Selling

Selling options is where many traders find consistent income – you collect premium upfront in exchange for taking on obligations. When you sell an option, whether it’s a put or a call, you’re taking what’s known as a “short” position. This means you’ve written the contract and have obligations to fulfill if the buyer exercises their rights. Your maximum profit is limited to the premium collected, while your potential risk can be substantial or even unlimited. Despite these risks, selling options is popular because it allows traders to profit from time decay and generate regular income, making it the foundation of strategies like the wheel.

What Happens When You Sell Options

When you sell an option, you:

  • Collect premium immediately (your maximum possible profit)
  • Accept obligations that you must fulfill if assigned
  • Create a “short” position
  • Can profit from time decay and stable prices
  • Can buy back the option before expiration
  • Must fulfill obligations if assigned
  • Keep premium if option expires worthless

The key advantage: time decay works in your favor and you can profit without predicting direction.

Selling Puts – The Obligation to Buy

When you sell a put option, you accept the obligation to purchase 100 shares at the strike price if assigned. Put sellers are typically:

  • Neutral to bullish on the stock
  • Seeking income from their cash
  • Willing to own shares at a lower price

Example: Selling a Cash Secured Put

XYZ stock is at $50, you sell a weekly $48 put for $0.50:

  • Premium Collected: $50 (100 × $0.50)
  • Cash Secured: $4,800
  • Return: 1.04% for one week ($50/$4,800)
  • Annualized Return: 54.2%
  • If stock stays above $48: Keep the $50 premium
  • If stock falls to $46: Buy 100 shares at $48 (cost basis $47.50 after premium)

Selling Calls – The Obligation to Sell

When you sell a call option, you accept the obligation to sell 100 shares at the strike price if assigned. Call sellers are typically:

  • Neutral to bearish on the stock
  • Own shares (covered calls) or don’t (naked calls)
  • Seeking income from their holdings

Example: Selling a Covered Call

You own 100 shares of XYZ at $48 cost basis, current price $50. You sell a weekly $52 call for $0.40:

  • Premium Collected: $40 (100 × $0.40)
  • Return on Strike: 0.77% for one week ($40/$5,200)
  • Annualized Return: 40.1%
  • If stock stays below $52: Keep shares and the $40 premium
  • If stock rises to $54: Sell shares at $52, total profit $440

The Income Generation Advantage

Selling options provides several income advantages:

  • Immediate Premium: Cash hits your account right away
  • High Probability: Most options expire worthless (good for sellers)
  • Time Decay: Every day that passes benefits you
  • Flexibility: Can manage positions before expiration
  • Consistency: Small regular gains compound over time

Time is Your Friend When Selling

When you sell options, time decay (theta) works for you:

  • Options lose value each day, benefiting sellers
  • Decay accelerates near expiration
  • Weekly options provide 52 income opportunities per year
  • You profit from stocks going sideways

This is why selling options is often compared to being “the house” in a casino – statistical edge over time.

Capital Requirements

Selling options requires significant capital:

Cash Secured Puts: Need cash equal to 100 shares at strike price

  • $50 strike = $5,000 required

Covered Calls: Must own 100 shares

  • $50 stock = $5,000 position

Naked Options: Requires margin (not recommended for beginners)

Managing Risk When Selling

Risk management is crucial when selling options:

Define Your Comfort Zone: Only sell puts on stocks you want to own Strike Selection: Choose strikes with good premium/risk balance Position Sizing: Never allocate more than 5-10% to one position Have an Exit Plan: Know when to cut losses or roll positions Avoid Naked Calls: Unlimited risk is unacceptable for most traders

When to Sell Options

Consider selling options when:

  • You want consistent income
  • IV is elevated (higher premiums)
  • You’re neutral to slightly directional
  • You have adequate capital
  • You understand the obligations
  • You’re comfortable with assignment

Rolling Positions

When your short option is challenged, you can “roll” it:

  1. Buy back the current option (close position)
  2. Sell a new option with later expiration
  3. Potentially adjust strike price
  4. Ideally collect net credit

Example: Rolling a Put

Your $48 put is at risk with stock at $47:

  • Buy to close weekly $48 put: -$1.20
  • Sell to open next week $48 put: +$1.35
  • Net credit: $0.15 (bought time for stock to recover)

Common Mistakes When Selling Options

Selling Naked Calls: Unlimited risk for limited reward Poor Stock Selection: Selling puts on declining companies Overleveraging: Using too much capital on one position Panic Closing: Buying back at a loss too quickly Ignoring Assignment: Not being prepared to own shares

Assignment: Part of the Process

Assignment isn’t failure – it’s part of selling options:

  • Put Assignment: You buy shares at a predetermined “discount”
  • Call Assignment: You sell shares at a predetermined “profit”
  • Both scenarios were acceptable when you sold the option
  • Have a plan for after assignment (hold, sell calls, etc.)

The Psychology of Selling Options

Selling options requires different mindset than buying:

  • Small consistent gains vs home runs
  • Managing winners (often close at 50% profit)
  • Patience during drawdowns
  • Comfort with assignment
  • Focus on probability over possibility

Building Wealth Through Premium

Successful option sellers focus on:

  • Weekly 1% Returns: Compound to significant annual returns
  • Risk Management: Preserve capital above all
  • Consistency: Base hits, not home runs
  • Quality Underlyings: Only trade stocks you understand
  • Mechanical Approach: Remove emotion from decisions

Tax Treatment for Option Sellers

When you sell options:

  • Premium is typically short-term capital gains
  • Assignment affects stock basis (puts) or sale price (calls)
  • Frequent trading generates ordinary income tax rates
  • Keep detailed records for tax reporting

Key Takeaways

Selling Options:

  • Creates short positions with immediate income
  • Collects premium but accepts obligations
  • Benefits from time decay
  • Profits from sideways or favorable movement
  • Requires significant capital
  • Good for income generation
  • Maximum profit = premium collected

Remember: When you sell options, you’re exchanging unlimited upside for consistent income. Time decay is your ally, and you can profit even when stocks don’t move. This is why many experienced traders prefer selling options to buying them – becoming the “house” rather than the “gambler.”