In 1946, Major League Baseball player Leo Durocher was chatting with sportswriter Frank Graham. They were discussing the competition that year, and the differences in strategies and mindsets among the major league teams.

During their chat, Leo looked across the field at one of the opposing teams, the New York Giants, and commented... “The nice guys are all over there, in seventh place.”

And the phrase caught on, becoming the version we know today...

“Nice guys finish last.”

At BROJO we’ve developed something of a specialty of working with “Nice Guys.”

Nice guys are everywhere, because it’s a mindset that’s engendered by most modern societies. Its also a mindset that affected my own personal life, and the lives of BROJO's coaches for many years.

Over and over again, we see the same problems... weak & shallow relationships, struggles with self-esteem, a craving for social approval, and many others.

The problems are so consistent and pervasive that the moment someone brings one of these problems up - this is known as a front door problem - we immediately start exploring the other patterns in their behavior and life.

And... almost always, the trail leads to some form of a “Nice Guy” mindset.

These problems are so consistent, they're almost a form of diagnosis.

So, What is a “Nice Guy”?

The term “Nice Guy'' comes from Dr. Robert Glover’s work titled No More Mr. Nice Guy in which he introduces the term “Mr. Nice Guy Syndrome.”

At its core Nice Guy Syndrome is a form of people-pleasing, but it is people-pleasing with an agenda- the desire to control of your world and the people around you through subtle strategies of manipulation.

A nice guy might seem nice, treat you well, and seem wonderful on the surface, but make no mistake- he sees that behavior as a payment towards something he wants in return.

That niceness is a strategy... a gift with strings attached.

Lots of strings.

Dr. Glover’s work is worthy of a deep read and a lot of reflection, because most men that grow up in modern society are in some way shaped by the “Nice Guy” mindset.

What’s important to understand here is that “Nice Guy” is a frame. It’s a set of perspectives, beliefs, and principles that form a social operating system.

And the truth is, it doesn’t work.

Nice guys suffer.

They struggle to create the life, and the relationship they want.

Their friendships, romantic partners, workplace relationships all suffer too.

The truth is that people pleasing and manipulation strategies create shitty relationships.

Here's how this happens, and why.

How Nice Guys Suffer

A few months ago I started building a map of "common Nice Guy afflictions."  Very quickly the list grew out of control and I began organizing it into related groups.

Here’s a tiny excerpt of some of the suffering we see.

• Weak, shallow relationships
• > Difficulty forming deep connections, despite an overwhelming desire to
• > Most especially, romantic connections
• > Pedestal problems, imbalance in the adorer v. adored relationship
• Strong dependence on social validation
• > Approval-seeking behaviors
• > An over-sensitivity to rejection
• > Avoidance of confrontation
• > > Difficulty setting boundaries
• > Tendency to mimic the behavior of those around them
• > > Sometimes, discomfort in large groups, or in mixing friend groups. Worlds collide.
• > Need for approval by everyone
• > > Multiple personalities and behavior sets, depending on who they're with
• > Taken advantage of
• > > Bullied - emotional punching bag
• > “Victim hero” syndrome
• “Control freak” - Tendency to create rigid expectations and rules
• > Over-commitment to the expectations of others
• > Self-sacrifice
• > Covert contracts
• > > Strong attachment to “sunk costs” - investment fallacy
• Perfectionism
• Low self-esteem
• > Self-sabotage
• > Depression
• > Strong attachment to comfort and security
• > > “Pain is bad” mentality, difficulty pushing oneself
• > > Comfort-seeking behaviors
• > > > Porn addiction, recreational drugs, self-medication
• > > Clinginess to a sub-par life
• Workplace dissatisfaction
• > Responsibility imbalances and self sacrifice ( the victim hero )
• > Difficulty delegating responsibility
• > Discomfort working in closely-knit teams, due to issues with boundary-setting and responsibility-sharing
• > Burn out.
• Escapism & self-medication
• > Over-attachment to fantasy worlds
• > > Video games
• > > Social media
• > > Porn
• > > Recreational drugs & alcohol

And these are just a few.

Do you see any here that you relate to?

The 4 Pillars of the Nice Guy Mindset

If you look at the list above, you can see that things naturally begin to form groupings that imply some of the underlying causes.

Among the people-pleasers I’ve worked with - both men and women, I see 4 common characteristics that stand out to me.

When you read these, think about your own thoughts and behaviors, and those of people you know well. Consider how they interconnect, and the resulting life they create.

