1. You’re Hungry for Self-Determination
For me, one of the biggest shifts came when I realized I didn’t want to spend the best hours of my day doing what someone else required of me. I wanted to use that energy for the things that mattered to me. Not because I’m lazy. Not because I don’t like working. But because I was tired of feeling chained to a paycheck—trading my time for tasks that didn’t always align with who I was or what I cared about.
I wanted to travel. I wanted to pursue my own projects—not at the end of a long workday, not as a side hustle squeezed into the margins. I didn’t want to be too tired to live the life I envisioned. I wanted autonomy over my time, space to breathe, and the ability to take a vacation when I needed it—without waiting for someone else’s approval.
If you’ve started to feel that same disconnect—like your days are filled with obligation instead of intention—it may be a sign you’re ready to be your own boss.
Being your own boss isn’t just about working less—it’s about working on something that actually fulfills you.2. You’re a Dreamer
One thing I’ve learned is that dreamers make incredible entrepreneurs. Not just because they have big ideas, but because they believe in something that doesn’t exist yet. For me, that meant reimagining how systems could work more efficiently. I’ve always had a drive to improve the way things flow—that passion led me to business process automation and eventually to launching Backbone America.
Maybe your dream is to open a salon, write a book, or run a boutique that brings joy to your community. Maybe you imagine a business that gives you more time with your kids, or one that lets you travel while still earning a living.
If you often find your mind drifting toward what could be—if you imagine new ways to live, create, serve, or lead—you’re already tapping into the spirit of an entrepreneur. Those dreams aren’t distractions; they’re opportunities waiting to be fulfilled. If that sounds like you, it’s another clear sign you may be ready to be your own boss.
3. You Feel Boxed In, Not Lifted Up
It’s one thing to feel tired or stressed. But when your role starts to feel like a box instead of a stepping stone—when your potential feels capped—it might be time to ask: How can I create better opportunities for myself?
I’ve always loved learning. When I was younger, I even dreamed of becoming a professional student. That exact dream faded, but my drive to grow, explore, and push myself never did. Unfortunately, companies have needs—and those needs don’t always align with our growth. I found myself being steered into the areas I did well, over and over. That might sound like a compliment, but it began to feel like confinement.
The more I stayed in that loop, the more I started to question my adaptability. I worried about how my highly specialized experience would translate if I ever wanted to move on. I saw it happening to others around me too—good people with big talents getting stuck in sameness. And for me, that sameness bred imposter syndrome. I wasn’t expanding. I wasn’t evolving.
I knew I had more to offer—and I was tired of waiting for someone else to give me opportunites. That’s what pushed me to resurrect the business I started years ago. I didn’t want to keep asking for permission to grow. I wanted to create space where I could grow on my own terms.
If you’re starting to feel like your role is holding you back more than lifting you up, it may be a clear sign you’re ready to be your own boss.
4. You Want to Leave Your Mark
I’ve never wanted to work just for the sake of working—or to spend decades doing something that only pays the bills. I want my work to mean something. I want to leave a mark.
When I was a business advisor for the SBDC, that meaning was crystal clear. I could walk into a neighborhood and see the storefronts of people I had guided through the process. Their families, their hope, their hustle fueled my motivation. I wasn’t just checking off tasks—I was helping real people build real futures. Even now, with Backbone America, that sense of impact keeps me going.
Don’t get me wrong—there’s a certain satisfaction in seeing the end users benefit from the work I do as an employee. But helping entrepreneurs launch and grow their businesses? That’s a whole different level of value add. It’s personal. It’s transformative. It’s lasting.
When I was working for someone else, I often found myself asking, What good am I really adding? I struggled to see where my personal touch landed in the world. That question never comes up when I’m working for my own mission.
If you’ve been craving that deeper sense of alignment with your passions, values, and life vision than you’re receiving as an employee, it’s a strong signal that you’re ready to be your own boss.
5. You’re Done Waiting
This is the shift that matters most. When you go from “Maybe someday” to “What steps do I need to take today?”—everything changes.
I’ve always been a goal-oriented person. I decide what I want, then start finding ways to make it happen. I let my ideas percolate—but I don’t leave them sitting on the back burner forever. While others say, “I wish I could do that,” I say, “You can.” And I mean it. Because I’ve done it.
As a single mom, I earned a bachelor’s degree and two master’s degrees while raising my children. I’ve traveled to more than 20 countries and continue to plan and go on new adventures every year. I’ve written books. And when I realized the solution to my career disillusionment was starting my own business, I didn’t wait. I created a plan and started taking action.
Were all my milestones met perfectly? No. But every one gave me a target to work toward. I’ve had hiccups. I’ve paused and recalibrated. But I never stopped moving forward—because each step brought me closer to a life that feels like mine.
If you’re ready to stop daydreaming and start doing—if you’re setting goals, researching, experimenting, or even reading this post—it’s a flashing neon sign: you may be ready to be your own boss.
Final Thoughts: Are You Ready to Be Your Own Boss?
Being ready to be your own boss isn’t about having every detail figured out. It’s about recognizing that the life you want is possible—and you’re done waiting for permission to live it.
If this post hit home, you’re not alone. I’ve walked this road, and I created Backbone America to help others take that same leap with clarity and confidence.
If you’re ready to stop spinning your wheels and start building a business that fits your life—not the other way around—the 31-Day Business Startup Challenge is your next step. It’s designed to help first-time entrepreneurs move from idea to execution with structure, support, and momentum. You don’t have to figure it all out on your own.
Let’s build your business—step by step, with purpose and a plan.
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