239: Why So Many Women Entrepreneurs Feel Lonely (Even at the Top)

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. Welcome if you've never been here before. This really is a podcast for ambitious women who are building businesses and lives that work for them, not the other way around.

I know it sounds super cliché, but it's hard to do. It's hard to build a business and a life that works for you, not a business that you feel like hinders your life, or a life that gets in the way of your business.

So today we're going to talk about something that doesn't show up on your calendar, but it takes up an awful lot of headspace. In fact, last episode, we did talk about your calendar and feeling like you never have enough time. But today I want to ask you this question: "How can you have that full calendar and a full book of business or a full roster of clients, but still feel completely alone?"

How can it be that you are so busy, but you still feel completely alone? So this episode is for you. I know this is you. You built something really successful, but you're finding yourself with no one to bounce ideas off of. No sounding board for tough decisions. No space to just be in the mess and the magic of entrepreneurship. This is the loneliness that no one talks about.

It's so true. It's so true. This is the loneliness that no one talks about. I've said it before, but it bears repeating. The buck stops with you, right? There is this invisible weight of decision fatigue because things stop with you.

I feel that sometimes in my own business. When you're the CEO, every decision, even the small ones, can feel like they carry the weight of the whole business. When there's no one in the room who truly gets what you're holding, it can be very isolating. Again, I feel all of this, okay?

But what I work with my clients a lot on is creating that support system so that you do not feel that isolation. A client once told me, "I don't need a team of people doing more for me. I need a space where I can think out loud where I'm not the only one at the top." Okay?

So when you're inside a coaching container, for example, you can think out loud and you're not the only one in there. She really just nailed it. We don't always need help executing. We just need help processing.

You can outsource things, right? You can hire experts, but you can't outsource to being the one in charge. I think that's where the loneliness creeps in. You can outsource tasks, but you can't outsource being the CEO or being the one in charge. It feels very lonely knowing that.

Here's the thing. Research shows that over 50% of CEOs say they've felt lonely at some point in their journey. And of those, more than half say it negatively affects their performance. Let that sink in.

Even the most successful leaders—the ones with titles and teams and traction—are quietly struggling with isolation. It's not just a feeling. It's a performance risk, right? If you're feeling isolated, it's impacting your performance.

So you could have a title and a team and you could have traction, but in the background, you're feeling pretty alone. I think there's some decision fatigue that sets in. I looked at this in preparing for this episode, tried to explore what are the stages of entrepreneurial loneliness. I see it evolve in three main stages.

So stage one. I want you to picture yourself, think about where you are. I want you to know by the end of the next couple of minutes what stage you're on.

Stage one is it's me, myself, and I. You're just starting out. Friends don't understand why you're so obsessed with your calendar. They're asking, "When are you going to slow down? Are you loving what you're doing?" And you start to question yourself. You start to wonder, "Is it just me?" No one is really getting this because they haven't lived it.

You could go back—if you have a copy of She Thinks Big, the book—go back to, I think, chapter two. I talk about the parking lots. Maybe it's in chapter one. This aligns with these parking lots a little bit.

So stage one: me, myself, and I. No one gets it because they haven't lived it. It's lonely. All right. Stage two. You've hired the help, but you're still holding it all together. Now you've brought in a contractor, maybe even a team, but you're still the one signing the checks, making the decisions, setting the vision.

You start to wonder, "How much can I really share?" And you start to tiptoe between transparency and leadership, which adds another layer of distance because you're still holding it all. You've got the help, but you're like, "Can I share my numbers with them? Can I share where I really want this to go?" And you're still holding everything together. That's stage two.

Now, stage three—and this is the stage that no one really, really warned you about—you've made it. But now you feel more isolated than ever. You've made it. You're running the six, seven-figure business. You have traction. People think you've arrived. But now the pressure is bigger. The team is bigger. The decisions feel heavier. Ironically, you feel even more alone.

This recently came up in an episode I recorded with my client, Andrea Liddane. I don't think that episode—you might've heard that already, but maybe not. I don't know. It's coming up. If we have aired it, then the link will be in the show notes.

We were both struck in our conversation by how easy it is, even in successful seasons, to really feel like you're navigating the wilderness with no compass. We agreed, she and I, what most entrepreneurs need isn't another productivity tool. It's really a trusted circle.

Okay, it's a trusted circle. It's some place where you can say your ideas out loud, where someone's listening.

I want you to use this visual here, the iceberg you're living on. You've seen the iceberg image, right? The tip above the water is what people see. Then they label it, if we're using this in a business sense, the growth, the rebrand, the podcast, the client wins. They see that growth, that little part that's sticking up above the water.

That image of an iceberg, there's a little tip and that's what people see. It symbolizes growth. For me, it might be a rebrand or a podcast or a client win or a book.

But underneath the surface, underneath the water, that's where the stress lives. The indecision. The Sundays where you question everything. The moments where you think, "Is this what I signed up for?" And the truth is that 90% of what it takes to run a business happens beneath the surface. And often, you're navigating it alone. And like that iceberg, you're floating solo.

