Frameworks and mental models for evaluating your relationships, whether in love, life or work.

Human beings move on impulse. You can fight it, or you can recognize that it’s our evolutionary biology–that we’re still operating on 50,000 year old software–and prepare yourself to deal with it. 

Relationships should be easy. The reason they are not is because we are afraid to communicate openly, and the reason we do not communicate openly is because we feel partially ashamed of ourselves. I, for one, have battled bouts with cynicism and sexual anxiety for most of my adult life. It’s not easy for me to make that public, but I can’t preach something I’m not willing to practice. 

The first step to better relationships is to learn to love your shame, and realize that being imperfect, having things you’re embarrassed about even, is being human. Once you can do that, it becomes much easier to empower yourself to take control of the things you can control, and there are aspects of every relationship you can control. 

It’s simple conceptually, much harder to execute. But it all stems from communication and self-empowerment, and when you find a dance partner of a similar mindset, it’s amazing how easy a relationship can become. I’ve thought about this a lot as I’ve grown up, and have captured 14 rules that I believe can help anyone both find and be a better dance partner. 

First, let’s take ownership of our past.  

We all have our battle scars from relationships. And since we have them anyway, we might as well get some benefit from them. No matter how you may have been hurt, wronged or misled in the past, lingering in a state of victimhood only gives whoever hurt you in the past a stronger grip over your future. We can’t control what happens to us in life, but we can always control how we respond. We all have that power. To start, we should look back on our past relationships the way an NFL quarterback studies the previous game’s film to pick up cues to prepare for the next one.

Rule #1: Don’t blame someone else if you get hurt based on something you wanted  to be true

Accountability is the foundation for progress. Just like an alcoholic will never sober up without first acknowledging he has a problem, we can’t use our failed relationships to set the stage for better future relationships without taking ownership of the part we played.

I get it–men (and women) can be vile. The dating world seems to have an eternal shortage of self-awareness. Some people may have more dignity than others, but we are all capable of being manipulative or misleading to get something we want. The sooner we can acknowledge that, the better. 

That’s not meant to be pessimistic, but a practical exercise of making sure that we are willing to see the world for what it really is. From what I’ve seen, it’s usually the person who swears “my woman/man could never do that!” who is the easiest to fool. That’s what they want to be true, not the reality of who their partner actually is. But just like a blanket judgment of good character (“He could never!”) doesn’t make it true, acknowledging that we are all capable of deception also doesn’t mean we will deceive.

Most of the rules to follow involve some level of assumptions and people wanting something to be true. As a foundation, we need to be willing to acknowledge this and take responsibility for it, or else we will find ourselves in the same situations over and over again. 

Rule #2: Embrace the fact that nobody owes you anything

This is our second foundational rule, and accepting it will make things a lot easier. If you fight it, you’re fighting something that’s completely outside of your control. It’s easy for us to think that because we make time and effort for someone or do something thoughtful that we can expect the same in return. We can’t. 

The principle of reciprocity generally holds true in most situations; strangers will almost always return your favor of holding the door by holding the next one. But when it comes to early-stage dating, all bets are off. Like self-awareness, some people have different levels of manners than others, but at the core we are all selfishly motivated in searching for a partner. 

Whatever thought or effort you put forth, do so expecting nothing in return. This way, you won’t be wrecked when nothing comes back, and you’ll enjoy it that much more when something does.

Rule #3: Don’t assume anything based on your  norms and values

This is usually where status and titles come into play. Quite simply, a lot of people (in this case, women mostly) have the idea that once they are sleeping with someone, it’s understood that they are exclusive. Sometimes that means officially in a relationship, but it’s amazing how many times I’ve heard people say they are not in a relationship but still “exclusive.”

My heart breaks a little bit each time. Let’s go back to reality. Divorce rates in the US are around 50%, and still pretty high around the world. That’s not only due to cheating, but infidelity is one of the primary causes. And that’s for marriage–people who have invested time, family energy, and financial resources into the relationship. I can only then assume that the rates of occasional cheating for people “in a relationship,” but not married, is a bit higher based on the lower barrier to entry. So, what do you think that would look like for people not even in a relationship?

