want to keep them your friends. They don’t want to hear the ins and outs. And your family is your family. You can’t really talk about it with the people in your organization, or only to a point.

Andrea Liddane: Yes, exactly. Exactly. So the story is I’m in the forest. I'm deep in. And there are so many forks in the road. And there are so many squirrels, because I always think about dogs and how they just get really distracted by squirrels.

That's how I have felt for my whole career. I've looked to all these different ways. And I have made so many great decisions. You know, I can be proud of what I've created.

But when I finally took the leap to hire you, I felt like I was standing there at a fork in this trail that I was going through. There were so many different options and squirrels everywhere.

There may be a hundred other ways to get through the forest, and maybe some of them would be better. But I decided to take the leap to trust you. And it's been the best decision. I cannot speak more highly of it.

Andrea Liebross: So now I get to go down a trail with you. We together choose what our next, are we going left or are we going right? We make that kind of thing. But I love the forest analogy because if you think about it, the trees were growing. The business is alive. You have clients. You've got a staff of 30 people.

So Andrea Liddane, so this is also a side note. This is a problem, everybody who's listening, that our names are so similar. But, well, it's a good problem to have.

There’s nothing like going wrong. There’s growth. But your business wasn’t growing at the rate you wanted it to grow. You felt like you were stuck in the mud a little too. Is that fair?

Andrea Liddane: Yeah. Oh, yeah. Yeah.

I'm going to just speak to money too, because I think it's really important. I've referenced the pandemic was hard for us as a business and we came through it. So it's not like, "Oh, I'm so flush. I can just like, I'll just hire a coach." But what I realize now is there's this whole thing about decision making that you talk about. I have realized in the time that I've worked with you that I have wasted so much time standing in the mud at the fork in this multi-pronged road going, "What do I do?" By the way, using that analogy, let's imagine if you've ever traveled overseas and you've gone to a museum or something like that, and there are a bunch of people standing outside and they want to be your guide. They're all trying to sell it to you. They're like, "I'm the best one. I do this." You know, there's also that I get emails every day for people wanting to show me this and that. How do I know how to decide?

Back to the name thing, I honestly felt like the reason, like the universe was yelling at me. You need to know this person. You cannot stop looking at this person's name. So just as an aside, because there was a whole fiasco with emails and things at the beginning of this relationship. But we figured it out.

To just have somebody there whom I've decided I'm going to trust and that I can turn to and ask questions and contemplate things. What Andrea does is she asks questions back that help me make the decisions more quickly. So I'm not standing in that mud for so long.

Andrea Liebross: Right.

Andrea Liddane: That I've chosen a route and we've chosen it together. I know she's there with me and she's going to call me out. If I start going down some other route, she's going to not call me out. I don't mean that in a negative way. You're going to ask me questions about this decision. Like, why are you making that? What's in it for you? That kind of thing.

Andrea Liebross: So, why, and you just said something and now I lost my train of thought. I was going to point out, why do you think, or what books, podcasts, I mean, you're also a lifelong learner. So I think it's a good thing to point out here is we can listen to all the books and the podcast and really talk to all the people, but those things aren't necessarily helping you make decisions faster. Is that what you think I'm right there?

Andrea Liddane: Yeah. I mean, I literally had the thought because I always joke, the only formal business class I ever took was typing in high school. That was a long time ago. Thank goodness. Because it's really come in handy, and I've worked for small businesses and I credit them with teaching me a lot, but you know every industry is different. I'm not doing what the people who have a staging business are doing. But the thing that is so amazing to me is that it feels really lonely at a certain point.

It feels like, yeah, I've gone down the path that employees pointed me toward. And it wasn't the right decision for the business. You have a voice for the business. That has been amazing.

