5 Questions You Need to Ask (To Avoid Ruining Your Life)

Somewhere, right now, some guy is sleeping under a bridge, or laying next to a dead hooker, or sitting in jail, wondering, "How the fuck did it come to this?"

The short answer is that when things are bad, you don't know they're bad. Humans are magical creatures who can completely disregard a raging fire, and then act confused at the sight of ashes. Trust me, I know.

So, if you are stopping to ask yourself one of the below questions -- all of which people have asked me at one point or another -- that's great. You've gotten further than a lot of people, just by asking. It takes a certain amount of courage to stop and ask ...

#5. "How Do I Know if I'm in an Unhealthy Relationship?"

This may be the single biggest "forest for the trees" question you'll ever encounter in life. Walk past the magazine rack at a grocery store, and half of the women's magazines offer to help you answer this, though they usually phrase it the opposite way, as in, "Is he the one? Our quiz will tell you!" But I think it's probably more relevant to answer the more urgent question of, "Is this relationship slowly murdering one or both of us?"

It's the "how to" murder articles you have to watch out for.

Fortunately, as one of America's foremost relationship experts, I've developed a sure-fire way to find out.

The Method:

It's very simple: Take a close look at the person you're in a relationship with. Now, marry that person. Then, stay married for a decade or so, then act completely baffled by the fact that they want a divorce. Then, about two years after the marriage has ended, you'll realize they were right all along and that you were never good for each other. Boom, there's your answer.


If you don't think you have the patience for that, I'm sorry, but you can't always just be taking the easy way out. A bad relationship is like a really good night's sleep -- you can't appreciate it until you wake up. The deeper the sleep, the less likely you are to consciously think, "God damn am I doin' some sleepin' right now! Fuck!" The worse the relationship, the less likely you are to see it.

After all, if it was just some comically horrible situation where the guy or girl screeches and throws balls of their own feces at you as soon as you walk in the door, that's easy to walk away from. It's bad, but on a level that's obvious and in a way that makes it easy to walk out. The truly bad relationships, the kind that hollow you out, are the ones where you actually feel something, and stay because you think you can't live without it. That's when you open up, and become exposed and vulnerable.

Opening up isn't a bad thing -- the ability to share yourself is what makes life worth living. But you both just get so good at pushing each other's buttons that those incompatibilities you have with one another become battlegrounds for subtle warfare and sabotage. Each learns to push the exact sequence of buttons that sets the other off. Problems are met with blame instead of solutions. And you won't see any of it as a problem, because you're tied down with a bundle of emotional needs that you mistakenly call "love."

If you are impatient and don't have time to do the full 12-Year John Cheese Relationship Stress Test, here's one warning sign you can look for: Is your love of this person based on some conditions you are hoping they'll fulfill later? Do you find yourself thinking, "I love him when he's not drinking" or "She'll be hot after she loses 50 pounds?" Yeah, that never works. Even on the rare occasion that it appears to work, even if you get them to change "for you," you're not seeing the hidden resentment festering in their minds. They won't like the fact that they had to modify themselves to suit your needs. Make no mistake, that resentment will one day manifest, and it won't be pretty.

But don't worry, it'll all be more than clear after it's over. After I got divorced, literally everyone I knew told me, "I can't believe you guys lasted as long as you did." I'm not mad they didn't tell me. I wouldn't have listened.

"When I take these out of my ears, if you're still talking, they go into your eyes."

#4. "How Do I Know if I've Picked the Right Job/Career?"

It's surprising how many people never actually stop to ask themselves this one. At least, not until they have that Office Space moment when they wake up and feel like they're dead inside, deciding that if they have to read one more memo about dress code, they're going to burn the whole fucking operation to the ground. Job breakups can take you by surprise just like the relationship breakups we were just talking about.

In order to research this article, I took several dozen horrible jobs over the course of 18 years or so, and left most of them on bad terms.

This is me during my two-year stint as "Bounty the Dog Hunter."

The Method:

I can hear it now:

"A 'shitty' job? Hey, at least I have a job, right? Not everyone can say that in this economy! I can think of two dozen people off the top of my head who would kill for a chance to make what I'm making!"

Yep, there's the trap. Because there have been wise people through history saying something to the effect of, "Be happy with what you have, because it could always be worse," it can get very easy to justify any job by comparing it, not to another job, but to starvation.

This can only hold you over for so long.

I have previously talked about how nearly impossible it is to get out of that "making enough to eat and nothing else" cycle. If a few odd things hadn't broken just the right way, I'd have stayed in it until I died. When friends asked me why I stayed in that shitty job, I would take offense.

