We don’t struggle with making decisions.

We struggle with trusting ourselves enough to act on what we already know.

Whether it’s applying for a job that feels out of reach or committing to a hobby you’re pretty sure you’ll love, overthinking often keeps us from experiencing the joy that’s already available to us.

Every week, I explore one small but meaningful shift I’m making in how I live, work, or create—and what it’s teaching me in real time.

This week, it’s self-trust.

The Back Story

Confession: I’m a recovering overthinker.

I can take a single decision and replay it endlessly—every possible outcome, every worst-case scenario—in hopes of making the “right” move.

But the people who actually move forward aren’t the ones with perfect clarity.

They’re the ones willing to act while things are still uncertain.

Somewhere along the way, I stopped trusting my gut and started outsourcing my belief—to clients, friends, mentors. People who weren’t actually living the life I was trying to build.

Toward the end of 2025, I decided to try something different.

Instead of waiting for confidence, I started building self-trust on purpose.

A quick ad break

For a long time, my own tiny experiment was simply… hitting send.

No perfect branding. No master plan. Just showing up in people’s inboxes consistently.

That one choice changed everything—paid speaking gigs, coaching clients, art commissions, and eventually the confidence to quit my full-time job.

This workshop is for multi-passionate creatives who know they want to start a newsletter, but keep overthinking it.

Inside, we focus on clarity over polish, momentum over perfection, and actually sending your first two emails to real humans.

It’s simple. It’s grounded. And it’s designed to help you stop circling the idea and start building trust with yourself through action.

If your next tiny experiment is finally hitting send, this might be for you.

→ Launch the Damn Newsletter Already

Currently $27. No fluff. Just forward motion.

The Framework

Self-trust doesn’t come from big, dramatic leaps.
It’s built through tiny experiments that create evidence.

Here’s how I think about it:

1. Define the direction, not the destination.

You don’t need a five-year plan. You just need a general pull.

What are you curious about? What do you want more of?

Those intuitive nudges are the universe—or God—or your future self offering a quiet hint about how to move forward.

2. Design an experiment that feels slightly uncomfortable—but safe.

Not terrifying. Not paralyzing. Just enough friction to stretch you without shutting you down.

If the experiment feels small, that’s the point.

Momentum grows when your nervous system learns that trying doesn’t equal danger.

3. Treat the result as information, not identity.

The goal isn’t success. It’s clarity.

What did you learn? What felt energizing? What drained you?

Every outcome is just feedback—and feedback is how self-trust compounds. 

A Real Life Example

Growing up, I was terrified of public speaking.

I have a lisp and I stutter when I get too excited.

But I was obsessed with the idea of standing on a stage and sharing ideas with confidence—like Eddie Murphy.

If I’m being completely honest, my lifelong career plan was simply: be Eddie Murphy.

So I didn’t start with a keynote.

I tried debate. Hated it. Quit.

I acted in a few plays. Struggled.

Then I became a TV anchor on my school news network. Mildly embarrassing, but incredibly fun.

In college, I hosted events—terrified, but doing it anyway.

After college, I volunteered for every speaking opportunity I could find.

And eventually, public speaking became part of my job—as a Creative Director and on 70+ stages so far.

The biggest one still surprises me: four thousand people at an AIGA conference.

None of that happened because I suddenly felt ready.

It happened because each experiment made the next one feel possible.

Additional Thoughts

A Few Things to Remember in Your Self-Trust Era

1. There are no permanent wrong decisions.

You can always adjust once you have more information. Learning by doing beats perfect planning every time.

2. Confidence is a byproduct, not a prerequisite.

You don’t build trust by waiting. You build it by taking deliberate, daily action.

3. You already know more than you think.

The experiment isn’t about proving anything to anyone else.

It’s about proving to yourself that you can respond to whatever happens next and continue to adapt and grow. 

If this idea of building self-trust through tiny experiments resonated, I shared a simple prompt inside the Reset Society to help you try one this week.

It’s a low-stakes way to name your curiosity, take a small step, and see what happens.

If you want to participate—or just be in the room with people doing the same—you’re welcome to join us on Skool.