Why do we stay in prison when there’s no lock holding us there?

By David McElroy · September 19, 2019

One of the restaurants where I go a lot lately is badly managed. I really like some of the employees and they talk with me about their frustrations quite a bit.

A few days ago, a couple of the employees had joined me at my table during their break. They were telling me the latest outrages they faced.

“Why in the world do they stay here if they’re so unhappy?” I thought to myself. I didn’t want to say that to them and sound condescending, but I was judging them for staying where they clearly didn’t want to be.

For a moment, I felt a little smug (and condescending), but then the smile disappeared from my face. In a painful flash, I saw my hypocrisy and felt really uncomfortable.

Why do people stay in places where they’re unhappy? I shouldn’t be pointing a finger at them. My smug question should be directed at myself.

I haven’t been able to get this uncomfortable question out of my mind since then. The more I think about it, the more I see this horrible tendency in a lot of people, including myself at times.

We sometimes feel as though we’re in prison. We don’t want to be where we are. We feel trapped. We’re quietly miserable, even though we might not admit that to others.

We have “good reasons” why we stay where we are. We’re envious of other people who can make changes and leave their prisons, but we think something is different for us. We might say we’re staying to protect someone else. We might think we’re protecting ourselves. We might even promise ourselves that we’re eventually going to leave.

But the simple truth is that we continue to endure long-term pain — over and over and over again — because we are unwilling to endure some short-term pain today.

When I used to work for myself, every day of the week seemed pretty much like any other. Depending on what was going on, I might work on any particular day. It didn’t matter whether it was Saturday or Sunday or a holiday. If something needed to be done, I was happy to do the work.

But I was just as likely to take an unplanned afternoon off to visit the zoo. Or go to a movie by myself in the afternoon while everybody else I knew was stuck at an office. Or get into the car and go visit someone I wanted to see, even if she lived hundreds of miles away. Or just take a day off and write whatever I wanted to write.

I had freedom to do what I wanted when I wanted to do it. As long as I got my work done — on my own schedule, for the most part — I was free and I was happy.

I don’t have that freedom today. I’ve tied myself to being at an office on someone else’s schedule. It’s not an unreasonable schedule. I can’t complain. I can get time off or re-arrange things when I really need to. But unless there’s a very good reason, I’m going to be in that office — doing work that matters to someone else — for those hours five days a week.

When I used to work for myself, Fridays were nothing special to me and I didn’t dread Mondays. Today, I live for the weekend. I feel like a prisoner who goes on parole each Friday at 5 p.m. and has to return on Monday.

Nobody forces me to do this. It was an opportunity that was handed to me and I took it. I’m certainly not unhappy with the person who offered me the job — who happens to be a long-time friend — but I know I’ve trapped myself in a velvet prison.

So why don’t I make a change?

That was the question that hit me pretty hard as I sat there and judged those restaurant employees the other day. Why don’t I make a change?

There’s inertia, of course. This is a well-established pattern. The company has come to depend on me, so I suppose I like to believe it would hurt my friend if I left. I don’t have to make a new plan to stick with this. I just get up each day and go solve problems for someone else — instead of myself.

I could ditch that job and keep my real estate license. I could go ahead and get a broker’s license in the next couple of months if I wanted to. I could replace the income from what I’m doing internally at the company — probably more easily than I want to admit — but it’s easier to just keep hating weekdays and praying for the arrival of the weekend.

I’m unhappy with myself about this, but so far, I haven’t done anything about it.

Everybody has done this. Most of us are doing it right now — about something. I don’t know what you need to change. I don’t know what your prison is. But I do know that your reasons for staying in your prison are terrible. I know the door is really open. All you have to do is screw up your courage and walk through the door which has been open all along.

You can either leave — and go do whatever else you ought to be doing instead — or you can waste more months or years or even decades of your life in this unlocked prison.

Eventually, it will be too late for whatever it is you want to be doing instead. You and I both need to find the courage to take action right now — not tomorrow or next week — to start walking through the prison doors which have held us in.

If we don’t, we will forever regret staying imprisoned in a place we could have left at any time.

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I’ve never been attracted to skinny women. There’s nothing wrong with someone who’s naturally thin, but it’s never been my preference. What has shocked me, though, is the judgment I’ve heard from women all through my life — about themselves and others — about who’s “fat.” I concluded long ago that most women in our culture have been brainwashed to believe that skinny is attractive — and that anything other than skinny is ugly. I first assumed that I was the oddball — for preferring women with bigger and heavier bodies — but I’m coming to the conclusion that most men naturally feel this way to one extent or another. I just ran across new research by a couple of Northwestern University psychology professors that shows that women seriously overestimate how much a straight man will be attracted to a skinny woman. In a perfect world, we would all be at a healthy weight, but when it comes to attractiveness, too heavy is more attractive than skinny. At least to me — and to a lot of men, too.

Years ago, I heard a question that seemed very insightful at the time. You’ve probably heard it, too. What would you do if you knew you couldn’t fail? The question is intended to help you uncover things you really want to do, but which you’re afraid to try — for fear of failure. In an interview today, I heard the great marketing guru Seth Godin give a different point of view. He said the better question is to ask what you would do even if you knew it would fail. That struck me as far more insightful than the original version. We ought to be doing what we know is right, not what will maximize our success or praise from others. There are some battles that are worth fighting even if you believe you’re doomed to failure. Those battles are often for love or important ideas or our children. Some things are simply worth fighting for — and the truth is that you might win anyway. Do the right thing. Take the chance.

The more I understand about myself, about human nature and about the nature of reality, the more I realize I’m a radical by the standards of both Modernism and Postmodernism. Seeing the things which I’m stumbling toward makes me an enemy of many of the core ideas upon which contemporary culture is built. It exposes the culture as a monstrous lie — like a dangerous infection that’s slowly destroying what human were created to be. My “inner observer” has always known that truth was found in the ideas of the Enlightenment, but I’m slowly finding words to explain what has merely been instinct until now. The Enlightenment was humanity’s great leap forward, but shallow and arrogant thinkers for the next two centuries threw away the fruits of that achievement. We can’t go forward as a species until we go back to correct this intellectual and spiritual error — and part of that is acknowledging that our collective attempts to do away with our Creator will always fail.

I’ve come to believe that some of us — including me — aren’t very good at knowing how to be happy. I don’t mean that in the sense that happy talk and positive thinking should be able to make us happy regardless of the circumstances. I mean that some of us had so much experience with being unhappy when we were young that we were trained to be unhappy — and that being happy is an unconsciously uncomfortable thing. When I look at times in my past when I should have been happy, it rarely lasted. I believe now that I found reasons to be unhappy — and caused real problems for myself — because being comfortable and happy felt so foreign to my programming. If I’m right, this means that some of us have to do more than just change our circumstances. It means we have to learn how to accept the happiness that we unconsciously fear we don’t deserve.

After I wrote last night about being happy, I thought of an old song that mirrored what I was feeling. After listening to the entire album, I found it remarkable how well the emotions of that music match my own heart at this point in my life. Bob Bennett’s “Matters of the Heart” came out while I was in college. Even after all these years, it holds up really well, and you can listen to the entire album on YouTube. The specific song which matched my feelings last night was “Madness Dancing,” but I still find every song on the album to be strong with the exception of the eighth and ninth. (The song about his parents, called “1951,” is especially poignant.) In fact, the opening and closing songs paint a picture of my heart at its best now in these lines: “A light shining in this heart of darkness, A new beginning and a miracle, Day by day the integration of the concrete and the spiritual.” It’s old music that you’ve probably never heard, but it means a lot to me.

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