Regret Is a Horrible Burden to Bear, Especially When You Are Homeless


Living with deep regret is a horrible burden to bear. It can be crippling. It is painful and often merciless. There is no way to go back in time and fix what went wrong, so you feel completely powerless and filled with remorse and sadness.

Many of us live with regret that is so oppressive it crushes your soul. When you’re homeless, you often find yourself ruminating over these thoughts of regret to the point of paralyzing you. It is a horrific way to exist.

My regrets may seem trivial to other people. I’m not guilty of harming others and have never done anything particularly bad. In my case, I regret my stupidity and bad choices. Though I never once used drugs or alcohol and never had gambling or other addictions, I have had a very bad habit of choosing the welfare of others above my own.

Do you know the advice about putting on your oxygen mask before attempting to assist others in an airplane disaster? Well, I am the fool who tried putting masks on other people first. I then ended up passing out on the floor while most people I helped ran, fleeing off the plane and leaving me on the floor. Some even trampled me on the way out. The few who stayed were too feeble or disabled to help me up, so now I lay in limbo between living and death.

I am very glad that my regrets aren’t things about hurting others because I could never live with myself if they were. But having regrets about your stupid errors in judgment still rips at the soul. In my case, life is a living punishment for those missteps. I am punished daily, brutally and unrelentingly, for trusting the wrong people.

I have often been very naive and have chosen to make excuses for people who never cared about me. Yes, I really am a jackass.

In normal circumstances, you could get therapy and find ways to move on with your life. But when you’re homeless, you can never move on. By definition, you are trapped in limbo. I would love to move on.

I would love to forget about my dirtbag ex and put that whole fiasco in the rearview mirror. But my stupidity in getting involved in a relationship, despite my advice never to do so, led to a series of regrettable events. Since then, I have paid the price daily. How can I move on when I am trapped in a prison? This isn’t living. It’s existing. Worse, it’s existing for absolutely no purpose.

I am worthless, with no value to anyone. I am not important. Life makes sure that I hear those messages all the time.

Regret is said not to be logical. It’s a waste of energy to ruminate on that which cannot be fixed. My intellect agrees with this. Unfortunately, my emotions do not let me forget my mistakes. So, I am trapped in a no-win situation with no viable way out, and all I have left is my pain and regret.

The expression, “Shoulda, coulda, woulda, didn’t” is one that doesn’t help me at all. I cannot dismiss the past when I live shackled in the bonds of the repercussions. However, that may be the point of regret.

Maybe regret is the emotion that helps teach us to avoid making the same mistake again. Isn’t that what prison is supposed to be for? Beyond mere punishment, it is a way to learn from your mistakes so that you won’t have to accumulate any more regrets. Regret can be a teacher.

When I converse with other homeless people, I often hear that regret is something they live with, too — trapped in the past. Isn’t that what any prison is? You are trapped in a place that you cannot get free of because of something that happened in the past.

I could elevate myself a little if I had a working RV to live in, where I could work on things to sell. I could try to have a small business selling my crafts and creations. As it is, I try to sell things I make, and I have had wonderful people buy from me. But it’s limiting what you can do without a studio. Again, I am trapped in the prison of my life, unable to fix what went wrong. I’m not able to move forward and fix my situation especially given my chronic illness and disability (made worse by long Covid).

How can a homeless person, sitting around in this “life prison,” do anything but ruminate about how we got here? Trust me, it’s hell on earth, and I wouldn’t wish it on anyone.

I want to point out that not all of this was my fault. Some of it was just sheer bad luck. Some people are born under lucky stars and just catch all the breaks in life. Others struggle from cradle to the grave.

I say that I was born cursed. Even people who do not believe in curses will eventually come back and tell me that, in my case, it really is true. No one they’ve ever met has such consistent bad luck as I do. This is a “truth is stranger than fiction” situation. Life simply refuses to give some of us a break.

I did get lucky in just one area, though. I have many great friends and loving people in my life who help me in all sorts of ways. My dear friend helps me with GoFundMe and PayPal, for example. I have another friend who helps me get my supplements. Friends have put me on family plans for streaming services. I have online friends who help boost my for-sale posts.

All these things matter a lot. I would be in even bigger trouble if I didn’t have all these wonderful people in my life. None of them are in a position to fix this for me, but the help and contributions of everyone in my life are the only things keeping me from total street-level homelessness. It’s so important to acknowledge the things you have to be grateful for.

Homeless Loki

Homeless Loki


Homeless Loki is a disabled homeless person also on the autism spectrum currently homeless in upstate New York

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