I didn't understand this concept that a "career" was not in fact just a job that you stayed at a long time, but could (and even should) involve something you actually care about doing. I kind of thought that everybody treated their hours at work like I did -- as a pure loss of time, energy and life that you have to pay as a tax in order to exist in a society. It was hard to imagine that there were people who didn't watch the clock and beg it to go faster, or ditch and go home at the slightest excuse. When I heard about people with jobs where they take their work home, and work over lunch, and on sick days, and during holidays, people who actually get excited when they talk about what they do in conversations, I just assumed they were crazy, or had nothing else in their lives.

There's no way these people don't make cocaine for a living.

I see it now, that I've moved on, that "be happy with what you have" is a bullshit idea when you're talking about work. You're obviously not suited for just any old job. Flipping burgers is perfectly fine if burger flipping is your passion and that's the best thing you can bring to the world. If not, if you picture your job as nothing more than a mean dog you have to feed in order to keep it from biting your nuts off, then you should know that it isn't like that for everybody. It doesn't have to be like that for you.

#3. "How Do I Know if I'm Ready to Have Kids?" (Or, "How Do I Know if I'm Being a Bad Parent?")

A lot of you are at the age where you're either considering having kids, fear having kids, or have kids and wonder if you've made a huge mistake. It's a reasonable concern, since this is the most important thing you'll probably ever do. You're in luck; I have forgotten more about bad parenting than most of you will ever know.

I'm still working on blocking the rest out.

The Method:

Fortunately for my kids, I didn't need to ruin them in the name of research into bad parenting methods. I had my own father, who was one of the great masters of the art. Based on having lived through that, and having kids of my own who so far don't show signs of growing up to be serial killers, I can say this:

If you're worried about having kids because you're not sure if that's what you want in your life right now, that's a bad sign.

If you're worried about having kids because you want to make sure you don't fuck up the kids, then you're probably fine.

"She doesn't really go with my purse -- should I just leave her there?"

In my experience, shitty parents don't usually care enough to analyze their performance from the kids' point of view, so they'll never ask the question to begin with. It's always about, "How will kids fit into my life?" rather than, "How will I not fuck up a kid's life?" To them, parenting is another obstacle they have to put up with, like a job or the flu. You grit your teeth and bear with it until the kids are out of the house, and then it's back to the normal life you had before they came along. To them, children are chores that have to be done.

For example, let me share a story about my father, and see if you can get a sense of where he went wrong here:

When I was 12, dad woke me and my brother on Easter Sunday. I remember that it was 8 a.m. because my grandmother, who we lived with at the time, had pointed out that he didn't need to be opening a beer that early. He told her to fuck off, shouted that he was a grown man and took us outside where we found two enormous Easter baskets on the porch. As we dove into the chocolate, he disappeared for a minute and returned with two six packs of beer, sitting one down in front of each of us.

"Awesome! Now who's ready for opium?"

He said that we were old enough to have our "first beer with the old man," and made us open one and drink it with him right there on the spot. Followed by the other five -- each. My brother was 11. To him, he was attempting to do something nice. Sharing something he loved (beer) with his children, and we should be appreciative of that, right? What he didn't know was that the only reason we drank that beer was because we knew that no matter how politely we turned down the offer, the rest of the day would have taken a dramatically violent turn. We joined him out of fear.

You can probably see the problem right away -- he never looked at it from our point of view. Parents make less horrifying versions of this mistake all the time. When you argue with your children, do you use the same tone of voice and tactics that you use with an adult? Because their brains haven't physically developed to that point yet. They haven't experienced anything that will let them put what you're doing in context. To them, you are just this screaming ball of anger and hateful facial expressions.

"Bitch, I'm 6."

And worse, they think they are what caused you to turn into that monster.

Kids have a tendency to blame themselves for all negative situations because by nature, they are biologically wired to be self-serving, to think they are the center of the universe. They learn to be compassionate and sharing, but they are not born with it. So when things go wrong and you erupt, their natural thought process is to assume that your reaction is their fault, even when it may be something else like a bad day at work. The only way to stop yourself is to continually stop and say, "How does this look from a kid's point of view?"

My dad didn't realize he was a bad parent until a few months before he died. Some people go to their grave never knowing. Which brings me back to my point, that if you're asking, "How do I know if I'm going to be (or am being) a shitty parent?" in the first place, there's a very good chance that you're not.

You're on track to becoming the metaphorical golden pick to a well groomed fro.

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