There's a special satisfaction that comes with checking your brokerage account on Monday morning and discovering that your cash-secured put order executed exactly as planned. In this complete workflow walkthrough, we track a cash-secured put on Bath & Body Works (BBWI) from order execution through expiration, demonstrating the ideal scenario where the option expires worthless and you pocket the full premium.
This trade generated $65 in gross premium (approximately $64.33 after fees) using $4,200 in collateral. The position was opened on Monday, January 29th at 8:31 AM—just one minute after market open—and expired worthless on Friday, February 2nd, allowing the entire premium to be captured as profit. With collateral now freed up, the same capital can be immediately redeployed into the next weekly position, creating a continuous cycle of premium income.
After confirming the order filled in the thinkorswim application at 8:31 AM on January 29th, the immediate next step is accurately tracking this transaction in your cost basis system. For paper trading or real money accounts alike, maintaining precise records from the moment of execution ensures you have an accurate picture of your overall position and performance.
Since this was the first BBWI trade in this particular account, the initial step in MyATMM's cost basis screen was to add the ticker symbol to the watchlist:
This one-time setup step is required before you can begin tracking positions on any new underlying stock. Once added, the ticker remains in your system permanently unless you manually remove it.
With BBWI added to the system, the next step is creating the actual position record for this cash-secured put:
After saving, MyATMM displays the position in two places: the active puts section (showing current open positions) and the proposed transactions section (showing pending cost basis adjustments that would occur if assigned).
The "proposed record" that appears after saving represents what would happen to your cost basis if the put is assigned. It shows you'll be purchasing 100 shares at $42 per share with an adjusted cost basis reflecting the $64.33 premium collected. This forward-looking visibility helps you plan for potential assignment scenarios before they occur.
While many paper trading simulations ignore transaction costs, thinkorswim's paper trading account includes realistic commission and fee structures. This presents an excellent opportunity to practice tracking these expenses, which significantly impact your actual net returns in live trading.
In the brokerage account view, the position showed $65.00 in gross premium minus $0.67 in total fees ($0.65 commission + $0.02 regulatory fees), resulting in $64.33 net credit. Many traders overlook these small fees, but they compound significantly over time:
MyATMM provides a streamlined fee entry process that automatically calculates net premium:
After saving the fee-adjusted transaction, MyATMM displays a $64.33 credit—matching exactly what appears in the thinkorswim account P&L. This one-to-one correspondence ensures your tracking system reflects reality, not gross estimates.
Pro Tip: To maintain perfect synchronization between MyATMM and your brokerage, set your initial deposit amount in MyATMM to match your brokerage account balance. This allows for exact balance matching as you track trades over time.
Once the transaction is fully recorded with fees included, MyATMM provides a comprehensive position overview that consolidates all key metrics in one view. This summary gives you an at-a-glance understanding of your exposure, capital requirements, and potential outcomes.
For this BBWI cash-secured put, the position overview displays:
| Metric | Value | Meaning |
|---|---|---|
| Shares from Puts | 100 | Number of shares you're obligated to purchase if assigned |
| Collateral in Play | $4,200 | Capital reserved in your account to cover potential assignment |
| Total Credits Received | $64.33 | Net premium collected after all fees and commissions |
| Strike Price | $42.00 | Price at which you'd purchase shares if assigned |
| Current Stock Price | $43.00 | Last traded price of BBWI (as of expiration) |
The relationship between strike price and current stock price is the critical factor that determines whether you'll be assigned shares or pocket the full premium.
With BBWI trading at $43.00 and the put strike at $42.00, the option is $1.00 out-of-the-money. This means no rational option holder would exercise their right to sell shares at $42 when they could sell at $43 in the open market. As a result, the option expires worthless on Friday, and you keep 100% of the $64.33 premium collected.
By the time Friday, February 2nd arrives, the position has run its full course. Since this video was recorded on February 4th (the following Sunday), the position had already expired out-of-the-money two days prior. This demonstrates the beauty of the "set and forget" weekly cash-secured put strategy—you don't need to monitor positions constantly throughout the week.
When a cash-secured put expires out-of-the-money, several things occur automatically:
Since the position has expired and requires no further action, the appropriate next step in MyATMM is removing it from your active positions:
While the premium collected remains in your transaction history permanently, removing the active position keeps your workspace clean and focused on current open positions. This becomes increasingly important as you scale to tracking multiple tickers with rolling weekly positions.
