⚠ Before you read any of this: everything in the Playbook is a record of my own trading decisions on my own positions – not a strategy guide, not a recommendation, and not financial advice. I’m documenting specific adjustments I’ve made when a trade moved against me, including why I made them and what could have gone wrong. What worked for me, with my own capital and risk tolerance, is not a template for what anyone else should do. Every entry includes a section on exactly when the technique I used stops working, because none of these are risk-free, and the market doesn’t care what worked last time.
This is where I write down the specific, real decisions I make in my own trading – not the strategy explainers you’ll find in the Options Strategies guide, but what I actually do with real positions. Most of it is about managing a trade that’s gone wrong: I roll spreads, I sell legs early, I turn defined-risk trades into undefined-risk ones on purpose sometimes, and I don’t always get it right. Some of it is proactive instead – ways I structure an entry into a position I already wanted. Either way, the Playbook is where I document it honestly, including the parts where it could have gone worse than it did.
What’s in the Playbook
Each entry below walks through a real technique I use, with a worked example, a clear point on when I’d stop using it, and the risks that go beyond the obvious ones.
How to Read These
Every entry follows the same shape: a warning at the top before any technique is explained, a real (or realistically reconstructed) worked example with actual numbers, and a dedicated section on when the technique breaks down – not buried in a footnote, but called out on its own. If you’re looking for how a strategy works in general, the Options Strategies guide is the better starting point. If you want to see how I’ve actually handled a trade that moved against me, that’s what’s here.
Frequently Asked Questions
Is the Playbook financial advice?
No. The Playbook documents personal trade management decisions from my own trading. Nothing here is a recommendation to use these techniques, and none of it is financial advice. What I do with my own positions may not be appropriate for anyone else’s capital, risk tolerance, or account size.
Do these techniques always work?
No. Every article in the Playbook includes a section on when the technique stops working, because it does – if the market keeps moving against the position, these adjustments extend or increase risk rather than removing it. I’m documenting what I actually do, including the possibility that it doesn’t work out.
Why does the Playbook read differently from the Options Strategies guides?
The Options Strategies section explains how strategies work in general terms. The Playbook is different on purpose – it’s written from my own trading, in the first person, documenting specific decisions I made on real positions, not a general how-to.