The Shamed Ambitious

…

This year of 2026 brings new challenges.

There’s a stickiness dissolving, and only enough momentum through orbit will eventually release me from gravity’s pull.

At some point, I think we have to reflect on all the change that has happened — and the change that hasn’t.

Side note: you do not have all the time in the world…

…

I’ve realized that power is something you choose to take a hold of, not something you find.

But it’s hard to see that when so much happens outside of our control. We sometimes convince ourselves of our powerlessness because there’s so much happening around us.

Is the world rotating without us?

It’s a very convincing argument for the slippery slope into nihilism and meaninglessness.

Here’s the thing though.

Meaning is made, not provided.

…

I’m not one to sit back and say that I have to be lucky, or that there’s too much outside of my control, or that what I want wasn’t meant to be.

I learned a long time ago, that responsibility of everything in my life is mine. And even when outside factors and circumstances need considering, it’s my responsibility to pivot and get past them.

Time is what we can’t get back, ever.

And it’s our job to realize that life isn’t about patience or waiting for the right moment.

It’s right now.

…

It’s weird to be 38 and not want what most people have.

And its not that I don’t want anything, like Diogenes.

It’s just the things that others prioritize less, I prioritize more:

Limitless self-governance, personal transcendence, fulfilling a legacy, building businesses, changing the world, traveling to the most sacred and remote locations around the globe, and saturating myself in a meaningful life.

And things that others prioritize more, I prioritize less:

I don’t want weekend dinners and camping vacations every summer. I don’t want a big nice house with a yard that takes 3 hours to mow. I don’t want hobbies that I only get to do in my garage, and fishing to get away from the family and work. I don’t want save for retirement and buy an RV to travel the states. I don’t want to watch Sunday night football and spend weeknights watching the latest episodes of the most dramatic tv show.

Meaning, Reader, is defined by you and only you.

I want what most people never realize or are too afraid to pursue. And I won’t apologize for that anymore.

And you shouldn’t either.

…

Insanity waits for those who ignore the whispers of their own soul.

We’re all looking for the answers to something.

And it’s more difficult than we realize.

Because true, authentic ambition means change in a way that goes far deeper than just how we act.

It’s a change in our mindset, our character, our personality, and how we show up(or don’t) with our loved ones, and how we show up for ourselves when no one is watching to find our answers.

EVERYTHING has to change.

It’s difficult.

And it often means creating distance between us and most of the people and community we know.

It’s the courageous step out of the garden of Eden and into the wild.

…

Committing to our ambitions changes us.

And if you’ve ever felt shame about being ambitious, or creative, or being ‘too much’ for society, now’s the time to accept:

Your ambition is necessary and needed. When we let go and give in to our true compass, we create space for others to do the same.

And it’s that resistance that is the only thing that is really keeping you from the real you.

Steven Pressfield said:

“Most of us have two lives. The life we live, and the unlived life within us. Between the two stands Resistance.” — The War of Art

…

The last 10 years for me has been about asking questions.

From the start, the overall theme was: Who am I?

The question itself is so philosophically large, it’s amazingly daunting.

Where the f*ck do you start??

Believe me, I asked the same thing.

It has to be narrowed down by testing your theories and your character.

How do you pivot when things go wrong?

How do you change when you realize your direction isn’t quite right?

What do you do when people around you question your intentions or belittle your craft?

Theory is never enough. It’s the science of action that gives you more breadcrumbs.

Theory and action are the duality of all success, and you must do both, even when it sucks.

That’s the resistance.

…

What I needed to know the answer to came from a frantic realization that my future had been pre-determined by a type of common “coma”.

A hypnotic trance I didn’t realize I was under.

The Matrix, in a sense…

I was conditioned by my upbringing and of a society that never promoted self-discovery.

…

How could we have known?

It’s this thing that I’ve found which was made — consciously or subconsciously — by society, culture, and industry that keeps us as far….and I mean far….away from the most impactful and fulfilled human we can be.

