The Most Important Rules To Break Are Your Own

When I first began learning how to live a better life, I decided to watch a video every day. After 67 days, I branched into more specific habits. With every individual habit, I took the same approach: do it every day.

  • When I stopped drinking, I didn’t drink for two years.
  • When I started writing down my priorities, I did it every day for a year.
  • When I quit coffee, I didn’t have any for 100 days.

Once I started coaching people and helping them with their habits, I found a tool called The Habit Tendency Quiz. I’m an Upholder. The creator of the quiz, Gretchen Rubin, says Upholders are great at picking up and letting go of habits for one reason: they play really well by the rules.

Whether I set them for myself or am handed a guidebook, once I know what the expectations are, I’ll work my ass off to live up to them. But this is also the dark side, Gretchen says:

“Upholders are too driven by getting the Goldstar. They look for the rules beyond the rules. It’s too important for them to know what the rules are. They’re almost boxed in by the rules. They don’t know what to do when there aren’t any.”

In 2014, I decided to take online business seriously. In 2015, I decided writing would be my way to win. So I lived by the rule I knew to have worked, the only rule I knew: write every day.

For over two years, I have lived by this rule.

In 2015, I wrote 250,000 words. In 2016, I published a book summary each day. 500,000 words. In 2017, I kickstarted my journey on Quora the same way.

For a while now I’ve known it’s time to let go of this rule. I wanted to finish my year of daily answers and then quit. But once you’ve chosen a new path, there’s no use in delaying it. That’s a new rule I’d like to try.

The most important rules to break are your own.

Replace them with better rules. When you find a better rule, it’s your responsibility to implement it immediately. So today, I’m moving into new territory.

The land of no rules. When a post takes me three days, it takes me three days. If I feel like writing three answers in one day, that’s what I’ll do. And if I don’t feel good about any piece for a week, I won’t publish.


Knowing the rules is important. It allows you to pinpoint which ones you better follow and which ones must be broken to win. But on top of the rules of the game, you’re playing by your own.

These rules are invisible. They’re hard to see. You may never have consciously set them. Some serve you for a while. Others keep you from moving forward.

You can’t find these rules in a guidebook. They’re part of who you are. Which makes them hard to let go. Much harder to reject than others’ rules.

When you discover your own rules, do you have the courage to break them?

“I am free, no matter what rules surround me. If I find them tolerable, I tolerate them; if I find them too obnoxious, I break them. I am free because I know that I alone am morally responsible for everything I do.” ― Robert A. Heinlein

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