the bossbabe podcast - 463: Why Most Entrepreneurs Stay Stuck at Six Figures (And How to Break Through)

Episode Date: May 15, 2025

Everyone online talks about reaching six-figures like it’s the ultimate goal, but what happens when you get there and realize you’re still overwhelmed, overworked, and underpaid? In this episode, Natalie breaks down why so many entrepreneurs get stuck at $100K and what it actually takes to break through. She shares the common myths keeping people spinning (like “just add more offers” or “wait to hire until you can afford it”) and reveals the real shifts, both strategic and mindset, that unlock sustainable growth. If you’re ready to simplify, systemize, and scale in a way that actually feels good, this one’s for you. TIMESTAMPS 00:00 - Why six figures isn’t the freedom milestone you thought it’d be 01:03 - The real reason hustle stops working when you try to scale 02:36 - What it looks like to wear every hat (and why it’s unsustainable) 03:06 - The sneaky mindset traps that turn a plateau into your ceiling 04:03 - Three growth myths that sound smart, but actually keep you stuck 05:34 - Why the fastest growth often comes from doing less, not more 06:04 - Step 1: Simplify - get radically clear on what’s working 06:34 - Step 2: Automate - how tech can become your first hire 07:29 - Step 3: Delegate - and finally stop doing it all yourself 07:59 - How to shift from operator to true CEO (without losing momentum) 10:12 - What high-level CEOs actually spend their time on 12:13 - Why scaling revenue without profit leads straight to burnout 15:33 - The silent profit leaks draining your business behind the scenes 16:20 - The middle-class business trap + how to break free from it 17:35 - The shift that turns your business into a freedom vehicle RESOURCES + LINKS Join The Société: Our Exclusive Membership To Help You Build A Freedom-Based Business - start today for just $97.  Learn how to Start or Scale a Freedom-Based Business with this free training: bossbabe.com/class.  Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).

Let's talk about something no one warns you about when you're chasing that first six-figure year. Everyone online is shouting about hitting $100,000, that's the finish line. But what no one tells you is six figures is not financial freedom. In fact, for most entrepreneurs, hitting $100,000 feels harder than it looks. And when they finally get there, they realize they're working more than ever, they're more stressed than ever, and somehow they're not actually keeping more money. Because what gets you to six figures is hustle. You grind, you wear every single hat,

you make it work by sheer force. But that same hustle-based strategy that gets you to $100,000, it is the exact thing that keeps you stuck there. So if you're hovering at that six-figure mark feeling like you're working way too much, way too hard for the money you're making, then this is for you.

I've made over $33 million, so I know a thing or two about driving revenue. And today I'm breaking down exactly why most entrepreneurs stay stuck at six figures and what it really takes to break through that plateau and scale to multi-six and beyond without burning out. Let's dive in. All right, so let's break down exactly why most entrepreneurs get stuck at six figures.

Here's the hard truth. The strategies that got you to a hundred thousand in revenue, they're usually the same ones that stop breaking the second you try to scale past it. So at six figures, most entrepreneurs are running a business that is a hundred percent dependent on them. They are the marketer, they are the salesperson, they are the service provider, the project manager, the face of the brand, the operations manager. If they stop, the business stops.

And let me tell you from experience, that's not necessarily a business. That is an expensive job. What starts to break down looks like this. You might be managing too many offers or products. Maybe you launched a new course, you're still running a one-on-one consulting. You've got a group program, maybe an affiliate thing on the side. And instead of one clear message driving your marketing, you are just so scattered.

Your energy is diluted and so is your audience's attention. Now your content can start to feel all over the place because you don't even know which offer to talk about today. And then when marketing feels confusing, guess what? People don't buy. Then there's the backend. No real systems at all. Lead generation, you're probably winging it, hoping your next post somehow gets traction. Sales, you might be sending DMs, manually following up, chasing leads down.

In terms of delivery, you're onboard sending DMs, manually falling up, chasing leads down. In terms of delivery, you're onboarding the clients yourself because no one else knows the process or because the process is literally only in your head. Do you feel called out? And when that's the setup, growth feels heavy. You are maxed out. Adding another client or launching another offer does not feel exciting. It feels like a burden. And let's not forget the most common sticking point. Fear of hiring, delegating or raising your prices. You tell yourself, I'll just wait until I make a little more and then I'll hire some support. Or people just won't pay any more than this.

