This episode elucidates the profound lessons derived from my two-decade journey in entrepreneurship, particularly emphasizing the notion that the path to freedom is often fraught with strategic failures. I recount my personal experiences of significant loss and subsequent rebuilding, illustrating that most conventional business advice tends to cultivate business owners rather than free individuals. I then articulate four essential lessons: the inevitability of discomfort in the pursuit of true freedom, the necessity of ownership over one's circumstances, the importance of embracing doubt as a catalyst for growth, and the value of committing to a singular path rather than succumbing to emotional relief-seeking. Ultimately, I encourage listeners to reflect on whether they are constructing a business that serves their life or merely entangling themselves within the confines of their enterprise. This episode serves as a clarion call to redefine success and freedom on one's own terms.
Takeaways:
The path to entrepreneurial freedom is often paved with strategic failures that provide invaluable lessons.
True freedom in business requires embracing discomfort rather than seeking relief from it.
Doubt is a pervasive presence in entrepreneurship, but it should not dictate our actions.
Ownership of one’s results empowers individuals, transforming blame into proactive responsibility for outcomes.
Link notes: https://cart.kreativedigitalmediainc.com/ai-work-week-slayer/
TRANSCRIPT:
Hello, my friends, and welcome back to another episode of Design your dream life. I am your host, Kara, and this is episode number 32. And today I want to share something really personal with you.
The lessons that I have learned from over two decades of building businesses, losing businesses, rebuilding businesses, and finally creating something that actually gives me the freedom that I always wanted. And I am not just talking about the highlight reel here. No, I am talking about the real lessons.
The ones that come from spectacular failures, my friends, from making expensive mistakes, from learning the hard way to what actually works and. And what's just shiny object syndrome dressed up as strategy. Because here's what I've realized.
Most of the business advice out there is designed to create more business owners, not more free people. I want to say that one more time. Most of the business advice out there is designed to create more business owners, not more free people.
And there is a huge difference between the two. So let me start by telling you how I got here. In case you haven't heard, and if you have, well, repetition's the second law of learning.
Because my path was not your typical entrepreneur success story that you hear about. I started with a multi million dollar real estate empire in my 20s. And from the outside, it looked incredible.
We had this 7,000 square foot mansion, multiple properties, the works. I thought I had made it. And then 2008 happened. I lost everything. Not just some things, you guys like everything. We went through bankruptcy.
We lost the mansion, we lost all the properties. I lost my identity as this successful young entrepreneur. And you know what? It was the best thing that ever happened to me. And I will say this.
Well, I would never wish this on my worst enemy. I am so grateful for that experience because it taught me the first critical lesson about building a freedom first business.
And here is lesson number one, my friends. The path to freedom is paved with strategic failures. Yes, it is. Here is what that bankruptcy taught me.
I had built the multimillion dollar business that was actually a house of cards.
It looked successful from the outside, but it was built on guru strategies that teach you how to over leverage yourself so that when bad times hit, everything collapses. And I was following a playbook that prioritized like rapid growth and impressive numbers over sustainability and actual freedom.
The real estate crash didn't just take my money.
It showed me that I had been building someone else's version of success, that I was following a playbook that prioritized rapid growth and impressive numbers over sustainability and actual freedom. Now, that failure also taught me to ask different questions. So instead of how can I make this bigger?
I started asking, how can I make this more sustainable? Instead of asking, how can I impress people? I started asking, how can I sleep better at night? Because a good night, peaceful sleep.
Oh, it is the best. And here is the thing about strategic failures, my friends. They are expensive. Yeah, they certainly are. In the short term, they are expensive.
But they are so invaluable in the long term, because every failure teaches you what doesn't work, which is just as important into learning what does work. And I see this all the time with my clients.
They're so afraid of failing, especially when they start working with me and I tell them we're going to fail. I fail all the time. I fail 80% of the time, and I win 20% of the time.
But I will tell you that 20% that I win, I knock it out of the park, my friends. And so I want you to adapt that. Like, I fail a lot. And if you're a business owner, you should embrace that failure, too.
But my clients, when I start working with them, they are. They're so afraid of failing that they never try anything bold enough to actually create the freedom that they want.
And they keep optimizing the same tired strategies of testing new approaches that could completely change their business. But there's a difference between failing forward and failing because you never tried.
Failing forward means you took a calculated risk based on a hypothesis and it didn't work out, and now you have data. Failing because you never tried means you let fear keep you playing small. The entrepreneurs who create real freedom are the ones who fail fast.
