Learning What Courage Actually Costs | 012
The simple math I'd been avoiding
Wednesday at 10:07 AM, changed something.
I was on a call with a mentor, and he immediately called out what he was seeing, "I got a different vibe from your last email than the one you're putting off right now."
He was right. I'd already been wrestling with the question I'd asked him the week before, "How do you build something sustainable around something that refuses to be systematized?"
Simple Math I'd Been Avoiding
We talked through my summer of free conversations. Sometimes 10 one-on-ones a week, each one energizing me in ways I'd never experienced before.
When he asked how this connected to making money, I gave him some vague answer about trusting the universe.
"If you want to have a sense of what value you're providing, one of the only ways you'll learn that is by asking people to pay for it," he said.
Then he asked, "This is just simple math. Let's say you had 10 conversations a week, and you wanted to make $500 a month. That's only $12.50 per conversation. Do you think it's worth $10 to sit and have a deep conversation with you Brad?"
Simple math. Embarrassingly simple math that I'd been avoiding because I was too busy trying to systematize concepts like “emergence” and "witnessing".
Why I Was Avoiding Simple
"Create an Office of Deep Conversations, $10. And see what happens," he suggested.
The simplicity was terrifying. No safety net of sophisticated frameworks. Just pure vulnerability about whether my gifts have market value.
But as we kept talking, something shifted. His $10 suggestion broke through my resistance to charging anything.
And once I could imagine people paying $10, I started wondering what 90 minutes of genuine witnessing was actually worth.
"So why do you even need to put a name to what you do?" he pointed out.
He was right. I'd been avoiding the simple experiment because I was afraid it wasn’t complex enough to be valuable.
Measuring Curiosity
Near the end of our call, my mentor asked what I wanted to learn from this experiment.
The answer came to me immediately, "Can I still find deep connection with someone even when I'm charging them?"
And just like that… my metrics shifted.
From the predictable marketing funnels I’d found myself drooling over for years… to whether someone books a session for genuine connection.
The Email I Almost Didn't Send
That night, I wrote the scariest email I've ever sent.
"I've been having conversations with strangers all summer. Sometimes 30 minutes, sometimes 3 hours. No agenda except showing up honestly and ready to listen.
I'm scared to put a price on this because it feels like commodifying something that matters so much to me. But I also can't do it for free forever.
$150 for 90 minutes feels both too much and too little. I'm starting with 5 people in September to see what this actually is.
Does this make sense to you?"
The $10 breakthrough gave me permission to charge something. But my instinct said 90 minutes of witnessing work was worth more than coffee money.
$150 felt both terrifying and honest.
My finger hovered over send for twenty minutes. Every marketing rule screamed this was wrong. Too vulnerable. Too uncertain.
But my mentor's voice echoed: "And see what happens."
So I sent it.
What Zero Bookings Showed Me
48 hours later… zero calendar bookings.
But something more interesting happened. Three people wrote back. Not to book sessions, but to think alongside me.
One asked, "What happens after someone has a successful conversation with you?"
I had no answer. I'd been so focused on figuring out what these conversations are that I'd never considered what comes after someone feels truly heard and seen.
The zero bookings are information.
They're telling me something about timing, relationship, and the difference between quick hit transactional thinking and slow transformational work.
Here's what I'm discovering about a business model that might actually honor my approach…
It feels like connection, not conquest.
It trusts natural timing instead of manufactured urgency.
It creates relationships where some people naturally want to pay for deeper witnessing work.
No avatars. No copywriting. No lead magnets. No sales funnels.
Just genuine expression drawing the right people naturally.
My Body's Response
Thursday and Friday this week were spent working through what it feels like to have that level of vulnerability out in the world.
My nervous system cycling between excitement and terror. Checking email obsessively, then forcing myself to step away and breathe.
Here's what these feelings are teaching me in the slow burn of this experiment.
When you share something you're genuinely uncertain about, people don't need you to have it figured out.
They’re more interested in how you are figuring it out.
This week someone in my online community mentioned that last week's vulnerable newsletter "cut through the noise" for them even though they don't usually follow my content closely.
That feedback confirms something that I’ve been discovering…
My uncertainty is a feature, not a bug and resonates more than polished expertise.
I also had a connect call with someone exploring a corporate transition. Ten minutes in, they started sharing deeper struggles about what they really want to do next.
Witnessing work is still hard for me to explain, describing it as "having things emerge." But they immediately understood the value and asked for the link to book a session to go deeper when they’re ready.
Providing my value comes from witnessing questions while they're still forming.
This is radically different from the corporate world, where uncertainty was something to hide, manage, or spin into confidence. Where admitting you didn't know something felt like career suicide.
But in the space after corporate, uncertainty has become a doorway.
Not knowing has become an invitation for others to not know alongside me.
The Real Experiment
This experiment isn't just about making money. It's learning about what I have to offer. It's about finding out whether deep connection can survive the introduction of money?"
I'll let you know what I discover.
P.S. Some of you reading this might be the ones who need someone to witness you but aren't ready to recognize that yet. Others might forward this to someone who needs permission to be seen without judgment.
What do you think would happen if we let people witness our uncertainty instead of waiting until we have it all figured out?
Interesting piece, Brad. Thanks and good luck as you continue to explore.