This is part of my series on How To Be A Good Person.

A reader wrote, “Stewie, how do I be more assertive in discussions? I feel like I should be assertive all the time, but I’m scared of stepping on toes.”

This is a great question. Western culture glorifies the assertive cowboy who is commanding and always has the right answer. Think of John Wayne, Jack Bauer, and James Bond. These caricatures make for entertaining movies and TV but have no place in real-life situations. Their behavior in your workplace would alienate everyone else.

Being assertive all the time would absolutely step on toes. Don’t do that. But you already know this because you have empathy for others. And that’s part of what makes you a good person.

So, here’s my rule of thumb: be assertive (e.g., self-assured and confident) when discussing something that you’re responsible for.

For example, a ship’s captain is accountable for everything on their ship, e.g., its people, its cargo, and the ship itself. As such, the captain will assert their views about anything concerning their ship and its voyage. And though a prudent captain will listen to recommendations, in the end, they decide what’s best.

Be like a ship’s captain: assert yourself when you’re the one responsible.

Specifically, your responsibilities fall into three categories:

  1. Yourself: your time, health, appearance, personal space, etc.
  2. Your stuff: your phone, car, home, etc.
  3. Your obligations: work responsibilities, family responsibilities, etc.

Assert yourself when discussing any of these things. At the same time—and this is important—do not assert yourself on issues you’re not responsible for. You can even say, “I don’t know—I’m not responsible for that.”

The 5% Rule

In my 30s, I had a significant realization: I’m responsible for very few things in this world. Consequently, I don’t need to assert myself about most topics.


  1. How other folks look or eat
  2. How other people manage their possessions
  3. How others handle their work obligations

In fact, only 5%1 of conversations center on things I’m responsible for. Once I figured this out, I stopped asserting myself about others’ responsibilities. I also stopped worrying about how others live. This freed up time and emotional energy to improve my life.

And my life has never been better.


Many people struggle with being assertive. They worry about stepping on toes and offending folks. As a result, some folks don’t speak up at critical moments and feel resentment later.

The solution is to assert yourself when discussing things you’re responsible for and go with the flow the rest of the time. You’ll find that 95% of conversations have nothing to do with your responsibilities, and therefore you don’t need to assert yourself.

When you stop asserting yourself about others’ responsibilities, you’ll have more mental space and energy to focus on your own life. And your life will get better.


  1. This is a personal estimate. It’s based on gut feelings, and I could be way off.