Are you Sure you Want to be Your Own Boss?

What is the #1 thing that it seems that most entrepreneurs say they love about being self employed and also the #1 thing that most aspiring entrepreneurs point to as being the best part about the “job” of being an entrepreneur? The fact that you get to be your own boss! While this certainly sounds like a great thing are you really 100% sure that you want to be your own boss? For me the answer is a resounding yes. That being said, there are certainly some very important things to keep in mind before you jump out on your own and think that being your own boss is all rainbows, cotton candy, and lollipops. As someone who has had many different bosses over the years while working for “the man” and as someone who has been their own boss for the last 6 years here are a few observations to consider.

The Pressure is All on You

If you love pressure then you will love being your own boss. If you break out in a cold sweat just thinking about your company’s current ratio tanking and potentially not being able to meet payroll, or pay the business credit card balance off, or having to not pay yourself a salary while your startup company is just getting off the ground then guess what? Many first time business owners find themselves in that scenario over and over until either their cash flow situation stabilizes or they go out of business. When you are your own boss the pressure is all on you. Some people love the pressure and some people get paralyzed under the weight of the pressure. Being the boss is not for everyone.

No One Tells You What to Do

“Yes!!! No one is telling me what to do! I am my own boss! I can do whatever I want! Yesss!!!” …. “Wait… what am I supposed to do exactly and how am I supposed to do it?” If you are someone who just simply works better when someone else lays out a clear plan of action for you with specific tasks to accomplish then you are probably not cut out for being the boss and especially not cut out for being your own boss.

Being your own boss means that you often have to make order out of disorder, deal with ambiguity, and make tough decisions on a daily basis. If you are not a highly motivated person that is comfortable with attacking projects and tasks where there is a lot of uncertainty about how to accomplish the task then welcome to being your own boss and starting a company where you are often learning many new things as you go (paying taxes, health insurance benefits, business licenses, etc.).

Yes, it is important to rely on trusted outside advisors and the more you learn then the more experienced you become but the fact remains that if you are unwilling to be self motivated and constantly learning then you may not be so thrilled with being your own boss as you maybe think you might.

You Have to Pick up the Slack, Jack

In the corporate world when things go wrong then you likely turn to your superior for guidance, assistance, and maybe even a little good old fashioned “cover your rear” precautionary “if something goes wrong then it’s not my fault” evasive maneuvers that one sees so often in corporate America. Well, if you are your own boss then there is certainly none of that because when things go wrong then the cleanup usually falls right at the big boss’s feet (Hint: If you are your own boss then that’s you). It’s up to you and you alone and that can be either a good thing or a bad thing. Your company may have great customer service and that is a good thing but when things go bad in a small business then it’s usually the boss and not one of the underlings that has to make things right.

So – Do YOU Really Want to be Your Own Boss?

I love being my own boss but it’s certainly not for everyone as there are both pros and cons to being your own boss. What about you? Do you want to be your own boss? Do you think that you are cut out for being your own boss? If you already are you own boss then what other pros and cons to being your own boss do you have?

This was a guest post by Joel. Joel is a CFP® and serial entrepreneur that loves working for himself (although he sometimes gets sick of how “his boss” makes him work such long hours). He has been working lately on a website for comparing insurance providers and also a website for comparing car insurance companies.


1 Forest March 18, 2010 at 1:06 am

I love being my own boss but I don’t think I ever want to employ anyone as such. I am happy to hire contractors but just don’t want responsibility outside of me!
.-= Forest´s last blog ..FREE DOWNLOAD -Tribes: We Need You to Lead Us by Seth Godin =-.

2 Credit Card Chaser March 18, 2010 at 2:12 am

Yep, I am a big fan of using independent contractors rather than employees as well when possible but of course a lot depends on the type of business you have because if you own say a grocery store than you can’t have independent contractor cashiers!
.-= Credit Card Chaser´s last blog ..Ever Had Your Credit Card Declined? Mischa Barton Says Join the Club. =-.

3 Chris Holdheide March 18, 2010 at 12:19 pm

I took over my fathers manufactoring business about a year ago and let me tell you being your own boss is no picnic. I retrospect I don’t really make any more than I did before I took over the business but now I have all the responcabilities on me. Everything from the employee issues to the financial issues.

Do like it? Yeah, but I believe I was much happier and less stressed when I was just getting a paycheck as an employee.
.-= Chris Holdheide´s last blog ..Debt Consolidation Care Review =-.

4 Simple in France March 18, 2010 at 12:48 pm

I’ve worked for myself before and would do it again! But I would not want employees–too stressful.

I think also that you could add that in addition to being self-motivated, it usually helps to know how to make good use of your time and be organized!

As for the cleaning up your own mess, you make a good point.

And, your boss might still be a jerk 😉
.-= Simple in France´s last blog ..What do YOU gain by living simply? =-.

5 Christina March 19, 2010 at 2:22 am

When I was a bit younger, I want to be employed for security reason…for 4 years of being employed, I realized that it’s time to get out of my comfort and earn twice, thrice or what I’m earning. I want to be secured yes, but I can be more secured if I work harder, be my own boss and be in control of my finances. Yes, I have to clean up my own slack, I have to manage some people but there are ways to handle everything, like you guys, I only employ individual contractors for a certain job that requires one…most of them work at home. Less expense – more productive. I guess if a person is afraid of responsibility then he/she can never be his/her own boss.

Another great post…

6 Stephen March 20, 2010 at 4:16 pm

I’m glad you wrote this. A lot of people do not realize how stressful it can be at times to run your own business. I would say the best part about being an entrepreneur is the freedom. Freedom has a very broad meaning, which does include not having a boss and making the strategic decisions on your own, but it also means freedom to take a 2 hour lunch break, go to happy hour with friends, etc. At the same time, being an entrepreneur means tough days, lots of work, no lunch breaks and having to pass on happy hours with your friends every once in a while to get everything done. It’s a balancing act, just like everything else in life.

Comments on this entry are closed.

Previous post:

Next post: