August 23, 2018

5 Ways we Self-Sabotage.

I have to admit something to you—I haven’t always had it together.

Yes, I know what you’re thinking, “You? No way!”

But, it’s true. When I was in my mid 30s, I stumbled into an addiction support group meeting and found some solace after many years of tragic events and circumstances that quite typically go along with alcohol and substance abuse.

It was a major turning point for me. For the first time in decades I achieved the kind of clarity that I don’t think I ever had. Not because I was using substances since early childhood, but because prior to using them, I had a lot of issues that were clouding my judgement and actually led me toward that life in the first place.

So, it was a magical period where I didn’t just get better—I got better than I ever was, even as far back as middle school.

This lasted for about a year. Somewhere in the middle of my great awakening, I met a beautiful woman who started to pay a lot of attention to me, and this triggered a lot of my core issues. Faced with the choice of cleaning up my psychic junkyard once and for all, or littering it with a few more years’ worth of garbage, I chose the latter.

I’ll give it to you short and sweet: when I returned to the support group—missing three years of my life and two feet of my large intestine—I was fortunate. I can name at least a dozen people I know who followed in my footsteps and only made it as far as a memorial service in their honor. It’s a tough way to go.

This is my story and I am sure that even if yours is not quite as tragic or horrifying, you can remember a time in your life when you “got in your own way” or were “your own worst enemy.”

All of these clichés describe this inexplicable trait known as “self-sabotage.” So, what makes us do that? It turns out it comes down to five reasons, really.

The inner struggle with self-worth.

A lot of times, those of us who race toward lofty goals are the very ones who struggle with self-worth and self-esteem. It should seem obvious why this is. If we walked around feeling completely comfortable with who we are, we wouldn’t be “shooting for the stars” 24 hours a day. Unfortunately, when we don’t see our own self-worth we wind up missing the stars and shooting ourselves in the foot.

Distrust in ourselves.

This is tied in a little to self-esteem, but as we climb higher and higher up the ladder, on a purely subconscious level, we begin to wonder if people are going to start to notice if we are faking it. It is this strange belief that success is for others, just not for us.

The need to stay in familiar territory.

Success is wonderful. Success feels great. But success also tends to scare the hell out of us when we’ve never experienced it before. Again, this takes place on a psychological level that exists a little beneath conscious thought. But, think about the possibility whenever you see yourself doing really horrendous things right before a major breakthrough in your life and career.

Addiction to chaos.

This is a big one for me, and I just had a brush with this recently. There is this woman in my town who, while very nice, is not a good choice to date.

One of my friends who dated her wound up in handcuffs at the end of their relationship. Another friend wound up in a sticky situation with Child Protective Services. Now, I’ve known both of these guys for years, so to put it as delicately as possible, I suspect this woman has a habit of weaponizing government agencies against lovers when she feels slighted. Needless to say, breaking up is really hard to do when it comes to this person, so all signs point to it being best to not engage.

A few days ago, I woke up when my alarm went off and I ran my current scenario over in my mind. Why is it, that after I finally gained the interest of a literary agent, and my public persona is squeaky clean, that I am friend- requesting this person on Facebook with the hope of asking her out on a date?

When things start to go really well for me—this is my common path. Glad I caught that one in time!


A lot of times when success seems like it’s right around the corner, it threatens our ability to be in control of our own situations. Failure is awful, sure. But believe it or not, many times we feel much more in control of failure than success.

I can almost promise you that if you find yourself getting in the way of your own success or self-sabotaging, the answer to why you are doing it lies somewhere in these five reasons or even, perhaps, a combination of more than one of them.

Have no fear!

When you are made aware of these things, you can catch yourself in the act and, you can follow in my footsteps by asking yourself very lovingly : “What the hell are you doing?”

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