Week 1: Foundations (Days 1-7)
Day 1: What Are Options?
Read one comprehensive overview of options. Understand that a call gives you the right to buy, a put gives you the right to sell, and both have expiration dates and strike prices. Don't go deeper today.Day 2: Calls Explained
Focus exclusively on call options. Understand buying calls (bullish bet) and selling calls (income collection). Watch one video explanation, then read one article.Day 3: Puts Explained
Same process for puts. Understand buying puts (bearish bet or insurance) and selling puts (income or stock acquisition). The symmetry with calls should start clicking.Day 4: The Options Chain
Open your broker's options chain for a stock you know (Apple, Microsoft, or similar). Identify the strike prices, expirations, bid/ask prices, volume, and open interest. Don't trade—just look.Day 5: Premium, Intrinsic Value, and Time Value
Learn what makes up an option's price. Intrinsic value is the real value (how far in the money). Time value is everything else. Premium = intrinsic + time value.Day 6: In the Money, At the Money, Out of the Money
Understand these three states for both calls and puts. Practice by looking at a real options chain and identifying which strikes are ITM, ATM, and OTM.Day 7: Week 1 Review
Review everything from the week. Write down 5 things you learned and 3 things that still confuse you. Research those 3 things.Week 1 milestone: You can explain what an option is to a friend in plain English.
Week 2: Core Concepts (Days 8-14)
Day 8: Time Decay (Theta)
Understand why options lose value over time and why this accelerates near expiration. This is the single most important concept for income strategies.Day 9: Implied Volatility
Learn what IV means, how it affects premiums, and why options are expensive before earnings. Don't worry about the math—focus on the concept.Day 10: Delta Basics
Delta tells you how much the option moves per $1 stock move and approximates the probability of expiring in the money. Both uses matter.Day 11: Covered Calls
Deep dive into covered calls. Understand the mechanics, profit/loss scenarios, and when this strategy makes sense. This is the most important strategy for income investors.Day 12: Cash-Secured Puts
Same deep dive for cash-secured puts. Understand how selling puts can be a way to buy stock at a discount or generate income.Day 13: Open a Paper Trading Account
Set up paper trading on thinkorswim or your broker's simulator. Fund it with an amount matching your planned real capital.Day 14: Week 2 Review
Review the week. You should now understand time decay, volatility's impact on premiums, and two core strategies.Week 2 milestone: You can explain why a covered call works and identify one on an options chain.
Week 3: Paper Trading (Days 15-21)
Day 15: First Paper Trade - Covered Call
If your paper account has stock, sell a covered call. Choose a 30-day expiration and a strike about 5% above current price.Day 16: Second Paper Trade - Long Call
Buy a call on a stock you think will go up. Choose 30-45 days out, near the money. Spend no more than 5% of your paper account.Day 17: Monitor and Journal
Check both positions. Record the P&L and what drove the changes. Did the stock move? Did time decay affect the values?Day 18: Third Paper Trade - Cash-Secured Put
Sell a put on a stock you'd want to own at a lower price. Set aside the cash in your paper account.Day 19: Learn to Read P&L
Study your paper positions. Understand why each is up or down. Compare option price changes to stock price changes.Day 20: Practice Closing a Trade
Close one of your paper positions. Practice the mechanics of sell-to-close or buy-to-close. Note the bid-ask spread impact.Day 21: Week 3 Review
You now have real (simulated) experience. Review what surprised you and what matched expectations.Week 3 milestone: You've placed and closed paper trades in three different strategies.
Week 4: Refinement (Days 22-30)
Day 22: Analyze Your Paper Trades
Use OptionsPilot to analyze covered call opportunities and compare them to the paper trades you placed. Were there better strikes or expirations available?Day 23: Risk Management
Learn position sizing. No single trade should risk more than 5% of your account. Practice applying this to your paper trades.Day 24-25: Place 3-5 More Paper Trades
Apply everything you've learned. Focus on covered calls and cash-secured puts. Journal each trade.Day 26: Learn About Rolling
Study how to roll an option to a new expiration or strike. Practice on one of your paper positions.Day 27: Read About Common Mistakes
Research the top 10 beginner options mistakes. Check if you've made any in your paper trading.Day 28-29: Full Portfolio Review
Review all paper trades from the month. Calculate your total P&L, win rate, and average gain/loss.Day 30: Decision Day
Based on your 30-day experience, decide: continue paper trading, start with real money (small), or conclude that options aren't for you right now. All three are valid outcomes.Week 4 milestone: You have a documented track record and a clear next step.
After Day 30
If you're ready for real money, start with one contract per trade. Keep the journal going. The learning doesn't stop—it accelerates when real money is involved.