You can save yourself a lot of emotional anguish if you simply acknowledge a few things:

  1. Your partner, no matter who s/he is, is capable of cheating (going back to Rule #1). This doesn’t mean that s/he is cheating, but it is within the range of possibilities. 
  2. There is no such thing as “exclusive but not in a relationship.” That’s a contradiction, because “exclusive” already is framing a relationship. The only reason someone would try to spin this is because they want to be open to dating others without feeling guilty about it.
  3. If you haven’t had an explicit conversation about your relationship status, don’t assume you are in one. You are not. 

Rule #4: Don’t cling too tightly to your righteous belief system

We never want to get to a point of being jaded, but if we want to find a healthy relationship, we also can’t afford to live in total oblivion. In talking to many friends and colleagues about their relationships over the years, one thing I’ve heard over and over again (again, usually from women) is “I always see the good in people.” 

It’s nonsense. People will always show you who they are. Let them.

This is different from starting from a position of default trust, which I’ll get to later. What I’ve seen over and over is someone using the “see the good in people” line as a badge of honor to blind themselves to very obvious red flags in a partner’s behavior, whether that’s addiction, aggression, dishonesty, racism or any number of other legitimate causes for alarm. You want to be understanding and accepting, and you identify your character as being someone who can overlook bad things and always see the good. That’s a noble, well-intentioned recipe for finding yourself locked into a painful relationship for as long as you can hang on. 

Rule #5: Don’t draw the wrong conclusions

I’ve had various conversations with people who speak in absolutes:

I’m thinking single might be the way to go based on divorce rates…

I gave up on people nowadays…

All wo/men are bad…

All of this kind of talk is disempowering and sends you right back into victim mode. And while you might think it makes you sound mature, it is really just a veiled declaration that you won’t take responsibility for any of your relationships.

It’s not easy to have your heart broken, or be burned a few times, and remain optimistic. But drawing the wrong conclusions, like thinking an entire gender is somehow flawed or that divorce is inevitable, only allows the people who hurt you before to continue to hold you back from finding a happy relationship going forward. You’re essentially putting up a shield as a defense mechanism, but that shield works like hand sanitizer that kills the good germs along with the bad. 

The harder work is to really self-reflect on your past experiences and see where you perhaps started to see and ignore red flags, or let what you hoped would be true prevail over what your eyes, ears, and gut were actually telling you. Once you do that, you can start to isolate individual behaviors and character traits to be mindful of going forward, and when you see them again, react accordingly. Your gut generally doesn’t lie; you just need to have the courage and strength to listen to it even when it goes against what you might be hoping for.

Rule #6: Don’t waste time destroying someone

Destroying someone is never worth the energy. I’ve yet to encounter a situation where the best approach was anything besides leaving the past behind and moving forward. 

In defaming someone, all you’re doing is taking your immature death grip on your victimhood and making it public. And for what? Do you expect the person to change? Maybe s/he will, maybe s/he won’t, but either way, that’s not your problem anymore. 

Just in case it’s not obvious, I’m not suggesting you let real crimes be swept under the rug. If you’re a victim of sexual harassment or something related, by all means report it to proper authorities; real crimes demand real consequences. 

But assuming what hurt you was within legal bounds, let it go. Trying to drag someone down in these cases says a lot more about you than about that person, and gives the person the ego boost of knowing you can’t get over them. Even if you wish to be vengeful, one of the most effective ways to do this is to signal to the person that you barely even remember who they are. 

Next, let’s look ahead…

Now that we have a firmer grip on our past, let’s build some frameworks for our future relationships.

Rule #7: Do live in reality

Embrace the world as it is and understand systems. 

A constant of the past few thousand years is that technology always pushes culture and its associated norms forward. If you’re grateful to be able to fly around the world, you also need to acknowledge that some 50,000 people have died in plane crashes over the years. The benefits of technology always come with costs, and it’s no different with online dating. Don’t blame apps for their shortcomings unless you also blame beer for alcoholism or ice cream for obesity.

