Why Your Income Plateau Isn't a Strategy Problem | Jess Pinili

Key Takeaways

• 1Your capacity for success is your tolerance for change. If you want more success, you have to get comfortable with being uncomfortable.
• 2Procrastination isn’t always laziness. It can be a way to regulate your emotions when you’re scared of what success might bring.
• 3'Every new level has a new devil.' The same fears and patterns show up at $10k months and $100k months, they just look different.
• 4Childhood conditioning is 100% connected to how you run your business. Beliefs like 'I have to work hard for money' come from what we learned growing up.
• 5When your brain feels scared about a big decision, it's not a real tiger. Jess uses a 90-second trick to calm her nervous system.
• 6You might be tweaking your strategy because of emotion, not data. It’s a way to feel in control when you’re scared of what could happen if you succeed.
• 7When your revenue doubles and then drops, it's often because your nervous system isn't ready to hold that level of success.
• 8The woman who breaks through is the one who chooses to do things differently, even when she does not know what the result will be.

Jess Pinili called her dad crying one morning because she didn't want to go to work. He asked her, 'If you're not happy, what are you actually doing about it?' Six months later, she quit her job, moved to Bali with $700, and started her business. But this isn't about that big leap. It's about what happens next, when you keep hitting a ceiling in your business no matter what you try.

What if your life looks good but feels wrong?

Have you ever looked at your life and thought, "I should be happy"? You've checked all the boxes. You have a good job, you can pay your bills, and you've got great friends. But deep down, something just feels off. It’s a strange feeling, and it can make you feel guilty and confused.

Jess Pinili knows that feeling all too well. Before starting her own business, she was a fitness manager for a couple of gyms. On the outside, her life looked perfect. She was doing everything she was "supposed" to do.

I was working as a fitness manager for a couple of gyms. And even though on paper, everything looked great. You know, I was making money, I could pay my bills, I had a great friendship group, I liked where I lived. Jess said

Things were good, but she felt a huge gap between the life she was living and the one she felt she was meant for. She felt disconnected from what she really wanted to do with her life. This feeling kept growing until one morning, it was too much to ignore. She woke up and just could not bring herself to go to work. Feeling terrible and guilty, she picked up the phone.

I called my dad crying and I had told him, like, what do I do? Do I just pretend I'm sick? Do I take a bit of time off? I'm just not enjoying this. Jess said

Her dad didn't tell her to just push through it. He didn't tell her she was being silly. Instead, he asked her a simple question that changed everything.

But the overall question is, you know, if you're not happy, what are you actually doing about it? Jess said

That question hit home. It was the wake up call she needed. Six months later, Jess had quit her job, moved from Australia to Bali, and started the business she's still running today.

That feeling that something is "off" is a real thing. It’s easy to dismiss because on the surface, your life might look totally fine. Maybe you can relate. Your life might look something like this:

• You have a steady job with a decent salary.
• You have friends and family who care about you.
• You pay your bills on time and have a safe place to live.
• There's no big, obvious crisis happening.

But inside, you just feel stuck or uninspired. It feels like you’re just going through the motions. That feeling isn’t something to ignore or feel bad about. It’s a signal. It’s your gut telling you that the path you're on might not be the right one for you anymore, even if it’s a perfectly good path for someone else.

So, what can you do about it? You can start by asking yourself the same question Jess's dad asked her. You don't need a grand plan or all the answers right away. Just take a quiet moment and ask yourself, "If I'm not happy, what am I actually doing about it?" Just asking the question is the first step. It's about being honest with yourself that something needs to change.

That feeling that something is wrong is a sign that it’s time to be honest about what you really want.

Moving to Bali with $700 in savings

Have you ever dreaded going to work so much you thought about calling in sick? Jess Pinili knows that feeling. On the outside, her life looked great. She was a fitness manager, paid her bills, and had good friends. But inside, something felt wrong. She felt disconnected from what she really wanted to do with her life.

One morning, she just couldn't face her job. She called her dad crying, asking what she should do. He gave her some simple advice that changed everything. He told her life was too short to feel that way and then asked a question.

