Considering Self-Employment? 7 Questions to Ask Yourself

03/24/2015 05:04 pm ET | Updated May 24, 2015

Part of the fun of owning my own business are the conversations that I have with my friends that work for employers. As the conversations go, we debate over benefits, perks, responsibilities, the economy and various other subjects. One thing for sure (I say tongue and cheek), I am gainfully unemployable, and for me, that is a good thing. Actually, it's a great thing. I've invested many years in my "work in progress" attitude and how to balance my business and personal life, weaving them together like a tailor made suit. I deal with the risks of self employment because, to me, they are far outweighed by the rewards offered.

Some would characterize me as a workaholic. Others might suggest that I am too focused on success. And a small segment of those I know say what I do isn't work because I have too much fun doing it. There is probably an element of truth in each. I love what I do and I do what I love.

The thought of having responsibilities that fit into a company's policies and procedures manual makes me weak in the knees.

As for me, I would hate to think that I would fit into a neat little box and labeled as "employee." The thought of having responsibilities that fit into a company's Policies and Procedures Manual makes me weak in the knees. I only say this because of all the horror stories I hear about clock punching, allowable sick days, cost of living increases and a whole host of other standard operating procedures found as a result of working for "The Man." I am not down on "The Man" for some, but being employed just isn't my "thing" at this point in my life.

Simply put, I love the idea of working as hard, or as little as I want, while being compensated for the results of my energy expended, and good old fashioned luck. Many would argue that it's the economy and external factors that control income and not how hard or smart one works. Pardon my directness, but that is just downright wrong. Want to make more money or have more free time? That is 100 percent up to you, regardless of the external forces at work against you. Where there is a will to succeed, there's a way to succeed.

Let's face it, you are either a part of your own plan or a part of someone else's plan and even though I truly believe (and live by) the philosophy of nice guys finishing first, I never said nice guys need to work on someone else's dreams and goals to finish first. Conversely, you can still win if you work for someone else, but you will be playing by their rules in the process. I recently heard a speaker talking about a philosophy of not thinking inside or outside the box, but rather, not having any box at all. I choose no box.

All that stuff aside, the views stated here are just my opinion and although I love working for myself, I must admit the security of salary, benefits, and protocol is sometimes alluring. Fortunately, if I ever find myself in a position of envy, I put my head down and work harder towards my goals until the feeling passes.

Fortunately, if I ever find myself in a position of envy, I put my head down and work harder towards my goals until the feeling passes.

I am looking to open up lines of dialogue with this post so please tell me what you think in the comments section below. In your opinion, if I am way off, let me know why you think I am off base. For the sake of examining the list below and defining self employment or business ownership, I consider anyone that has no guarantee of salary, benefits, stipend, draw, points or anything of value to be considered self employed or a business owner.

If there is ever any question as to whether you should either take the leap to the world of self-employment or to continue to work for a stable paycheck from a company, I encourage you to examine the list of seven questions below prior to making the jump. I am not claiming self employment is better or worse, I am only stating what my observations are regarding self employment as I pose these seven questions.

Do you like to work longs hours? Business owners get to choose which 18 hours they work each day. If you are ok with the risk of putting all of your free time, TV time, vacation time, weekends, family time and personal time on hold while you build your business, then you are prime for the rewards found in self employment. You will be amazed how your time management skills improve when you are self employed, busy, and dealing with a to do list a mile long.

Are challenging customers going to be challenging for you? I hope you brushed up on your psychology courses in college because you will need to be as good at analyzing your customer's mental state as much as you will need to understand your product offerings.

Business owners get to choose which 18 hours they work each day.

Do you like to wear many hats at work? Business owners sell, market, account, and engineer all while being the boss. If you have one speed and specialty for business, and you feel as though that will be good enough for the world of self employment, think again. While it is true that you should focus on what you are good at and let others do the rest, in the beginning, you will need to do all the work yourself, so you better brush up on HTML 101, read Business Plans for Dummies and overdose on self help and motivational podcasts.

Are you ok with zero benefits? Business owners have none unless they buy their own. 401K, health, dental and prescription benefits are costly, so be prepared to comparison shop, pick higher deductibles and have high premiums for insurance and benefits when you are self employed.

Do you realize the down economy is not an excuse for poor business results? Business owners are fully committed and still have to pay bills even when the economy is down. Mortgage companies, credit card institutions and my bank do not take good intentions, only legal tender. Long gone are the ideas of recession, inflation, depression and market bubble; yes those things still exist, but so does the mortgage payment. Three words: Figure it out.

Don't like working for the man? Try being The Man.

How many sick days and vacation days do you have? If you are self employed, you have the reward of 365 vacation days a year as long as you are ok with losing all of your customers for lack of servicing. Want to take a trip to Paris? Excellent, make sure you are prepared to work twice as hard before you go and three times harder when you get back to make up for the lost time at work.

Want a raise? Don't worry, eventually you will get one but be prepared to get paid last. The benefit to unlimited income potential is just that; it's unlimited. The downside is being acutely aware of the potential to have an entire week, month or quarter go by without a paycheck. Get very good at managing cash flow peaks and valleys if you are considering self employment.

BONUS: Don't like working for "the man?" Try being "The Man." Try not to go on a power trip with this move to self employment. People will not want to do business with you if you have an ego larger than life and you are unable to fit it into your hat. Be relatable, humble, empathetic and flexible when you make the move or consider other options other than self employment.

On the other side of the subject, I enjoyed many years of learning from my experience being an employee and find I am richer as a result of working for someone else. I left full time employment around 1998 and have loved the rewards provided by self employment since then. Yes I have sacrificed many things along the way but I understood the risks when I took the leap over 15 years ago. Before you take the plunge I encourage you to carefully examine the questions above. Even if you decide not to follow the advice I offer, I can assure you, blazing your own trail will be amazingly rewarding.

I would love to have you as a reader of my regular posts available on my website at I have a book, available on in paperback or Kindle versions now. The book Ranked #1 New Release for Business Communications and climbing the Kindle ranks for Customer Service publications as well.

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