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Stoic Street Smarts

8 Counterintuitive Strategies To Make A Relationship Last

Published 4 months ago • 3 min read

Today's newsletter is about the experiences and insights I've made on what makes a strong, happy relationship.

My readers are a mix—some of you have 20-year+ marriages. Others are single. I don't claim to be an expert. I just know what's worked for over the past 11 years. No matter where you are, there's some value for you.

Before we get to that, a brief announcement in the form of today's "sponsor"


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8 Counterintuitive Strategies To Make A Relationship Last

A big reason relationships fail today is the assumption that healthy relationships are entirely subjective. While every couple has unique dynamics, the fundamentals of a strong partnership are largely universal. As Tolstoy wrote, "Happy families are all alike; every unhappy family is unhappy in its own way."

Every relationship is great when things are going well. Even two toxic, narcissistic drug addicts can look like the perfect image of love and happiness if you catch them at the right time. If you don't know the backstory of someone's relationship, the smiling photos on social media and public loving demeanor could be the eye of the storm in their dysfunctional relationship.

You can’t judge a relationship based on the good times. Accordingly, one of the biggest mistakes you can make is looking for a relationship based on how good it makes you feel.

Don’t take this to mean that you shouldn’t be with someone who treats you well and whose company you enjoy. But if you get into a relationship based only on the good times, then you are potentially setting yourself up for a heavy dose of dysfunction.

Your romantic relationship is second only to the relationship you will have with your children. If you decide not to have children, then this is the person you will spend most of your time with. For that reason alone, it’s important that you don’t mess this up. Notice that I didn’t say it’s important that you “get it right.”

No one gets it right. Even the happiest relationship has trying moments that inspire you to wonder if you’ve made a mistake. That’s to be expected when you take two people—with different backgrounds, experiences, and perspectives—and attempt to create a lasting union. The point isn’t for relationships to be perfect or even consistently pleasant, but the good should outweigh the bad by a significant margin.

This post blends my personal experience, general observations, and scientific research about what makes a relationship a fruitful, positive experience. I don’t know if these points will be new or groundbreaking, but they are useful and have served me and others well.

Whether you're single or 20 years into a relationship, there is value here.


Social media round-up

  • On YouTube, I warned people why they shouldn't date drug addicts. This seems obvious, but based on the responses, people got a lot out of it. Or they were just entertained.
  • On Twitter, I explained how the following graph paints a dishonest picture of poor and rich people having more children than the middle class.


Cool content I've read

  • A Personal Reflection On Social Media: Zac Small wrote a great essay on why he chose to heavily reduce his social media presence to focus on photography, family, and landscaping. Zac is one of the friends I've made since being heavily involved in the online space, so I thought this was an interesting read. This section of the essay really hits home:

  • Perfection or routine: Zach Homol (I swear this isn't a theme. It's just a coincidence that both these guys are named Zach) has one of the hardest roads to success I know of. The guy worked in the coal mines of West Virginia, one of the poorest states in America, and clawed his way out to something better. This essay is a reflection on how he uses routines to reduce friction in his daily life. Reading this, I thought of how my wife insists everything stays clean and orderly, even when we have a lot of work. It feels like it takes away valuable time, but it makes everything easier.
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