Like anything else, the new dating norms are useful and can work for you if you’re in control of them; they can also pull you down a slippery slope and control you. Sure, the common ways we meet people today have drawbacks. You are undoubtedly competing against an endless pool of people for attention. If you’re a woman, you will undoubtedly get unwanted sexual advances and the occasional explicit picture. Does it mean the world has gone to hell?

That’s where understanding the system comes into play. People (men) are not any “worse” today than they were before. The reason you’re getting that dick pic, especially in a massive city like Tokyo where I live, is that there is an endless resource supply. The man who sends that picture knows he will come across as an asshole to 99% of women who see his profile. He is also banking that 1% is lonely, desperate, horny, or maybe looking for revenge on someone who cheated. If he finds that 1% every week or two in a pool of tens of thousands, he gets what he’s looking for. To him, it’s practical, if also completely classless. 

You can either get angry about it and let it discourage you, or ignore/block that guy (or guys), and understand that the technology also gives you a much bigger search pool to be able to find the qualities you are most compatible with in someone. In the past, you were limited to whoever happened to live in your village, or whoever was friends with your friends at school. Some people found love this way, and a lot more just tolerated someone for as long as they could. The key point here is that there are unintended consequences to any system, and we shouldn’t let those discourage us from taking advantage of the benefits the system affords.

And I want to add a little side thought here: If you really don’t like online dating, there is still an analog world out there, which is easy to lose sight of. I recently had a random conversation with a Gen-Z colleague. She told me that she only meets men from apps, and that if a guy approached her in the gym or in a supermarket, she’d find it “creepy.” Oh, the irony.

Sure, if someone makes an in-person approach in an aggressive or rude way, or cannot take a signal that you are not interested, by all means it is creepy and should be judged as such. But assuming the person is respectful and quick to move along if you’re not interested, let’s again consider the system. 

For the person who hits on you (respectfully) at the supermarket, the worst case scenario is that he is a seasoned pick-up artist and does this on a regular basis. Even then, he is limited to only so many hours in a day, and so many women who happen to walk by and catch his eye. The best case scenario is that he is actually a nice guy who finds you uniquely attractive, in which case he has already demonstrated social skill and the confidence to be able to risk rejection in public. The most likely scenario is somewhere in the middle. 

But consider the app. Even in the best case scenario, he is swiping and sending a flirty introduction to you and dozens of other women. The good ones on there are essentially mirroring the worst case supermarket scenario: casually chatting up scores of women. And the worst case scenario here is (referenced above) too explicit for the street pickup artist to pull off without being arrested. And of course, the app swiper didn’t demonstrate any real confidence and didn’t have the hurdle of risking public rejection for the chance to meet you–he had no barrier to entry. 

I’m not saying one is bad or one is good. I’m just giving this example as a reminder to understand the reality of the systems you’re playing in so that you can control them rather than allowing them to control you. 

Rule #8: Don’t take anything too personally

This is basically piggybacking on the systems discussion from Rule #7, but worth a short behavioral psychology lesson. 

Occam’s Razor is a neat little mental model that says the simplest explanation for something, all other things being equal, is most likely to be true. Hanlon’s Razor is a close cousin, which warns against assuming malice when something could just be mere neglect. We are much more likely to be distracted, forgetful or just outright stupid than we are to be malicious. 

We too often curse the person who cuts us off on the highway and project all sorts of evil intent onto them, but the vast majority of the time they just didn’t see us. This is logical, too, because for the intent to be truly evil, more things would have to be true: they would have to see us, have to want to do something bad to us, have to be willing to risk an accident, decide to act on that evil intent, and then actually steer the car in front of us. That’s a lot of conditions to have to be true; whereas simply not seeing us requires just one. 

The same goes with relationships. When your boss fails to reply to your email, or a match fails to reply on a dating app, they could be out to get you. But it’s far, far more likely that they just overlooked the message (there are endless distractions all around us), are dealing with some stressful situation, or any number of other explanations that have absolutely nothing to do with you. Stay calm and carry on. 

