Square Peg, Meet Round Hole

I have friend who was a very successful entrepreneur. For the first 2/3 of his working life, he never worked for anyone in any organization, starting his first company in college and growing it enough to eventually sell it. That business he walked away from after the sale and invested that money in his next venture – which was another success. It was enough of a success to attract the attention of a multinational company who wanted to buy it, which they eventually did.

They asked him to stay on and run the business, something he agreed to do and something I advised him not to do – three years into a five year contract, he quit (and left a ton of cash behind in the process). He didn’t quit because the business was unsuccessful, quite the contrary – with the access to capital the bigger company had, the business was able to grow far beyond where he would have been able to grow it. His problem was because he had never had a boss, he was never able to adjust to working for someone in an environment where someone else made the rules.

The “corporate” environment fit him like a straight jacket. What was right for the greater success of the business was totally wrong for him on a personal level. It wasn’t that he was a rebellious sort, he just couldn’t deal with the deliberate pace, the constraints of having someone review his decisions and not being able to do what he wanted at exactly the time he wanted. Prior to the sale, he had shareholders, investors and boards to deal with in his company but they were always passive and benign and he was able to do whatever he wanted because he was successful. They were never much of an impediment to what he wanted to do – so he really was an independent actor.

The business environment his company operated in also changed after the sale – instead of his company being able to do anything he wanted at any time, it had become an integral cog of a larger business where the business units had to coordinate and move at the same pace toward the same goals and he found that gratingly frustrating. He is retired now and while he is financially secure, he is not happy. Nearly 5 years on, he still constantly grouses about his decision to sell his company – regrets it to the point of getting angry about it – the experience changed him. He is far more cynical and far less optimistic today than he used to be.

I think this is a problem for the current GOP front-runner. He, like my friend, has never really had a “boss” and now he wants to be the head of one of the most regimented, slowest moving dinosaurs in the world. He talks like an unrepentant entrepreneur now but if elected, will have to adjust to a situation where he will have many “bosses” – Congress, the judiciary, the media and most of all, the American people. He is going to have to answer for his decisions. His current behavior indicates that he is not comfortable answering to anyone and his past indicates that when things don’t go his way, he folds his tent and goes home. I can’t see him successfully adapting to a new reality.

Yet another reason I can’t support Donald Trump.

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7 thoughts on “Square Peg, Meet Round Hole

  1. I understand this fellow. I have worked for myself since I finished my residency, and I come from a long line of small business owners. As I near retirement, I am about to sell my practice to a venture capital group that has been very successful buying practices in my specialty, so I am going to have to get used to being an employee for the first time in years. The only good thing about it is that it will enable me to get out of debt, and there is light at the end of the tunnel. Solo medical practice is no longer financially viable.

  2. I understand your point, prez………………….. but I doubt that I could say that OWEbozo had “many “bosses” – Congress, the judiciary, the media and most of all, the American people. ” Or at least he has never listened to what any of them have said if it went against his plans for America’s transformation.

    • His “bosses” have been more like my friends passive and benign investors, shareholders and boards – he was doing what they wanted him to do, so no need to start trouble.

  3. Obama, has a boss and has never run anything on his own. Bought and paid for by the George Soros network. Trump, has been on his own and would be incapable of working in the bureaucratic nightmare that is now the US Government. In 6 moths he would be a stark raving lunatic (if not already).

    Of all those still in the hunt Ted Cruz is the only choice. Although he does not look the part he could orchestrate the system the best to salvage whats left of the USA for at least 4 years. If Hillary gets elected and the Republicans actually accept one of her SCOTUS appointee’s, you can rest assure the 2nd Amendment will be rendered useless.

    There are some, including Glen Beck, that are saying Hillary is better than Trump as the Republicans in Congress could control her. My response to that is they had 6 of the last eight years to stop Obama and we got zero.

    • Why do you say Cruz doesn’t look the part ? He seems very Presidential to me when he speaks . And his knowledge is vast.

      You are correct about Hillary and about the Establishment GOP.
      Glenn Beck is completely wrong. And he in fact Deconstructs himself constantly as he claims Trump works with both parties, so there is indeed a vector for republicans ” controlling” Trump. His base of course is hoping for the OPPOSITE…..That Trump will control the GOP sellout to the Democrat Left.

  4. Now you have found an Achilles heel regarding Trump that I think is an accurate concern. Its been my experience leaders often face these sort of challenges, some do better than others in handling them.

    • Both my wife and I have had similar experiences…..being hired as “consultants” after selling businesses.

      I kind of see this situation with Trump. He’s being hired as a consultant by the People to use his expertise on solving problems that he’s been used to solving as sole decision maker.

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