Or this is what the market can handle. And that's the moment that the plateau can become permanent. Because until you shift out of that thinking, you'll keep spinning your wheels at six figures, wondering why the money isn't flowing the way that it should. So before we get into what actually breaks you out of this plateau, let me just call out a few scaling myths that are keeping way too many entrepreneurs stuck spinning their wheels, because it isn't just strategy that's slowing you down. It's also what you believe about growth.

So the first myth is if I add more offers or more products, I will make more money. And it does sound logical, right? I get it. More ways to buy means more sales. But here's the truth. Complexity kills scale. So more offers means more content to create, more funnels to manage, more customer journeys to optimize.

Like when you think about the details, it can dilute your message. It can split your audience's attention and ultimately burn you out. And the businesses that scale the fastest, they actually double down on one clear proven offer and they get known for that. The second myth is you should hire help once you can afford it. This one keeps people broke for years. And here's the reframe.

You afford help by buying back your time sooner. So you can focus on revenue generating work. Hiring the right support is not actually a cost. It is a multiplier if and only if you do it strategically. The longer you wait, the longer you might stay stuck in say $10 an hour tasks and then wondering why you can't break through. Another myth is passive income is the goal. Listen, there is nothing wrong with leverage, but the idea that you are going to build this

set it and forget it passive machine that just prints money while you're on a beach, total fantasy. Unless you have serious systems, team, and traffic behind it. The truth is most of what's marketed as passive is actually the hardest to scale profitably without a machine. And if you're chasing passive before you've built a solid scalable offer, you are setting yourself up for disappointment. So here is the shift. Scaling isn't about adding, it's about removing. solid scalable offer, you are setting yourself up for disappointment. So here is the shift. Scaling isn't about adding, it's about removing.

Removing anything that does not move the needle. The businesses that grow cleanly, profitably and sustainably, they are really ruthless about focus. They are really clear on what works and they're not chasing vanity metrics. They are building machines. So how do you break through that six-figure plateau? Because the answer isn't more. It's not adding more, more offers,

more marketing channels or more hours. It's doing fewer things better. And I know it sounds simple, but this is where most entrepreneurs get it wrong because they think that scaling means expanding when in reality, the next level is all about refining. So let me just break it down. Step one, simplify.

So at Multi Six Figures, the businesses that scale the fastest, they are the ones who have stripped it all back, most often to one core offer, one traffic source, and one sales system. And they run that over and over until it prints money. So that means getting radically honest about what your highest leverage offer really is. So which offer delivers the best results and creates the most profit with the least complexity. Because once you know that, everything else either supports that offer or it goes. Step two is automate. If you are still doing every single follow-up manually, if your onboarding process depends on you remembering to

send a welcome email, if your client delivery feels heavy because there's no repeatable system, you've got to stop thinking like a solopreneur. Technology is your first hire. You should be building automations that can handle things like lead follow-up, nurture sequences, client onboarding, even recurring tasks like delivery tasks, like sending reports or gathering feedback because the real bottleneck at this level is not often your audience size,

it's the operational drag that is slowing down every single sale. Then step three is delegate. You really shouldn't be carrying a $500,000 business on your back completely alone. You probably will burn out. And so I don't just mean outsourcing admin tasks. I mean hiring revenue driving support.

So maybe that's a setter for your DMs, a closer for sales calls, a community manager who keeps clients engaged so you can stay focused on what grows the business. Maybe it is a virtual assistant who can just take some admin off your plate. The mindset shift is the team is what buys back your brain so you can zoom out, think strategically,

and operate like the CEO, not the assistant, the coach, and the virtual assistant, all rolled into one role, which likely you are feeling right now. Solopreneurship is a thing, but people are still outsourcing a lot of the admin things that are taking up space in their brain. Now another part that people don't talk about enough is that scaling isn't just strategy, it is identity. And the reason that a lot of entrepreneurs can stay stuck at six figures

is not always because they don't know what to do, but it can be because deep down they are still operating with that solopreneur mindset when they don't want to be a solopreneur anymore. So they might be thinking like the coach, the service provider, the content creator, not the CEO of a company. And here's the shift you have to make if you want to break through. Stop asking, how can I do more? Maybe start asking, how do I build a business that runs without me being in every single part of it?