Andrea Liebross: So let's dig into that a little bit. So I think what you're referring to is some of your employees have said, "Hey, Andrea, I think we should change our pricing or invest in this software or offer different tutoring hours," like whatever it might be. So those employees have come to you with suggestions. Then you have thought, "Hmm, maybe they have a point. Hmm, maybe I should do that." Probably over the last 24 years, you've done some of those things. Some of them have worked out. Some of them haven't. But probably what you're recognizing now is that in that decision-making process, you weren't always considering what was best for the business. You were going off of what? What do you think you were going off of?

Andrea Liddane: I was going off of trust. Maybe, I mean, I was naive. So, again, back to the money. Like I have wasted so much money doing things and it's all about making mistakes. I mean, I own a tutoring business. We talk about making mistakes all the time. Like, yeah. That's just part of life. I can have regrets about some of those things, but I try not to, because that's just where I was.

Andrea Liebross: Right.

Andrea Liddane: Yeah. But now if I can have another person who really doesn't have any, I mean, you don't have anything to win in this game.

Andrea Liebross: Your wins are my wins. If you feel like you're winning, or if you are winning, then I'm winning. That's it. I have no vested interest. It's not like I own stock in Liddane Tutoring. Maybe I should. Maybe I should.

Andrea Liddane: Would you figure out that piece for me, please?

Andrea Liebross: All right, next. That'll be our next thing. So squirrels. Let's talk about the squirrels. Can you give an example of a squirrel? But maybe something that's been distracting you or was distracting you.

Andrea Liddane: Yeah. Well, again, I'm in an industry where I've had a lot of feedback. I've had some amazing employees, employees who were so vested in the business and have given such great, valuable information and have helped me to see and have strengthened my belief in this dream. I'm quite fortunate because I've had this dream for a really long time. I mean, since I can remember.

So I've turned to different people and a lot of people have supported me. But the problem is that most of them don't have business backgrounds either. They've never guided a business through some of the turmoil. Now being with you and being able to ask those questions, but also to be able to be part of the group. The group is a piece that we're not speaking to. Andrea convinced me to do the full Runway to Freedom. Again, one of the best decisions. I can't wait to be with these people again.

But I also have them to watch. It's funny when you're doing coaching on one of our calls with one of the other people in the group, I learn so much because it's a lot easier to be super critical of somebody else. Like, "Well, of course you're going to do that." Like, and then you go, "Oh yeah, look at that."

Andrea Liebross: I'm doing the same thing or what they're receiving coaching on relates to me in this way. So that's super powerful. So lots of squirrels that you learned through, we'll call it, you always learn mistakes or whatever, but...

Andrea Liddane: That includes clients, that includes employees, that includes people who just find my name and send me something in my inbox. Like it can be at so many different levels, so many different levels.

Andrea Liebross: But I guess, I think what's interesting here, when you say that, you never have had really a filter to put things through, except rolling around in your own head. I think now you're approaching things in a much more, just from my observation and working with you, in a much more systematic way or what's important right now.

That is important. We're going to put it on the shelf for now because we're focusing on this. So then it kind of puts the squirrels to the side.

Andrea Liddane: Yeah. I recently had to make a big decision and I was much, much more intentional about how that decision played out and what the steps were. So I wasn't trying to do it all at one time. I think having you there where I was like, again, using this analogy, so Andrea's standing there in the fray of all of these squirrels and all of these different options of ways to go saying, "Follow me, I will help you, or let's go through this together."

I just want to say that finding that person, it's really a gift, but it's also one of those things that I think about in my own business that we really try hard to pair a student with someone who can guide them on their journey through the forest. I mean, maybe it's just for a few steps. Maybe they just need to their calculus exam so that they can get a decent grade in it or something like that. But the squirrels are out there for them too. Parents, the most common conversation or question or statement that I get from parents, and I've done thousands of intake calls in my life. That's part of what we do.

In that time, I've heard every parent almost say to me, "I could help my kid." I know how to get through the forest. I did it. I've had my own journey and I can look up things and there's every different podcast and everybody but what we offer and what you're offering is like, here is a way through this forest and I'll be with you and I'll be honest with you. I have experience. I've been through the forest many, many, many, many, many, many, many, many times. I've got the background.

