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To Quit or Not to Quit

March 5, 2024

I’m reading Annie Duke’s latest book “Quit: The Power of Knowing When to Walk Away.” Though I’m only about halfway through it I can already confidently recommend this book to traders.

The book isn’t addressed to traders, though it frequently references our profession in its anecdotes and many of the stories are very relatable.

And it certainly has me thinking about better ways to decide to quit a trade, quit a strategy, or quit a product.

I frequently go down rabbit holes, experimenting with models to extract consistent, repeatable, acceptably risk-adjusted returns via index options. I’ve written about my near-constant obsession with this project numerous times. It continues.

As a trader, it's always good to be working on some kind of “side hustle.” In our cases, this is more likely to look like building a new strategy, fine-tuning a scanning method, or constructing a money management scheme that can propel us into becoming more profitable traders.

The nature of experimenting in the markets is to lose money in the service of learning what definitely doesn’t work, so that we can continue stripping away until we get to the very essence of what does work.

But when do we quit?

How much money is too much money to lose while experimenting? How much time is too much time to invest in discovery? How much opportunity cost am I willing to bear?

The thing that is always front and center with me when I feel like I’m approaching a crossroads is: What if I quit digging when I’m just inches from the gold?

I don’t have any answers here. This is a very real and ongoing struggle for me.

If anyone has any good ideas, please share them.

Maybe when I get to the end of Annie’s book I’ll have some tools that will help me better design guardrails for my experimentation sandbox.

Here’s hoping…

Trade 'em Well,

Sean McLaughlin
Chief Options Strategist
All Star Charts, Technical Analysis Research

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