The Reluctant Entrepreneur

Reluctant Entrepreneur

I was on the phone last night with my older brother who is in the process of starting his first business. Unlike myself, my brother shied away from the entrepreneurial track and has spent his entire working life after college in the mental health field as a psychologist. It’s funny how I just assumed that my brother would be adept at navigating the entrepreneur minefield based on his high level of intelligence; but that’s when reality took hold of me again and I remembered why I do what I do. I am a serial entrepreneur and  business coach for a reason; my passion is building businesses and teaching others how to do the same. Some of the questions he asked me put me back in my teaching mode as I began to rattle off important resource information and strategies to help his transition into entrepreneurship. My brother is what I call a        ”reluctant entrepreneur”; not because he isn’t excited about starting his business, but because he was almost forced into it after he was passed over for a promotion that he was more than qualified for that was given to a person almost half his age and with half the experience.

My brother was at that stage in his career where his salary was becoming an issue and it was now the cause of him being passed over for a deserved promotion. My family used to tell him that the state mental health department would function just fine if he missed a few weeks of work and came to visit the family every once in a while. My brother lives in the Midwest and most of our family is here on the East Coast. Due to his lack of visibility my brother had two nicknames; one was the “grim reaper” because the only time we would see him was if someone died. And the other was “Claude Raines”; the actor that played the title character in the movie “The Invisible Man”.  We actually didn’t see him for a six year period because he was working sixty to seventy hours a week and was always under staffed. We used to tell him that when he keeled over from working so hard that the state would have his seat filled before he was cold. Well that didn’t happen, but the fact that he got passed over for the promotion probably bothered him more than falling out at the job. He realized what his true worth to the organization was.

The day he found out he was passed over for the promotion in favor of someone with half of his experience, half of his age, and most importantly, half of his salary; he was furious. My brother is one of the nicest most gentle human beings that I know; but oh when he gets heated, he’s like a fire breathing dragon. I haven’t seen him that mad since two teenagers on my block growing up were trying to beat up my next door neighbor and myself (we were about nine years old and they were fifteen or sixteen – not too much of a contest I’d say). My brother took out the trusty baseball bat and went looking for those jokers, but he never found them. I know if he could have taken out that baseball bat and redecorated that state mental health office I’m sure he would have.

So now here is the quandary, my brother is in his mid fifties and now has to decide to either look for a job or start his own practice. Now mind you, he had been frustrated at the job before because he was understaffed and overworked. So every few years he would grumble about starting his own business, but you knew as soon as he cooled down that that would just be a fleeting thought. After a few months of putting out resumes and barely getting a sniff of an interview, he decided to finally move forward with his new business. I guess he was tired of relaxing and working on cutting down that never ending “honey-do” list. As we spoke last night, I made sure he had his checklist so he could move smoothly through the paperwork process necessary to file his LLC and get his business in order. I stressed to him that it is best to start correctly so everything is in order. We had a long conversation about bookkeeping where I told him he needs to use Quickbooks as opposed to his self constructed excel spreadsheet. I told him that he could file for his EIN (employee identification number form SS-4) directly on the IRS website ( for free. I explained to him that many incorporation companies will charge you for that service even though it is just a matter of completing an online application. I explained to him how as an LLC his business profits and losses flow through to his personal income. I had to remind myself that my brother had no experience with starting a business before and that his masters degree in psychology was virtually useless when it comes to entrepreneurship. Entrepreneurship is an occupation, it’s not what you do; it is a learned skill; just like becoming a skilled professional athlete. You must spend time honing your craft and learning from your inevitable mistakes.

I realize that there are many people that fall into the “reluctant entrepreneur” category for many different reasons. They may be like my big brother who was expendable because they could replace him with someone with half of his salary. The “reluctant entrepreneur” could fit the profile of a salesperson that got let go. They could also fall into the category of what I call the “unemployable”. These are people that may have a criminal record that will keep them from getting hired for a position that pays the required amount of money they need to live. It may also be the person who does not have the educational background, technical skill, or any type of skill set that would make them marketable to a prospective employer. People who fall into this category many times become the “reluctant entrepreneur” for lack of better options. If you or anyone you know becomes the “reluctant entrepreneur” please let them know that it may be a blessing in disguise. They may actually be more suited for running their own business than working for someone else. I tell my employees (in a nice way of course) that I have certain policies and procedures that must be followed in order for my business to run the way I want and need it to run; and if they are not able to conform then they may need to go and create their own environment where they are more comfortable. I say it with love as I have helped several former employees start their own businesses. I will never hold anyone back if they feel they need to put themselves and their families in a better position by starting their own business (as long as you are not stealing from me and my company). I learned a long time ago that there are many great ideas, and that the truly successful people are the ones who can execute on those ideas.

Are you a “reluctant entrepreneur”? Do you know a “reluctant entrepreneur”? Please email me or leave a comment and tell me what you think about my article. I also may request to interview you for my new book.


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