- The Essential Military-to-Civilian Transition Resource

The Boss of Me

Eight Things to Factor in When Considering Self-Employment

by Tom Wolfe, Career Coach and Contributing Editor

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Article Sponsored by: Epes Transport System, Postal Connections

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transitioning military hired for operations managementDuring a recent career coaching session with Charles P., an Army Major who was about to retire, I asked him what he would really like to do in his civilian career. He said that figuring out the answer to that question was his biggest stumbling block. That is not uncommon for people in his situation, so I asked him the same question, but in a different way. I said, “OK, forget about the titles and instead just give me the elements or characteristics of what you would be good at and what would make you happy.” He smiled and said, “That’s easy, Tom. I want to control my destiny, sink or swim on my own merits. Call my own shots. Get my hands dirty. Work hard and get paid for it. Not have to relocate, and be home most nights for dinner.” I said, “Charles, have you thought about going into business for yourself?”


Perhaps your skills and needs and wants are similar to those of Charles’. Is self-employment a good choice for you? Maybe yes, maybe no.


Self-employment offers many advantages to former military. You get to call the shots. Decide where you want to live. Wear what you want to wear. Associate with people and products that matter to you. Determine your own working hours. Hire and fire as needed and according to your standards. Reap the rewards of your success. The appeal of self-employment is understandable. But be careful - although you may have a clear view of the tip of the iceberg, you also need to take a look below the waterline. Here are eight factors to consider as you learn more about this type of employment.


1. Risk


According to the Small Business Administration, more than 70 percent of self-employment business ventures fail in the first two years. Can you afford the risk?


2. Accountability


There will be a big scoreboard up there with your name on it. The numbers next to your name are your numbers. Nobody can take credit for your success, and nobody will cover up your failure.


3. Financing/cash flow/credit


Starting your own business requires seed money. Do you have it? If you have to borrow it, how is your credit rating? Some franchising opportunities require an up-front investment of $5,000 to $100,000. Many business failures can be attributed to running out of cash in the first year.


4. Time off


How important are vacation days, holidays and sick days to you? Have you been using those 30 days of annual leave? Being off work on those federal holidays is kind of nice. Guess what? Self-employment often means no vacation, no holidays and no weekends. This can be true until your business is well-established and you can leave the keys with trusted employees when you’re out of town.


5. Working hours


Yes, your military experience has conditioned you to work 12-14-hour days. Were you thinking about cutting back a little? Forget it. Being your own boss is a 24/7 endeavor.


6. Employees


Will you need them? As much as you relish the thought of not having a boss, do you really want to be one? If so, how many employees and what kind of talent will you need? Will you be able to find them? Most business owners will tell you that their No. 1 problem is finding and retaining good employees.

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