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Opinion

BYOB: Who is in charge around here?

Mark Henderson
By Mark Henderson May 5, 2023
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When I am asked to mentor entrepreneurs, I often hear the phrase: “I want to be my own boss.” Those words make me shudder. The people using this phrase have no appreciation for what it means. The only job on the planet where you can be your own boss is Evil Dictator of a Third-World Country, and that usually doesn’t end well.

Being your own boss doesn’t mean that you have no boss. Ironically, it means you have all the bosses. Seasoned entrepreneurs deeply appreciate that their chosen path makes them directly responsible to everyone. The “Boss” doesn’t have to make any one person happy. They must make everyone happy: vendors, suppliers, employees, government agencies, regulators, politicians, (and most critically) customers.

Aspiring entrepreneurs are often rebelling against a lack of transparency in their organization. They don’t understand why the leaders make the decisions they do. They feel like their own ideas, thoughts, and concerns are ignored. These can be the best employees if they truly care about the organization’s mission, product(s), team, and customers. Great leaders and managers help these fantastic employees become entrepreneurs inside of the organization. Everyone wins. Average bosses push them out by not listening, unintentionally creating aspiring entrepreneurs on the outside.

I’ll present an entire article on this subject later, but I wanted to touch on it briefly here. You can teach almost anyone almost anything, but I have never taught an employee to care. Caring either exists or it doesn’t. You can nurture and direct it. But if an employee is self-absorbed or apathetic, you will never change that.

Realize that when you say the words, “I want to be my own boss,”  you aren’t giving up a boss, you are inheriting thousands of bosses. Each of those bosses has their own agenda, and they will generate very real constraints on your ability to execute your plans.

During my career, I have been criticized by nearly everyone, at least it feels that way. Everyone gets to poke something I have done, a decision I have made, or a way that I failed. Most employees only suffer job evaluations once per year, and those are often done by a boss with some sensitivity training and usually come with a raise or bonus. I have been forced to endure daily evaluations that never come with a raise and usually cost me something. These evaluations are often direct and insensitive. Some are sly and passive-aggressive. Many are back-handed or self-serving. Occasionally, that criticism comes from a place of actual caring and a desire to help. They all contain at least a nugget of truth, and that’s what makes them sting so badly.

Being your own boss requires working with contradictory constraints: You need to make investments, but you are out of cash. You need to fire that person because of their toxic behavior, but they are very technically competent. Your distributor demands that you release a new product this month, but the product isn’t ready for market yet.

If you really want to be your own boss, you have to be prepared to meet everyone else’s needs and expectations first. Simon Sinek said, “Leaders Eat Last.”  So do entrepreneurs.

ICYMI: Brewing your own business column one

The views expressed by contributors are their own and not the views of SuperTalk Mississippi Media.

Copyright 2025 SuperTalk Mississippi Media. All rights reserved.

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