...if you're not happy, what are you actually doing about it? Jess quoting her dad

That question hit home. Six months later, Jess quit her job, packed her bags, and moved from Australia to Bali to start her own business. She did all of this with only $700 in savings. It was a huge leap. When she looks back on that time, she remembers a strange mix of feelings.

I feel like the first three months, I was terrified, yes, but also fearless at the same time. Jess said

For those first few months, a deep gut feeling told her she was on the right path. The fear of running out of money didn't really sink in right away. She knew she had to make it work. The thought of failing and having to move back to Australia, live with her dad, and get another job was her worst-case scenario. For her, going back to her old life was not an option.

What’s interesting is that her biggest fear wasn't about money or failing at business. It was something else entirely. She worried about what people back home would think. In Bali, working online was normal. But in Australia, it wasn't as common back then.

a deep, a deep one was definitely, what are my friends in Australia going to think about this? Jess said

She was scared of being misunderstood by her friends. This fear of being judged was even bigger than the fear of moving to a new country and starting from scratch. She had to push past that feeling to build the life she wanted.

If you're thinking about making a big change, it helps to get really clear about your fears. Sometimes the thing we think we're afraid of isn't the real problem. Try asking yourself these questions:

• What’s the actual worst thing that could happen?
• What happens if I do nothing and stay where I am?
• Is there a smaller, hidden fear, like being judged, that's really holding me back?

Thinking about these things can help you see what’s truly stopping you. It can give you the clarity you need to move forward, even when it feels scary.

Sometimes the fear of staying the same is the biggest risk of all.

Why is your tolerance for change so important?

Have you ever felt like you were about to burst when trying something new with your business? It's that antsy, nervous, almost scary feeling in your stomach. Most of us think that feeling is a stop sign. We think it means we’re doing something wrong or that our plan isn't working. But what if that feeling was actually a good sign? What if it just meant you were growing?

Jess Pinili has a totally different way of looking at this. When she first started her business, it was a huge change. She had quit her job, moved from Australia to Bali with only $700, and was trying to build something from scratch. Desi asked her what it actually felt like in her body to make such a big shift.

Jess explained that growing your business isn't just about strategy. It’s about how much new stuff you can handle at once. She said:

the way that I teach all my clients about expansion is really your tolerance for change.

Jess said

For her, starting her business was exciting, but underneath all the excitement, there was a different feeling. It was a feeling of intense pressure, like a pot of water about to boil over.

it's almost like a pressure cooker in your body of waiting for the results that you're working towards.

Jess said

This pressure wasn't just about whether the business would work. It was also about how people would see her. She came from a fitness background, but now she was talking about confidence and mindset for women. Everything was changing, and it was deeply uncomfortable.

The pressure came from a lot of different places:

• Showing up on social media stories and trying to sell something.
• Pivoting her content to talk about new ideas.
• Worrying about how her friends and family would react to the "new Jess."
• Feeling like she was being watched and judged for trying to create something different.

The really interesting part is that Jess wasn't scared of the work. She knew what to do and was driven to get it done. The hard part was handling the uncomfortable feelings inside her body. It was the fear of being seen differently, of not fitting into the box her friends and family had her in.

And that’s the key. She learned that she had to just sit with that pressure cooker feeling. She couldn't run from it. She had to learn to tolerate it and trust that she could handle it. She had to tell herself:

okay, I'm not going to burst. It's okay, I can keep doing this.

Jess said

So the next time you feel that squirmy, uncomfortable feeling when you're trying to grow, remember this. It might not be a sign that you're on the wrong path. It might just be the feeling of your tolerance for change getting bigger. Instead of stopping, try sitting with the feeling for a minute. Notice it. And remind yourself that this feeling is part of the process.

Growing your business often feels uncomfortable, and learning to handle that feeling is the real work.

Are you watering down who you are for your friends?

When we make big life changes, it's not always the hard work that scares us. A lot of the time, the biggest fear is what other people will think. This is especially true when it comes to our friends and family.

For Jess, this was a huge deal. When she quit her job and moved from Australia to Bali to start her business, it wasn't just about leaving her old life behind. She had lots of fears, like running out of money, but one fear stood out more than any other.

