10. How You Know When It’s Time to Grow

How You Know When It’s Time to Grow

When is it time to level up? To bust out? It’s time when your outer world feels too small for your inner reality. People may say this is greedy, but it isn’t. This episode explains why. 


  • How you’ll know when it’s time to grow
  • Why growth is never greedy
  • What you need to know if you’re waiting for applause
  • Why self-concept is such an important part of entrepreneurship




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Welcome to Episode 10 of HOW TO MAKE MORE MONEY, a podcast that helps you get seriously good at the game of making serious money.

I’m your host Kelly Hollingsworth. I’m so glad you’re here. If you’ve been following along, you know that we are at the home plate. This is the seventh episode in our seven-episode series discussing the seven skills that take your income to seven figures and beyond. Is that enough sevens for you? It’s a lot of sevens. Today we are on skill #7. This is the funnest topic of all, and it’s where we really get into it. What we’re talking about today is the topic that separates the contenders from the pretenders.

Are you ready? Good. Because this is the episode where everything shifts. It’s where the gloves come off and you really see what you’re made of, and who you want to be in the world.

What is this topic? Today, we’re focusing on YOU. The six skills we covered prior to this episode are about your client:

  • Skill #1, creating the click through commercial storytelling, is devoted to identifying, communicating, and offering the happy ending that your business creates.
  • Skill #2, spreading the word, is about getting out into the world and inviting your people to join you on that journey.
  • Skill #3, high-profit thinking, is where you learn to manage your vibe so you attract customers rather than repel them. At first glance, this may seem like it’s about you, but it actually isn’t. It’s about you getting yourself together enough that you don’t get in the way of your customers getting what they want, which is the happy ending that your business creates.
  • Skill #4, coaching, is completely about your clients. With the skill of coaching, you are helping your clients do some high-profit thinking on their own, so they can get out of their own way and avail themselves of the happy ending your business creates.
  • Skill #5, service, is where you scrub your business of all indulgences. Indulgences are about serving your emotional needs. Service is about serving your clients’ needs and desires. And service is what every high-earning entrepreneur needs, because that’s where the money comes from. When you deliver the happy ending, that’s when you get paid.
  • In the last episode, we talked about skill #6. Skill #6 is severing. This is the process of cutting yourself from the weight of conventional wisdom, so you can shorten the critical path to your clients’ happy ending. Make it shorter. Make it more efficient. Make it as pleasant and enjoyable as possible for your client, and that’s another aspect of delivery that every high-earning entrepreneur needs.

All of these skills thus far have been all about your client. Today we’re going to focus on you. And specifically what are we going to focus on? You, letting go of all the garbage you have been fed about yourself and entrepreneurship and making money. You, letting go of the story you have been telling yourself about yourself. And you letting go of other people’s ideas of what your place in the world is, should be, and will be.

What we’re talking about today is basically a giant identity shift. It starts when you invite yourself to make more money. We talked about that way back in, I think, episode 3. And the journey is complete when you get to that point of recognizing that you are that person. In story terms you can call this the aha moment. It involves you recognizing that you have shed your old identity—that persona you’ve been living in that was never really you—it never really fit you–and stepping into your true self as the entrepreneur who runs a seven-plus figure business.

When you do this, you are at that moment in your own journey when suddenly all the planets come into alignment and you get everything you wanted. You get the money. You get the meaning. You’re creating transformation for your clients because you lived the transformation for yourself. It’s when your business suddenly feels effortless, because you’re no longer in your own way.

How do you get this? With the seventh skill that creates a business that goes to seven figures and beyond. It’s the skill of shedding your old self-concept. It’s where you take off that tired old coat you’ve been wearing, and you leave it where it lays. You decide, that’s gone. It doesn’t even exist. This is who I am. This is who I’ve always been. I just didn’t know it before because I was covered up with an untruth about who I thought I was supposed to be.

As I think about this shedding of an identity that isn’t really you, I wish I could show you a movie of my life. If I could, you would see how important it is to let yourself pursue your dream. Making more money, on its face may seem shallow to some, but true entrepreneurs are drawn to it because on some level they understand that the money isn’t really what it’s about. The money is merely a byproduct of the realization of two very important, inextricably intertwined desires. The first is the desire to be who you really are in the world. And the second is to help the world by achieving that self-concept of yourself. By achieving something that you were put on this earth to achieve.

