"The Price of Freedom: What They Don’t Tell You About Being a Boss"
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The Price of Freedom: What They Don’t Tell You About Being a Boss
Being your own boss—it sounds like a dream, right? No one telling you what to do, the freedom to set your own schedule, and the ability to build something you can truly call your own. But here’s the truth: the price of freedom is steep, and most people don’t talk about the sacrifices it takes to get there. Let me break it down for you
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Always Being Available
One of the hardest sacrifices I’ve had to make is being constantly available. When you’re self-employed, your time isn’t really your own. The work doesn’t stop when you clock out because there is no clocking out.
This took a toll on my personal relationships. My most recent relationship ended because, in her eyes, one key point that she mentioned constantly throughout our relationship was I was working too much. From my perspective, I didn’t understand it—I was always home before she was. But the truth is, women, just like anyone else, need quality time and attention. And when you’re so locked into your vision, so consumed by what you’re building, it’s easy to develop tunnel vision. You’re thinking about the next move, the next dollar, the next step forward. But relationships? They don’t wait for you to “get it together later.” They need nurturing, too, and sometimes, as a boss, that’s a sacrifice you end up making.
Financial Struggles
Let’s talk money because this is where it really gets real. As your own boss, every single thing in your life has a price tag attached to it, and you’re footing the bill. Your healthcare, your life insurance, your investments—nobody sets that up for you. There’s no HR department telling you what to contribute to your retirement fund or offering you a match. You’ve got to figure it out.
I remember the first time I realized I had to pay my own taxes quarterly. I mean I don’t but that’s what they recommend at least. It felt like I got punched in the gut. No one prepares you for that. I had to learn, on my own, how to budget for taxes, set up investment accounts, and prioritize life insurance. It’s not optional—it’s survival. But when you’re just starting out, that survival feels like it’s being paid for with every dollar you’ve got.
Sometimes, you’re down to rice and beans, Dave Ramsey style. You’ve got to stretch every penny because the business comes first. And if you don’t hit big right away, you’re going to feel every financial strain. But that’s part of the price of freedom—the freedom to bet on yourself.
At this very moment, as I write this article, I’m staring at nearly $10,000 legal bill just to file for joint custody of my youngest child. Let that sink in—ten grand, just to do what’s right as a father. And even in the midst of this financial punch to the chest, I have to remain calm, steadfast, and focused. I still have to be a father in real-time—showing up for my kids, being present for them—while balancing the weight of this burden.
On top of that, the grind doesn’t stop. I still have to get up and go to work, still have to stay creative, and still have to be organized every single day. Why? Because I don’t just depend on me—I’ve got two kids who rely on me to keep things together. And as much as I’d like to vent to the world about how heavy it all feels, like Killer Mike said, you can cry, but then you’ve got to get back to it. You’ve got to lead. Because at the end of the day, it feels like the world doesn’t really care about what you’re going through. You have to find a way to push through because if you don’t, no one else will.
That’s the real price of freedom—the weight of responsibility that doesn’t pause for your pain. It’s tough, but that’s what being a man, a father, and a leader is about.
Loneliness and Isolation
Another thing they don’t tell you about being your own boss? It can be lonely. You’re the one responsible for every decision. When something goes wrong, there’s no team or manager to fall back on. It’s all on you.
There were nights I sat by myself, questioning whether I’d made the right choice, doubting the path I was on. You’re not just carrying the weight of your dreams—you’re carrying the weight of everything that depends on those dreams. And sometimes, the isolation of carrying that alone can be overwhelming.
One of the toughest parts of choosing myself and my dreams over everything else is that, sometimes, I find myself by myself. When you commit to building something on your own terms, not everyone understands your grind—or your vision. And, honestly, it’s not their fault. Most people aren’t built to handle the level of sacrifice and focus this path requires. But that doesn’t make it any less isolating.
There are times when I’m out here grinding—putting in the hours, making that money—where I feel like I’m hustling on a corner, just like back in the day. Metaphorically speaking, of course (because you know the feds might be reading). But seriously, it’s that same energy, that same hunger, where you’re standing there waiting for the next opportunity, the next move, the next serve. You’re always on, always thinking, “What’s next?” And while everyone else is home, comfortable, watching TV or hanging with loved ones, you’re out in the field, hustling like your life depends on it—because it does.
The truth is, when you choose yourself, you sacrifice the comfort of being understood. It can feel like no one really gets it—the long hours, the pressure to deliver, the constant drive to prove that this isn’t just a dream but a reality you’re fighting to create. It’s lonely, but it’s part of the deal. When you put yourself out there and refuse to settle, you realize that not everyone is going to stick around for that journey. And honestly, sometimes you don’t even blame them. This life isn’t easy, and it’s not for everyone.
But here’s the flip side: choosing yourself means betting on yourself. And while it comes with moments of isolation, it also comes with a deeper understanding of who you are and what you’re capable of. Even when you’re by yourself, you learn to stand tall, because you know what you’re grinding for is worth it
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The Constant Need to Innovate
When you’re an entrepreneur, the world doesn’t stop moving, and neither can you. You can’t afford to get comfortable. The moment you stop innovating, you risk losing everything you’ve built.
Unlike a traditional job where the work stays steady, being your own boss means you’re always solving the next problem or chasing the next opportunity. You don’t have the security of a paycheck that’s coming no matter what. If you don’t figure it out, the money doesn’t come, and the business doesn’t grow. That constant pressure can push you to new heights, but it can also wear you down.
Heavy Is the Crown
There’s a saying: “Heavy is the head that wears the crown.” And it’s true. Being a boss isn’t just about the freedom to call the shots—it’s about shouldering the weight of everything that comes with it.
But here’s the thing: I wouldn’t trade it for anything. The sacrifices, the struggles, the sleepless nights—they’ve taught me resilience. They’ve shown me what I’m capable of. And even though the journey is hard, the freedom to build something that’s mine makes it worth it.
To anyone considering this path, be where your feet are. Understand that being a boss comes with costs that no one will prepare you for. But if you’re willing to pay the price, you’ll discover that freedom—real freedom—is priceless.
Closing Thought:
The price of freedom isn’t just financial—it’s emotional, mental, and physical. It’s about stepping into the unknown and taking on responsibilities most people never see. It’s heavy, but if you can carry it, the rewards go far beyond what money can buy.