What’s Stopping You From Becoming Your Own Boss?

In this never-ending World of 9-5 jobs demanding everything from our first-born to our death benefits, more and more are opting to create their own Business and Become their own Boss. However, as many of us already know, it’s just not that dang easy.

What’s Stopping You From Becoming Your Own Boss?

If you already work in Corporate America, like I do, you have to think about what you would be giving up.

  • Steady paycheck
  • Medical benefits
  • Paid sick leave
  • Paid vacation time
  • 401k or other savings-type plans
  • Pension/Retirement

But in the grand scheme of the whole “Be Your Own Boss” things, do those things really matter?

As I begin to help a very dear friend of mine venture out on his home, it made me think again of my “once upon a time dream” of working at home. It also made me question others who would love to be their own boss, what’s stopping them?

When I think of my own plans, that have been halted, for now, the top three things that have stopped me are:

#1 Financial Security

It’s important to know where your monies are coming from. If you have a mortgage, car payment, family, and other pertinent material things in your life, you need to know how you are going to keep them. Will you be able to feed you and your dogs this week? This month? What about your car insurance? Medical issues that come up or other “unexpected” expenses and repairs.What's Stopping You From Becoming Your Own Boss?

#2 Medical Benefits

You may not think it is a huge issue if you are young or not often sick, however, for many that are older or those who may depend on medical benefits to help, what do you do? Are there companies out there that specialize in offering medical benefits for Entrepreneurs and Small Businesses? Are these type of plans affordable or are they outrageously priced like the “so-called” Affordable Care Act?

If you have family and children that are currently dependent on your Corporate America provided medical insurance, what do you do? How do you cover yourself and your loved ones, if and when, you become your own boss?

#3 Fear of Failure

When you think about giving up all of the above Corporate America benefits, it can be detrimental in you making your move to Entrepreneurship or not.

Going out on your own can be a scary thought. Nailing down your product(s), services, and niche can be difficult, especially in an ever-growing World of Freelancers and Entrepreneurs. Wondering if you have what it takes to “bring home the bacon” and not fall flat on your face can be another HUGE determination of you taking that leap.

I personally, find that Fear of Failure really shouldn’t be a deterrent for me but way in the back of my head, it is. When I think about all that I would be giving up to not be a success, could be devastating to our mind and soul.

Will you be able to “measure up” to those already in your field?

The one thing we must remember her is at one time or another, everyone has “failed”. Those who got back up and tried again and the ones who conquer the fear and become successful.

Don’t Overthink It

There are many additional reasons why people fail to go out on their own and become their own boss. Sometimes the fear is greater than the will. Sometimes the “means” just aren’t there and one can’t possibly take that leap. Don’t beat yourself up about it. Maybe it wasn’t your path, to begin with.

But I want to hear from you. If you are one that would love to ditch that 9-5 job and be your own “person”, what’s stopping you?

Let’s chat!


10 thoughts on “What’s Stopping You From Becoming Your Own Boss?

  1. Hi Bren! Great article! For me, financial security was the reason I wanted to become an entrepreneur. I realized that the 9-5 is not enough to pay for what I wanted, and I would’ve probably still been paying debt now. So, I decided to spend a couple more hours after work learning online and finding new opportunities. Yes, it is exhausting, but it necessary. I couldn’t just quit without a backup plan. So, I made sure my plan has a good potential success before deciding that I’m not waking up at 6 to go to a desk job. Now, I’m financially secure, paid my debt, and planning vacations all over the world. They are paid vacations because my online work pays for itself. Thanks again for sharing this article!

    1. Hi Stefan and Welcome to my little World!

      I’m so happy that you shared your success story with us! Financial security is a huge reason. It is one reason that continues to stop me today and the benefits of my full-time job. Making a plan is key in obtaining what you want. It seems you did just exactly that and are making it happen. Big props for living your dream, Stefan. We only get but one life to live. Do it YOUR way. 🙂


  2. Hi Bren, to be honest, I think I limited my own potential. It goes hand in hand with the fear of failure but kind of stopped me in my tracks as I was just getting started. Yes…. You’ve got me thinking here…

    1. Hi Amanda,

      It happens to all of us. Once we can push ourselves past that threshold of doubt, we’ve got it made. You are very talented and by God, don’t hold back girl. Get out there and slay it!


  3. Great post Bren!

    Fear is what stopped me from starting my own business. It still does. There are some things like getting in front of the camera that scares me half to death. I don’t know what it is. I’ve tried but I freeze up. You’d like as much as I like to talk and shoot the sh*t that I’d be aching to get in front of the camera, lol.

    Thanks for the motivating us to go after our dream of being our own boss!

    You know I’m sharing this one gf!


    1. Thanks, Cori!

      You and I both have that camera thing going on. But maybe it’s more because I don’t really like watching videos so I don’t want to do them. 🙂 You are a BOSS girl. That fear is in your head. I don’t think there isn’t anything you can’t do if you put your mind to it. Just remember, if you can dream it, you can HAVE it! Go for it girl! Slay it!


  4. Hey Bren,

    People always have a fear of failing which stops them from becoming their own boss. I have seen many people who were doing great but due to their fear, they stopped writing.
    It varies person to person and it’s hard to tell what exactly people have in their mind.

    Thanks for sharing with us.
    Enjoy your day.

    1. Hi Ravi,

      You said it. Fear can stop a “boss to be” in their footsteps. I think fear of not succeeding is the biggest one. However, isn’t each person’s success different? I say kick Fear in the butt and out the door. Just do it! You are! And nailing it!


  5. Hi Bren,

    Great article and I think that one of the reasons that many people don’t take the leap is because they’re afraid of failure. We all know that it’s scary to leave the security of that JOB.

    Well, it’s not really security as you can get laid off and you don’t have any control. However, some people just need that comfort knowing that they’re getting a paycheck every week.

    Failure can be a scary thing, I’ve failed many times. It’s not too bad and while I don’t like the failure, unfortunately, that’s just a part of life. When you venture out to do things that you’ve never done, you have to give yourself time to learn how to do things correctly.

    Like you said, you just can’t overthink it. You just have to be willing to follow your dreams.

    Thanks for sharing this, have a great day 🙂


    1. So very true, Susan!

      I think people put too much emphasis on failure. Failure is an event. Not who we are. I believe we practice until we achieve the goals we want. Failure is not an option and shouldn’t be for anyone, imo.

      I’m happy to read your thoughts. I know you must have had some fear but didn’t let that deter you. Keep kicking it, Susan! Great to see you here!


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