Hi, I'm Jon.

I'm a digital nomad, traveling around the world while working full-time as a founder, engineer, and activist. I document my work, thoughts, and discoveries here.

When to Say "No More"

When to Say "No More"

I think eventually every person finds themselves in a difficult relationship with someone or something in their life that they can't seem to get themselves out of. Perhaps it's a job that you feel treats you unfairly or a difficult friend who comes off as disrespectful more than occasionally. These are relationships that seem like endless fountains of anguish and pain that drain the energy out of you. They exhaust you. Yet, for some reason or another, we find some sort of justification for staying in these relationships:

"My job is completely chaotic and it's not what I want to do, but I need the money right now and think I can make things better with my team."

"I'm fighting almost every day with my mother for weeks, but I can see that she's trying to make things better and she just gets carried away with her emotions."

"My friend keeps flaking on me, but we've been close since we were kids and I know they're just really busy all the time."

What is hardest about these kinds of relationships is that they make you feel trapped. You don't know where to draw the line and declare bankruptcy. Should you stick it out and keep hoping that it's going to improve with time? Do you have enough energy and the patience to wait for it to improve? I've found myself in this kind of relationship multiple times in my life, and I've built up a framework to help me make a decision around these sorts of relationships easier. I've figured out a way to know when to say "no more."


A State of Doubt

The first step in this framework is figuring out if you are in a state of doubt about the relationship. In other words, you need to recognize if you have serious existential uncertainty about the relationship for an extended period of time.

This is different from the normal feelings of ambivalence that come with rough patches in a relationship. Every relationship, whether it is with someone you're dating, or a client, or anything else, is bound to encounter conflict at some point or another. Couples will fight occasionally over things like who did the dishes last time or how to spend their holiday bonuses on a vacation. Jobs will have their demanding moments during peak seasons and you'll have disagreements over the way forward with your colleagues. Relationships are rarely completely devoid of conflict, and conflict that is dealt with maturely and constructively is perfectly normal and to be expected.

However, there are situations where unhealthy conflict, chaos, and strife on a regular basis will have you thinking about the relationship in existential terms for relatively long periods of time. These thoughts endure and can't be easily shaken off. You start wondering if this is the right person for you in a long-term romantic relationship, and thoughts about breaking up continuously glance your mind for weeks or even months. You suffer multiple 80-hour work weeks that affect your friends and family without much respite, and you start wondering if you should start looking for another job. When you start lingering about whether you should stay in a relationship for extended periods of time, you are in what I call a state of doubt.

It’s also worth mentioning that what you're pinpointing is what you feel about the relationship. You are not considering whether the doubt you feel is warranted or if there is a good excuse for the questions you have in mind. You are simply wondering if true, unmistakable doubt is present in the relationship or not. It's there or it isn't there. Just focus on the feeling, and instinctively, you'll know if you're in a state of doubt.


A Dangerous Dance

Once you recognize you are in a state of doubt, this doesn't mean the relationship is doomed. In fact, this moment might be the best opportunity of turning your relationship around. You are simply aware that your relationship is in peril, and that means you already are or probably should be engaged in seriously addressing the apprehension. At this point, the goal is to actively work on the relationship to take yourself out of that state of doubt, and if you can do so, you should feel glad you were able to bring things back on course.

If you're having trouble with a friend who's not dependable, this is the time to sit them down and have a frank conversation about why you're not a priority and how to rebuild trust. If you're overworked at your job, now is the time to talk to your boss about shifting responsibilities or getting a raise so you feel valued for the effort. This process of working at the relationship is always a difficult one, and it probably won't get resolved quickly. However, being honest with yourself about whether a relationship is in danger is the first and best chance you have at recourse.

That being said, there is another thing to keep in mind once you recognize your state of doubt: you are now in a dangerous dance with hope. Chances are, you are staying in painful relationships because you are clinging to the possibility that things will get better with time and effort. As you work through the issues in your relationship, you may see that there is clear progress in how you are being treated. The fights are getting shorter, the conflicts are less emotional, and perhaps the other party is even becoming more self-aware of their behavior. What is important to recognize while you are working towards getting out of doubt is that you are racing against your time, your energy, and your patience. Hope is making you stay in this relationship, and what will happen if an offense reoccurs is that you will find every excuse to forgive the incident. Your hope will convince you forgive missteps and keep working at the relationship at great cost. You have to remember that being in a state of doubt and trying to actively resolve the dysfunction is a dangerous dance.


Three Strikes

So, knowing the danger of staying in a perpetual state of doubt and locked in this dance, you must also set a clear limit to your efforts the moment you recognize the doubt. The worst thing you can do is skip this step because your instincts, your emotional core, your hope will lead you to come up with every excuse to continue repairing your relationship no matter the personal cost. This is dangerous. Not setting up a pre-emptive bright line to your efforts may crush you emotionally and lead to an explosive end to the affair. Once you recognize the state of doubt, set a limit at the outset and stick to it.