They fail cheap, and they fail forward. They are not reckless, but they are not paralyzed by the possibility of failure either. So lesson number two.
Discomfort is the price of true freedom, my friends. So after bankruptcy, I thought I wanted security. I honestly did.
So I went back to the corporate world, climbed the ladder, became a coo, had what everyone thought was the dream job, great salary, working from home, respected position. And this was working from home way before it was the trend. But I was miserable, Absolutely miserable. Like, I had honestly lost myself in that role.
I was working, like, 60 hours a week. I didn't like who I'd become as a leader, and I felt like I was living someone else's life. And this taught me lesson number two.
Because success doesn't eliminate discomfort, it just changes the flavor of it. When I was broke after bankruptcy, I was uncomfortable because I didn't have a lot of money. And when I was a COO making great money, I.
I was uncomfortable because I didn't have the freedom or fulfillment. The discomfort never goes away. You just get to choose what kind of discomfort you want to experience.
So most entrepreneurs think that once they hit a certain revenue number or they get to a certain level of success, that they will finally feel comfortable all the time. And that is just bullshit. It's a lie. That is actually the lie that keeps people trapped in businesses that drain them.
You know what real freedom feels like? It feels like choosing your discomfort.
It feels like being uncomfortable in service of something that you actually care about instead of being uncomfortable because you're trapped in someone else's system.
So when I got laid off and downsized from that CEO position, which felt devastating at the time, I had to face the most uncomfortable question of my life. Can I really make it on my own?
I mean, that question terrified me, but it also liberated me because I realized that the discomfort of uncertainty was nothing compared to the discomfort of living a life that wasn't mine. And so now let me tell you about doubt, because that is lesson number three.
Doubt will try to keep you small, my friends, because doubt is going to be your constant comparison as an entrepreneur, and you need to learn how to manage it. Doubt shows up every single time you're about to level up.
Every time you're about to make a decision that could change everything, doubt will be whispering in your ear. When I decided to retire my husband, doubt was screaming at me. What if the business doesn't sustain both of you? What if you're being irresponsible?
What if this is all just a fantasy? What if all of this just goes away tomorrow? And when I decided to raise my prices, doubt was there. What if no one pays? What if I lose clients?
What if I'm being greedy?
When I decided to build my freedom business and I shifted my entire business model and I wanted a business that I could run anywhere in the world and also that I didn't let my calendar dictate my life? Man, doubt was there. What if it doesn't work? What if you need something more hands on? What if you're being naive? And here's what I learned.
Doubt is just your brain trying to keep you safe. It is not giving you accurate information about what's possible. It's just trying to protect you from the unknown. And that is totally normal.
The entrepreneurs who create real freedom learn to hear doubt as background noise instead of gospel truth. They acknowledge it. They consider whether there are any legitimate concerns buried within it, and then they move forward anyways.
Because here's the thing. If you wait until doubt goes away before you take action, you are never going to take action. Never. Because doubt doesn't go away, I promise you.
You just get better at dancing with it and embracing it. Lesson number four, changing your mind is expensive. This is a big one, especially for my digital entrepreneur friends.
I see this pattern constantly with friends in the industry. I have even done this. I am so guilty of this myself. I am not gonna lie.
I literally had this happen to me this week, and I had one of my business besties slap it right out of me. I'm serious. Like, it happens at every level. And so, again, here's the pattern.
You get uncomfortable with a current strategy, so you change your mind and try something completely different. So you spend months building out a course, then you decide it's not perfect, and you scrap it for a different idea.
You might work on your signature funnel for weeks and then see someone else's approach and decide to start over completely with a new strategy. Oh, my goodness. I will tell you this. I, like I said, I suffered from this.
This week, I went down a whole rabbit hole of, like, maybe I want, like, a faceless YouTube channel. Isn't that the dream? And da, da, da.
And I was like, boxing my girlfriend, and she's like, girl, I'm gonna call you on your shit, because that's what I'm here for. Don't do this. You do this, and I'm calling you on this. And I'm like, oh, I know. I just need to go all in and stay here.
I even questioned, do I continue to keep doing this podcast? And I had someone reach out to me saying how much they enjoyed it and to not stop doing it. And so I will say, like, it is easy to try and pivot.
You know, I also have a friend who changed her business model four times in six months.
And every time she hit resistance or things got difficult, she would convince herself that the problem was her business model and not her commitment to seeing it through. And so every time you change your mind to get relief from discomfort, it actually costs you.
