Question #2: What would it mean if I were wrong?
Many people are able to ask themselves if they’re wrong, but few are able to go the extra step and admit what it would mean if they were wrong. That’s because the potential meaning behind our wrongness is often painful. Not only does it call into question our values, but it forces us to consider what a different, contradictory value could potentially look and feel like.
Aristotle wrote, “It is the mark of an educated mind to be able to entertain a thought without accepting it.” Being able to look at and evaluate different values without necessarily adopting them is perhaps the central skill required in changing one’s own life in a meaningful way.
As for my friend’s brother, his question to himself should be, “What would it mean if I were wrong about my sister’s wedding?” Often the answer to such a question is pretty straightforward (and some form of “I’m being a selfish/insecure/narcissistic asshole”). If he is wrong, and his sister’s engagement is fine and healthy and happy, there’s really no way to explain his own behavior other than through his own insecurities and fucked-up values. He assumes that he knows what’s best for his sister and that she can’t make major life decisions for herself; he assumes that he has the right and responsibility to make decisions for her; he is certain that he’s right and everyone else must be wrong.
Even once uncovered, whether in my friend’s brother or in ourselves, that sort of entitlement is hard to admit. It hurts. That’s why few people ask the difficult questions. But probing questions are necessary in order to get at the core problems that are motivating his, and our, dickish behavior.
Question #3: Would being wrong create a better or a worse problem than my current problem, for both myself and others?
This is the litmus test for determining whether we’ve got some pretty solid values going on, or we’re totally neurotic fuckwads taking our fucks out on everyone, including ourselves.
The goal here is to look at which problem is better. Because after all, as Disappointment Panda said, life’s problems are endless.
My friend’s brother, what are his options?
A. Continue causing drama and friction within the family, complicating what should otherwise be a happy moment, and damage the trust and respect he has with his sister, all because he has a hunch (some might call it an intuition) that this guy is bad for her.
B. Mistrust his own ability to determine what’s right or wrong for his sister’s life and remain humble, trust her ability to make her own decisions, and even if he doesn’t, live with the results out of his love and respect for her.
Most people choose option A. That’s because option A is the easier path. It requires little thought, no second-guessing, and zero tolerance of decisions other people make that you don’t like.
It also creates the most misery for everyone involved.
It’s option B that sustains healthy and happy relationships built on trust and respect. It’s option B that forces people to remain humble and admit ignorance. It’s option B that allows people to grow beyond their insecurities and recognize situations where they’re being impulsive or unfair or selfish.
But option B is hard and painful, so most people don’t choose it.
My friend’s brother, in protesting her engagement, entered into an imaginary battle with himself. Sure, he believed he was trying to protect his sister, but as we’ve seen, beliefs are arbitrary; worse yet, they’re often made up after the fact to justify whatever values and metrics we’ve chosen for ourselves. The truth is, he would rather fuck up his relationship with his sister than consider that he might be wrong—even though the latter could help him to grow out of the insecurities that made him wrong in the first place.
I try to live with few rules, but one that I’ve adopted over the years is this: if it’s down to me being screwed up, or everybody else being screwed up, it is far, far, far more likely that I’m the one who’s screwed up. I have learned this from experience. I have been the asshole acting out based on my own insecurities and flawed certainties more times than I can count. It’s not pretty.
That’s not to say there aren’t certain ways in which most people are screwed up. And that’s not to say that there aren’t times when you’ll be more right than most other people.
That’s simply reality: if it feels like it’s you versus the world, chances are it’s really just you versus yourself.
CHAPTER 7
Failure Is the Way Forward
I really mean it when I say it: I was fortunate.
I graduated college in 2007, just in time for the financial collapse and Great Recession, and attempted to enter the worst job market in more than eighty years.
Around the same time, I found out that the person who was subletting one of the rooms in my apartment hadn’t paid any rent for three months. When confronted about this, she cried and then disappeared, leaving my other roommate and me to cover everything. Goodbye, savings. I spent the next six months living on a friend’s couch, stringing together odd jobs and trying to stay in as little debt as possible while looking for a “real job.”
I say I was fortunate because I entered the adult world already a failure. I started out at rock bottom. That’s basically everybody’s biggest fear later on in life, when confronted with starting a new business or changing careers or quitting an awful job, and I got to experience it right out of the gates. Things could only get better.
So yeah, lucky. When you’re sleeping on a smelly futon and have to count coins to figure out whether you can afford McDonald’s this week and you’ve sent out twenty résumés without hearing a single word back, then starting a blog and a stupid Internet business doesn’t sound like such a scary idea. If every project I started failed, if every post I wrote went unread, I’d only be back exactly where I started. So why not try?
Failure itself is a relative concept. If my metric had been to become an anarcho-communist revolutionary, then my complete failure to make any money between 2007 and 2008 would have been a raving success. But if, like most people, my metric had been to simply find a first serious job that could pay some bills right out of school, I was a dismal failure.
I grew up in a wealthy family. Money was never a problem. On the contrary, I grew up in a wealthy family where money was more often used to avoid problems than solve them. I was again fortunate, because this taught me at an early age that making money, by itself, was a lousy metric for myself. You could make plenty of money and be miserable, just as you could be broke and be pretty happy. Therefore, why use money as a means to measure my self-worth?
Instead, my value was something else. It was freedom, autonomy. The idea of being an entrepreneur had always appealed to me because I hated being told what to do and preferred to do things my way. The idea of working on the Internet appealed to me because I could do it from anywhere and work whenever I wanted.
I asked myself a simple question: “Would I rather make decent money and work a job I hated, or play at Internet entrepreneur and be broke for a while?” The answer was immediate and clear for me: the latter. I then asked myself, “If I try this thing and fail in a few years and have to go get a job anyway, will I have really lost anything?” The answer was no. Instead of a broke and unemployed twenty-two-year-old with no experience, I’d be a broke and unemployed twenty-five-year-old with no experience. Who cares?
With this value, to not pursue my own projects became the failure—not a lack of money, not sleeping on friends’ and family’s couches (which I continued to do for most of the next two years), and not an empty résumé.
The Failure/Success Paradox