I don’t typically talk about my own journey in much detail. When I talk about my life, I generally just hit the high points. I grew up in poverty. I started a housekeeping business at age 13, cleaning houses… five bucks an hour. And I became one of the few female hedge fund managers in the world. These few sentences hint at a journey of inner transformation that’s pretty big, but as I look back, it is in fact so profound I can’t even begin to describe it.

It started with my housekeeping business. The seed of that business began when I was so small. I grew up in a pretty normal household. Dad was an accountant. Mom was a housewife. Everyone drank too much. But it was the 70s—everyone drank back then. Have you watched Guess Who’s Coming to Dinner lately? Every third line in that movie is about alcohol. They went for a drink. Let’s have a drink. Can you meet for a drink? No, but only because we’re meeting someone else for a drink. So, in the beginning, all the drinking in my family, and all the other shenanigans, felt pretty normal.

But then everything started to spin out of control. At first it was just once in a while. I remember my mom waking us up in the middle of the night, so we could drive around strange neighborhoods looking for my dad’s car. I remember finding his car, at 2 o’clock in the morning, parked in front of some other woman’s house. And my mom driving us home and telling us it was all going to be fine. By the next day, it seemed that all was forgotten. We were still a family.

Then, when I was older, about third or fourth grade, I remember my dad being gone for days. Maybe it was weeks. When he finally came home, we learned that he had lost our house on a craps table in Las Vegas.

My mom still didn’t leave him. My dad got fired from his job at Boise Cascade, and we sold the big house in Boise and we moved to Coeur d’Alene, where my grandparents lived. My dad went early to get our new house while my mom stayed back in the old house to pack it up. When we arrived in Coeur d’Alene, we saw that our new house had a freeway running through the backyard. And my mother asked, “Who would buy a house that has a freeway running through the backyard?” At that point, my grandmother told her that my dad had been drunk when he bought the house.

You can smell a divorce coming, can’t you? When it happened,  my mom started running a newspaper route to put food on the table, and going to college to get a degree so she could eventually get a daytime job.

That was great that she was getting out there and making things happen, but our homelife went seriously downhill from there. Pre-divorce, our house had been ultra-clean. Post-divorce, it often felt cluttered and dirty. I didn’t realize quite how dirty until a neighborhood friend came over to my house, and later we went over to his house. His mother asked, “What is that smell?” And he took off the jacket he had been wearing at my house, and he handed it to his mother and said, “This is what their house smells like.”

It was an awakening. I remember thinking to myself, “Oh. I guess poverty has a smell. And whatever it smells like, it’s in our house.”

I went home, looked around, and I thought, This is not who I am. This is not what my life is going to be about.

That’s when I started cleaning. And I mean seriously cleaning. My mom had taught me to clean when she was a housewife. And I always did chores as a kid. But I hadn’t considered that I should take over the cleaning of the entire house until that moment when I realized that my house didn’t smell good anymore, because my mom couldn’t take care of it anymore. If it was going to get better, I was going to have to do it. So I decided to become the person who lived in a clean house, and from there it was effortless. I didn’t spend one second thinking about, should I or shouldn’t I? At that point, it was simply who I was.

Once that was clear to me, inside, This is who I am, it was easy for me to turn that into a business. So I went and told people about it—“Our house doesn’t just look clean. It smells clean, because I know how to make that happen. I can do it for you, too.” And people hired me to make their houses not just look clean, but smell clean, too.

In a nutshell, I figured out how to solve the problem of a poverty-scented house in my own life. And then I shared that story with others. And then they hired me to do the same for them. So check out the three layers of story: Layer 1: going through hell—from a house that smells bad to a house that smells good. This matched layer 2, the story you tell. I went out and told the neighbors about the happy ending of a house that doesn’t just look clean, but it also smells clean. And this matched layer 3, the journey you sell. I sold them the end result of a house so clean that it smells clean.

