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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.

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Lets start with some simple definitions:

A job is work you do to earn a wage but you don’t see yourself pursuing as a permanent line of employment a means to reach you desired job.

A career is work you do to earn a wage where the work is related to your desired job or position in line with your long term goals.

When you were 15 and working as a stock boy at the gas station it was a job. When you are 28 working at a nuclear power plant as a nuclear engineer you have a career, provided that is what you wanted to do. What may be a job to me may be a career to you. Working as a waiter is a job to me, but if you want to be a restaurant manager later in life it is essential to your career and therefore it is your career.

The Problem Today

In the current economic downturn people are losing their jobs by the thousands. They are being thrust out of their chosen career and left on the side of the road to fend for themselves. All of these people are looking for work doing what they have always done. They want to stay in their career of choice. The problem is all of their coworkers do as well. The marketplace is becoming much more saturated with job seekers and less saturated with openings. This means career type jobs may be more difficult to obtain.

The ranks of unemployed are pulling their unemployment checks and searching for their ideal job. At some point the unemployment checks are going to stop rolling in. What do you do then. Unfortunately more often than not people are starting to live off their families, parents are asking their children to “donate” money to keep them rolling. In most cases they don’t have an income by choice. There are jobs out there, not your career work but job. Walmart, McDonalds, other employers who pay money, it may not be much, but something is better than nothing. When I worked collections I talked to people who had been out of work for over a year, they were 2 almost 3 months behind on their mortgage their car had been repossessed but they still stubbornly refused to go out and get a job. They wanted their ideal career.

I would like to think if I get laid off and fail to find adequate employment within my chosen career path I would get out there and find a job doing something that pays. Some amount of income coming in to support my family or myself is more important than stubborn pride. At the very least I will be able to show my creditors that I am doing everything I can to pay back my obligations. Sitting on your laurels and farting around on the Internet should not be a part you play when you have no income coming in. Some money is better than no money. I am not saying stop looking for a job, but you have to draw the line somewhere and say enough is enough, I have to have some income.

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Lets face it, the job market sucks right now. Companies are shrinking, banks are closing left and right, and automobile factories are closing everywhere. For those of us that still have a job we are counting our blessings, those of you who are looking for jobs are trying to find someone willing to hire. One thing people tend to overlook when job hunting is the benefits outside of just the face dollar value of a job. When you go in for an interview they always give you a chance to ask questions at the end. You don’t want to screw up your interview so make sure you use that opportuinty to ask about the job. Better yet, ask the interviewee’s what, other than the money, is awesome about this employer. The answers to that question could very well seal the deal for you.

401k Match

Everyone talks about how great matching is. The fact is every employer doesn’t offer matching. There is nothing that says they have to so don’t expect your future employer to do it. For those of us who do get matching, it is “free” money on top of what we are getting as a base salary. I say “free” because you usually have a set period of time you have to work for an employer before you are fully vested in their matching portion of your 401k. Free money is free money though so don’t count this benefit out when looking for a job.


Pensions seem to be going the way of the dinosaur. I personally lucked into working for an employer that still offers pensions. Whether or not it will still be around 90 years from now when I am able to retire I don’t know. Pensions are just another source of  “free” money. Again you are going to have to wait a specified amount of time until you are vested, but anytime after that you can retire. I only have one more year until I can “retire”” as a fully vested employee.

Flex Hours

Flex hours are basically a fluid kind of work day. You have a set number of hours and the option of when to work them. For instance you could work four 9 hour days and one 4 hour day starting a 7am every day. Or you could work 5 8 hour days starting at 8:30 every day. Either way you are working 40 hours a week but the flexibility in setting your schedule allows you the time to take care of what you need to. If you have to get kids to school in the morning it may work better for you to start later in the day. Having an employer who participates in this kind of scheduling is great, especially for working parents.


Flex hours are pretty cool, they let you get some stuff done. If you add to that the ability to work from home, well then you are onto something.  If you happen upon an employer who not only supports, but encourages you to work from home you should jump on it. Working from home is a benefit most people don’t get, but it rocks. I work from home 90% of the time and I love every minute of it. Your phone rings less, less people bother you, and you can get more done with you music blaring. It is my number one benefit of where I work and I wouldn’t give it up for the world, well maybe $30k, that would do it.


When you sit down to a panel interview with the people who are going to be your peers and they say how great management is, they are probably telling the truth. They have no incentive to lie to you unless they are trying hire you to be their manager or their bitch.  A good manager is worth a lot of money even if you don’t think so right now. You can learn more in one year of working for a quality boss than you could making $20k more working for a POS leader. A good boss cares about your development and trains you to replace them. Look for one of those regardless of your starting salary.

Health Care

Most employers offer health benefits, the thing you need to be wary of is just how much those benefits are going to cost you. You could have two separate job offers on the table but if one of them is a lot less but  includes free health benefits and the other charges you $200 per paycheck but pays you more you could be better off with the lesser paying job. Make sure you take into account the costs of your healthcare benefits when looking at competing job offers.

I know I could probably find a job making more money for another employer, the fact is though I get almost every benefit I just listed. Health care isn’t free with my employer, but it is through my wifes. Still, I think you would be hard pressed to find an employer that has great management, flex hours, telework, 401k matching, and a pension. It would take a considerably larger chunk of change for me to give up my current job to go work for someone who didn’t offer me these same array of non salary benefits. Did I mention I get a pension?

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CashCrate Review

April 9, 2009

CashCrate is one of those Get Paid To (GPT) Sites where you are paid to complete offers, some free and some not so much. It has become tremendously popular with stay at home moms, college students, and just about anyone else with a few minutes and a desire to make some money at home.  There […]

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What NOT to do in an Interview

March 11, 2009

I have spent a lot of time interviewing people lately. We are currently hiring at my day job for two positions and I have the “joy” of being on the interview panel.  I know that a lot of people are having a hard time right now and there is record numbers of people looking for […]

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