What I've come up with as a limit is three emotional strikes. Strikes are offenses that are so severe that they take you from a state of doubt into a deep, sharp sense of violation. In other words, these are offenses that cross a line from being a forgivable speed bump on the way to recovery and into something that is memorably damaging. Your friend who regularly flakes out on you misses a concert last minute. You saved up for weeks to buy these expensive tickets and you can't get a refund and can't resell. You've talked to them about this several times and already expressed your concerns seriously, but the friend shows little remorse. Your boss tells you last minute that you can’t take the day off so you’ll miss your flight, even after a month's heads up that you're planning a family trip to see an aging relative. This is weeks after he's given you the approval and promised you he could find a replacement if an emergency came up, which he’s clearly failed to do. You'll know in your gut when someone violates your trust and gets a strike. Like recognizing a state of doubt, what is important is recognizing the feeling of violation, and not the reasons for it. You're not choosing to give someone a strike, you feel the offense as an emotion. Remember that you are in a dangerous dance with hope, and you are fighting the instinctual reaction to excuse the violation. You have the feeling or you don't, and it's not something you can ignore.

Now that you know what an emotional strike is, it's also important to know how many to have. I give myself three. The first strike is an excusable violation to me. I feel they get a clear pass if I'm actively working on the relationship, they are really trying, and the incident is just a forgivable stumble I've come to expect as I work through our issues. The second is sign that violations are developing into a pattern, and emergency steps need to be taken. This is when my state of doubt tends to really solidify and the canary flees the coalmine. Finally, the third strike is pulling out the white flag and surrendering. The violations are clearly a pattern, and my state of doubt has turned into flat out rejection despite my best efforts to repair the damage.

When the final strike you've set up for yourself is hit, that's when it's time to say "no more." It doesn't matter how many strikes you give yourself, as long as you have a number in mind at the outset and you stick to it. I personally choose three for most relationships. One of my closest friends said he'd only give one to any relationship. However many it may be, crossing the final strike is when to go. You may not need to tell the other party you’re finished with the relationship immediately, but this is when you have to be determined to get yourself out of the arrangement and actively plan your exit. This may be before you have completely run out of options to address the dysfunction, before you feel utterly exhausted and spent, but that's the entire point. The purpose of the strike framework is to decide to get yourself out of a toxic relationship before it turns disastrous and really runs you dry.

What I find most useful about this framework is that it takes the agency out of making a difficult decision like this. Every step of the framework has clear instructions about what to do and the emotional turning points are large and bright. The way I explain this to my friends is that it feels like following directions on a clearly marked highway instead of wandering through a labyrinthine parking lot looking for an exit. It turns the emotions you are feeling into signposts on a road towards recovery instead of putting these untamed feelings in the driver’s seat so the wild ride never ends. The decision is made outside of you. You're not personally giving up on the relationship and not giving in to the guilt of abandoning what feels like an unhealthy arrangement. Instead, it feels like you’re just following the rules of a framework that you know is sensible, well outside the irrational, emotional turmoil of the parties involved.


Remember to Forgive

Finally, regardless of how this framework works for you - whether you need just one strike or five, whether you have a different bar for what constitutes an emotional strike, anything - after the dust settles, remember to forgive. Being in a difficult relationship is a draining affair, especially if it is entered into with the best intentions and it's arduous for an extended period of time. Because of the pain you've experienced, it's tempting to hold on to hard feelings even after you finally exit your state of doubt. That's both for relationships that recover to a healthy state and those that end entirely after the final strike.

"Why should I forgive someone that has caused me so much pain?" people ask me. I can write a whole other post about forgiveness (and I probably will one day). The best reason I can give is not to forgive just for the sake of the other person, but for yourself. You don't need to forgive because someone deserves it. You don't need to forgive because you think someone's behavior was excusable and you're saying it's okay. You forgive for yourself. Holding onto the anger, frustration, and pain after going through such a taxing ordeal means you will continue to suffer even after the episode is over. If you do not forgive, you will never really be free from the anguish you worked so hard to escape in the first place. Forgiveness is the final step of the framework, and for many, it's almost always the hardest part.

So if and when you find yourself in a difficult relationship, I hope that working through your issues will eventually take you out of doubt before you reach your emotional limit. If you do end up passing that final strike, remember that leaving a toxic relationship is for your own health and well-being, and there is no shame in looking out for yourself. Regardless of how things pan out, remember to forgive and it will finally set you free from your pain. I hope this framework provides some clarity in what I know is a harrowing experience for anyone who goes through a difficult relationship. It's saved my life more than a few times.



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