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Issue #35: Nice Guy or Arsehole? The Real Question

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Mike, let me introduce you to the question so many Nice Guys get wrong.

Nice Guy or arsehole? 

They answer this incorrectly because it’s the wrong question to ask.

I’ve talked about ‘black and white’ / all-or-nothing thinking in this newsletter before.

We guys are shockers for it.

If it’s not one thing then it must be the opposite.

If it’s not yes, it’s no.


Sometimes it’s both and…

We crave certainty.


We want a detail we can focus on and get to work on – fixing, doing, creating, achieving a result.

It’s hard-wired in us to find a detail to apply ourselves to, from hunting to protecting to parenting.

We balls it up now by applying it to almost everything even when it’s glaringly inappropriate and not working for us.

Health, fitness, diet? All or nothing.


Work-life balance? Same 🤷


Drinking? Shitfaced or sober.


Giving a fuck about what others think? Obsessive or #zerofucksgiven

We mess up what are generally nuanced things.

But nuance needs us to play in the grey space.


And when you’ve spent a lifetime in the black or white, grey feels daunting.

It IS the unknown.

Yet – cheese incoming – when we learn to live and play in the grey, life has more COLOUR.


The voice of your insecurity

It couldn’t be truer for Nice Guys – who, as a rule, tend to outsource their sense of security and safety in the world to others.


That means chasing, needing, and surviving off the approval and validation from the external world.

If I don’t have that… well, I have no worth.

The nice guy thinks if he isn’t in his head about what others think of him he needs to not care at all about what anyone thinks of him.

This is expecting yourself to be inhuman.

Of course we need to care about what some people think some of the time.

Discerning when and who and why – that’s the grey space.

Where uncertainty exists, the nice guy resists.

He will avoid it. Move away from it.

Ultimately, it’s because he has a deep sense of uncertainty within himself. So, he chases certainty from the world – i.e. belonging – knowing he is liked and safe in the world.

This way of being is reinforced each time a nice guy contemplates the alternative.

He asks this poorly thought out black or white question:


Do I be a nice guy or an arsehole?

It leaves no room for anything different and continues to paint himself into a corner of “If being an arsehole is my option, I’m best to remain a nice guy.”

It’s kind of a cozy-sounding justification not to change.

It lacks nuance, courage, and any kind of mature thought.

Nice Guy and Arsehole are two opposing ends of a long spectrum.

However, when the nice guy believes this is ‘one or the other’, he doesn’t have to take any courageous action.

At some point, you must squash the arsehole idea – and explore the nuance.

Setting a boundary – not an arsehole.


Saying no to something you don’t want to or can’t do –  not an arsehole.


Asking for what you want – not an arsehole.


Being honest with someone –  not an arsehole.

Honouring your needs, looking after yourself, initiating an uncomfortable conversation,  communicating something upsetting, letting someone have their own emotional experience without trying to manage it for them or take it away –  not an arsehole.

I could go on there.


This is a small list of things a nice guy will avoid for fear of being seen as an arsehole.

Selfish, self-centred, not nice.

Yet, as we know – unless you’re new here – being nice simply to be seen as nice (conditional kindness) is not nice. It’s a subtle form of manipulation that serves your insecurity, not the person you’re being nice to.

Looking after yourself, honouring your needs, wants, energy, and time – are based in self-respect.

And this is what so many nice guys struggle to choose and embody.

When you continue to believe that the ONLY alternative to being a nice guy is to be an arsehole, you continue to deceive yourself. And others.

The painful irony for so many nice guys is that they often let things slide, sweep issues under the rug, accommodate and absorb, overload themselves and do their best to maintain a calm exterior.

Until… BOOM, there is a straw that breaks the back – and some kind of overreaction happens.

The kind of arsehole inappropriate behaviour they fear just blurts out.

Like the nice guy who finally tells people to get fucked – furious at them for bumping up against his weak or nonexistent boundaries.

How dare someone ask me something and make me communicate and enforce a boundary of MINE!

He fires his internal disappointment at them.

The answer here is courage and self-respect.

It’s a willingness to let other people be annoyed at you, disappointed in you, pissed off even.

Without intentionally setting out to do so.

This is such a vital difference – a willingness to disappoint others vs intending to disappoint them.

This is the wrestle for the nice guy.

He is so uncomfortable with people disliking him, being annoyed, disappointed, pissed off at him, and having some kind of negative emotional experience that can be attributed to him, that he will abandon and disappoint himself time and time again to avoid it happening.

The long-term consequence here is an eroded soul, a weak spirit, and one frustrated individual.



The Four keys to communicating with courage


You are not responsible for how someone feels or what they choose to do with your words.

What you are responsible for is how you communicate and how you act.

As long as you communicate with the following four things, you can put down responsibility for their reaction and pick up your self-respect.  Your integrity. Your backbone.

Start letting people think and feel what they like – especially about you. It might sting, but you can handle that. As long as you respect yourself. That’s what matters more than anything.

These 4 keys for communicating challenging things are:

  • Respect
  • Honesty
  • Kindness
  • Compassion

If you reflect that you have communicated in this way, you can feel safe that you’ve done your part, now it’s up to the other person how they interpret that, what they do with it, and how they feel.

Remind yourself:


“That is not mine. I have to let them have that and be ok with how they view me or feel towards me.”

Develop the ability and willingness to piss people off – without the intention to do so.

In a relationship – if you cannot handle your partner’s disappointment, if you can’t be ok in the presence of her being annoyed at you, you will always be responsible for a lack of safety in the relationship.

You’ll constantly work to manage her state – at the detriment of your own. And your integrity.

That weakness you and it weakens a relationship.

You need to be able to piss your partner off.


This doesn’t mean intentionally pissing her off.


It means being willing to stand for something even if it pisses her off.

Be willing to maintain integrity, act from self-respect even at the risk of her being disappointed or pissed off in the short term.

Because if you can act from this place, it will provide a sense of safety, something to respect and depend on in the longer term. Which is infinitely more valuable in a relationship.