Building Courage
How to Build Self-Trust in a Weekend
A story about fear, embodiment, and the 30-pound boa constrictor that taught a room full of leaders how self-trust is actually built.
This is a real 30-pound boa constrictor snake.
And in just a second we’re going to wrap it around someone's neck.
Actually, around several necks.
One at a time.
While they’re blindfolded.
In a secluded mansion in the vineyards of Southern California.
If you’ve been reading my newsletters for a while, this is far from the craziest thing I’ve sent to your inbox.
But still…it probably deserves a bit of explanation.
Setting The Stage
This was Memorial Day weekend 2023 and I was leading a retreat entitled *Power & Flow*.
It was 4 days of intense eye-opening exercises that about a dozen leaders signed up for who felt like they weren’t getting everything out of their lives that they wanted.
As I was putting together this event, I was reflecting on what stops people in life and found one thing to be the common denominator:
Fear.
If an artist is afraid his music won’t sell, it’ll be hard for him to find flow state during a studio session. If a middle manager is afraid of his boss, he won’t muster the courage or power to ask for a promotion.
For most people, fear isn’t some rare dramatic event.
It’s not a snake.
It’s not a burning building.
It’s Tuesday.
It’s the email you don’t send.
The conversation you avoid.
The business you keep “almost” starting.
The relationship you keep negotiating yourself into staying in.
The problem isn’t that fear exists, it’s when it starts making your calendar.
Choosing your relationships.
Writing your emails.
Setting your prices.
If you live in fear, you will not live fully.
Full stop. Period.
Everyone knows this, so the people who signed up for this retreat weren’t there to find out how to be fearless, they were there to learn how to respond to it.
Four Days of Fear
Now, this retreat was the exact opposite of a corporate seminar.
No fluorescent lights.
No sandwich trays.
No Zoom breakout rooms.
These people came because they wanted to change their lives.
And my belief about change is pretty simple:
At some point, if you want a different life, you have to give your body a different experience.
Something your body remembers.
So, throughout the weekend they were confronted with unexpected battles with fear — whether that was being stuck in a dark forest at 4am or doing improv comedy in front of a live audience.
For some, the scariest part of the weekend was just being honest about how far away from their ideal life they were.
And when fear threatened to make their choices and reinforce their habits, we ran them through breathwork techniques, habit building frameworks, and psychological reframes that they could call on whenever they needed.
We didn’t want them to just see what calm courage looked like, we wanted them to know what it felt like.
A lot of the techniques were new for these folks — but none of them mattered unless they worked.
So we had to put them to the test.
The Snake
On the last night of the retreat, we blindfolded them and one by one we told them they were about to experience the scariest moment of the weekend.
And before the snake came out, I reminded each person to become the version of themselves they had been building all weekend.
Not in theory.
In their body.
The version that breathes.
Stays present.
And chooses.
Then we put the snake on them.
And while everyone had their own response, one man’s reaction stuck out to me in particular.
He’d been scared of snakes his whole life.
He’d never touched one and never wanted to.
But during the exercise, with this giant boa still sliding across his chest, he said:
“I feel at peace.”
I asked him why.
“…because I trust myself.”
That’s the sentence.
That’s the whole retreat.
That’s the thing I care about.
Self-trust is not built by telling yourself you’re powerful.
It’s built by accumulating evidence.
You said the hard thing.
You took the risk.
You stayed present and you didn’t let fear drive.
And now your body believes you a little more.
That’s why I design experiences this way.
Because I’m not that interested in giving people more concepts.
None of it matters if it doesn’t change what you do when you’re afraid.
When the snake shows up in your life — literal or otherwise — I want some deeper part of you to recognize the moment.
That you’ve been here before.
You know how to breathe.
You know what to say.
Because one day, the snake will not be a snake.
It will be your partner saying the thing that hits the wound.
It will be your boss questioning your value.
It will be your bank account looking thinner than your ambition.
It will be the moment right before you ask for what you actually want.
Can you breathe then?
Can you choose then?
That’s power.
That’s how you stay in flow.
Not being calm because nothing is happening.
Being calm while something is.
Key takeaways
- Self-trust is built through evidence, not affirmations.
- Fear is not the problem. The problem is when fear starts making your decisions.
- Your body needs lived experiences that prove a new identity is possible.
- Courage does not mean waiting until you feel calm. It means learning how to stay present while something is happening.
- The snake in your life may not be a snake. It may be a conversation, a risk, a price, a relationship, a creative leap, or the moment right before you ask for what you actually want.
Questions this insight opens
How do you build self-trust?
You build self-trust by repeatedly giving yourself evidence that you can handle the truth, take meaningful action, and stay present under pressure. Self-trust is not something you think your way into. It is something your body starts to believe after you prove it to yourself enough times.
Can self-trust be built quickly?
A single powerful experience can create evidence, but lasting self-trust comes from repetition. One weekend can show you what is possible. The rest of your life becomes the practice of proving it again in smaller, ordinary moments.
Why does fear make it hard to trust yourself?
Fear narrows your attention and tries to protect you from risk, rejection, embarrassment, or discomfort. When fear starts making your choices for you, you stop collecting evidence that you can handle life.
What is embodied transformation?
Embodied transformation is change that your body has experienced, not just an idea your mind understands. It is the difference between knowing you should be courageous and having a lived memory of staying present while afraid.
How can coaching help build self-trust?
Coaching can help you notice where fear is quietly making decisions for you, clarify what you actually want, and create practical experiences that build evidence. For many creative leaders, founders, and high-achievers, self-trust grows when insight becomes action.
If this insight named something you’re navigating in your own life or leadership, explore coaching with Imari.
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