Are you hearing the “click” that we talked about in Episode 4? I hope so, because it works every time, but that’s not what this episode is about. This episode is about why we’re drawn to entrepreneurship in the first place–it comes from the inextricably intertwined desire to be who you actually are, to have your external life reflect that, while helping others to do the same thing.

Case in point: When I realized that living in a dirty house wasn’t who I was, I shed the gunky outer layer that had accumulated on the surface of the real me. I rolled up my sleeves, and I got to work. At age 13, I was solely responsible for cleaning not just our family home, but the homes of other families.

So notice what happened. I was living in a circumstance—a dirty house—that didn’t match my self-concept. The awareness of the gap between those two things is what caused me to grow. I had to stretch. I had to do hard things. When I did, my outside—my external reality–began to match my inside—the self-concept that I had of myself. I’m not a person who lives in a dirty house. When I had the inner awareness that this is not who I am my outer world shifted. The house was spotless. And it smelled good, too. And so did my clients’ houses. Through the self-growth that can only come from making your outer world match your inner understanding of who you are and what your life should look like, I made money. It wasn’t the point. The profits were a byproduct of the growth that comes from shedding an identity that wasn’t really me. And doing the work to step into more of who I really was at the same time that I helped others to do the same. We were all stepping into more of who we really were, when our houses were cleaner and smelled better.

The same thing happened when I started my hedge fund. I was working at a hedge fund that invests in other hedge funds. (It’s called a “Fund of hedge funds” if you’re interested in the terminology.) And this fund of hedge funds had a policy that they would only invest in other hedge funds of a certain size. But at the same time, they were acknowledging that the best returns typically occur when a fund is smaller–before it met their investment threshold. Why is this the case? It’s the difference between a cruise ship and a speed boat. If you want to pick off profits in the market, a speed boat is better. A cruise ship isn’t nimble, so it’s harder to go pick up that money.

Knowing this, my employers still adhered to a rigid policy of not investing in a fund until it got to a certain size. Why? Because buying into the larger, more established hedge funds on behalf of one’s investors is more judgment-proof. In other words, people are less likely to judge you, and to sue you and be awarded a judgment, in which you have to reimburse them for their losses, if any. In my mind, this practice was just like my neighborhood friend’s jacket. There was a smell there. And specifically it was the smell of a whole bunch of people doing things that looked good on paper—that would placate plaintiffs’ lawyers and regulators if they ever got sued–but that didn’t actually work very well for the investors in the fund.

I decided I wanted to invest where the best returns were. I didn’t want to give up return just because I was pandering to potential plaintiffs’ lawyers. So I went on a hunt around the world, looking for the best trading talent I could find, but that a whole bunch of other people hadn’t already invested in. In other words, I was looking for trading talent that still had a lot of open capacity.

And I found it. When I did, I built a fund around it. That was the outer journey. The stuff you could see on a movie screen if we were watching this in a theater. But what’s the meaning behind it? All of this was done because I needed to grow in my own life. How did I know I needed to grow? I couldn’t have articulated this at the time, but I needed to grow because my inner view of myself simply didn’t match the external reality.

Before I started my fund, I was basically a desk jockey. I was working for the guys who ran that fund-of-hedge funds. The guys who would only invest in other funds if they were of a certain size. They were setting up deals that didn’t make a whole lot of sense to me, and I was writing the documents that made those deals happen. They would tell me the terms of the deals they were putting together, and I was basically the “princess of fine print,” making those deals happen by creating all the paperwork that makes those kinds of deals happen. And I was chained to a computer for ten, twelve, sometimes fifteen hours a day.

I remember one time, all of my bosses were in Asia setting up a fund that I knew was never going to get off the ground. Yet they were very excited about it, and they were insisting that I get a bunch of documents done and Fed Exed to them in Asia by some insane and completely arbitrary deadline. It took until late into the night to write the documents, and I missed all the Fed Ex pick up times. So I had to race to the Fed Ex Drop at Atlanta Hartsfield Airport in the middle of the night and drop the package off there. Did I mention this was in the middle of the night?