Andrea Liebross: That's a good analogy. Also for the listeners who are most, a lot of my listeners are parents. It's like you could figure stuff out for your kid. You could also, if we're talking about tutoring, like we could go on YouTube and watch Khan Academy videos.

Andrea Liddane: For days.

Andrea Liebross: But that's not the same as having a live or virtual, but a human tutor. It's not the same. I think that's also, as business owners, we can watch a million videos and listen to YouTube, podcasts, books, everything. But it's not the same to almost have someone in your court.

Andrea Liddane: Yeah, exactly. Again, all the people who are sitting at whatever top of little entity, it could be three people, whatever, one person, you're sitting there trying to make the decisions which way to go.

Again, like as a tutor, might I not know the latest, greatest thing, or might I, but I'm going to get to know the student and I'm going to add my experience and my background. I mean, you have this background and you've seen all of these people go through business and you've learned so many things in your life. So I'm going to trust that, because I mean, otherwise I'm just dinking around over here, like standing in the mud.

Andrea Liebross: I think you mentioned before we started recording, like jumping over a stream? Kind of. It's like being able to jump over the stream. I think recently, Andrea Liddane made a big decision in her business. I think you knew when we were approaching that that in the end, something had to change and be different. But to figure out how to make that happen in a way that felt actually authentic to you, that felt good, that felt like it was the right thing to do for the business, “if the business had a vote,” which we say—the business had a vote—felt the right way, vote for the business, but also allowed you to explore options along the way, like get a taste: “If we go this way, is it going to feel okay?”

Andrea Liddane: Yeah.

Andrea Liebross: I think either you probably never would have made that decision or jumped over the stream, okay? If we hadn’t worked through that together, that never would’ve happened. Or you just would’ve made that decision, I don’t want to say too fast, but not as carefully orchestrated as you did.

So that’s almost like, we took out the map, we contemplated the ways we could go, we chose like one route, not knowing halfway through which fork we would take, but we’re going to go in this direction. Then we can make that next decision when we get there. Right. And then in the end, I think it's worked out.

So I think I find business owners either want to kind of like rip off the band-aid way too fast or they never rip off the band-aid at all. And then the band-aid becomes part of their skin and then they just go back to, “Well, this is just the way we've always done it.”

I think businesses that have been in existence for a long time, that’s even more true.

Andrea Liddane: There are so many things. I mean, you know, and I make jokes like, it wasn't that long ago that I was taking client notes by hand, basically like on a napkin in the back of my minivan. I mean, that's really how I started. And there's certain parts of the business that aren't that far from that.

But how do I know—because everything can always be improved and everything—but how do I know what are the most important parts? And again, which trail to go?

Thinking about the stream, I want to go back to that. I hope this doesn't get too corny with this whole thing that we're using here.

Andrea Liebross: But analogies are good. I love them.

Andrea Liddane: Yeah. So again, we're on this trail. There are like a hundred different ways to go. There are squirrels at every place, people at every place offering to guide.

I think what it felt like when I called you the first time—and that was a hard moment in my life—was like, “Please just get me across this stream, and then I'm going to trust you.” There was such a sense of relief with that.

Almost like, you're crossing the stream, you don't know, if you've never done it before, is this rock going to give out and you're going to end up in water up to your waist? You know, how do you get across?

Andrea's standing on the other side, “Step on that rock. Step on that rock. Have you considered this?”

Now that we're here on the other side, I feel like going along on the journey, I just have somebody who's learning about my business, who's understanding some of the sticking points, but also can make those decisions in the best interest of me as a human.

Again, I’ve worked so hard, as so many people have. If you're not quite there, it's like, “Well, what should I do?”

Andrea Liebross: Right. So how do you think you make decisions differently now?

Andrea Liddane: Such a good question. Because I think this is probably the biggest—and I was just giving feedback to a shared person of ours this morning about not getting stuck in the decision-making of whom to talk to.

Andrea Liebross: I think I might know who that is.

