Hellhounds: The Fear of Failure
Hellhounds on your trail, boy, hellhounds on your trail.

Hellhounds on your trail, boy, hellhounds on your trail.
The quote above is from one of my favorite movies of all time: Crossroads. (No, not that Crossroads — the other one.) If you haven’t seen this mid-80s gem, I’d highly recommend it — particularly if you play guitar or have an appreciation for the blues.
As a young man, Willie Brown made a deal with the devil at a certain crossroads deep in the Mississippi Delta — the same crossroads where Robert Johnson struck a similar bargain. Like the blues guitar legend, Willie exchanged the eternal rights to his soul for musical ability. Although Willie had fleeting moments of fame as Willie “Blind Dog Fulton”, his life hadn’t turned out the way he wanted. The due date of Willie’s eternal payment was quickly approaching. At the end of his life, detained in a correctional medical facility, he was vexed by that inevitability. Hellhounds were on his trail.
Hellhound Inevitability
Have you ever wrestled with hellhound inevitability? Is there a dark or negative force in your life that has achieved relative omnipresence? That’s what I think of as a hellhound. Sometimes you hear distant barking. Other times the beast comes so close you can feel its dank breath as it nips at your heels. If you sit still, it will get you. There is a constant, nagging pressure to outrun it, outperform it, outsmart it.
If there are actual demon dogs chasing you and you came here in search of a 10 Steps to Escape Hellish Canines type of how-to guide, this post will not help you. In fact, you should stop reading this immediately and call Animal Control. They won’t be able to stop the evil mutts, of course, but it could buy you some time. While the mongrels feast on the flesh of an unlucky county worker, I’d recommend you rent a canoe and head out into the middle of a lake. I’m no expert, but I’d be surprised if the pooches can swim. If they can swim, at least you’d have the tactical advantage. Have you ever seen a dog swim? It’s neither scary nor fast. If you had to, you could whack the supernatural puppers with your paddle as they approach. Be strong, my friend.
Nay, we’re squarely in the realm of the metaphorical. A hellhound could be anything, really: a medical diagnosis, hurtful words or actions from a loved one, childhood trauma, or any number of fears. For me, it’s anxiety anchored in the fear of failure.
Nonfailure
Failure avoidance, or nonfailure as I like to call it, has been the biggest negative-motivator in my adult life. Personally, professionally, and everything in between, my existence as a human is marked by an intense desire not to fail — to avoid living in a van down by the river. (I do realize that some people are really into Van Life. However, this is not that. I’m not talking about spending weekends glamping in a custom Mercedes Sprinter. I’m talking about the last-resort inhabitation of a rusty 1982 Ford Econoline that smells of gasoline and stale Marlboros.)
I don’t go through each day continuously, or even consciously, thinking about failure. It’s something that ebbs and flows in the recesses of my gooey gray matter. Left unchecked, the nonfailure signals color my thoughts and actions. In my professional life, I’ve come to realize that my workaholic tendencies, including my longtime side-hustling entrepreneurship, have often been rooted in failure avoidance. When living life from this vantage point, I grind out every angle and consider every possible outcome. Every task, assignment, project, and interaction is make or break, do or die. I’m hyper-vigilant about my words — particularly my emails and texts. My OODA loop gets bogged down in the ‘A’ as I dot the i’s and cross the t’s. I always need a contingency plan — my eggs require a level of distribution betwixt multiple baskets.
“A lot of what you shared just sounds logical,” you’re thinking. “Being diligent, cautious, analytical, and self-aware is just part of being a good adult earthling.”
On the surface, I agree with you. The net result of my hypervigilance is generally positive and thus you might consider these characteristics beneficial in diverse dimensions of existence. While the ends are positive, the means totally suck. Operating from a posture of anxiety, taking actions motivated by the avoidance of a perceived impending calamity, tends to bludgeon one’s innards. At best, it makes internal weather conditions dark and stormy. At worst, it results in living in a perpetual state of “fight or flight.” Either way, it’s not great.
What’s chasing you?