Dear Corporate Shrink,

I have been working for an information technology company for the past eight years. I am bored and tired of working for the man. The money is ok but I keep wondering if I should test the waters of self-employment. How do I determine whether the right move is to take the plunge?

Bored and tired of working for The Man

Dear Bored and tired of working for The Man,

First, let me congratulate you on not being impulsive and jumping in without contemplating the pros and cons of your decision.

People leave situations when there is too much pain in staying or when an alternative situation offers more rewards. Basically, you have to try to, objectively, to measure the pain you are in and clarify the assumptions about the alternative. You have to diligently examine the present situation and ways to significantly improve it. Then, you have to add courage. Sometimes it’s more courageous to stay than to leave. As when an individual decides to stay and work on saving a marriage, rather than leave to pursue another relationship, less known, that "seems" and "feels" more promising.

What are your expectations about self-employment? Many people assume it means a more flexible schedule - that is not always true. There’s an adage that says that when you start a business you should expect to work twice as hard for half the money - at least in the start-up phase, which could last months or years.

Is your expertise in an industry that is growing, shrinking, or oversaturated with professionals? Obviously, if going independent means facing stiff competition, one may be better off staying with a secure company - unless you can develop a new product or find a specialty niche. The information technology industry has certainly been going through hard economic times for the past several years.

Have you tried improving the present situation? This is hard to even think about when you are in the midst of an especially frustrating period or there’s a fresh incident that is making you feel negative about your work. Try to sit down during a calm, non-emotional phase and write down three lists. First, the negative aspects of your present job situation (lack of recognition, overworked, underpaid, boredom, too much politics, problems with supervisor, unstable company or industry, co-workers, etc.). The second list involves the positives (good salary, stable company, enjoyable co-workers, exciting work, advancement opportunities, good relationship with management, flexible schedule, good insurance and benefits, etc). The third list is those negatives that you might be able to turn into positives. Some negatives, such as an unstable company or industry, will be out of your control. However, maybe you can be creative and try to promote a project that would be interesting to work on. Or you can deliver a consistent message to co-workers that you prefer not getting involved in office politics. If your company has an employee assistance program you can obtain the input of a professional. Or maybe you can consult with a trusted colleague?

The objective is to shrink the list of negatives to the point where you can live with them as they outweigh the risks of going off on your own. This is an important project that may need to take several weeks or months. If you make an objective and thorough attempt in this exercise and in the end you feel the risk of leaving the nest is worthwhile, then you turn your attention to developing an exit strategy and a solid business plan for your own enterprise.

Do you have an entrepreneurial personality? For instance, it helps to have a balanced mix of practical realism, optimism, and ambition. You need to be practical to expect long work hours and gradual progress; your optimism needs to carry you during tough times; and your ambition will help you take necessary risks.

Does your personal vision match your business vision? Crafting your personal vision involves making some fundamental choices about what you want to create with your life. Usually this life plan revolves around personal values, such as integrity, family, serving others, etc. It’s important to examine how your personal values can be promoted and supported by your business. For instance, if you value family time but the business you are contemplating as an independent consultant will have you flying out of state one week out of every three, you may have a conflict between personal and business values.

The support of your family is essential. Try to get their honest opinions. Check with that trusted friend or mentor. In situations where the spouse tends to be conservative but the business plan is solid and personal values do match business values, a successful friend with a business background can help present your ideas to the family.

I’m trying to sound cautious. It is true, most attempts at self-employment fail sooner or later. However, I do know of many success stories. There’s the philosophy professor who opened a bird seed kiosk and was happy as a lark (pun intended) with the change it brought to his life. I myself only worked for The Man for 2 1/2 years and then made a solemn vow, which I’ve kept, to never work for someone else. However, do understand that when you are self employed, you are working for more than one Man, you are working for many clients, and not all those situations will be rewarding - but in the end, you make the decisions, You are The Man.

This entry was posted on Saturday, September 15th, 2007 at 4:12 pm and is filed under ownership, strategy, thinking, career issues, vision, family, small business, values, entrepreneurs. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.