Andrea Liddane: Yeah, I think you do too. So I think in the past, I have felt that in order to be a good business person, I have to research. I'm a learner. I have to research every step of the way: “Should I do it this way? Should I do it that way?” Almost like looking at a Google map and zooming way out, “Well, I want to get to there, and let me see all the options.”

Sometimes it's just not that important. If somebody else can go, “Hey, this is the way I think you should go. These are the reasons why,” and they're sound, make the decision and move on. Because otherwise, you're just stuck there. That’s what you’re spending all your time doing.

Andrea Liebross: Yes. Being stuck there. You have, in the past few months, you’ve hired a virtual assistant. You’ve brought on a new marketing agency. What do you think would have kept you stuck in indecision before? Why didn’t those things occur before?

Andrea Liddane: Well, first of all, I’ve never done this before.

Andrea Liebross: Yeah. So this is interesting. Like, even though we've been around for 24 years, never done it before, right?

Andrea Liddane: Nope. Nope. As a human being, I've never done a lot of these things. Like, I don't know. The world has really changed.

Andrea Liebross: Yeah. But you’ve hired tons of people. Your business can't run without other tutors. So you've hired tutors. That doesn't stress you out at all. But hiring a different type of person or someone to fill a different role or capacity, never done it before.

So I think that's what keeps people stuck. Like, “I don't know how to do this. I've never done this before.” They overanalyze, like the person we’re talking about this morning who is overanalyzing how to approach something, then you just go, “Well, maybe I’ll get to it next week.” Or, “I’m going to wait till”—we're recording this right before July 4th—“I’m going to wait till after July 4th. It’s not a good time now.” Versus just, “Let’s just try it on. Let’s see what happens. What’ve we got to lose?”

Andrea Liddane: Exactly. Knowing when to do that. Because there are certain things that are just easier to—I mean, I've started this in my business. There are a lot of different kinds of customers. It's a flow. We have people who’ve stuck with us for many, many, many years. But there are people coming in and coming out, and that’s how we work it.

But I think also part of this is—I don't know how I learned this through you, but I know I did—is having avatars for certain people and situations so that you're not reinventing this wheel every single time.

Even when an employee behaves a certain way, or there's something going on, or even if they're an amazing person, how are we going to treat that person? What is the real estate that it's going to take up in my brain? Or customer.

There’s a certain kind of customer that I’ve seen a hundred million times in this business. You can't always tell when they first walk in the door. So how are we going to deal with that and not sit there and ruminate?

Andrea Liebross: Take up real estate in your brain. Andrea was here when she was here for our last retreat. While you were here, you had a client, a parent, reach out with a problem/taking up real estate in your brain: “What am I going to do? How am I going to answer?”

And I remember you saying, “Can I just ask one question? I don't even know what we’re talking about, but I gotta solve this problem right now because it’s taking up too much space.”

I think that's something that becomes different when you have a strategic thought partner, when you have a sounding board, when you start to create momentum and you just make decisions quicker.

Andrea Liddane: Yeah. But knowing that you and everyone else at the retreat were on my side, that was a crazy experience to have. Everyone was so interested. If I would have been at home, I might’ve mentioned this to my husband or maybe my friend or whatever, but it's not the same as somebody else who's like, “Yeah, that's hard when you have to deal with that kind of person or that sort of situation.”

Again, I don't have other people in my life who run businesses the size of mine. You also always talk—I have so many Andrea-isms. If you know Andrea's content, you'll understand all the things I'm referencing here. But one of the things is resources.

Andrea Liebross: Yeah.

Andrea Liddane: I'm going to let you put it in your words.

Andrea Liebross: So I say we have our four most valuable resources: time, money, people, and then we could say energy or brainpower, kind of like what comes from within.

You may think that time is your most valuable resource. You can make an argument for that. You could say money is your most valuable resource—we can make an argument for that—or the people you have. But really, your most valuable resource is your own brainpower and your own energy and figuring out what to do with that in order to create more time, money, and better relationships. I mean, that's what we should be focusing on. I don't know if that's what you're getting at. Is that what you're getting at?