Rule #9: Know that you don’t owe anybody anything, either

A close cousin to Rule #2. Just like you can’t expect anything from anyone, also free yourself from the burden of feeling that you owe anything either.

I once had a friend tell me that marriage (and having a family) is the most unselfish thing you’ll ever have to do, so you should be as selfish as you’ll ever be in choosing who you build that family with. I think it makes a lot of sense. 

I believe that everyone who is actually hoping for a long-term relationship should have a list of non-negotiables and nice-to-haves. Love is obviously more art than science, not something that can be treated with analytics. But I think it’s important to have at least a few hard requirements–non-negotiables where 3 out of 4 or 4 out of 5 doesn’t cut it. This list can’t be too long–there’s no perfect person out there–but I don’t think it’s unreasonable to hold out for someone who is a good communicator, has a sense of humor, is open-minded to new ideas, and who you’re attracted to (for example). 

Of course there are ten thousand other preferences you might have, and if the few must-haves are met, then you can consider those as bonus points that you’re willing to compromise on. But if you find that some of your non-negotiables are missing, you don’t owe the person any reason for not wanting to continue exploring the relationship. 

As for work, it never fails to amaze me that many people feel guilty about submitting their resignation to a job. Business is business; if business slowed down, your company would find a way to send people on their way. Never lose sight of that, and never feel guilty about doing what’s best for you. 

Rule #10: Do value actions over words

This loosely ties to Rule #4. People will show you who they are, so let them.

Do you find that she never has time for you on weekends? Is he always working late and that’s why you can’t have dinner together? 

These things do happen, and they can be telling the truth. But usually it means you’ll see some kind of tangible output (e.g. a product launch, a book they published, etc.). Once they start to happen on a regular basis, you need to start to consider the prospect that the person just isn’t very invested in you. 

I can’t tell you how many times I’ve heard people say they don’t see their partner often because the partner is busy with work. Fool me once, shame on you. Fool me twice, shame on me. If you continue to buy this, at some point you need to accept responsibility for whatever happens next. Most jobs just aren’t that busy, and we spend most weekends with the people we actually want to hang out with. And regardless of whether they are telling the truth or hiding something, if they prioritize work and/or other people now, you can’t expect that to change in the future. 

I can’t repeat it enough: people will show you who they are, so let them. 

Rule #11: Learn to scope for self-awareness

Over the past few years I’ve come to realize that self-awareness is probably the most critical thing I’d consider in deciding who I want to spend my time with, whether that’s a relationship, a friendship, a business partner, or a boss. I never even considered it before, probably because I wasn’t very self-aware. Funny, huh.

Testing for self-awareness is a great heuristic for evaluating so many other traits that make for a healthy relationship, most importantly with communication. People who are highly self-aware are usually also deeply introspective and don’t clutch too tightly onto any particular belief. I’ve also found that they can communicate about sensitive things without feeling attacked, which makes a relationship much easier to have. 

Scoping out self-awareness in a stranger can be tricky, but I’ve found a few things that help me look for it in a potential partner or even a boss at work. 


I don’t expect anyone to have a spotless past, in any context (when it comes to workplaces, I’ve written before about how recruiters shouldn’t seek perfection as they often try to do). We all make mistakes. But I’ve found that most people repeat the same cycles. 

I’m interested in seeing how someone is able to reflect on mistakes, what they learned from them, and how they’ve pivoted. First, are they even able to acknowledge mistakes and shortcomings? If they are, do they demonstrate some accountability for the past or are they stuck in victim mode? 

Now, when I’m considering working with someone, I want to make sure they can pinpoint some mistakes they’ve made in the past and how they’ve grown from them. The same goes for relationships. I recently had a conversation with a (never married) female friend who was starting to date a man who was previously divorced. When she asked what I thought about the relationship, I turned the questions back around and asked her about her partner. He had a fantastic story about how his ex-wife never made time for him and how he was devastated. 

