Options Trading: Risk-First Strategies That Work

The 90-Day Options💡 Definition:Options are contracts that grant the right to buy or sell an asset at a set price, offering potential profit with limited risk. Makeover

Meet Jordan. Same $10,000 account, two very different outcomes:

• Week 1: YOLO weekly calls → -48% drawdown in 6 trades
• 90 days later: Risk-capped spreads, +7.4% with max loss per trade capped at 1%

The difference? Not “secret indicators.” A risk-first framework and position sizing.

Sources: Options accounts with frequent short-dated buying underperform due to time decay and volatility💡 Definition:How much an investment's price or returns bounce around over time—higher volatility means larger swings and higher risk. drag (CBOE, SEC). Retail performance improves when risk is capped and trades are structured with limited loss (CME).

What Options Are (And Why They’re Dangerous Without Rules)

• A call = right to buy; a put = right to sell; both decay over time (theta)
• Price is driven by underlying price, time, rates, dividends💡 Definition:A payment made by a corporation to its shareholders, usually as a distribution of profits., and implied volatility (Black–Scholes overview – Khan Academy)
• Time decay is relentless for buyers; sellers earn decay but take tail risk

💡 Definition:A voluntary payment given to service workers in addition to the bill amount, typically based on quality of service.Tip💡 Definition:A voluntary payment to service workers, typically a percentage of the bill, given as thanks for good service.: Before placing any trade, sketch the payoff diagram and list your worst-case outcome.

The Core, Repeatable Strategies

1) Covered Calls (Income on Stocks You Already Own)

• Own 100 shares; sell out-of-the-money (OTM) calls 30–45 DTE; exit at 50% profit or roll
• Works best on range-bound, lower-IV names; target annualized yield💡 Definition:The return an investor earns on a bond, expressed as a percentage, which can be calculated as current yield (annual interest ÷ current price) or yield to maturity (total return if held until maturity). 6–12%
• Risk: You cap upside; assignment risk around 💡 Definition:Income is the money you earn, essential for budgeting and financial planning.earnings💡 Definition:Profit is the financial gain from business activities, crucial for growth and sustainability.

Reference: Covered-call performance vs buy-and-hold in low-vol regimes (CBOE BXM Index).

2) Protective Puts (Insurance You Hope to Never Use)

• Long stock💡 Definition:Stocks are shares in a company, offering potential growth and dividends to investors. + long OTM put 60–120 DTE during elevated uncertainty💡 Definition:Risk is the chance of losing money on an investment, which helps you assess potential returns.
• Converts unknown downside into known max loss; think of premium💡 Definition:The amount you pay (monthly, quarterly, or annually) to maintain active insurance coverage. as insurance

Reference: Drawdown control improves long-horizon geometric returns (AQR).

3) Vertical Spreads (Defined Risk, Defined Reward)

• Bull call or bear put spreads 30–60 DTE; risk capped to net debit; place where probability-of-touch fits thesis
• Use when you have directional view but want limited risk and lower cost than single-leg options

4) Cash‑Secured Puts (Get Paid to Set Your Buy Price)

• Sell OTM puts on stocks you want to own; hold cash to purchase at strike if assigned
• Target IV rank > 30; avoid into earnings unless intentional

Reference: Option income with equity💡 Definition:Equity represents ownership in an asset, crucial for wealth building and financial security.-like risk when managed prudently (CBOE PUT Index).

Risk Management💡 Definition:The process of identifying, assessing, and controlling threats to your financial security and goals. You’ll Actually Follow

• Position size: Max 1% account risk per trade; total options exposure ≤ 25% of account
• No earnings roulette: Avoid short premium through binary events unless hedged
• Use stop-at-a-loss of 2× credit for short spreads; 50% profit take on short premium
• Trade log: Record thesis, greeks, IV rank, exit rules; review weekly

Behavior matters more than math: Most blow-ups are position-sizing errors, not bad ideas (Dalbar).

Psychology: Beat FOMO, Respect Theta

• Have a written checklist; act only when all criteria pass
• Pre-commit exits (profit target, max loss, time stop). No “I’ll just give it one more day.”
• When IV spikes, think like an insurer (sell spreads); when IV compresses, be a buyer (debits)

Practical Setups (Repeatable Playbooks)

• Trend pullback: Debit spread with 30–45 DTE in direction of trend; exit on prior high/low
• Range fade: Short iron condor when IV rank > 30 and price mid-range; exit at 50% max profit
• Hedge on cue: Buy puts when 20D/50D moving averages cross down and VIX > 20; remove on recapture

Use our calculators to sanity‑check assumptions:

• Stock Returns Calculator: /tools/investment/stock-returns-calculator
• Rebalancing Impact: /tools/investment/rebalancing-impact

What to Avoid (Common, Expensive Errors)

• Buying weeklies because “cheap” → fastest theta decay
• Naked short options without defined risk → tail events end accounts
• All-in trades, martingales, or revenge trading → psychological traps

Bottom Line

Options are powerful, but only when risk is defined, exits are pre‑planned, and sizing is small. Start with covered calls, protective puts, cash‑secured puts, and vertical spreads. Measure twice, size once, then let time and discipline do the 💡 Definition:Interest calculated on both principal and accumulated interest, creating exponential growth over time.compounding💡 Definition:Compounding is earning interest on interest, maximizing your investment growth over time..