Andrea Liddane: Definitely. Definitely. If I'm brewing over a certain kind of customer or a certain kind of employee, or some decision that other people have made—again, standing at that fork in the road—but I have Andrea with me, like we’re holding hands, we’re going down this path, it’s far more powerful to make those decisions.

What I've realized too is that the revenue that I'm managing—and this revenue is different from profit—but I don't have any background in understanding how to do this well, even just that piece: “Should I spend money on this? Should I hire a virtual assistant?”

I can do all the things that she's doing. I know how. I'm telling her how.

Andrea Liebross: Yeah.

Andrea Liddane: That takes a lot of time.

Andrea Liebross: It does. So is that a cost? Is that an investment? So that's another thing you've figured out. And mulling that over in your own head, you can convince yourself either way.

But I think having this strategic partner, this forum, this community to help weigh those things makes things smoother. It doesn’t create business lag either.

So I think it's fair to say you were experiencing a little bit of business lag. You didn’t have the momentum you wanted. It was hanging out. It was fine, but it was just there. I think that you’ve seen huge momentum in the last handful of months. Fair?

Andrea Liddane: Yeah.

Andrea Liebross: I’ve seen it. I’ve seen it for you. I don’t know, but I’ve seen it. Sometimes you're in your own peanut butter jar. You can't see it, but I've seen it.

Andrea Liddane: That's another Andreaism. I love the peanut butter jar. Yes. Swirling around.

Andrea Liebross: Swirling around. A lot of women might assume that coaching is just for startups. Or that at this point in your career, I mean, you should have been able to figure this out. What would you say to someone who thinks that by year five or fifteen or twenty-five, they already should have had this figured out?

Andrea Liddane: Again—and here's my story, just quickly—is that I decided consciously to scale my business in 2018 and then got stuck in the peanut butter jar of the pandemic. So coming out of that and looking around, I mean, again, had I had this resource early on, it would have saved me so much money. It would have saved me so much.

Andrea Liebross: So what would you say? Like, what do you wish you would have said to your 2001 self? Or maybe your 2014—the earlier self, the younger self? If she could sit on one of our coaching calls, what do you think she'd say? Or how would you have even told her to get on a coaching call?

Andrea Liddane: I would tell her to get on a coaching call for sure. It may not be obvious at first. That’s the other thing. You know what? Again, this is just like—I’m going to run the parallel here—it’s like hiring a tutor. You can lead your child through their calculus course because you have a degree in blah, blah, blah.

But the cost is that the laundry might not get done, or you might be arguing with that person. Maybe the person I’m arguing with is myself, or it can be people from outside.

Right now, I have a great opportunity coming to me from one of my tutors. But having somebody standing there with all the resources in front of them alongside me saying, “Is this the right thing?” I think finding a coach as early as possible, if you’re serious about this whole thing you’re about to do or doing, is invaluable.

But for me, it’s not too late. In fact, it's right on time because I’ve now built this thing with so many different hands and beautiful minds of people who have helped me to create it, some people who have helped and wanted to destroy it, and I protected it.

Now it's time for me to get it to the point that it's capable of getting. But I need guidance because, well, look at me. I don’t want to spend the next 20 years trying to figure out what the next step should be and making all the mistakes.

So now I want to get to the other side of this forest, and I want to do it with integrity, and I want to have a good life, and I want to reap the rewards. But I don’t know how to do that because there are so many things I’ve never done before, and I’ve learned them along the way, but it’s not very efficient. It’s really inefficient to do it without a coach sometimes.

Andrea Liebross: Yeah. I would say it creates efficiency a hundred percent.

Andrea Liddane: It does. A hundred percent.

Andrea Liebross: How have you also—because I've heard you talk about this—how has this helped you reclaim inspiration for your work? Because I know you are very passionate about what you're doing, but sometimes it's hard to keep that at the forefront.

