May 27, 2026 May 27, 2026 2026-05-27

In 2009 I wrote seven ways to say no, motivated by the observation that most people don’t practice the word. My framing was almost entirely technical: saying no is a skill, you just need to work out the right muscle for the right context, here are seven variations. I was right in that saying no is very important. I wasn’t quite spot on about the technique, I think now there’s a little more to it than just that.

What Technique Doesn’t Touch

The seven methods in the original post were about phrasing — ways to decline that are clear, honest, and calibrated to different social situations. That part is technically correct. What the post ignored at that time was the hidden layer, the “why”. The right approach was not about which type of negation to choose, but why it’s genuinely hard to say no in the first place.

It’s not that people don’t know the word. It’s that saying no activates something that feels a lot like danger. You risk disappointing someone. You risk being seen as difficult, unhelpful, selfish. For a lot of people — and I include myself here — that conditioning runs very deep. I reckon this must have been useful at some point. Being agreeable is a social survival strategy that works well in certain environments and certain phases of life.

The problem is that the survival strategy doesn’t automatically adjust – it still lingers long after it’s needed.

The technique advice is: say no clearly and without excessive explanation. The psychological reality is: you first have to convince yourself that you’re allowed to.

These are 2 different problems, and solving the first one doesn’t necessarily solve the second.

Where I’ve Gotten Better, Where I Haven’t

Seventeen years of practice means I can give an honest accounting.

I’ve gotten significantly better at saying no to new projects that arrive with energy and enthusiasm but no clear fit with what I’m actually trying to build. The older version of me would say yes and find out later that the enthusiasm was borrowed, or shallow. I’ve done that enough times to recognize the pattern early now.

I’ve gotten better at saying no to the version of myself that wants to explain, justify, and soften every refusal until the no becomes a maybe. A no that takes three paragraphs to deliver isn’t actually a no — it’s an invitation to negotiate. I can give very short “no”-s now.

Where I still struggle: I guess I’m still underselling myself sometimes, still don’t know how to say no to giving discounts (and that goes from financial discounts, up to attention discounts, so to speak).

On “Boundaries” and What the Word Gets Right and Wrong

The “boundaries” conversation that went mainstream in the 2020s is partly covering the same territory as my original post, and I have mixed feelings about it.

What it gets right: it moved the conversation from technique to permission. You’re not just learning how to decline — you’re recognizing that you have the right to. That’s the layer the 2009 post mostly skipped. The cultural normalization of saying “I’m not available for that” without elaborate justification is genuinely useful.

What gets lost: the word “boundaries” has been used so much that it’s started to mean almost anything — sometimes legitimate self-protection, sometimes just preferring not to be bothered. When everything is a boundary violation, the word stops doing work. And the framing can shift the focus from “what do I actually want?” to “what can I get away with refusing?” — which is a different and less interesting question.

The Most Important No

The most important no I’ve said recently wasn’t dramatic. It was turning down a business arrangement that had all the surface features of a good opportunity — credible people, reasonable terms, interesting problem space — but required me to be present and available in a way that would have consumed the time I currently use for building my own things.

The pull was strong because the opportunity was real. The no was uncomfortable because it wasn’t obviously the right call — it was a judgment call about what I’m building and what I’m protecting. Six months later, the time I protected has gone into ten apps and a steady writing practice and being more present with my family. The opportunity I declined has moved on without me and is fine.

That’s almost always how it goes. The thing you protect time for turns out to be the important one. The thing you said no to finds another way to exist without you.

This is something I try to keep in mind every time I find it difficult to say no.