It costs you time, it costs you money, it costs you momentum, and more importantly, it costs you the confidence that comes from seeing something through to completion. And I get it. Like, I'm an ideas person. I think that is why I am so brilliant at marketing.
I just have all of these amazing ideas, like, I can come into a business, and I'm like, ooh, we should do this, this, this, and this and this, right? And.
But my problem for me, right, is that I have to focus on just this, because I have a bazillion ideas that I could also do, but if I try and do all of them, I'll never get anything done right. And so I have to keep coming back and being like, no, this is the focus. This is where I want to make the most impact.
So I am not saying that you should never pivot or adjust your strategy. I am just saying that you need to distinguish between strategically pivoting or emotional relief seeking. Hi, I'm Cara.
I like to have emotional relief seeking behavior. And hopefully you have somebody that can pull you back if you start doing that.
So strategic pivoting happens when you have data that shows you that your current approach isn't working and you have a clear idea about what would work better.
Now, emotional relief seeking, that happens when you're uncomfortable with where you are and you want to change something, anything to make that discomfort go away. And the most successful entrepreneurs that I know, they pick a lane, they stay in it long enough to actually see the results.
Actually, once heard somebody say they stay in it one or two years before they're allowed to pivot, I should probably give myself that rule because I do have that pattern. I'll come out here and I'll play a little bit and then I'll be like, oh, I'm so much better.
I get, I'm such a winner over at scaling other people's businesses that, that scale so easy for me.
But I want to now bring it to the level where I'm teaching a wide market, a bunch of people instead of like the very few selected people that I get to work with. I want to have more impact. And having that more impact means that I have to show up in different ways.
And so again, I'm definitely that emotional relief seeking person. Right?
And so again, I've, I, I really do think that committing and I should make that declaration, I should make the declaration at least right now to this podcast, that I will be doing it for at least a year. And so I don't even know how many months they've started. We're on episode 30 something. But to @ least doing this podcast for a solid year.
I will commit to that right now.
But anyways, when I was saying is, is that the most successful entrepreneurs I know, they pick a lane, they stay long enough to actually see the result, they optimize, they, they improve, right? And they keep going. Instead of constantly jumping to new approaches, they keep going.
And so I feel like that is something that is so extremely important. And again, you Guys, perfection's an illusion, right? And so before I get on to number five, I just want to share that with you.
Like, I've helped my clients create so much money, and again, there is. You will never have perfect. Like, life is always going to be 50, 50, and there's always going to be the good and the bad at every single.
At every single stage, at every single level that you. That you do. And I think the more that you can push yourself and the more that you're willing to go outside of your comfort zone.
And I used to push myself really hard outside the comfort zone, and then I got pretty comfy in my comfort zone, and I built a mansion in here, and now I'm pushing myself out again and putting myself out there. So instead of, you know, meeting people and being referred to as this brilliant strategist, now I'm like, okay, I'm going to general population.
And that is scary. And it's okay, but it's up leveling in a different way. All right, so lesson number five. Ownership changes everything.
And this might be one of the most important lessons of all. Taking a hundred percent responsibility for your result can change everything. When I got laid off from my COO position, I had a choice.
I could blame the company for not valuing me. I could blame the economy. I could blame timing. I could blame a lot of things. And instead, I chose to take full responsibility.
Not because everything was my fault, but because blame keeps you powerless and ownership gives you power.
So when you take a hundred percent responsibility for your result, suddenly every decision becomes clearer, every next step becomes obvious because you are not waiting for anyone else to change, right? You're not looking for your circumstances to be different. You are focused on what you can control. Right? We had this family motto.
I'm like, what is it? Of course I know what it is. And I used to say to the kids growing up, our family motto was, do your best, forget the rest, right?
And as long as we taught our children to show up and give it their all, the rest is that like, I'm. I'm going to show up, I'm going to own a hundred percent of what I can control, and I'm going to release the things that I can't. Right?
And I see entrepreneurs struggle with this all the time. They blame the algorithm for their low engagement. They blame their audience for not buying.
They blame the economy for their lack of sales, and they look at external factors that. That do affect our businesses. But successful entrepreneurs, they focus on what they can control within those external factors.
So instead of using it as an excuse, when you take full ownership of your success, you also get to take full credit for it. And there is something incredibly empowering about knowing that you created something through your own decisions and actions. Actions.
Here is something that I learned that might surprise you. Earning your success feels completely different from stumbling into it or having it handled to you.