Andrea Liddane: It's getting more and more rekindled. And I see a way. And I'll be honest with you, I am tired. I'm running all the operations of my business right now. I'm doing all these things.

But not for long. I’m pretty exhausted by that. It's the same thing for parents. I’d say to clients all the time, “You have to help your kid make sure they bathe and that they have clean clothes and they have what they need to go to school.” Is this something that is worth, you should be doing this? Is that net result something that I should be making all these decisions by myself and handling all these things and experimenting?

I feel like I don't want to do that anymore. I want to take, last week we were talking about bold leaps rather than next steps. And that's what I want to do. I hope I answered that question.

Andrea Liebross: Yeah, you did. You did. You've taken bold leaps rather than next steps. I love it. So, all right, two last questions while we wrap up.

You’ve said to me, “This is the best investment that I have made.” So if someone said to you, “What do you think the return on your investment has been thus far, emotionally or strategically, or financially?” How would you answer that?

Andrea Liddane: Well, again, you can juggle all the balls, you can sit tight, but it’s a lot of energy going out. My balance of my energy, it’s not where I’m enjoying my work anymore all the time. I have these moments that are amazing.

I really want to love this because I am super passionate for it. I know that I understand things in a different way than some people, and I want to share that and give some guidance in my own work. But I also need the time and the permission to do that.

So I think what I’ve learned from the coaching is that the rest, and the carving out time for my brain to really dream and wrap itself around what I want to create, is extremely critical.

So chasing the squirrels or making a decision to go in a certain path, I couldn’t do all the paths, but I’m just running around. I’m not really doing what is in my best self.

Andrea Liebross: Yeah. So I think by seeing that you can make decisions faster and clearer, with more clarity, you’ve been able to reclaim some of your own time.

I mean, I know you said to me once, “I haven’t been in my house by myself for more than 48 hours ever.” You had a whole week. You just took it off. And you took it off for time for yourself. Or you’ve been doing tons of camping. And you’ve been kind of working while you’re camping, but you’ve definitely been okay with having that space. I think that’s a huge return on investment.

Andrea Liddane: Yeah. I mean, I can’t wait to get to the next step with your guidance so that I can hire a Director of Operations. Because I know that my brain worrying about accounts receivable, let’s say, like, somebody needs to do that, but does it need to be me every single week?

Probably not, what I should be doing or can be doing for my business, even just trying to make that decision, “What is worth my time?” it's hard to see that in yourself. Because I can do these. I know my business inside and out. I can do it all. All the pieces, pretty much, I mean, other than the bookkeeping and all that.

Andrea Liebross: You’re capable.

Andrea Liddane: I’m capable.

Andrea Liebross: Do you have the capacity, or do you want to use the capacity you have for it? That's the thing.

Andrea Liddane: Yeah. That's not the dream. The dream isn't for me to be stuck in all of that.

Andrea Liebross: Yeah. So, all right, last question. How would you describe how you feel about the future of your business now?

Andrea Liddane: I'm so excited. I mean, I'm excited. I'm excited because I feel so much more confident now in the decisions I'm making.

Again, just having another person come in who's watching, who's tracking, who's listening, Andrea listens to those of us who are in Runway to Freedom. I leave her messages about the most random ideas I have, and sometimes she gloms onto them and says, “Hey, that's really great,” and other times I can tell, she'll ask me questions that will guide me to a different direction.

With the coaching and even with the support from the other women in this program, it's not that any of us feels like we have the answer, but just that reflection time and giving space. I can't wait for our next retreat because giving myself the space to really work and think—even if it's not “productive time” in terms of we did blah, blah, blah, blah—how critical that is. I'm now giving myself that permission, and I can't wait for more.

Andrea Liebross: I can't wait either. I'm excited too. I'm excited to see where you go next and how this all shakes out. I'm excited for our next retreat. So if you're listening and you want to be there, come, message me, tell me, and we will get you going on that. We'll talk about what that looks like and what that means and what it involves.