A deep, a deep one was definitely, what are my friends in Australia going to think about this? Jess said

She explained that Bali is a place where lots of people work online from cafes. It's totally normal there. But back in Australia, it wasn't as common. She was nervous about what her friends would think as they saw her posting on social media about her new business. She worried they would see her on her stories and think, "What is Jess doing? What is this thing she's trying to start?"

Jess even said this fear was bigger than the fear of moving to a new country or quitting her job with only $700 in savings. That's a pretty big statement.

I think that in itself, over moving country, quitting my job, starting something new, I think that was probably the biggest fear that came up and one of the biggest shifts within myself that I had to overcome. Jess said

It's a feeling a lot of us can relate to. When you start to change, you wonder how this new version of you will fit in with the people who have known you forever. Jess described it as a deeply uncomfortable feeling. She wondered, "how is this new version of me going to fit in the reality of my friends and family's minds?"

It’s scary because we all want to be loved and accepted by our friends. We worry that if we change too much, they might not get it. You might worry about things like:

• They'll think I'm trying to be someone I'm not.
• They'll make fun of me behind my back.
• We won't have anything in common anymore.
• They won't accept this "new me."

Jess realized that we all tend to put people in boxes. Our friends have an idea of who we are, and they put us in a box based on that idea. When you start doing something completely new, you're basically jumping out of that box. It can be confusing for them and scary for you.

So what can you do about it? Over time, Jess learned she had to let go of trying to control what other people thought of her.

I had to let go of needing to control the narrative of what anyone perceives of me when I look at friends and family. Jess said

She accepted that everyone has their own opinions and that's okay. It doesn't mean it's not scary or that it won't hurt sometimes. But trying to manage everyone's idea of you is an impossible job. The real peace comes from knowing you're living a life that feels right for you, even if others don't totally understand it yet.

You can't control what other people think, but you can always choose to be true to yourself.

Your business problems started before your business

Ever wonder where your bad habits in business come from? It's easy to think they're new problems that popped up when you started your company. But what if they started way before that, when you were just a kid?

Desi asked Jess a great question about this. She wanted to know how much of what holds us back started before our business ever did. Jess’s answer was pretty direct.

I would say a hundred percent. All of it. Jess said

That’s right. One hundred percent. Jess believes that all the stuff holding you back today is tied to your childhood. It’s not about your marketing plan or your sales funnel. It's about the ideas and habits you learned a long, long time ago.

Think about it. When we’re little, we learn how the world works from our parents or the people who raise us. We watch how they act, how they talk about money, and how they deal with success or failure. We soak it all up like a sponge without even realizing it. These lessons become our unconscious habits and beliefs as adults. Jess finds that when she works with women, their biggest challenges in business always connect back to these early lessons.

She sees a few common patterns that show up again and again. These might sound familiar to you:

• You have to work super hard for money. Jess says this is a very common belief. You might have seen your parents work long hours and struggle. So now, you believe that making money has to be difficult. If it starts to feel easy, you might even mess things up because it doesn't feel right.
• You're afraid of being truly seen. This isn't just a fear of public speaking. It's the fear of showing people who you really are and then being misunderstood or rejected. As Jess explains, it's the...

  ...fear of being seen. Seen for who you truly are, and afraid beyond that of being misunderstood, being rejected, not being accepted. Jess said So you might water down your message or hide parts of your personality to feel safe.

• You put things off because you’re scared of success. This one is tricky. You might think you're just a procrastinator. But Jess says it's often a deep fear of what will happen if you actually succeed. Will you have more responsibility? Will people treat you differently? So your brain tries to keep you safe by making you scroll on your phone instead of doing the thing that could move your business forward.

It sounds a bit heavy, I know. But here’s the good news. Just because you learned these things doesn't mean you're stuck with them forever. The first step is just to see the connection.

...when you recognize that it's just as easily as you picked it up, you can change it... I think that's the beauty in recognizing where it came from, understanding who you picked it up from, and thinking, okay, if I don't like that about myself or the way it's it's hindering my growth of my evolution, I can change that. Jess said

So start by getting curious. The next time you feel stuck or find yourself falling into an old habit, ask yourself where that feeling might have come from. You don't have to fix it all at once. Just noticing the pattern is a huge first step.