It was ridiculous. And I went home, and I slept a few hours, and then, when I got to the office the next morning, I realized that I had Fed Exed the documents TO MYSELF. In a fog of exhaustion, my assistant or I had put our office address on the air bill where the recipient’s address was supposed to go. Isn’t it funny? In the last episode we talked about a Fed Ex snafu, and today we’re talking about exactly the same thing. I promise this is not going to be a trend. In any case, instead of the documents going from Atlanta to Asia, they went from Atlanta, all the way back to Atlanta. The whole effort was for NOTHING.

So there I was, sitting on the floor inspecting the Fed Ex box, and I had to call my bosses and explain what had happened and why. And they said, “Oh, no big deal. We don’t really need the hard copies. Just email the documents to us.”

At that point, reality smacked me in the face. It was just like when I was in my little friend’s house in the neighborhood, and he said that my house didn’t smell good to his mother. I was working for people to whom I’d given all my power. I’d put them in a position where they could destroy my life, or at least huge chunks of it. They could sabotage my schedule, whittle away at my sleep, send me on a wild goose chase in the middle of the night—to complete a task that didn’t require completion. To do something that they didn’t even need. For a fund that was never going to go anywhere anyway. I had become a high-level janitor, cleaning up the dingleberries off of stupid deals that didn’t serve anyone.

As I sat there on the floor, slumped over in exhaustion, I thought to myself, THIS IS NOT WHO I AM. It was just like when I was a little kid in the neighborhood, recognizing this is not who I am. I am not a kid who lives in a stinky house. It was the same thing. I realized, I am not going to be janitor to dingleberry deals anymore.

That’s when I put things in motion to start my own fund. And within not too much time, I was living on a beach in the Virgin Islands, managing my fund and living life on my terms.

Why am I telling you these stories? Because this is what happened to me, over and over again, at every stage of my life where I leveled up in my business. There was a disconnect between who I knew I was on the inside, and the life I was living on the outside. My circumstances felt uncomfortable because they did not match my self-concept. I was like a potted plant that had outgrown the pot, and it was time to bust out. When I became aware that I was uncomfortable because that was not who I was, I embarked on a period of growth. And each time I grew, I made more money.

Some people may call the desire for something more “greedy.” They may call it selfish. But it’s actually just a human desire to grow. When your inner reality doesn’t match your external circumstances, you feel uncomfortable because it’s a sign. It’s a sign that it’s time to grow.

And the way you grow is to help yourself while helping others. This, too, sounds selfish to some. It sounds greedy. But it’s human nature to want to do this. When we help others, we help ourselves. That’s the way of commerce. It’s as natural as giving a daisy water and sunshine. Those two ingredients guarantee growth. The desire to help yourself by helping others is like water and sunshine for a human. These are the two ingredients that guarantee human growth. So they’re never something to be ashamed of. You should embrace them. Because it means you want to grow and you want to serve.

This brings me to skill #7. The seventh skill that takes your business to seven figures and beyond is the skill of shedding who you were for who you are on the inside, and who you know you need to become on the outside. It’s about embracing an ever-increasing concept of yourself by allowing yourself to shed the old self-concept. Your self-concept is how you think about yourself. Who you are on the inside, who you can become on the outside, what you can create in the process of having your outer world reflect your inner world, and what will come into your life—what you will receive—as a byproduct of having gone through that process.

In a nutshell, when you embrace your higher self-concept and shed the old one, you are embracing your inextricably intertwined desires to help others and help yourself. In this embrace, money will come your way. Money is the inherent byproduct of satisfying the very human, inextricably intertwined desire to grow and to serve at the same time.

Doing this requires an awareness of two things. One, this is the process of human growth. You feel it on the inside, and you let it happen on the outside. The second thing you need to know is doing this quickly requires the willingness to allow it to happen and to speed it along. This is a skill. And it’s critical that you understand that this skill is essential to human growth and to helping humanity, because many stakeholders in your life—maybe even your own brain–are going to try to sandbag you and prevent you from growing and serving.

They will tell you that it’s selfish and greedy to focus on your business to the extent that you want to.

They will whine, “Why are you doing that? Then you won’t have time for us.”

They will tell you, “Don’t rock the boat. Just stay where you are. It’s so much safer here.”

