Years of Destroying What Actually Works | 017

I’m writing this from my usual corner at the coffee shop. Back to the wall, watching everyone come and go. And I keep starting this newsletter different ways because I don’t know how to tell you about the pattern I finally saw this week, at the end of my September experiment.

Actually, that’s not true. I know how to tell it. I’m just scared to.

The thing is... I’ve been having the same conversation with myself for nine years. Not the productive part of me. The other part. The one that just watches. That notices what’s true while the rest of me is busy building.

And this week something became clear. I’m still not sure what to do with it.

So let me try to explain “the loop”.

I see patterns everywhere. Get excited about possibilities. Build systems to capture them. Push harder. Ignore the back pain and migraines. Push through the chest tightness. Just...one…more…optimization.

My body trying to get my attention and I keep treating physical symptoms like they’re interrupting the most crucial work in the entire world.

For three of those nine years I basically checked out. Couldn’t see patterns anymore. Just went through the motions while some part of me tried to recover from how hard I’d been pushing.

I thought I was broken with what I called a “squishy brain”. What was actually happening... that watching part was staging an intervention. Forcing me to stop by making it impossible to keep running.

Then I’d recover enough to start again.

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What finally broke the loop

Two people paid me $150 for witnessing conversations this month. One immediately booked a followup.

I’m back at the coffee shop when I get the second booking confirmation. And my chest gets tight. Like physically tight. The migraines started coming back. Like I wrote about in early September in [What Exhaustion Actually Teaches].

But this time I could hear both parts at the same time.

The part seeing all the possibilities, wanting to build systems and scale this and make it professional.

And the part that’s been trying to get my attention for nine years saying “you’re about to do the thing again.”

I’m sitting here and I can feel it. That specific frenetic energy that means I’m ignoring what’s actually working to chase what looks legitimate.

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The part that matters

Wait. I need to back up and tell you something else first.

September. I threw something at my thirteen year old daughter during an argument.

It was small and didn’t physically hurt her but that’s not the point.

The point is... I don’t know. The point is this wasn’t just about business anymore. The loop I’d been running for nine years, it was spreading again, aggressively everywhere.

I contacted my former therapist from my three years stuck on the couch. Got the help I’d been avoiding this year. Started treating the anxiety symptoms as information instead of disease.

Emotional and physical stability had to come first for myself and my family. That seems obvious now. It wasn’t obvious while I was in it.

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What keeps showing up

Anyway. Back to the coffee shop. Staring at these booking confirmations. Chest tight.

And I’m realizing... every single person who hired me did it for the same reason.

Not my frameworks. Not my systems. Not my ideas about their projects.

They wanted to be seen. They wanted me to reflect back what they couldn’t see themselves.

One friend called it “arbitraging people’s thoughts.” Another said I was “extracting trapped value from their own thinking.”

And I keep feeling... what if that’s the actual work? What if witnessing itself is the professional competency?

My shoulders are tight just typing that because it sounds too vulnerable. Too uncertain. Too much like I’m just being myself and charging for it.

But that watching part keeps pointing to what actually happened.

I launched Corporate Dropouts in September 2024. A weekly community where people showed up to have supportive conversations about life after corporate. I wrote about starting that in [Welcome to the Escape Plan]. Ran it for six months. People loved it.

And I dropped it because I couldn’t figure out how to optimize it. I talked about that pattern back in March in [Can I Trust Myself to Keep Going?]. Got frustrated that people just wanted me to witness their journey instead of optimizing it for them.

Then I tried a Wayfinding Group with actual structure. As I wrote about in August in [I Thought I Was Gandalf]... people got frustrated when I added all frameworks and systems to their exploration. They wanted the witnessing, not the “expert” guidance.

Over the summer I wrote about how [I Opened My Calendar to Complete Strangers]. People loved those connect calls. They kept showing up.

Corporate Dropouts worked until I tried to optimize it. Wayfinding frustrated people when I added structure. Summer connect conversations worked until I tried to force my ideas into them as I wrote about last week in [Choosing Connection or Money]

The moment I try to package witnessing, I lose what makes it valuable.

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Learning to listen to both parts

I’m looking around the coffee shop now. People working on laptops. Having meetings. Doing the normal business things.

I just took a breath.

There are two parts of me. The part that sees patterns and possibilities everywhere and tries to capture them. And the part that watches, that notices what’s actually true.

For nine years the first part has been drowning out the second part.

I’m learning to trust the watching part more than the possibilities part.

This means building something I can’t fully explain. Around emergence instead of methodology. Around relationship instead of curriculum.

Positioning ongoing uncertainty as the feature, not the bug.

You’re probably thinking this sounds like terrible business strategy. And yeah, every instinct I have about how business works says this won’t scale, this isn’t professional, this isn’t legitimate.

But the people who’ve actually hired me haven’t wanted my certainty. They wanted permission to live in their own uncertainty without shame.

And that watching part keeps saying “this is sustainable”. “This honors both parts. This doesn’t require you to choose between seeing possibilities and staying regulated.”

Not perfectly. I’m already catching myself starting the loop again at the end of this September experiment and having to course correct.

Sometimes it takes months of hosting corporate dropouts, guiding wayfinders, recording podcasts, publishing newsletters, showing up for connect calls, and yes, getting paid for witnessing conversations… over a year of reckonings, to finally hear what’s been trying to get your attention for nine.

My body knew before I did.

That watching part knew before I did.

Probably some of you knew before I did.

I’m learning to listen... now.

P.S. This Wednesday I’m sharing all about my September experiment with Witnessing Conversations, at the School of the Possible Open House. October 8th, 11am-12:30pm Eastern Time. It’s not a presentation, more like a gallery opening where we show what we’ve been working on. Come hang out if you’re curious. RSVP here

P.P.S. I’ve got spots open for more Witnessing Conversations in October if this resonates. Not because I have it figured out. Because I’m willing to sit with you while you figure it out. BradDid.com/conversation