To me, this was a huge red flag. A self-aware person would be able to find some way in which he contributed, and be willing to be vulnerable enough to admit that to someone clearly open to giving him a chance. The fact that he could so easily sweep aside any personal accountability and place 100% of the blame on his ex eliminates his credibility, with me anyway.

Statistically speaking, infidelity is one of the main reasons for divorce, and men are more likely to cheat than women. These numbers aren’t foolproof, but it’s safe to say there’s a large number of divorces that were caused by men cheating. I can assure you that most of them have a perfectly convenient story about their ex not having time for them (or something similar) to tell their next prospects. 

I don’t believe that someone having cheated before is an accurate predictor that they are going to cheat again. People learn lessons in different ways, and sometimes we need to experience tangible loss, or see pain in someone we care about, to spur maturity and growth. But this only happens when the person truly internalizes their mistake. Who knows if my friend’s new boyfriend cheated before, but his ease of pinning his failed marriage 100% on his partner would make me think it’s pretty likely that he’s full of shit. Because with self-awareness, even the most considerate of partners would find some way in which to hold themselves accountable. 


Getting a feel for someone’s willingness and ability to reflect is nuanced, but there are clues that are pretty easy to read if you know how to look. The way people answer questions can reveal a lot, and it’s usually obvious when someone has the answer they think you want to hear queued up. 

I see this a lot in rocky, on-and-off relationships. When the couple hits bumps, usually one person will express a desire to split, cite a reason or two, and the other will immediately promise the sun and the moon to address whatever reason was given. Loss aversion is a real thing, but this kind of reaction can’t possibly be credible without the person first taking some time to reflect on the feedback s/he was just given. 

It would give me a lot more confidence in the person if they just listened, took a bit of time to reflect on it, and then came back a few days later and said they really believed they could commit to whatever changes need to be made. Usually, though (and usually men are the guilty party here), the response is an impulsive sales pitch, which might as well be a declaration that they didn’t actually take on board any of the feedback at all.

The next might be a little nitpicky, but I also try to read cues about whether the person is in need of constant stimulation, or are they intentional about how they give attention. In a work context this can be a leader who is always chasing fires, or thinking too short-term, rather than sticking to a well-thought out long-term vision. In a personal context, it could be whether someone is addicted to doom scrolling or feels the need to be out getting attention from someone every Friday night. As a general rule, I don’t believe people can really grow when they are in constant need to be entertained. 


Finally, I generally like to be around people who are well aware of their own strengths and weaknesses. Having confidence in our strengths is a great quality that I think most people have, but a lot fewer are introspective about what they struggle with. 

One idea I’ve shared before is that, if I was building a company from scratch, I’d require everyone to write down (for all team members to see) three reasons we’ll love working with them and three reasons we might struggle working with them. This makes for an easy self-awareness test, because you can easily see it lacking in people who talk about being “too much of a perfectionist” or “caring too much” (or, in a dating context, “being too horny,” which is actually something a friend told me she heard recently, and is obviously a manipulative answer fishing for a particular response). 

Everyone has their own issues, but as a universal rule I’ll only go deeper professionally or personally with people who can be honest about their own limitations. 

Small bonus point: Keep an ear out for when, in getting to know people, they throw unnecessary superlatives in the conversation. Since I moved to Tokyo, I rarely meet someone (especially true amongst expats) who works in, say, marketing. They run marketing. This may be a subtle point, but I’ve found this to be a pretty accurate heuristic to reveal narcissism (applicable to both work and personal relationships).

If you meet someone at a networking event specifically for entrepreneurs, then maybe it’s relevant to mention that you founded a company. If you’re meeting someone at the gym, it’s surely not. The funny thing is, so many people I’ve met puff up their past experiences “running” this or “heading up” that, and their entire career may be only one or two companies so farl. Most of us started as a junior executive or whatever it is; no need to inflate what it was in hindsight. 

Rule #12: Empower yourself

This is the natural extension to Rule #5, and it takes courage. Take ownership of what you can control.

Do you have trust issues stemming from your past? Ask hard questions about a person’s transparency on a first date. Have you been frustrated by an overbearing boss before? Ask hard questions about what development areas your new hiring manager is pursuing during the interview. 