You should come be with the two Andreas and all of the other people. Maybe there'll be three Andreas. If there's some other Andrea listening, come on over.

Andrea Liddane: Her last name is L-I.

Andrea Liebross: Yes. Yes. Come on over. Well, this has been such a pleasure. Thank you for sharing and for being so honest and open with everybody. You do tutoring all over the country. They don't have to live in Seattle, do they?

Andrea Liddane: Nope. Nope.

Andrea Liebross: How are they going to find you?

Andrea Liddane: Great online tutors. Great people working for me. Our website is www.liddanetutoring.com.

There are so many tutors in the world. But if you're looking for somebody who, again, can be that guide for your student, because I can tell you how that's a whole different piece. We can't control our children. So giving them someone that we say, “Let this person help you through this moment,” is really powerful.

Andrea Liebross: Yeah. All right, we’ll have all the links to Andrea’s business in the show notes, so go capture those.

Okay, my friends, thank you for being with us today.

Andrea Liddane: Thank you, Andrea. We all love you so much. That’s great. It’s a pleasure to be interviewed by you.

Andrea Liebross: I appreciate you being here.

So friends, I hope you loved listening to Andrea as much as I did. I always say two Andreas are better than one, even if it does confuse our inboxes and links and probably our VA from time to time.

But what Andrea shared is so important. Just because you can do it alone doesn’t mean you should. Just because you’ve built a business and had it for many years doesn’t mean that you need to continue building it alone. You’ve done it with heart and grit and pure tenacity, but transformation doesn’t necessarily always happen until you get yourself the right kind of support. That is what working with me and working with a coach is really all about.

So sneak peek, I’m tweaking the names of some of my coaching programs. That mastermind, that Runway to Freedom mastermind, is soon going to be called The Ascension Collective. That really is what Andrea Liddane is in, is part of. It’s my high-touch, multi-point coaching experience for female entrepreneurs who aren’t just building anymore, they’re optimizing, they’re evaluating, they’re leading.

It’s for that woman who knows she could keep doing all the things, but is really ready to finally stop being the bottleneck and start being the CEO. Kind of what Andrea described.

So if this conversation that I just had with Andrea Liddane stirred something up in you, come find me on Instagram @andrealiebrosscoaching or click the link in the show notes and learn more about what I am doing with my clients like Andrea.

I hope this episode has created awareness. But now, take action. It’s time to make your business feel the way you imagined it could feel, and it could be, when you started. You built the business, but let’s build the feeling. Reach out. I’m here to help.

Until next time, remember: She thinks big. So do you. Talk to you soon. See you next week.

Thanks for tuning into the She Thinks Big! Podcast. If you're ready to learn the secret to unleashing your full potential, don't forget to grab a copy of my book, She Thinks Big: The Entrepreneurial Woman's Guide to Moving Past the Messy Middle and Into the Extraordinary. It's available on Amazon and at your favorite bookstore.

And while you're there, grab a copy for a friend. Inside, you'll both find actionable strategies and empowering insights to help you navigate the complexities of entrepreneurship and life, and step confidently into your extraordinary future.

If you found value in today's episode, please consider leaving us a review on your favorite podcast platform. And if you're ready to take this learning a step further and apply it to your own business and life, head to andreaslinks.com and click the button to schedule a discovery call. Until next time, keep thinking big.

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Who_s the Best Business and Life Coach in Indiana - AndreaLiebross.com

I'm Andrea Liebross.

I am the big thinking expert for high-achieving women entrepreneurs. I help these bold, ambitious women make the shift from thinking small and feeling overwhelmed in business and life to getting the clarity, confidence and freedom they crave. I believe that the secret sauce to thinking big and creating big results (that you’re worthy and capable of) has just two ingredients – solid systems and the right (big) mindset. I am the author of best seller She Thinks Big: The Entrepreneurial Woman’s Guide to Moving Past the Messy Middle and Into the Extraordinary and host of the She Thinks Big podcast.