That difference really is huge. So solopreneurs might wake up every day and be wondering, what should I be posting? How could I get more clients or even the next sale? How do I fix this problem? And CEOs probably wake up thinking, who is solving this problem? What system ensures that this never happens again? Maybe how do I optimize what's already working at scale?

And here's the uncomfortable part. Most of us say we want to scale our business, but I'll have it's proof otherwise. So we might still be pricing like freelancers, terrified to raise rates because what if nobody buys at that increased rate? Maybe we are still hoarding tasks because there's belief that no one can do it like me.

Maybe we're scared to invest in help because we've convinced ourselves it's way safer to stay super lean, even though it's literally what is keeping us stuck. But let me tell you this, the leap from six to multi six figures is not necessarily a grind harder, post more, add another funnel kind of leap,

but it could be a leadership leap for you. It could be becoming a version of you who is willing to trust, delegate, and operate from vision and not fear. It's the moment you realize your time is the most expensive resource in the business. Like, I really want you to hear that. And your job isn't to be the best at doing everything.

It's to build the machine that does it without you. That is the mindset shift. And until you make it, you'll probably stay stuck. So let me paint a picture of what actually changes for you when you do take a step into that CEO role, because I know right now a lot of your day probably is spent inside the weeds. Like you can't even see the wood for the trees. You're writing the emails, chasing down the clients, making Canva graphics,

scheduling, posting content. And here's the thing, that's most of the time not what CEOs would spend their time on. And so when you make the shift from solo printer to CEO, your role will change. And so here's what you want to consider being focused on versus where you're actually focused. So first, think about auditing the data and actually making decisions. So the CEOs that are scaling cleanly, they know their numbers. They do not delegate the numbers. They know their numbers. They're looking at what's working, what's not and where the money is leaking and they are fixing it fast. Second is strengthening the core offer. They're not creating new programs or products every single quarter because they're bored.

They are obsessing over making the one they already have so much better. Better results, higher prices, better client experience, stronger retention, because scaling happens when you optimize, not when you keep starting over, not when you keep starting from scratch. And then third, managing the team and not the tasks. They are leading strategy. They really shouldn't be following up on deadlines and following up on tasks not done. They are coaching the people who are running the day to day,

because that's what actually creates scale. And then last, creating leverage, not scrambling for content ideas. Maybe looking at new partnerships, new revenue streams, new ways to grow without adding loads more work. Maybe they're asking, what creates the biggest impact with the least amount of me? Because here's the truth, no seven-figure CEO is waking up wondering, what should I post on Instagram today? They're probably waking up asking, where's the next bottleneck? Or what decision moves us forward?

Or is there an interesting position I could take on social media? It's a shift, right? That is what changes everything. So you stop spending your time getting through this endless to-do list and you start spending your time building the machine that grows, whether you are sitting at your desk or your laptop or not. And that's what becoming the CEO actually looks like in practice. Okay, let's talk about another shift.

Again, that is not talked about enough when it comes to breaking past six figures. At some point, the goal has to stop being grow revenue and start becoming grow profit. Because I see this trap all the time and it kills me. You hit 10,000, then 20,000 months and your brain instantly says, cool, how do I double this? How can I hit 50,000 months? And so you're adding offers, you're cranking up ad spend, you are launching more, you're doing all the things. But what no one tells you is growth mode without profit mode is how you scale yourself straight into burnout. Revenue grows, expenses grow faster. And somehow you can end up

feeling poorer at $300,000 in revenue than you did at $100,000 in revenue. And that is a truth that most people avoid. If your model isn't profitable at $100,000, scaling it probably won't fix the problem but actually could make it worse. And that is why it's so important once you hit that first six figures you do have to zoom out and stop chasing that top line growth and actually start asking where might we be leaking margin what is bloated or unnecessary or how do we make more from what we're already doing instead of just adding more. So you're shifting from how do I sell more to how do I run this tighter, cleaner, and more profitably.

And trust me, you guys, that is a game changer. One of the best ways to do that is actually to model your revenue backwards from your profit goals. This is something that, you know, multiple eight figures later, I'm still doing. If you want to keep and take home $200,000 a year, what revenue number and margin gets you there? What offers, team structure and systems support that without dragging you into complexity? Because the real flex isn't hitting $500,000 in revenue and keeping $50,000.