The first step to fixing your business problems is realizing they probably aren't business problems at all.

Do any of these common money stories sound familiar?

Sometimes, the thing holding you back isn't your business plan. It's an old story you've been telling yourself for years without even realizing it. These old ideas about money, work, and success often come from way back when we were kids. Jess Pinili says that these hidden beliefs are almost always the real reason someone gets stuck.

She sees the same few stories pop up again and again with the women she works with. They are super common, so if one of these sounds like you, you are definitely not alone. Jess explained that these patterns usually start long before someone even thinks about starting a business.

I would say a couple of common patterns that I see in my client, I have seen in my clients over the past few years is number one around money mindset.

Jess said

When you see how these stories play out, it makes a lot of sense. Here are the big ones Jess pointed out:

• You have to work really hard for money. This is a huge one. Maybe you saw your parents work long hours and came to believe that being exhausted is what it takes to earn a living. So you get stuck in a loop of working harder and harder but never actually making more money.

• You're afraid of being seen and misunderstood. This was a big one for Jess personally. When she first moved to Bali to start her business, she was terrified of what her friends back home would think. Would they get what she was doing? Would they judge her for it? She said that this fear was even bigger than the fear of quitting her job or moving to a new country. She worried about how this new version of her would fit into the box her friends had her in. The fear of being rejected by people we care about can make us play small without even knowing it.

• You put things off because you're scared of success. This one might sound backward, but it’s really common. Jess explained that procrastination isn't always about being lazy. A lot of the time, it's our body's way of protecting us from a big change, even a good one. If you keep putting off a task that could grow your business, it might be because you're secretly nervous about what happens next.

Jess finds that people don't always connect their actions to this deeper fear. They just think they're bad at something.

It's not necessarily, oh, you're just not good at content... It's actually what do you think is going to happen beyond that the success if you break it down?

Jess said

If you finally make that video or launch that thing, what happens then? Do you get more money? Jess asks what that success really means to you.

Does it mean more responsibility? Does it mean that people are gonna treat you differently?

Jess said

These are the hidden questions that can keep us stuck procrastinating on the important stuff. The first step is just to see if any of these sound familiar. You don't have to fix it all at once. Just noticing which story you might be living in is a great start.

Noticing these old stories is the first step to changing them.

Procrastination is not what you think it is

Do you ever have something really important to do, but you just keep putting it off? Most people call this procrastination and then feel bad about being lazy. But Jess Pinili says it might not be about laziness at all. It could be that you're secretly afraid of what happens if you actually succeed.

Jess gives a great example of this. Picture a business owner who knows she needs to create long-form content, like YouTube videos, to grow her business. She adds it to her calendar, ready to go. But when it's time to film, she suddenly finds a million other things to do. She might start doing laundry, scrolling on her phone for hours, or convincing herself she just doesn't know what to say.

On the surface, she might think, "I'm just not good at making videos." But Jess says the real problem is usually something else. It’s not about the task itself. It’s about managing our feelings.

procrastination, but in the sense of when they have a fear of success. Jess said

When we put things off, our body is often just trying to protect us from a scary feeling. We do something easy, like scrolling social media, to feel better in the moment. According to Jess, procrastination is a way our body tries to get back to feeling normal and stable. But what’s so scary about making a video? It's not the filming. It’s the success that might come after.

And beyond that, and why we do that is because beyond that, we're scared of perceived success. Jess said

Jess asks her clients to think about what happens after the video does well. What happens when it brings in more customers and more money? That's where the real fear is hiding.

...what do you think is going to happen beyond that the success if you break it down? Okay, you create this piece of content, and to make it simple, you you get more money. And then what does that mean? That success, if it's money, does it mean more responsibility? Does it mean that people are gonna treat you differently? Jess said

All of a sudden, success doesn't sound so simple anymore. We start to worry about all the things that could come with it. Things like:

• Having to manage a lot more money
• Feeling pressure to keep doing better and better
• Worrying about what our friends and family will think
• The responsibility of hiring a team
• The fear of failing after you've had a big win

Faced with all these new, scary possibilities, our brain looks for an escape. It wants to go back to what feels familiar and safe. So, we procrastinate. It's not because you're lazy. It's because your body is trying to keep you safe from change, even good change.

