Free Advice with Richard: To Be Or Not To Be, Employee or Proprietor?

Write in to get clarity on Relationship Difficulties, Work/Career Questions, Family Troubles, or Social Life issues. Email me at rzradvise@gmail.com. Or leave your question or issue in the comment box below. Also see the "Tip or Quote of the Week" below.

Issue of the Week:  "To Be Or Not To Be, Employee Or Proprietor?"

I’m fifty years old and specialize in financial analysis software. Previously, I worked for a consulting firm for 17 years, during which I was always torn between working for a company or starting my own company and being my own boss. Since then I had move to another company where I continue to work in my highly specialized field with good pay and benefits. 

Now, even though this is a better job, I’m always thinking about going out on my own. As with my old job and this one, I like the fact that I have a steady paycheck, health insurance and a continuous source of work, which gives me a fairly good sense of security. I’m a full-time employee, so whether I work 40 hours in a week or 12, I come home with the same amount of pay. 

I realize that if I go out on my own I will have to find the business for myself. Also that, in this profession, one has to keep up with technology and new developments. I feel reasonably confident that I will be able to do that. But that does require a  considerable amount of time as does finding customers.

I have a friend in the same field, also working for a corporation, and we talk about starting a business together, as partners, but have not moved ahead on this.  

I’m fifty years old and I think that holds me back a little. I continue to live with that desire to make the change, but don’t.

Do you have any feedback that might help me decide?

Dear undecided,

I can certainly appreciate the, yes I will, no I won’t, space you are in.

Not being in your 20’s or 30’s any longer surely contributes to a reserved and cautious outlook when the option for major change presents itself.  However, that this betwixt and between state of mind has been ongoing for a number of years, suggests to me that there may be some issues in your life, outside of this choice to remain an employee or become a proprietor, that may well deserve some attention.

As for the practical situation, I would suggest that you ask yourself a few questions.  

The two major areas that come up for me are:

1) How good are you, and how willing are you to work at generating business on your own. I would guess that you have some contacts, since you’ve been in this line of work for a long time, but the sales and marketing you will apparently have to do will require great effort and time. Do you see yourself as a salesman? How comfortable are you with this role?

2) You mention the essential need to stay current and be on top of new developments in financial analysis software. As we all know, and you especially must be aware, that technology in the computer world moves fast.

Here again, such due diligence to stay knowledgeable and sharp will take considerable time. How good are you at scheduling your time to handle these vital areas?  

In terms of taking this leap on your own: You spoke of a colleague that, like you, entertains this idea of self-employment. And, that you have talked about it a number of times. A little analysis of these previous talks may also be in order. Are they conversations or serious discussions? 

These talks should not be discussions, but meetings to plan strategy. Meet as though you are actually starting a business. 

What I allude to here is that your talk may not be specific enough. For example: What needs to be done first? second? third? What will it take to accomplish these first steps, e.g., money, time, other people, contractors, marketing companies, and who will do what. Write it all down. Who between the two of you is more the salesman, the tech person, the numbers man? Sound out each others abilities and preferences. I’m not familiar your particular business, but perhaps after considerable exploration you begin to feel that such an enterprise might require a third partner.

Fashioning these meetings in this way will help move your dream of independence from idle rumination to the reality of how possible is this endeavor? 

If you get a little anxious from these meetings, don’t let it worry you, that’s probably a good sign. It means you’re getting serious. And if you begin to experience excitement before the next meeting, you’ll know you're on the right track. 

One supportive fact is that you say this field of yours is not only highly specialized, but that there are also few people that do this kind of systems work. The indication here is that you appear to have a pretty good fall back situation, should your move to business owner prove to be to difficult.

Now, since (I think) we covered the practical characteristics, I would like to touch on  my earlier statement, with reference to the extended discussion of plans to consider a major change that does not grow beyond the talking stage.

There may be nothing here beyond the practical, but significant challenges to cause considerable concern. However, when indecision continues to be carried on and on, in the bubble of new dreams, and does not get acted upon, it would be healthy to consider exploring what may be going on intra-psychically. Sorry for the clinical term, but merely allow yourself to examine what, or where, or when, this behavior shows up, or has shown up in other areas of your life. One can do this with a little self diligence, and or, get some help on a short term basis. 

If you have any questions about that, please email me, or leave a message in the comments box at the bottom of the column.

Best of luck,


Tip of the Week: A Quote. "Every worthwhile accomplishment, big or little, has its stages of drudgery and triumph; a beginning, a struggle and a victory." Ghandi

If you have a question or an issue, or a suggestion for the “Tip of the Week,” email it to Richard at rzradvise@gmail.com or leave it in comment box at the bottom. Always confidential. Names do not appear in the column.

We always welcome your comments.

For information on Richard's approach to psychotherapy and counseling, click on: Richard Z. Ross, MA, CGP, LMHC, LP


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