Lessons on people pleasing from Machiavelli and Robert Glover: From Nice Guy to the Assertive Man

A prince ought to have no other aim or thought, nor select anything else for his study, than war and its rules and discipline. – The Prince

When I was 18 years old, I lived on a ship. It was a large ship, an aircraft carrier, over 3000 people when deployed out to sea.

For the first time in my life, I was on my own in the world. I lived 8000 miles from my closest family, in a country where I didn’t know the language. In hindsight it was the greatest thing that could have happened to me.

Most people go their whole lives without even leaving their own state, or country. They never get to experience life outside their own borders. They never get to find out who they really are, and instead lead lives of quiet desperation, or with a yearning for what could have been.

However, the best part about all of it, is you learn to fail, to be tested, to make big mistakes, and learn that you can recover from all of them as long as you take responsibility for your actions.

I spent 4 years living in Japan, and I had the biggest failures of my life during that time, and learned some of the greatest life lessons.

During those formative years, I picked up a book titled “The Prince” by Machiavelli. I had been put in a leadership position and had no idea how to lead anyone, truth be told, I wasn’t really leading myself. I found this book from a google search on best leadership books for new leaders. So I bought it, and read it, or should I say…devoured it.

It was unlike anything I had ever read.

I was really having a hard time distinguishing myself from being a nice guy, someone who everyone loved, and trying to please others, to someone that people respected and listened to.

I couldn’t find a balance. This book helped, and so have the last 12 years.

I was definitely a people pleaser, and would never say what I actually meant. I had extremely low self-esteem as a teenager and would always prioritize others over myself. This continued until I was about 19 years old, then I became a guy who thought he needed to say everything on his mind.

This ended up backfiring on me, because I thought that’s how tough hardcore men talked and acted.

Slowly over time, I learned that it isn’t about acting a certain way, it’s about character, discipline and being who you were made to be, and not who you think you should be.

Machiavelli writes a chapter in the book titled: One should avoid being hated or despised

A prince is despised if he is considered changeable, foolish, weak, mean, and uncertain. A prince should avoid these characteristics. In his actions he should try to show greatness, courage, seriousness, and strength. In his private dealings with his subjects he should show that his judgments must be followed, and he should maintain himself with such a reputation that no one can hope either to deceive him or to get round him.

There are a couple things that can be taken from this:

  • Be the same person in public as you are in private.
  • Make a decision and stick to it, good leaders are good at making decisions
  • Strength is learned, I would say that Being Stoic is one of the best qualities of a leader. Keeping emotions out of decisions and debates is paramount
  • You can’t please everyone, so don’t try

You shouldn’t try to avoid being despised for the sake of being despised. It’s going to happen. Not everyone will like you or the decisions and actions that you take.

However, if you keep others in mind when making your decisions you will fare better.


10 Days of Skill


From Nice Guy to Assertive Man

I was a “Nice Guy”, who was timid and scared. I didn’t like people to be mad at me, and would do everything to seek their approval.

What a wimp right?

Maybe you are too…

What exactly is a nice guy, and how do you stop being one?

Source: No More Mr. NIce Guy BOOK By Robert Glover

Source: No More Mr. NIce Guy BOOK By Robert Glover


  • Nice guys are dishonest – They hide their mistakes, and avoid conflict
  • Nice Guys are secretive – Nice guys hide anything that will upset anyone
  • Nice Guys are manipulative – They have a hard time making their needs a priority, so they feel powerless and use manipulation to get their needs met.
  • Nice Guys are Passive Aggressive – They tend to express their frustration or resentment in indirect, round-about, and not so nice ways. This includes being unavailable, forgetting, being late, not following through, not being able to get an erection, climaxing too quickly, and repeating the same annoying behaviors they promised to never do again.
  • The list goes on...

 I don’t know about you, but I was that guy for a long time. Not only that, but I become that guy sometimes when I’m tired or after a particularly trying day.

I would be a liar if I didn’t admit it.

We all have the makings of “Nice Guys”, and our culture loves for us to be those guys, but the people around us suffer for it, our society suffers. What we need are assertive men, that get in front of problems, confront stuff that is wrong, say what they mean, and learn how to have their needs met and fulfilled without means of manipulation, secrecy or deception.

Here is my advice:

Stop Being a Nice Guy. You are not fooling anyone, and you are not fooling yourself. Everyone sees you walking around with slumped shoulders, hiding your true feelings.

I see men that let their wives run their lives. It makes me sad.

How do you know if your wife or spouse is running your life?

  • She plans out your day for you without asking your input
  • She spends all of the money in the household and you let it go on and on
  • She does not respect you and withholds sex from you
  • She makes you “earn” stuff
  • She says that you are emotionally unavailbale and she uses guilt to get her eway

Do you know why she is running your life?

Because you are a “Nice Guy”

Robert Glover helps men go from “Nice Guy” to an Integrated (Assertive) Man:

The Integrated man

  • He has a strong sense of self. He likes himself just the way he is.
  • He takes responsibility for getting his needs met.
  • He is comfortable with his masculinity and sexuality
  • He has integrity. He does what is right, not what is expected.
  • He is a leader. He is willing to provide and protect those he cares about.
  • He is clear, direct, and expressive of his feelings.
  • He knows how to set boundaries, and is not afraid to work through conflict.

You know what has made me overcome all of these “Nice Guy” Tendencies or Behaviors?

  • I wake up at 4:00 am with an Action Plan
  • I execute on the plan
  • I get ahead of problems and issues and confront them head on. I always feel a rush of adrenaline and am excited when I Confront people.
  • Look people in the eye, and say what I mean
  • Let people know where I stand right away

If you want a model of men who have these characteristics on television and in the movies.

Here are a few of my favorite. (They are all Cowboys).

  • John Wayne – Watch True Grit
  • Clint Eastwood – Watch all the westerns
  • Robert Taylor – Longmire (He was also an Agent in “The Matrix”)

Moving from a “Nice Guy” to an integrated man is going to take time and intentionality.

You need to make a constant effort.




Have you read Robert Glovers book? If so, what kind of impact did it have on you?

How have you had success moving from a “Nice Guy” to an Integrated Man?

Are you a “Nice Guy” who wants to recover?


Start taking responsibility and Ownership, it’s time to be who you were made to be.



Philosopher Photo credit: kosmolaut on Visualhunt / CC BY