They will ask, “Who do you think you are? The Queen of England? Get over yourself. You’re just like all the rest of us.”

They will warn you with harrowing tales of others, who are ostensibly better than you, smarter than you, and who have more resources than you, but who failed. The implication will be that if this other, better person couldn’t do it, you can’t either.

To all of this, all I can say is two things. One, all of this criticizing and warning and whining comes from a well-meaning place. These people really do love you. If you were ten years old in this situation, they would just buy you new shoes when your feet got too big for the old ones. If you were a potted plant that they cared about even a fraction as much as they care about you, they’d get you a new pot. They wouldn’t think a thing of it.

Which brings me to the second thing. It’s not that these folks want to bring you down or keep you small. More likely, what’s happening is that they just don’t understand something very important. That your desire to create a different external reality from the current circumstances of your life is simply an expression of discomfort that comes from shoes you’ve outgrown. And what you need to know is that the most uncomfortable place a human can be is a life they’ve outgrown. Small shoes that pinch your toes and blister your heels are nothing compared to this.

If you’re feeling that discomfort, you have to bust out. You do it by shedding your old self-concept, and stepping into who you really are. This is where the money comes from, my friends. It comes from human growth that serves humanity, and if you hear nothing else I ever say, please hear this. You have to know this one thing to the depths of your soul, because there are no cheerleaders before you make the money. The cheerleaders only come later, after you’ve made the money.

When I look back on my life, I can tell you that when I was about to do the thing that I really needed to do to grow, there was no applause. There were, however, many serious conversations involving deep concern. Involving a lot of, “Do you know what you’re doing?” And “We’re worried about you. This is dangerous. I don’t think this is a good idea. Why don’t you just stay at your job? Why do you have to rock the boat? I’d feel better if you didn’t.”

So what you need to know, to the depths of your soul, is that the antidote to all of this naysaying is simply to have a deeper understanding of human growth than those around you who are concerned about you. From this deep understanding, you develop the skill of leaning into the inextricably intertwined desire to grow and the desire to serve, and to receive the money that’s an inherent byproduct of this process.

Why do you need this understanding? Why do you need this skill? The reason is because when you’re not making the money you want to make, a big part of the reason for that is that if you don’t understand growth, you’re in danger of mistaking growth for greed.

This is a big thing that holds entrepreneurs back. When you have the skill of shedding your prior self-concept, and you know that that’s where the money comes from, you realize there is no “greed” that you should be ashamed of. What is labeled as greed is usually a desire for growth. To bust out of circumstances that have grown too tight. That don’t fit you. You do this because you’re wanting to serve at a higher level, and you’re wanting to grow, in a manner that’s consistent with who you really are on the inside. When you do this, you help yourself. And you help humanity. And the byproduct of that growth and that service is money.

This is how the seventh skill—shedding your old self-concept—helps you with the fourth essential function of every business. With the first six skills, we covered attracting, converting, and delivering. Three essential functions of every business for sure. What’s left? Collecting. If you don’t have the skill of shedding your old self-concept to match the inner you—who you really are on the inside–you won’t collect. You won’t get to seven figures and beyond because it will feel greedy. It will feel inappropriate. It will feel selfish. Shedding the old self-concept means rejecting that tired old notion of “It’s greedy to want money.” And stepping into the version of you who, deep down inside, knows the truth—that money is the scorecard for how much you’re growing and how much you’re serving. And that’s all it is.

When a daisy grows, you see lots of green. Add water and sunlight and you get green. It’s exactly the same with a human being. Add growth and service, and you see green.


If it’s time for you to start seeing green, then what’s next? Stay tuned for the next episode. You’ve heard all about the five fears that are keeping you stuck. You’ve heard about the seven skills that dissolve fear and that make you unstoppable in business. If it’s time for you to step into a one-of-a-kind community where you can acquire these skills to create an income that goes to seven figures and beyond, then stay tuned for the next episode. Because we’re going to discuss you crossing the threshold into your own high-earning life. That threshold is called Gateway to Seven, and I’m going to tell you exactly what you’ll find there, and why it’s the thing that’s going to change your life. Stay tuned for that, and thank you so much for being here today.