And I had my wake up call when someone I thought was my “forever” asked me to commit to the next level of life. An instance that shed all of my falsehoods in the moment, and revealed to me what I’d never understood, but deeply and darkly felt:

“I have no idea what I want my life to look like…and it looks alarmingly similar to life that fills me with regret and emptiness.”

I knew what I would have been committing to was a mask I couldn’t handle wearing.

…

I think my whole life since I was 28 has been:

What does it mean to be a man?

I tore myself apart trying to find it.

To find such answers, one must question all of the things in character.

Responsibility.

I no longer got to have a bias. I no longer got to blame women for not seeing me, men for judging me, government for taxing me, and society for not understanding me.

…

Beyond victimhood is humility, I think.

We have to step down from wanting to be recognized as a pained human, and see that strength is not in vocalizing how much we’ve been wronged, but in taking responsibility of how we’ve wronged ourselves.

And the real test is how we show up when that happens.

Can we accept it?

Can we take the burden of it?

…

Finding ourselves means making ourselves a priority.

I spent so many years giving everyone else space, thinking that I would be considered and loved endlessly for never stepping on anyone’s toes or taking up space that would put them in a shadow.

And so I had to return from taking on all responsibility, with a new acknowledgement that I am only responsible for myself.

Not all of humanity’s emotions, feelings, shortcomings, and pain.

I had to join responsibility with self-pride.

In a sense, we have to become big enough to cast a shadow, and let others worry about stepping out of it.

…

There’s a difference between shame and guilt that I heard in conversation:

Shame is the thing we do when we unfairly judge ourselves for being and expressing who we are…just because it didn’t get embraced by the world.

(Learned ideas often from poor family dynamics and demanding social standards)

Guilt is what we feel when we actually do something that is morally wrong or inconsiderate.

Shame is a reaction of insecurity.

Guilt is what keeps us correcting ourselves after things we did we know weren’t right.

…

There’s something very disturbing when we feel wrong or ashamed about who we are at our core. When we hide our true self for the sake of others.

There’s something very suppressed when we consider that our insecurities and doubts are what we accept as true.

You should never feel wrong about your ambitions and aspirations, your beliefs and spirituality, your work ethic, your style, and your creations.

And if you do, ask yourself what you’ve spent most of your life keeping hidden.

…

Who’s approval have you ever needed besides your own?

And how long before you stop assuming that you need it and decide to show up and pursue your life?

I’ve found that defining man is the wrong question:

Instead of, “What does it mean to be a man?”

The right question is and always was:

“What does it mean for me to be a man?”

And the difference between the two would seem obvious.

Unless you’re me.

…

That thing your after is the thing that no one else will be able to tell you.

And it’s probably going to be the most challenging thing you ever chase.

Which means the question of what it means to be a man or woman to yourself is more justified and cataclysmic to your positive change than asking society to answer it for you.

It’s not about the key that changes all people.

It’s about the key that changes you.

…

The best version of ourselves doesn’t lie just in the questions we ask of and about the world, but how we answer them.

And that means answering them with ourselves in mind.

It means shedding our shame.

It means showing up deliberately and with conviction.

And without first worrying about how someone else will take it, because it’s not your responsibility to make sure they’re comfortable with it…

…

Life doesn’t change unless we can show up with pride and optimism first, not everyone else’s feelings.

Ambitious without shame.

Authenticity without shame.

Creativity without shame.

Action without shame.

Love for ourselves and our aspirations….without shame.

…

So…

Will you remove your veil?

Will you stand up for yourself and your beliefs and your creativity?

Will you stop considering everyone else besides yourself?

Will you stop suffocating who you really are?

Truth and Love, Reader.

If you like my writing and the things I question, you might(I mean…probably) also like my newsletter. If not, you can still get all my stories here on Medium!

Substack is where you can subscribe to my newsletter and get not just my medium stories, but chat with me directly, have access to all of my content in one place, and have access to The Art of Questioning audio. Only at https://zackaryhenson.substack.com

There are so many great stories on Medium! If you want to have access to some of the best writing by thousands of creators, start your membership with the link below, which will also support my writing.

Remember…question everything! https://zackaryhenson.medium.com/subscribe