It is running a $300,000 business that pays you like it's a $500,000 business because it's clean, it's optimized, and it's actually designed for profit. That's the shift that gets you out of this endless hamster wheel and into the kind of business that feels good to run. And digging deeper into this, the truth is most entrepreneurs don't stay stuck at six figures because they're not making enough. They stay stuck because they are not keeping enough. Because listen, hitting $100 thousand dollars a year sounds great

until you realize that you're spending $80,000 to make it between team costs, ad spend, tools, subscriptions, random expenses that slowly bleed the business. And what no one talks about is that at this stage, and to be honest, at every stage, profit margins shrink really, really fast if you're not paying attention. I still have to pay so much attention to this because here's what's happening. You start outsourcing, which is great, but instead of optimizing delivery,

maybe you're just throwing bodies at the problem. Maybe you're hiring people, but there's no clear KPIs or efficiency systems. So things are feeling like they get messier, not easier. Or you add software, but you never cancel anything. Been there, done that way too many times. Or you're paying for tools that you forgot you had. Maybe you're taking on clients that drain you

and you actually don't enjoy working with because it's good money. But then you forget to factor in how much time and energy and emotional bandwidth they cost you. And then suddenly, yeah, you're making $10,000 a month, but you are barely keeping yourself enough to pay your rent. Revenue is vanity. Profit is freedom.

So breaking out of the six figure plateau is really not just about making more. It is tightening up how you run the business. So you actually keep more. Simplify delivery so that every client is profitable. Audit your expenses quarterly. Ruthlessly cut down what is not driving growth. Start looking at lifetime value per client, not just those front end first time sales. And think about building in recurring revenue wherever possible,

so you're not starting from zero every single month. Because scaling does not matter if you're scaling stress. I think the real flex is building a business that pays you well, that funds your life and still has margin left over. That's the shift that we're not talking about enough. It's the one that truly can unlock multi six figures and the freedom that you thought you would feel at $100,000 in revenue.

Now let me name something that most entrepreneurs do feel, but again, I feel like we're just not talking about enough. I call this the middle-class business trap. This is the stage where your business is making enough to look successful from the outside. Maybe you're hitting eight to 10,000, maybe even $15,000 months, whatever the number is, but behind the scenes, it is heavy. It is hard.

It feels like the business fully owns you and not the other way around. You're making enough to stay afloat, but not enough to create any kind of real freedom. Maybe you're hiring enough to just survive, but not enough to actually buy back your time. Perhaps you're stuck taking clients you don't love because it's good money and you're scared to say no, quite frankly. And what's really wild is once you're here, it gets harder to change because the business technically works. It's just really exhausting.

And that's what I mean when I say six figures isn't always freedom. It is the middle class of entrepreneurship. It's comfortable enough to stay, but not profitable enough to grow or feel good. And often the only way out is you stop running the business like a solopreneur and you start building it like a solo printer and you start building it like a CEO would. Something really powerful is having a business that pays you well, it funds your life and it doesn't require you to carry it every single day.

So if you're sitting at six figures right now wondering why it still feels hard, wondering why you're working more, stressing more and somehow keeping less, this is why. The strategy that got you here, it won't take you where you're trying to go. Breaking through is not about adding more offers, posting more content, or just working more hours. It is about simplifying, systemizing. It's about shifting out of solopreneur mode and finally leading like the CEO that you know your business actually needs, because the truth is real

scale doesn't happen when you do more. It happens when you build the machine that works with or without you. That's how you'll stop spinning. That's how you'll stop leaking profit. And that's how you'll be able to build a business that just doesn't look good on paper, but it feels really, really good to run. And so your move now is audit where you're still playing operator instead of CEO. Make those hard decisions, simplify and start

building the business that creates freedom not just revenue. I hope this was helpful I'll see you in the next episode. Wait wait wait before you go I would love to send you my seven-figure CEO operating system completely free as a gift. All you've got to do is leave us a review on this podcast because it really supports the growth of this show. This is my digital masterclass where I'll show you what my freedom-based daily, weekly, and monthly schedule looks like as an eight figure CEO, mama and high performer.

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