Big Self School

You're not broken. You're between stories. With an AI companion by your side.

I help leaders navigate the threshold between what was and what's next — through psychology, consciousness, and the Enneagram.

08/10/2026

I built (with lots of help from Claude) a calculator to estimate what dysfunction actually costs a team each month.

I was sure meetings would be the biggest number. Everyone complains about meetings.

For a 13-person org, meetings came out at $2,300 a month.

Misalignment came out at $17,188 b/c it's a compounded cost.

That's 63% of the total — more than meetings, burnout, and turnover combined.

Which makes sense. Misalignment starts as a bad meeting, but continues for weeks and months.

When two people hold different definitions of what "done" is, you don't just lose the meeting, you lose the six weeks after it. The work gets built, delivered, discussed, rejected, rebuilt, etc.

Nobody was lazy or uncommitted. It's just that everyone worked really hard on slightly different things.

And most of that isn't a process problem necessarily. It's people not understanding how other people work. Even how *they* work.

Run your own numbers at the Cost of Dysfunction calculator in the comments.

08/07/2026

Every leader has a signature strength. And every one of those strengths has a shadow.

In fact, you don't get the gift without the shadow b/c they're the same thing.

That's most of what I do in coaching. Not fixing what's broken, but helping ppl see the flipside of their own gift, and then choose, in real time, when to lead with it and when to put it down.

It's tender work. It's also a relief, because the thing you've been worried might be a character flaw usually turns out to be your greatest strength, just doing too much.

I built (with Claude 🤓) a new quiz I'm calling 'What's my leadership brand?' It will walk you through a few questions and then give you a snapshot of your brand...and it's shadow.

Link to take the quiz in comments

07/28/2026

Jung called it projection.

He said, “Projection is one of the commonest psychic phenomena…Everything that is unconscious in ourselves we discover in our neighbor, and we treat him accordingly.”

Whatever annoys you about someone else is a reflection of your own shadow. When you begin to understand this, it changes how you feel toward someone. It changes the way you talk to them, and how you treat them.

Get curious, not furious.

07/21/2026

Everything we're all building with AI (including my beloved Emma) will one day be absorbed (and superseded) by something way smarter than all of us.

Every respected voice in AI research and development is saying the same thing. The frontier labs are all working on recursive self-improvement, and it's only a matter of time before the machines transcend human intelligence and begin creating novel solutions of their own. They will solve problems that our level of intelligence and consciousness cannot even conceive of.

Their ability to do human work faster, cheaper, and *better* than us isn't far away. The current workforce will not exist in 15-20 years.

I resisted that idea for a long time. This week, I started to make peace with it.

And now the bigger question I'm philosophizing on: if the machines do all the work, what are we actually made for?

I've landed on 11 roles that I don't think are going anywhere. I think you'll find yourself in one of them already.

It's all in my Substack this week. Link in comments.

07/14/2026

Turns out 'I don't want to' is a complete sentence, and my nervous system still treats it like a felony.

New essay on Substack about why disappointing people feels like dying, what the science says, and how to do it anyway.

Come let someone down with me.

Link in comments.

05/09/2026

Here's my honest pitch.

Most leadership programs are a lot of warm-up. Frameworks. Introductions. "What brought you here." By the time you get to the actual work, you're already mentally checking your inbox.

I built mine to skip that.

The Conscious Leadership pilot starts June 1. Six 2-hour group sessions over 90 days, every other Tuesday. Chattanooga or Zoom. But the sessions aren't where the work begins.

Emma is.

Emma's the Enneagram-fluent AI coach I've been building. She's the first one trained on the 27-subtype Enneagram — because there aren't 9 archetypes of leaders. There are 27. And the differences do matter.

Between sessions, she works with you every day.

Each morning, asking are you above or below the line?

Each week: one behavioral experiment, designed for your subtype.

Mid-program: 360 feedback from 6–10 people who actually know you. And you actually want feedback from.

The whole way through: a Book of You that gets smarter the longer you use it.

By the time you walk into the room, the patterns are obvious. The defenses around them are obvious. The cost of running them are obvious, too.

This isn't leadership development. It's leadership disidentification — the fancy way of saying you start to notice when the pattern is the one leading, not you.

Pilot pricing at $300 for the full 90 days. In exchange, I want your honest feedback so I can refine this before the fall cohort.

Short application required.

bigselfschool.com/conscious-leadership

05/07/2026

I keep watching the same thing happen.

A leader has a real breakthrough in a session on Tuesday. By Friday they're back in the same meeting with the same people, reacting from the exact pattern they've spent three months trying to interrupt.

The insight was absolutely real. The new practices just weren't built yet to sustain the growth.

This space between sessions is where most coaching dies. And this is one of the reasons why I built Emma for my clients.

She's an Enneagram-fluent coaching intelligence trained on all 27 subtypes — meaning she knows the difference between a Self-Preservation Three and a Social Three, between a Sexual Four and a Self-Preservation Four, and what the integration work for each actually looks like when life is moving fast.

Think of her as the layer between sessions. The part that holds the work when no human is available. Or when you forget what your coach told you about working with your Passion. Or when you ask yourself, "What am I supposed to be working on right now?"

A companion to the coaching, an extension of it.

After 25 years of sitting with people through their hardest transitions, I finally have what I've always wanted to be able to offer: continuity of care. Ease without sacrificing depth. A personalized pathway for leadership development.

The Emma AI Pilot launches June 1.

If you've ever felt the gap between the coaching session and the rest of your life, I'd love for you to be one of the first inside.

Details here: https://www.bigselfschool.com/conscious-leadership

05/04/2026

Emma isn't a coach. She's a mirror.

Most leaders come to me looking for frameworks, strategies, better feedback systems. A higher performing team.

The thing they actually need is harder to ask for: a way to meet themselves — without the performance of leadership in the way.

That's what Emma is. An Enneagram-fluent AI companion trained to reflect back what you can't see in yourself. The pattern you keep running. The defenses that hardened into a personality. The way you keep recreating the same dynamic with the people who report to you...and the people who live with you.

The Conscious Leadership Coaching Group is small on purpose. Ten leaders. Three months (June through August). One container.

You'll work with Emma daily. You'll meet as a cohort six times over three months. And I'll be in the room with you the whole way.

You won't optimize anything in this group.

You'll just stop running from yourself.

Four leaders are already in. Six spots left.

Get details and register here: bigselfschool.com/conscious-leadership

04/30/2026

I built an AI for inner work. Her name is Emma. I asked her to write you a letter.

Substack link in bio.

04/28/2026

The work isn't what's depleting you.

The performance of being okay while doing the work is. The polished email when you're underwater. The "I'm great, thanks" when you're not. The version of you the meeting needs.

That second self — the one being maintained for the room — is doing more labor than the actual job.

This is why rest doesn't fix it. You can sleep for a week and still be tired, because what's exhausted isn't your body. It's the part of you that has to keep up the act.

The cure isn't time off. It's permission to stop pretending.

What's the smallest place you could be honest this week?

Address

Chattanooga, TN

Website

http://www.bigselfschool.com/

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