And you're not broken, you're just kinda unsupported. Not kinda. You're just unsupported.

So I know this, and this is one of my missions in creating the coaching programs that I created. I know what a real community can look like. But let's talk about what it feels like, because it's not just networking or a Facebook group.

Inside something like Ascension, inside the coaching group that I have created, I've watched women exhale, literally, for the first time in months. I've watched women on my retreat in the middle of the day say, "I just need to go rest. I'm realizing that I haven't rested in months."

These women, they might sit in the metaphorical or literal white chair that I've talked about in previous episodes and say things like, "I didn't realize how lonely I was until I came here and met these women yesterday." Or they might say, "It's been so long since I had a conversation where I didn't have to explain myself and start from the beginning." That's because everybody knows each other in this room. We've been with each other—even if it was in a virtual Zoom room—they don't have to start from the beginning.

Or another woman said to me, "This room gets me. I don't have to be the boss, the leader, the fixer. I can just be me." So that's the magic of being surrounded by women who know what it's like to lead at this level.

Are you surrounded by women like that? I want to know. If you're not, you're missing out. Because it is heavy to both hold growth and doubt at the same time. It's heavy. That iceberg is heavy. The tip above the ocean level that people see, you're holding that. That's the growth. But you're also holding all of the decisions and the other things below the surface.

When you're in a room like this, people get it. They're not trying to fix you. They're just trying—these other women—to just be there beside you. So I want to invite you to come into a community like this. This is a place where you can exhale, where you can share your ideas, where people will listen, where people are not going to try to fix you. They're just going to try to support you in whatever is most helpful in that moment.

So here's your homework. I want you to check in with yourself. Who do you bounce business decisions off of without second-guessing yourself? Who challenges your thinking without competing with you? Who really understands what it's like to be in your shoes?

If your answer is no one, then that's your sign.

So who do you bounce business decisions off of without second-guessing yourself or without hesitation? Is it no one? Who challenges your thinking without competing with you? Is it no one? Who really understands what it's like to be inside your shoes? Is it no one? So if the answer is no one to any of the questions, that's your sign.

I want you to pick one person. This is your homework. I want you to pick one person you trust, someone who's in the arena with you, and send them a text and say, "Hey, what's something you're navigating in business right now that feels heavy?" And then share yours, what feels heavy to you. That's it. That's all. But the conversation has to start somewhere.

So here's your invitation from me. You can text me actually that thing. What are you navigating in your business right now that feels heavy? I will answer that question. You send it to me, and I will share my own real example. Then I will ask you what yours is.

But here's your invitation. If you're tired of doing this whole world and business and life alone—even if you've gotten really good at it—I want to invite you into something deeper.

Ascension is for women entrepreneurs who are done trying to outwork the loneliness, who are ready to lead their business with more clarity and more spaciousness and yes, more support.

This is not just a mastermind. It's a strategic accelerator. It's a circle of peers, a place where you don't have to explain yourself because the women inside here already get it.

Why do you need to be here? Because you can't build a successful business by yourself. I can't build a successful business by myself.

But building a sustainable one, a joyful one, a business that fuels your life instead of draining it? That's another level.

So I guess I could go back and I could say, you can build a successful business by yourself, but I don't think it can be successful in the sense of being sustainable or joyful or one that fuels you. That's what takes community.

It really starts here. Loneliness isn't something you grow out of, my friends. It is not that. You don't grow out of this. It's something you plan for because it can show up at any stage. Any stage.

You need to treat it like any other business risk and build in protection for this loneliness before it takes its toll. So yes, get ahead of it.

One, build your support systems early before you think you need them. Loneliness really grows in those spaces between the decision and the discussion. Don't wait until you're burnt out or stuck.

Number two, schedule connection with the same intention as strategy. Put it on your calendar. Join a room. Be inside a group. Create rhythm around reflection. So schedule connection with the same intention as strategy.

And choose spaces—number three—choose spaces where you can be real, not just impressive. So networking, sometimes we feel like we need to be impressive there. But I want you to choose a space where you can be real. The point isn't to show off what's working. It's to unpack what's not and to grow through it together.

And then fourth, treat community like infrastructure, not indulgence. This isn't a nice-to-have. I think this is a need-to-have. So just like a CRM or a payroll service, this is a system. Being inside a community like Ascension, it's a system that keeps your business and you operating at full capacity.

So there's no such thing as being done with being in a community. Nope. So if you're not building community in your business, you're leaving one of the most important growth tools on the table. I promise you.

Thanks for listening to this week's episode. If something I said resonated, I want you to send this episode to a fellow entrepreneur. Because we're not meant to do this alone.

Then I want you to visit andrealiebross.com and book a call with me and click on that coaching tab. Learn more about the Ascension Collective. DM me on Instagram. I would love to hear from you what is heavy in your business, and I'll share what's heavy in mine.

Remember, now is the time to level up. There has never been a better time. This community is not a nice-to-have. It's a need-to-have. Because loneliness happens at every stage. Alright, my friends, I will see you next week.

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