Illustration of two diverse, androgynous characters working together in a strategic setting, win-win thinking: image of collaboration under pressure on a chessboard floor.

Win/Win Thinking: Reframing Conflict Without Becoming What You Hate

Win/win thinking…it’s one of those things that sounds great at first, but when you get into the details of actually having to do it, it can quickly becomes overwhelming. It sounds like bullshit: all you have to do to succeed is never get taken advantage of again!!!

Uh. Easier said than done.

But let’s talk about it.

Most of us are scared of conflict–of saying no when the circumstances aren’t right. We get pressured into accepting craptastic situations in order to keep the peace.

This article is part of an ongoing project I’m working on, the Asshole Mitigation Plan, about learning to push assholes out of your circles while inviting in the truly good people who help lift you up, and how not to screw that up.

The Asshole Spectrum

1. Assholes

I’ve been working on how to resolve the asshole problem for a number of years now, more or less since 2016 when the daily harassment that I was getting online intensified during US. election season—then intensified again in 2020.

Assholes are everywhere. How do you build something that’s resilient in the face of people and institutions that are designed to exploit other people to increase short-term gains?

Years passed and I sorta have the asshole problem under control, at least on a personal level: I can define them, identify them, avoid them, shut them down, and make them uncomfortable enough to leave of their own “free” will. It’s not that I can’t get hurt by assholes, but that I no longer make the problem of assholes worse through my own actions—and assholes really depend on people letting themselves get hurt.

The best thing to do with a situation involving assholes is…leave. Or to call their bluff and let them leave.

Assholes, invariably and consistently, exploit other people. I’ve never had a regular, long-term connection with an asshole turn out to be a net gain in the long run, and usually not even in the short run.

An asshole, in case you haven’t heard me say it before, is someone who can’t understand that anything other than themselves, in the present moment, has a fundamental, emotionally meaningful existence.

These are people who can’t anticipate the consequences of their own past or future actions, and who don’t understand that other people aren’t programmable robots that lack the essential agency that they feel themselves to possess.

An asshole will gleefully fuck over their future self, because there is no real past or future, let alone other real people. The idea of investing their future self seems like just one more enemy putting constraints on them now.

2. Green Flags/Autonomists

Green flags are people who do things that are so good for you that no matter what happens, you’re going to invariably (and even a bit mysteriously) benefit more than whatever you invest in them. And so will they.

They’re generally not stereotypically good or nice people, but people who are authentic and don’t have hidden agendas. People who are green flags tend to have (or learn to have, eventually) excellent boundaries and say no a lot so they can say yes to the things they value.

Green flags act from a place of justice, fairness, and big-picture thinking. Lately, I’ve been calling them “autonomists” because they seem to value their own, and other people’s, autonomy.

Green flags/autonomists themselves aren’t a problem. My problem with them is letting myself trust them. It hurts.

When you’ve been under the control of an asshole for a while, it’s difficult to confront the existence of green flags. It’s hard to admit that you’ve been letting people use and abuse you, but it never had to be like that.

When you kinda suspect that everyone is an asshole, then it kinda becomes okay that you’re an asshole to everyone else.

But if there are people who don’t live life from a dog-eat-dog perspective, and they tend to come out on top, then…that kinda means that you living a dog-eat-dog life was just you being stupid and mean and small.

And that sucks to know. Once you can come to grips with that, though, then the green flags will sort of…gravitate toward you? And start treating you like one of their own?

As long as you respect their autonomy, they’re okay helping you find yours.

It’s weird. I like it. But it’s weird.

3. Everyone Else

The next problem is how to deal with everyone else.

I’ve been pondering it on and off for a couple of months, not really getting anywhere. If the general idea is to repel assholes and attract green flags, then for people who are neither, what’s the best strategy?

Do you just grit your teeth and hope for the best?

Do you start out trusting people, then turn your back on them if they betray you?

How do you even define a situation that involves someone who is an asshole, yet still might be worth your time? How do you even handle that?

I have wasted a lot of time on people who talked a good game but didn’t match actions to words, people who pushed me to work harder and faster without giving anything in return, people who were easily fooled, people who were committed to doing the stupid thing for just a little longer instead of walking away. People who were sinking and didn’t mind taking someone else with them.

