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April 22, 2026

My Friend Who Doesn't Make Plans

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Last week I texted a friend inviting him to join me and some other friends for a walk. He responded saying “Maybe, TBD”. Unfortunately he didn’t end up making it out. Reflecting on my relationship with him over the last year or two, I don’t know that we’ve spent time together outside of spontaneously bumping into each other.

He’s the type of person that doesn't like planning things.  Now it’s not like his way doesn’t work, he gets a lot done and is a functioning member of society. But what I’ve noticed is that our different ways of operating within the world are incompatible. I am pretty structured. I like making plans in advance and being proactive about allocating time for people and things that I want to do. 

It’s clearly not a good recipe for our friendship, but what does it mean about our different approaches to life? What are the tradeoffs?

I can certainly speak for myself. Being organized and structured helps me to live more intentionally. I design my days so that they’re full of the things I want to do. As a result I live a balanced life, make progress on things I care about, invest in the people I want to spend time with, and keep space for the personal time that I need.  The downside is, I’m less flexible and cannot accommodate new plans as well. I miss out on some great moments because I’m already committed to doing something else.  

On the flip side, my friend who is less scheduled and more open can feel into what he wants to do in the moment. He probably can be more present with what he’s doing because he doesn't have in the back of his mind what he needs to get to next, or what he was supposed to be doing. He probably meets the moment a little bit better because he chooses it in real-time rather than planning it in advance. However, I imagine the downside is that he’s not as deliberate about investing in things like relationships, and struggles to build momentum toward longer term goals.

Neither is better or worse. They’re different operating systems. I design what I want out of life, he responds to what life presents. Both can make a person happy. 

No matter the nature of the differences, It’s a bummer to me because I value his friendship and we don’t spend much quality time together. And I wonder if he notices that we aren’t as close as we could be. In any case, it’s interesting to observe how different people with different approaches to life attract different things into it.

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