An over-valuation of comfort

Nice guys tend have strong comfort-seeking behaviors. They self-medicate a lot. They avoid confrontations. The hard life is not for them.

A nice guy embraces challenge and growth, as long as it's not painful challenge and growth. How many pro athletes, Olympic superstars and business elites do you know who are Nice Guys?

Probably not many.

The reason is that Nice Guys struggle with a core point- real growth requires real pain. Physical, mental, and emotional pain. The pain of rejection. The pain of failure. The pain of change.

This holds us back, because most of the great things we want are on the other side of a mountain of challenge and risk. That great relationship. That epic career. That superstar skill. Nice Guys see the mountain. and quit before they start. ‍

A bit of a “control freak” persona

When was the last time you were a passenger in a car, and the driver was going just a little too fast around corners? Did you reach up and grab the “oh shit” handle?

It felt safer, didn’t it?

But how much safety did it really add? Were you even 1% safer in the case of an accident?

Probably not.

Nice Guys seem uncomfortable with uncertainty and unpredictability. They seek to control everything in their world, including people - and even prefer the illusion of control to a hands-off approach.

This shows up in all sorts of situations-

• Difficulty approaching new people, or expressing interest, when the person's reaction is unpredictable
• Taking measured risks, even when they are low. Nice Guys have a tendency to over-inflate risks
• Self-delusion. The tendency to turn a blind eye to problems, like a failing relationship, and pretend nothing is wrong. Until it's too late to do anything
• Fantasy-building. Fantasies are as "controlled" as you can get, and Nice Guys find comfort in imagining a world that behaves according to plan

Nice guys have a desire to control the world and to try to force it into a predictable structure. But is that even a little realistic?

The Illusion of Control

If you are familiar with 3 circles of control, you’ll remember that your world is loosely organized like this;

1. Circle of control. The things you can actually control.
2. Circle of influence. Things you don’t control, but you can perhaps influence to varying degrees.
3. Circle of concern. Things you care about, but... you don’t really control much at all. Most relationships lean heavily into this category.

If you think about this carefully, you’ll discover there's not much in that center circle.

Relationships? No way.

Happiness? Meh.

Career success? Not really.

Health? Well... no actually.

The options we have in a given situation? Again, no.

In fact the only thing we can really control is our choices, and maybe our thoughts... some of the time.

That illusion of control is strong, isn't it?

That center Circle of Control is vanishingly small... so small, that it’s nearly non-existent.

But if you recall, Nice Guys dislike uncertainty, and the antidote to that anxiety is to grip the "oh shit" handle fiercely- even if it’s not going to steer the car at all, or protect you one bit in a crash.

Really, it's kinda useless. Yet... it gives a comforting sense of security, even if it’s entirely fake.

In more technical terms, this fallacy is known as an Internal locus of control, and it is an important aspect of personality psychology. See the Addendum for more.

What's more important here is to notice the connection to our next pillar.

The desire to control people, even in a fantasy world, leads to...

A tendency to create covert contracts

Let's be real. Other people are one of the least "controllable" parts of our lives, because - if free will exists - then they have it just as much as you.

Nice Guys face a real problem here.

Sex, romantic relationships, friendships, and social approval are all things we want- but all of these require other people.

At the same time, Nice Guys desperately want to avoid confrontation, boundary setting, and the risk of rejection.

So what's a Nice Guy to do?

The "solution" is a to base our relationships on a totally unworkable gray area we call covert contracts.

A covert contract is an unspoken agreement or expectation that one person has toward another, with the belief that if they fulfill certain actions or behaviors, the other person will reciprocate in some way.

The "unworkable" aspect is that these expectations are not openly communicated or agreed upon by both parties. Instead, it exists solely in the mind of the person who has created it.

The result? Disappointment. Frustration. Resentment.

Weak and fragile relationships, for everyone involved.

Insecurity & low self-esteem

I see this one so often, that I have determined that it needs to be included as a pillar of the Nice Guy mindset as well.

In some ways, it feels like an outlier, but I suspect it is more deeply connected to the Nice Guy mindset than we know.

Nice Guys often struggle with a feeling of "not good enough," combined with some level of chronic anxiety and depression.

Afterword

Maybe someday I'll make a Nice Guy scoring system to help people evaluate where they're at, and where they're improving.

For now, it's useful to evaluate the pain points in your life, and especially in your relationships. They'll point you to where the work is needed most.

For anything to change, you must first see the problem that needs changing.

And if you need help, you know who to call.