Break Some Rules

I

Newsflash: you can just do stuff.

In other words, even if the rules dictate YOU MUST COMPLY WITH X, you can go do Y, or Z, or 3. It's your choice. No, I'm not calling for anarchy. But I am suggesting that microdosing-anarchy by finagling around dumb rules is a gateway drug to more fulfillment.

Need inspiration?

Here's some real examples:

1. For almost two years, my company was billed $300/month for an email software. We used only one of it's many features, so I tried negioating a fair rate, but they did not play ball. Last year I whipped together my own clunky version, deployed it to AWS, and have since paid ~$10/month in AWS fees instead.
2. We were asked to pay $16,000/year for a software service that was free for years because the provider changed its pricing model. Given that I balk at $300/month, I made a big scene: through a series of tense, yet professional, emails, I threatened to remake their product using Claude and then share it for free with the developer community. They made a "one-time exception" and now we can continue using their lovely product for free.
3. I use my old university email to verify my status as a student to unlock all sorts of great deals. For example, I pay like ~$4/month for both Apple Music and Apple TV+.
4. Buying a refundable airline ticket to get 1-day expedited passport renewal to go on a spontaneous roadtrip.

II

Rules are not made for regular people. Rules exist to dampen destruction by irregular people on the edges of a normal distribution. In other words, in any population there is a tiny subset of people who will abuse and exploit resources and in general do bad things. Rules help corral these free spirits.

Jim Jefferies has a fantastic stand-up piece on gun control that discusses this:

... “Why should I have my guns taken off me? I’ve done nothing wrong.” Look, I agree with you. If you’re a responsible gun owner and you don’t fuck around with them, then you should be allowed your guns. You really should. But that’s not how society works. We have to play to the 1% that are such fuckwits they ruin it for the rest of us. We have to walk as slow as our slowest person to keep society fucking moving, right?

... We should all be allowed to take fucking drugs, but we can’t, can we? Because Sarah took drugs and she stabbed her fucking kids. Oh! “Oh, thanks, Sarah. You fucked it up for everyone.” Right? Everyone should be allowed to drive their car as fast as they can do it, right? But we can’t because Jonathan got drunk and ran over a family. “Thanks, Jonathan! Now I have to drive at 30, you fucking idiot!”

And that's the point of rules: everyone has to give up a little bit of joy to subsidize outliers. It doesn't feel fair, but until we have some superintelligent AI Santa Claus that can make exhaustive naughty lists, the rules apply to everyone to evenly distribute the joy tax.

For our purposes here, let's avoid slinking into the expansive field of ethics, and assume there are two types of rules: big rules and small rules. Big rules are public laws to distinguish good and bad people in civilization—things like "don't murder, don't steal, drive safely, etc". Small rules are (1) boundaries set by private entities like "you must pay $300/mo to use our service", or (2) expectations set by society like "get a degree, get a job, etc."

Obviously, one should never break any big rules.

Less obviously, all small rules are optional. That's the open secret. You can get ahead of most people by being a tiny bit selfish and looking for a way around the small rule. My company is saving $16,000 on its bottom line at the cost of the folks at that company thinking I'm a jerk. That's okay because those dollars can be used somewhere else more productive. Voila, you're now slightly ahead of other people.

It's worth clarifying that opting-out of small rules does not mean you can violate big rules. For example, not wanting to pay quoted price is okay, but hacking the service provider is fundamentally wrong (big rule: one must respect sovereignty).

III

If you don't question rules and politely follow instructions, you're tacitly approving those rules.

As mentioned before, rules eat small bits of your joy. This presents itself in various forms: opportunity cost, inconvenience, etc. If you ignore some small rules, you retain some of that joy. If you do it often enough, it becomes a habit. You naturally negotiate quotes to cut costs; you palm the maître d' to get a nicer table. This is a beneficial skill to develop because you learn how to put yourself first. When you start doing that, you create more opportunities for yourself.

It's not selfish, it's an edge.