So what can you do about it? Jess says it starts with simply noticing. The next time you find yourself putting off a big task, just stop and ask yourself, "What am I doing right now?" By interrupting the pattern, you can start to see what's really going on. You might realize you're not avoiding the task; you're avoiding the scary "what ifs" that success might bring.

Procrastination is often your body trying to protect you from the uncomfortable feelings that come with growth.

Why does my income go up and then right back down?

Have you ever had a really great month in your business, only to watch your income drop right back down the next month? It's a common pattern, and it's super frustrating. It can feel like you took one big step forward and then two giant steps back, leaving you wondering what went wrong.

Jess Pinili told a story about a client that shows exactly why this happens. It's not because your strategy suddenly stopped working. It's something deeper. This client worked really hard for months. Then, in just two and a half weeks, her revenue doubled. At first, she was thrilled. She thought, "Holy crap, everything I've done has worked. This is great." But that celebration didn't last long.

Almost immediately, her brain started to panic. It was like a switch flipped. Suddenly, all she could think about were the problems this new money would create. Jess shared her client's train of thought, and it's something a lot of us can probably relate to.

"Am I a bad person? Because I make more money? Does that make me greedy that I celebrated this? To be a better person, do I need to? This is quite literally my members' train of thought. Do I need to donate to charity?" Jess said.

The client's mind just kept spinning. She started worrying about everything from paying more in taxes to what her friends and family would think. Her thoughts went a little something like this:

• Do I need a more expensive accountant now?
• Should I tell my friends? What if they aren't happy for me?
• Wait, was this just a fluke? I don't think I can do this again.
• Am I even worthy of this much success?

This new level of success felt so unfamiliar that her brain saw it as a threat. Our brains are designed to keep us safe, and to the brain, "safe" often means "familiar." Anything new or different can feel dangerous, even if it's something good, like more money.

"Well, the brain is wide for efficiency and familiarity is efficiency. And so what the brain is trying to do is to conserve energy." Jess said.

So, what happened next? Overwhelmed by all these new fears, the client pulled back. She completely ghosted her audience for a month and a half. She stopped creating content because it just felt too hard. As a result, her engagement dropped, traffic to her sales pages disappeared, and her sales dried up. Her income went right back down.

"What happened? She immediately revenue dropped down to under half that. And so belief came with, well, I can't sustain that. That's too hard. I'm on this income roller coaster and it solidifies all of that." Jess said.

She ended up right back where she started, but with a new belief that she wasn't capable of handling that success. This is what Jess calls a capacity issue. It’s not about just wanting more money; it’s about preparing your mind and body to actually hold it without freaking out. So, what can you do? Start by just paying attention. The next time you get a win, big or small, notice your first reaction. Do you celebrate it, or does your mind immediately jump to all the new responsibilities and potential problems? Just noticing that pattern is the first step to changing it.

Your income can only grow to the level that your mind feels safe holding.

How to tell your body it’s not being chased by a tiger

Have you ever made a big decision for your business and felt totally terrified? Maybe your heart started pounding or your stomach did a flip. Your brain knows you're just sending an email, but your body is acting like you're in real danger.

Jess Pinili says this is a super normal reaction. Our brains are old. They’re built to keep us safe from things like, well, tigers. When we do something new and scary, our body can't always tell the difference between a real threat and a business risk. It just feels the fear and sounds the alarm.

Jess explains that when we make a big choice that stretches us, our body can react like it’s in serious trouble.

...when we recognize how that feels in the body, is look at caveman times that was recognition of we're about to be chased by a tiger. Jess said

So what do you do when your brain says "go" but your body says "TIGER!"? You feel that panic. Your mind starts listing all the reasons this is a bad idea. And before you know it, you've backed away from the very thing that could help your business grow. It's an old safety program running in the background. Your brain loves what is familiar because it doesn't take much energy.