When I lost everything in 2008, I could have felt sorry for myself. Instead, I just realized something powerful. If I could build a multimillion dollar business once, I could do it again.
The skills, the mindset that created that success weren't tied to specific assets that I lost. And it has been true every step of the way. Every level of success I've earned has given me confidence that I can earn the next level too.
And I see this all the time. The ones who have worked for their success have unshakable confidence and belief because they know they created it.
They know they can recreate it, or scale it, or pivot it, because they understand the fundamentals of what makes it work. This is why I don't just give my clients strategies. I teach them how to think strategically. I don't just give them my systems.
I teach them how to create systems that work for their specific situation. Because the goal isn't to make them dependent on me.
The goal is to give them the tools and the mindset to create sustainable freedom in their own businesses. So let me share with you why I think the real reasons why most digital entrepreneurs fail to create the freedom that they want.
First, they are unwilling to be consistently uncomfortable. Right? They want the results of entrepreneurship without the emotional experience of being an entrepreneur.
But growth requires discomfort, innovation requires uncertainty, and success requires doing things before you feel ready. Second, they're obsessed with tactics.
Instead of mastering fundamentals, they want the newest funnel strategy or the latest social media hack instead of focusing on the boring fundamentals that actually create sustainable results, like understanding their mindset, creating genuine value, and building relationships. And third, that they're relief seeking instead of result seeking.
So every time they feel uncomfortable, they look for something to change, to make discomfort go away. But entrepreneurship is about learning to be comfortable with discomfort, not eliminating it.
Fourth, they're following everyone else's blueprint instead of designing their own.
And that is so powerful, they're trying to follow someone else's version of success or freedom instead of creating their own and getting inside of yourself. This is what I always say is like, I'm not a guru. You are your own guru. You have all the answers that you will ever need inside of yourself?
I find that it's my job to coach and guide for you to connect with yourself and design what works for you. Because what works for you doesn't work for another person, right? And so you are the rock star.
And so look at me for guidance and ideas and suggestions. But you're the author of your own story. Don't take what worked for me.
You've got to take the strategies and the ideas and then create what works for you. So here's something I want you to think about. Here's something I want you to think about.
What would change if you started treating yourself like a CEO treats their best employee? A good CEO sets high standards. They provide clear direction. They give honest feedback. They invest in their team's growth.
They hold people accountable to their commitments. And most entrepreneurs are terrible CEOs to themselves. They hold themselves at such an ungodly standard that you could never live up to right?
And they don't necessarily invest in their own development. And that is the mindset piece of honestly, it really is.
Like, what if you started expecting excellence from yourself in a way of growth that your business will only grow to the amount that you decide to grow? What if you started focusing on your business as the journey of yourself and becoming the person that you were always meant to be?
You deserve to that type of leadership and guidance from yourself. Here's something I don't think enough entrepreneurs talk about, which is building a successful business is an actual privilege.
And with that privilege comes responsibility. When you create financial freedom for yourself, you have the opportunity to create value for others.
When you build systems that work, you can teach those systems to others. When you solve your own problems, you can help solve similar problems for somebody else. I didn't build my business just to make money.
I built it to prove that it is possible for both success and freedom. I built it to show other entrepreneurs that they don't have to choose between making money and having a life.
And every client that I help create a freedom first Business is proof that this approach actually works. And every entrepreneur who breaks free from the hustle and grind mentality makes it easier for the next person to do the same.
That's kind of like the ripple effect of building something that actually serves your life instead of consuming it. So here's what I want you to take away from this episode. I want you to look at your own business and ask yourself these three questions.
Are you building toward your own definition of freedom or are you copying someone else's blueprint? Number two, are you making decisions from a place of strategic thinking or are you just following the latest trends?
Number three, Are you willing to be uncomfortable in service of your goals? Or are you constantly seeking relief from discomfort? 4. Most importantly, are you building a business that serves your life?
Or are you building your life around serving your business? Because here's what I know. I know this to be true. It is possible to have both success and freedom.
It is possible to build a business that makes you great money without consuming your entire life. And it is possible to create something that feels authentic and aligned instead of like you performing someone else's version of success.
But it also requires you to think differently. It requires you to be willing to do things that feel uncomfortable. And it requires you to trust yourself, which is huge.
Trust yourself enough to break the rules that do not serve you. All right, my friends, thank you for listening to another episode.
Remember, your version of success is valid, your definition of freedom matters, and you have everything you need to build a business that actually serves the life that you want to live. I will see you next week, my friends. I hope you have an amazing one.