The Rules We Live By

Hello, fellow thinker!

Before we dive into this week’s letter, I wanted to throw out an invite to any of my subscribers who might be interested in being a guest contributor to this letter. Do you have a story to share about a life lesson you learned? Would love to collaborate with you!

And now please enjoy my letter on Rules!

Rules are everywhere — in life, in work, in games, in faith. Some come from lawmakers or prophets; others emerge quietly through experience. Over time, I’ve realized that rules give shape to effort. They turn loose intention into something you can act on and create a sense of order that lets progress build over time.

In nearly every area of life, growth begins with learning the rules. Religion has its Commandments. Governments have their laws. Philosophy offers Meditations — Marcus Aurelius’ collection of Stoic reflections that outline a way to live with clarity, self-control, and purpose. The Stoics believed that following sound principles brings harmony between thought and action, allowing a person to move through life with steadiness and intention.

Investing follows the same principle. Every experienced investor develops rules that guide decisions — when to buy, when to sell, how much to risk, and how to stay patient. A common rule is to take profits once a stock rises by a set percentage or to sell quickly when a trade moves against you beyond a limit. Others focus on consistency, like buying a fixed amount each month regardless of market noise. These practices reduce emotion and create structure. Over time, that discipline often becomes the real source of success.

In my years helping people find jobs, I developed a rule that I now share with anyone considering a career move: never accept a counteroffer once you’ve decided to leave. I’ve watched this play out too many times to ignore. Candidates who stayed after accepting a counteroffer often found themselves looking again within months. The reasons that pushed them to explore new opportunities in the first place didn’t disappear — they only went quiet for a while. Eventually, they resurfaced, and the same frustrations returned. The rule holds up every time: once you’re ready to move on, trust that decision and follow it through.

I’ve also learned to look for good rules in the wisdom of others. When I was searching for a new home, a friend who invests in real estate gave me one of his own. He said he never buys houses on main roads — and absolutely avoids homes that sit on two. When I told him about a house I was considering on a corner lot between two busy streets, he immediately called it a “double no.” It made perfect sense the moment he said it. Since then, I’ve added that to my own list of rules. I never forgot it.

Many years ago, I created one rule for myself: every January would be Dry January. My goal wasn’t lifelong sobriety; I simply wanted to reset after the holidays, which were often filled with client dinners and long nights of celebration. I needed a break and a way to feel in control again. The first few days were always tough, but once momentum built, clarity returned. Each successful January reinforced my belief that I could set a rule and keep it.

That simple habit became one of the most important decisions of my life. By 2021, when the time came to quit drinking completely, the foundation was already there I could start clean on January 1st. The yearly reset gave me structure, confidence, and the strength to step fully into sobriety.

Rules like this act as anchors. They steady you during uncertainty and help decisions feel less chaotic. They also compound. Repeated over time, they build resilience and stability, just like small, consistent investments grow into wealth.

Wisdom grows through experience and endures in the rules we choose to live by.

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Keep thinking, my friends!

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