...the brain wants familiar. And so anything outside of familiar, what you've chosen, you will always go into those self-sabotaging behaviors... Jess said

But you can teach your body that it's okay. You can show it that hitting "publish" on a new offer isn't the same as running for your life. Jess shared a simple exercise that only takes 90 seconds. She says an emotion takes about that long to move through your body. If you can catch the fear before it takes over, you can change how you respond.

Here's how to do it the next time you feel that panic coming on:

• Notice the feeling. Instead of ignoring it, pay attention when your heart starts racing or your palms get sweaty after a scary choice.
• Put your hand on your heart. This is a simple physical action that helps you pause and notice what's going on inside.
• Talk to your body. You can literally have a little chat with yourself, either out loud or in your head.
• Tell it what’s really happening. Remind your body that this feeling is just change. It’s not an actual tiger.

Jess’s advice is to be really clear and direct with yourself.

...hey, this is just change. We're making this decision... but it's not a tiger. It's actually just us changing, and that's okay. Jess said

Just sit with that uncomfortable feeling for 90 seconds. You can even set a timer on your phone. You're not trying to make the fear disappear. You're just teaching your body that you can handle it. You're showing it that this new action is not a real danger.

At first, you might not feel a huge difference. But if you do it over and over, things will start to shift. After a month or two, you’ll look back and realize that the decision that used to feel like a tiger attack now just feels... normal.

Your body can learn that new business decisions aren't a real danger.

What’s the difference between the woman who breaks through and the one who stays stuck?

So, what makes some people seem to get ahead while others stay in the same place? It’s easy to think it’s just luck or that some people have it easier. But the real difference might be simpler than you think. It often comes down to one thing: being willing to do something different, even when it feels a little scary.

Jess told a great story about this. She was working with a client who has a product-based business. They were looking at her website together. The client had a form for a sizing guide, but it was set up to only accept 10 responses a month. When Jess asked about it, the client said she was only getting about 10 responses anyway, so why pay for more?

It sounds like a smart business decision, right? Don’t pay for what you don’t use. But Jess saw something else happening. She pointed out that by choosing the cheaper plan, her client was literally putting a cap on her own business.

So you think from a you're thinking, and this is where business owners, miss, you're thinking from a strategic perspective, well, I'm only getting 10 responses a month, so I'll only pay for this tier of the form. , Jess

The client admitted she was scared of getting more emails. More emails meant more conversions, which meant managing more stock and more work. She was afraid of the success she said she wanted. So she had, without realizing it, limited herself.

Jess suggested she upgrade the plan to allow 100 responses. The price difference was very small. The client chose to do it, even though she didn't know if it would work. A week and a half later, she told Jess she had already gotten 30 responses. She tripled her results just by making space for them to come in.

This story shows the difference perfectly. The woman who breaks through is the one who chooses to do something different without knowing what will happen. She pays a little extra for the bigger plan, just in case. The woman who stays stuck waits for the 100 responses to come in before she’s willing to pay for them. But they can’t come in if there’s no room.

the biggest difference is they choose the uncomfortability of doing something different and not knowing the result because we don't. , Jess

Getting unstuck isn't always about making huge changes. It’s about the small choices you make every day. It's about operating in a way that matches the person you want to become. You can’t wait until life calms down or until you have more time or money. Life is always going to happen.

And this is what I say to my business owners is life is always going to be busy. And life is always going to life. , Jess

So how can you start doing this now? Think about one area in your business or life where you feel like you’re not moving forward. Then, ask yourself a few honest questions:

• Am I putting a cap on what I can receive, like Jess's client did?
• Is there one small, different action I can take today, even if it feels odd?
• Am I waiting for a guarantee before I try something new?
• What would the version of me who already has what I want do in this situation?

You don’t have to know the outcome. You just have to be willing to try a new road.

The person who gets ahead is the one who chooses to act differently, even when it's uncomfortable and the result isn't guaranteed.

Listen to the full conversation

This conversation with Jess was full of moments that made me think. If you feel like you're doing all the right things but not getting results, you'll want to hear the whole episode. You can listen to the full conversation by playing the episode on this page. To see more from Jess, you can find her online at her website, womanmasteryhq.com, or on Instagram @jesspinili.