You have to take what you hear with a bit of a grain of salt, knowing that people are generally on their best behavior early on. But it will still give you more substantial surface area to read and form a gut instinct from, and that gut instinct is your biggest ally. And let’s be honest, most of the time we don’t even dare to ask any hard hitting questions early on in a relationship, even though that would serve our best interests almost always.

These kinds of questions might scare some people away. Good! Isn’t it better to find that now, before you’ve invested any time or emotion into someone who will end up becoming a pain point for you later? If introspective questions that demand self-awareness and vulnerability make a hiring manager uncomfortable, you are better off avoiding that person anyway, and the same goes for a possible relationship partner. 

Just like you can empower yourself by understanding your contribution to difficult relationships in the past, you can add to your toolkit by having the courage to go deep early. 

Rule #13: Re-learn trust by default

You have your fair share of battle scars from past relationships. So do I. Just about everybody else does, too. You’ve probably had your heart broken. Maybe you’ve been misled, manipulated, or deceived. You’ve probably heard some horror stories from your friends, or worse yet, maybe have one or two of your own. 

And yet, you are in total control of how you’ll approach future relationships. Will you be skeptical of everyone you meet and call it being “realistic.” Or will you extend trust by default until the person does something to lose it?

I can certainly see why a lot of people’s learned experience is to keep their guard up. Trusting requires vulnerability, and having our trust violated again and again doesn’t get easier. But I still believe that default trust is the way to go, and I can’t explain why better than author Jim Collins, who has spoken about the “trust wager” concept he learned from his mentor, Bill Lazier. 

Basically, Lazier explained that to have the best relationships, you need to surround yourself with the best people. The best people will be pushed away when they see you’re skeptical of them, so by being overly protective of yourself and starting people with distrust, you are essentially closing yourself off to the best of what’s out there. The concept of reciprocity also applies here: if you trust people, they are more likely to behave in a trustworthy way.

Will your trust be violated sometimes? Absolutely. Will that hurt? Yes. Chalk that up to being part of the cost of living. Over the course of a lifetime, you’ll be much better suited being surrounded by the trustworthy people who will be drawn to your trusting nature. 

Go positive, go first.

Rule #14: Know the rules of the game you choose to play

We often don’t really want what we think we want. 

Do you want feedback from your team at work? Then you have to understand that it might not be pretty; feedback doesn’t mean only praise. 

Do you want to drive innovation at work? Then you have to be willing to give creative people room to operate, and understand that change inherently alters the structure upon which you’ve built your power, and maybe even threatens you unless you can change with the environment.

Do you want a rich partner who wins you over with gifts even though he doesn’t have time for you? Then you should understand that you’ll probably always be an afterthought. And don’t forget that if he believes his wealth alone can get him what he wants, like a transaction, then he’s likely to be repeating the same cycle with some newer, fresher, younger girl a few years down the road. Just another transaction.

Do you want total transparency in your relationship? Then you need to be emotionally prepared for things you may not want to hear or know about your partner. You can’t expect someone to be willing to share everything with you unless you also create a safe space and prove that you can accept the things you may not love about them or their past. 

You’re entitled to pursue any kind of person, environment or relationship you want. But you should do so being fully aware of what your approach optimizes for (e.g. transaction, transparency) and the second-order effects that may make you uncomfortable, so that you know what you’re really signing up for. 


I have derived these rules over the years despite not having a history of great relationships myself. I think that actually helps me understand these things more, because we can all be so easily blinded to logical reality when it’s our emotions in play. Daniel Kahneman talks about this frequently, how even though he is literally the world’s top expert in cognitive biases, he still can’t prevent himself from being swayed by them at times. 

None of these rules will help you find a perfect workplace, friend, or partner. That takes some luck, and there aren’t any surefire hacks for that. But I’ve decided to organize my thoughts and share them now to hopefully help someone feel just a little bit more control over their fate, and maybe increase their odds ever so slightly of finding that luck.