Issue #73: How to Stop Being Afraid of Asking

Today I want to ask you a question.

Possibly a series of questions.

Mostly it’s this:

What do you enjoy from me in these newsletters and what would you like to see? More of the same, or new/different/something else, but really, really specific?

Or perhaps worded differently:

How can I help you?

I am happy to keep writing these on the topics I see come up time and time again, in the men I work with, in the men that reach out to me, and the partners of men.

Ultimately, though, I write these to support you.

I write these to provide insight, advice, guidance, and some loving challenge to help you move towards the man you want to be and the life you want to have.

If I can tailor that in some way to be more useful to you, then, well, the simplest way to ensure that is for you to ask me for what you want.

Asking for what you want

This is something I used to struggle with doing. Struggle.

I had this bullshit insecurity belief and fear that didn’t want to put people out, that “how dare I impose on others” - mostly a deep fear of people thinking ill of me. Rejecting me.

Underneath most of this was a subconscious belief about what I thought I deserved.

You might have this too.

The unease at burdening others or “putting them out” is driven by an insidious underlying idea: “that you don’t deserve to”.

Of course, it is usually bed mates with a mix of jealousy at those who can ask for what they want, with a ‘how dare they!?’

This reflects a deeper idea about yourself and what you think you deserve.

And the thing about your subconscious is that it will ensure you always act in ways that see you only ever get what you think you deserve.

So if you think you don’t deserve love, happiness, joy, belonging, ease as you are now - without earning it or being different, say - you won’t act in ways that see you get them.

Not consistently, with confidence and conviction.

You will deny those things. You’ll sabotage. You’ll hold yourself back from the things you want in some way.

You’ll also struggle to ask for what you want.

You probably have no idea what you actually want.

I’ve been that man. It sucks.

Putting so much into simple interactions, all because of my own shit.

My desire for you is to courageously ask for what you want; in life, in love, in business.

And in here, with me.

If I can make these emails more specific for you, if you’d like certain content, or for me to talk about the ongoing issues in the Middle East - ask.

One thing that is vital when it comes to asking for what you want is having the courage the ask.

The next, importantly, is the willingness to hear no.

You can ask. Someone can say no. End of.

Because, no, I won’t be talking about the geopolitics of the Middle East.

And I might not be able to deliver on some of your asks. That shouldn't stop you from asking.

The possibility of hearing ‘no’ shouldn’t stop you from asking.

Especially if you’re a man who has stunted your life by never asking for - or thinking about - what you want.

What have you got to lose?

Whatever it is, whoever it is, you can handle heating ‘no’.

If this resonates with you, if you’re someone who has let insecurity run too much of your life to the point that you struggle to ask for what you want, today I set you the challenge of doing exactly that.

This helps build confidence, self-trust, the ability to handle rejection, and sovereignty. Agency.

Do it in the smallest of ways, from asking me here to someone passing you the salt instead of getting it yourself.

The small helps build to the bigger.

Practise the bigger ways too.

You can handle hearing ‘no’.

Be it with me here or in your life, go do this - be in the practise of getting better at it. You can do that. For certain.

What else is happening?

I’ve spoken in here at length about many things, one of those being the work we do with men - more specifically, Nice Guys - in the Everyday Legends Academy. Helping you become an Unfuckwithable Good Man in life, love, and your work.

That is still rolling and helping men transform their lives. It is fucking great.

In fact, we just had our 36th group of men graduate.

I’ll tell you one thing I LOVE - seeing men move, first off, into the work. Taking the step into it when they can feel nervous, resistant, apprehensive, even. Choosing to trust themselves, open themselves to being coached, to feedback, direction, and growth.

When we commit to big, challenging things, we are immediately brought into confrontation with ourselves. With our edges, our insecurities and fears and all the bullshit beliefs we hold about ourselves, the world around us, and our place in it.

In that moment, you are invited to step out of the limitations that you have been honouring and into growth. Where expansion is necessary, and where the steps to get there emerge after you step.

Never before.

When the guys in ELA do that, man, then we can do the work, make the changes, do the transformation.

Anyway, spots in our next intake are still open (but closing soon).

I say that point to say this: coming up early next month, I am facilitating a BRAND NEW INITIATIVE.

And I am pumped about it.

It is called the HUNT & GATHER: An Adventure & Leadership Camp for reforming Nice Guys.

In short, me and one of my Inner Circle coaching guys - a vastly experienced hunter - will be taking a small group of men into the NZ wilderness.

They will be hunting deer and being stretched in all new ways to their edges and into new levels of personal leadership.

The hunting alone is an epic experience.

We will also utilise the many ways nature and an adventure like this provide us to see what the guys are made of, and test them mentally, emotionally, and physically.

An initiation of sorts.

Moving from the standard day-in-a-life and old personal agreements and patterns, to an arena that presents countless opportunities for them to meet themselves, and encounter growth and the man they want to and can be.

This one is sold out.

Our dates in the first half of 2026 are filling up quickly.

If this sounds like something you might be interested in, respond to me here and … ask.

Mike