I’m a confirmed idiot. After all, one time at a friend’s house I went to the bathroom and accidentally urinated entirely in my friend’s trash can (By the way, I was completely sober).
However, I am also awesome in this specific way: I value assholes.
Assholes, of course, can just be jerks who just enjoy hurting other people or don’t care when they do. These people are obnoxious. Nobody likes them, and for that reason, most of us are scared shitless at the idea of being thought of as one.
But I enjoy people who are willing to risk being mistaken for a jerk. I appreciate those willing to potentially hurt the other person for that person’s sake. They are willing to risk the relationship. They are willing to make you cry if it makes you better. I call them loving assholes.

Alicia took this picture when we were in Sri Lanka last summer. We think it looks cool. It is also very related to this post (it is not related to this post).
Loving assholes are quite possibly the most important type of close friend to have in your life. They are valuable precisely because they care more about you than about being in your life. They call you out when you are being mean to your wife. They let you know your fly is down. They insist that you apologize to your kids when you have done something wrong. They stop you from buying that last round of shots. If your inner-circle consists of yes-men or yes-women, you risk becoming abusive; nobody is above it. We can all fall into habits of being, for example, short-tempered, verbally abusive, or generally unkind towards the people we love. If nobody in your life is a loving asshole, than nobody will call you out.
I am a loving asshole. Consider this example: it was two months before my friends wedding and I was his best man. I became increasingly concerned about my friend’s marriage. After a few cautions, I reached the point that I could not in all honesty support their marriage and I stepped down as best-man. I risked my entire relationship with my friend in an attempt to help him.
Artists easily shoot themselves in the foot by not seeking out honest feedback. In college, a buddy of mine wrote and directed a six hour play and had his friends perform it. I saw it, the first 1.5 hours was pretty good, but on the whole it was awful. It tied up his friends lives for a big chunk of their senior year, and nobody had the heart to tell him what they thought.
To the extent that I am a good writer today is the same extent to which I have managed to cultivate honest feedback. I reccomend this loving-asshole-cultivation technique in particular: marry one of them. I can count on Alicia to give me an honest and frank appraisal on, for instance, this post. I see it now, “It was good. You probably said ‘asshole’ too often. You probably could have come off as slightly less self-congratulatory. I thought it was hilarious when you peed in Jim’s trash can.”
Of course, if artists do not cultivate an inner-circle of loving assholes, all they risk is being a bad artist. If you or I do not have any loving-assholes as friends, you risk being a bad person.
Of course, I am not alone in being a loving asshole. There are millions of us, and we are asshole-ish to different degrees and in different varieties. However, I doubt that truly loving assholes are much more than 5% of the population (total guess).
One loving asshole that comes to mind was Jesus. Throughout the gospels, Jesus constantly ‘sticks it’ to the pharisees and others. One example is Matthew 15: 1-7a.
Then some Pharisees and teachers of the law came to Jesus from Jerusalem and asked, “Why do your disciples break the tradition of the elders? They don’t wash their hands before they eat!” Jesus replied, “And why do you break the command of God for the sake of your tradition? For God said, ‘Honor your father and mother’ and ‘Anyone who curses their father or mother is to be put to death.’ But you say that if anyone declares that what might have been used to help their father or mother is ‘devoted to God,’ they are not to ‘honor their father or mother’ with it. Thus you nullify the word of God for the sake of your tradition. You hypocrites! Isaiah was right when he prophesied about you:
“These people honor me with their lips,
but their hearts are far from me.
They worship me in vain;
their teachings are merely human rules.” (NIV)
The Pharisees prided themselves on being extra-devoted to the Law. This would have really pissed them off. In fact, we know it did. Two verses later the disciples warned Jesus, “Do you know that the Pharisees took offense when they heard what you said?” Jesus replies, “Leave them alone; they are blind guides of the blind.”
Of course, Jesus can get away with that sort of innapropriate behavior because he is all-knowing and what not. You and I should emulate Jesus in the other, Philippians Christ hymn sort of way; by being really really humble. But being really humble means being willing to forsake your clean image as a good person and occasionally that might mean making someone sad.
Fortunately, the world is hungry for honest feedback. Instead of feeling sad, we often feel invigorated and closer than ever when we confront someone out of love. I was inspired to write this post because I have recently started some life-coaching sessions with an individual who simply wants to learn how to get better at making conversation. She is eager for some frank appraisal and discussion. It’s inspiring to see.
And it makes me want to ask my reader’s, who do you need to be a loving-asshole for today?
4 quick tips on being a loving asshole:
- Only be a loving asshole, generally, with people you know well. You can’t speak into someone’s life if you do not know what you are talking bout.
- Take responsibility for your very good friends. Know when it is likely that nobody will speak certain truths into someone’s life unless you do.
- When you confront as a loving asshole, you do so for the other person’s sake. Any defensiveness on your part when they push back (and they likely will), and you are just an asshole.
- Loving assholes are only loving assholes occasionally. Usually, they are just loving. Don’t go overboard.
This post is #2 in my “I’m a Confirmed Idiot” series. You see, sometimes I have thoughts worth sharing, but I don’t share them because they are in various ways self-congratulatory. If subtexts had vocal chords they might scream, “See! Aren’t I great?” Don’t get me wrong. That’s a wonderful message which the world needs to hear. It is just problematic when it is so obviously preached by me. So sometimes I avoid ideas and messages worth sharing, things I believe in, that may help people, in the pursuit of looking like a nice guy. So, in the “I’m a Confirmed Idiot” series, I am requiring myself to, before getting into obviously self-congratulatory prose, start with a formulation in which I confess an entirely true and unrelated personal epic fail. This frees me to make my points with righteous passion, holding nothing back, for, as it says in Leviticus 27:35, “If you are humble for a moment, feast on the joy that comes from being full of yourself the rest of the time.” Look it up; it’s in the Bible.
Incidentally, this is also #2 in my series “Old Jer Ideas” and remarkably similar to my first post.