People who wanted “advice,” but didn’t follow it.

Reframing Conflict Through Mutual Respect

1. Social greasers.

I played around with the idea of “everyone else” for a long time (several months after the start of writing this article, as it turns out; this is taking forever to finish). I wrote down examples, I fought with definitions. What makes everyone else different than assholes and autonomists? They aren’t just “normal.”

Just because there are a lot of something doesn’t mean they should be portrayed as “the norm,” and just because something is “the norm,” that doesn’t make it useful to portray it that way.

Plus, normal people seem to be able to change, at least a little. Which means their normalcy isn’t some kind of essential characteristic.

I’ve seen “normal” people slide into complete assholedom (particularly as they get older and have to face death, it seems like), and I’ve seen normal people claw themselves out of a rut and start taking real responsibility for their lives.

My best guess is that the “normal” people are doing something consistent and active that keeps them from becoming assholes or autonomists, and that thing trying to make everyone “just get along.”

They value social grease, conformity, and a sense of belonging.

Assholes and green flags both value some level of conflict.

An asshole doesn’t want to “just get along,” they want to take more than they give. They get into conflicts where their short-term thinking runs up against literally anything else. Ironically, an asshole in the right place at the right time with the right motivation can do a lot of good in the world, because they’re willing to rock the boat in exchange for being treated like saints. It’s rare but it happens. (Mostly they pretend to be good at something while taking credit for other people’s work.)

A green flag/autonomist doesn’t want to “just get along,” they want to be autonomous and authentic and help others do the same. They’re willing to face conflict rather than bend to other people’s demands to “just get along” or to give in to an asshole’s demands. Over the short term, they can make things very uncomfortable, because most of us don’t want to risk social ostracization over a minor point…we’d rather use little white lies to smooth things over.

This is not to say that social greasers are bad people.

But…we do play into a lot of assholes’ bullshit. And green flags tend to drift away from us, as they realize they can’t rely on us to not get sucked in by some asshole’s bullshit…repeatedly.

When things are bad, we social greasers tend to think things like, “If only we had tried harder, waited a little longer, or were more committed…then things would have gotten better. Right?”

When things are good (or at least good enough), why change them?

We don’t want a fight.

And that’s problematic. Because our energy goes toward preventing conflict or at least making sure other people have to bear the brunt of the conflict, no matter the cost.

2. Win/Win

Here’s my thought.

Most of us need a strategy to help guide us toward green flags and away from assholes. This is necessarily gonna help guide ourselves away from our own worst instincts, whether that’s to take advantage of the people around us or to just make everyone get along.

The thing is, wanting people to “just get along” is a terrible long-term strategy. It attracts assholes and pushes away green flags.

It enables assholes to be their worst selves while still getting the benefits of being part of a community, while preventing green flags from being their best selves—because speaking truth to a social greaser means getting pushed away.

This applies whether or not you yourself are an asshole, a green flag, or a social greaser. Assholes don’t thrive long-term in communities of assholes. Assholes prey on everyone, including each other. They disrupt functioning systems to no real benefit, even to themselves, because they can’t anticipate consequences to their actions.

The best way to deal with people who either are social greasers, or aren’t clear whether they’re social greasers or something else, should not have to depend on your assessment of the other person, or of yourself.

A successful strategy should be a clear direction for action that you can carry out when exhausted, depressed, hopeless, and grieving.

So: I propose that when you’re not sure what kind of person you’re dealing with, you should only get involved in win/win situations, where you estimate that everyone involved benefits, on the same level and in the same ways.

3. Exploitation

Now, this plan will not be perfect, but it should help weed out things that end up being a clear waste of your time, no matter what kind of person you are.

If you’re a green flag, you’re already doing this.

Examples:

If one person benefits with money and the other person benefits through “exposure,” then that is not a win/win situation, but one person using the other.

If one person benefits with profits and the other person benefits through “minimum wage,” that is, financial recompense that pays less than the replacement value of the time spent, then that is not a win/win situation.

If one person benefits with countless hours of skilled volunteer support (particularly in a way that leads to them making some sort of profit) and the other person benefits through “recognition,” then that is not a win/win situation.

Those things are exploitation.

