Bring your most expensive problem.
Leave with clarity, energy, and a way forward.
Who is this for?
You're high-functioning, creative, and entrepreneurial. You think from left field. You live for transformation. You've had sudden breakthroughs before, and you know it can happen again. You believe it's possible to shift your perspective in a weekend.
You are confident in your capacity to take action in your personal life or work. However, right now you're stuck. It's frustrating. Annoying. It drags at your attention. You can't quite put it down. You know that if you can move through it, life will feel different. You'll be free to act, to create, and to lead.
What's an expensive problem?
It's a problem that is costing you dearly. So much that you lose focus, or can't sleep at night. The cost may be money, or something you can't put a number on—time, peace of mind, energy. Whatever it is, the price is too high to ignore.
You'll bring your expensive problem to a small group of peers and work on it together.
Example Scenarios
You're burning out but the company can't afford for you to slow down, with no end in sight.
You're in a good, caring, and serious romantic partnership. They want marriage. You aren't sure. You don't know how to become sure, or whether you'd feel this way with anyone. The uncertainty infects every piece of your life.
Your company has hit a ceiling. You know the next stage of growth requires a fundamentally different strategy, or a different version of you. You can't see which, or how to get there.
You and your cofounder are close friends and strong partners. However, you have a significant conflict that seems impossible to talk about. The longer you wait, the harder the conversation becomes.
You are unusually talented, but your skills are hard to make legible. You could fit yourself into an established career path. It feels like a waste of your potential. You don't know whether that's wisdom or fear. With every month, the window narrows.
You want a life partner. But you keep attracting the wrong person, and breaking up at the same point. Something is repeating, and self-awareness isn't helping.
You've built a company where the product is you. You'd like to exit while the company continues to thrive, but you're afraid that if you leave, it all falls apart.
You were heading for your North Star. Everything was going perfectly. You, or your company, were amazing. Then an unexpected event hit like a tsunami and knocked you off course. You're completely adrift and you don't know what to do.
What you'll walk away with
On Sunday evening, you will have:
- The ability to see your problem from multiple perspectives—adult developmental psychology, systematization and automation, structural analysis of interactional power, metarationality.
- Understanding of your situation that you could not have reached on your own.
- Clarity of direction and renewed energy.
- Concrete next steps and the confidence to take them.
This is not about abstract ideas. It's about dismantling what's keeping you stuck, and being inspired to take practical action on the other side.
Who we are
We guide leaders and creators through life-changing turning points.
Charlie partners with tech founders and AI researchers, helping them lead with clarity and presence.
How the weekend works
The workshop takes place July 31st–August 1st, 2026 in New York City. Over two days, you'll participate in four sessions in a peer group of no more than twenty participants.
You'll work directly on your problem in small breakouts, applying frameworks for immediate insight. The process is rigorous, sometimes surprising. Spacious breaks are build in so understanding can land and conversations deepen.
You will leave not only with clarity on your own problem, but with new ways of seeing that extend far beyond it.
Confidentiality
The workshop is a safe place to explore difficult or painful situations. At the outset, you'll sign a binding agreement not to publicly share other participants' problems without their consent.
Early bird pricing
$500 discount available to April 1
Workshop
$2,000
The weekend event plus a Zoom call before and after
Workshop + Sessions
$4,500
The weekend event plus three individual sessions with both Charlie & Andrew
Apply
If you're interested, tell us about yourself and your expensive problem. We'll follow up if it seems like a good fit.
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