Many people say they want to be their own boss, conflating greater freedom of choice with personal pleasure.
But I suspect it’s not always pleasurable, because a good boss will know when to kick me in the ass and when to pat me on the back, even when I may not feel like receiving either action.
BEING that boss means I need clarity and discipline.
Some folks just don’t do well with that level of “freedom”. Being a boss is not necessarily freedom, anyway. To your point, there has to be discipline, but also the acceptance of responsibility for those that work for the boss. A good boss is not free to just shout orders. He has to create orders that optimizes the resources he has when trying to accomplish a task. We won’t even get started on the optimization part 😀
But the self-motivated employee doesn’t need to be kicked in the ass or patted on the back. I wouldn’t want to be a boss simply because I don’t want to carry the weight of more complex decisions. I like to be presented by a stream of bit-sized tasks which I can carry out efficiently, while leaving things like strategic planning and telling other people what to do to others. I don’t resent having a boss. Sometimes I disagree with their decisions, but very rarely with how the treat me. Maybe I’m just lucky.
I once had a boss that told me, “Don’t let the door hit you where the Good Lord Split you!” I am still pondering his words over 27 years onward…..
Kent Wayne 
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