Over time, fudging the line around exploitation, no matter how well-intentioned, is a waste of your time. If some people are bearing the brunt of the costs while others gain the rewards…it’s not sustainable. If everyone pays the costs and gains similar rewards proportionately to each other, then the situation is probably fine.

4. Getting Out

My experience of getting out of thinking in terms of greasing social situations has been uneven, imperfect, isolating, and rewarding. It sucks saying no when you’ve been taught that saying no will get you punished, saying yes will mean you don’t have to use your energy fighting a fight that will never be resolved, and walking away feels like a death sentence, or at least like abandoning your ethics (and your loved ones).

There are very real consequences of saying no and walking away from assholes. The consequence of saying no to a social greaser is less, but still pretty serious. 

I think everyone gets that. Telling your boss to piss off can make you homeless right quick.

What people struggle to understand is the rewards of walking away. Not stirring up trouble with people with more power or leverage than you, which is a satisfying idea but rarely pays off. But quietly and strategically getting out of the situation.

Talking about getting out of a deeply entangled situation is probably too big of a scope for this post.

So let’s talk about how to handle a situation you’re not involved in yet.

In my experience, this works:

  • Define a cold, hard number for what your time is worth. Like $50 an hour. (Rough guesstimate, take your day-job wages and double them to account for taxes and benefits.) Ask people you trust to gut-check you on this number. 
  • When a situation occurs, find out what the other person brings to the table. Is it the same type of value? Is it time if you’re providing time? Is it money if you’re providing money?
  • Is what the other person asking from you going to tend towards exploiting third parties? That is, is the other person treating you well, but treating other people like inferiors, slaves, objects, marks, or fools? Unethical bullshit tends to come back to haunt everyone involved.
  • If someone is making a worthwhile exchange that doesn’t take advantage of anyone and you want to do it, go for it.
  • Otherwise, deflect. “Thank you, but I’m not interested at this time.” You don’t have to say no, you just need to KICK THE CAN DOWN THE ROAD.

Some people find it easy to say no. If you can say no without tearing yourself to shreds, you probably already stopped reading this article! Go straight for the “no.” You already know how to live with the consequences of saying that.

The rest of us need to practice a few phrases to say in cases where we feel pressured to comply and fear the consequences (real or imagined) of getting out of an unprofitable situation.

Nobody should have to make sacrifices that don’t benefit them.

I mean, you can

But that shouldn’t be the expectation (well, except for kids and other people who aren’t capable of taking care of themselves).

You shouldn’t feel required to let yourself be exploited in order to belong to a group or in a relationship.

How to Practice Win/Win Without Losing Yourself

Asking myself the hard question of whether I’m benefiting other people the same way and with the same intensity that they benefit me is uncomfortable. Sometimes the answer is no. And sometimes it takes someone else pointing out to me that I’m screwing up, and that’s uncomfortable, too.

I’ve caught myself applying social grease to a few situations because it was easier to get away with what I wanted.

I’ve caught myself shutting down good things, green-flag things, just because they were uncomfortable in the moment.

I’ve caught myself pushing people away because they had time to spend with me but I didn’t have time to spend with them—and I could have just said that.

All sorts of dumb shit.

I don’t like it. It’s how I used to think all the time, back before I got divorced. I don’t want to be that person anymore; I don’t want to get sucked into some asshole’s world and trapped there again, and, even more than that, I don’t want to become that asshole.

I also don’t want to waste my time. I’m fifty. I have stuff to do. I don’t need to invest my time in people who want to start projects but not see them through. And that includes me.

What I’m learning is:

In order to respect others’ autonomy, I have to respect my own.

No amount of social greasing can replace my self-respect. No amount of compromise can repair my integrity.

It sucks to know it.

Fortunately, the green flags in my life don’t expect me to be perfect. (And they aren’t perfect themselves, either.)

It’s easier to move towards respecting your own and others’ autonomy if you have people who support that, both by helping you avoid the consequences of saying no, and by holding you accountable when you yourself are the problem.

And it all starts with saying noor at least not saying yes–to things that aren’t mutually beneficial.

This post is part of the Asshole Mitigation Plan, a series about staying grounded, kind, and smart in a world that rewards the opposite.

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