Dean Cross

Home The Options Strategy Series

Assigned: Selling Puts for Income

A Realist's Guide to Cash-Secured Puts

A cash-secured put is not free money. It's rent you collect for accepting someone else's downside.

No guru promises. No guaranteed income. Just the mechanics, the math, and the discipline to sell puts with your eyes open.

Most options books fall into one of two traps: they sell a fantasy of easy, endless income, or they bury a simple idea under a mountain of Greeks. Assigned does neither. It's a clear, jargon-light guide to the one options strategy a patient investor can actually run with real money, written by someone more interested in keeping you solvent than impressing you.

It starts with what a put really is and what “cash-secured” actually demands of your account, then walks the whole strategy one decision at a time.

It is just as direct about the downside. Three real, dated trades show what can go wrong, including the one that screened safest and still detonated, along with how to size positions so a bad month never becomes a disaster, and the truth about earnings and capped upside.

Whether you're selling your first put or have collected premium for years, it gives you a disciplined framework built on real prices and real outcomes, not back-tested fantasies.

Inside the book

  • Choosing what to sell puts on, from indexes and ETFs to single stocks, and why settlement type changes everything
  • Choosing strikes and expirations, and reading the premium for what it's really telling you
  • An eight-point checklist to gate every trade before you place it
  • Managing an open position, rolling, and what actually happens the day you're assigned
  • The wheel: turning assignment into an ongoing income cycle
  • Three real, dated trades, and position sizing so a bad month never becomes a disaster
  • The psychology of selling puts, and a repeatable system you can run for years

Look inside

A few pages from the paperback. Select a page to see it full size.

  • The contents
  • The opening of Chapter 1
  • Figure 4.1: three approaches, three strikes
  • Figure 13.2: the cushion that matters

Who it's for

Investors selling their first put, and experienced premium sellers who want a risk-first framework.

Where to go next