The transaction history preserves the record for performance analysis and tax reporting, while the active positions view shows only what requires ongoing monitoring or potential action.
At this point, you're no longer in any active positions on BBWI. The $64.33 premium has been successfully captured, and your $4,200 collateral is now available to deploy into a new cash-secured put for the upcoming week.
With the previous position successfully closed and capital freed up, the natural next step is evaluating whether to continue selling cash-secured puts on BBWI or move to a different underlying. The video demonstrates this analysis process using thinkorswim's Analyze tab to evaluate available premium for the upcoming weekly expiration.
Rather than automatically rolling into the next weekly position, prudent option sellers compare premium across multiple expiration dates to identify the most efficient deployment of capital:
| Expiration | Days Out | Strike | Premium Available | Analysis |
|---|---|---|---|---|
| February 9th | 5 days | $43 | $0.60 | Standard weekly premium, conservative strike |
| February 16th | 12 days | $43 | $1.25 | Two-week premium, more than double weekly |
| February 23rd | 19 days | $43 | $2.00 | Three-week premium, still pre-earnings |
| March 1st | 26 days | $43 | $2.75 | Premium jump due to February 29th earnings |
Notice the significant premium increase for the March 1st expiration—jumping 75 cents from the February 23rd expiration despite only representing one additional week. This premium expansion occurs because BBWI's earnings announcement is scheduled for February 29th.
Options premiums typically increase before earnings due to anticipated volatility. While this offers higher income potential, it also introduces additional risk:
Whenever you see an unusual premium jump between two consecutive expiration cycles, check for upcoming earnings announcements, Federal Reserve meetings, or other major market events. The additional premium compensates for heightened risk, but you must decide if that compensation is adequate for your risk tolerance.
After analyzing the available premium across multiple expirations, the decision was made to continue with the weekly approach, selling a cash-secured put for the February 9th expiration. This maintains consistency with the previous week's strategy and avoids the earnings volatility embedded in the longer-dated options.
The February 9th expiration at the $43 strike showed a bid-ask spread of $0.60 to $0.70. Rather than accepting the bid price ($0.60) or demanding the ask price ($0.70), the order was placed at $0.65—splitting the difference to increase fill probability while capturing more premium than the bid:
Ticker: BBWI
Action: Sell to Open
Option Type: Put
Quantity: 1 contract
Strike Price: $43
Expiration: Friday, February 9th
Limit Price: $0.65 per share
Order Type: Limit (Good-Til-Cancelled)
Expected Net Premium: $64.35 (after estimated $0.65 commission)
After confirming all order parameters, the order was submitted through thinkorswim with an expected execution time of Monday morning after market open. Interestingly, the estimated net credit showed $64.35 instead of the $64.33 from the previous week, despite identical gross premium and commission structure. This small variation likely results from rounding differences in how the platform calculates regulatory fees.
The order now sits in the system waiting for Monday's market open. If conditions remain favorable and the stock doesn't gap significantly overnight, the order should fill at $0.65 or potentially better—creating another opportunity for weekly premium collection.
As emphasized in the video, one of the major advantages of weekly cash-secured put selling is the minimal time commitment required. You can place the order Sunday evening, let it execute Monday morning, forget about it all week, then return the following Sunday to repeat the process. If the put expires worthless, you pocket the profit. If assigned, you own shares and transition to selling covered calls. Either outcome generates income and continues the wheel strategy cycle.
This BBWI example demonstrates the full lifecycle of a weekly cash-secured put trade from start to finish. By understanding each step in the process, you can replicate this workflow consistently across multiple tickers and build a systematic income-generation strategy.
The sustainability of weekly cash-secured put selling rests on several key principles demonstrated in this walkthrough:
The $64.33 premium on $4,200 collateral represents 1.53% weekly ROI. If you could maintain this exact return every week for a full year:
Simple Annualization: 1.53% × 52 weeks = 79.6% annual return
Compounded Weekly: (1.0153)^52 = 2.17 or 117% annual return with reinvestment
Reality Check: These calculations assume consistent weekly performance, which is unrealistic. Some weeks will deliver higher premiums, others lower. Assignment events, market volatility, and position adjustments will all impact actual annual returns. However, the calculation demonstrates the income potential when consistently executing the strategy.
Throughout this trade walkthrough, MyATMM served as the central hub for recording transactions, calculating net premium after fees, and maintaining position-level visibility. For traders executing the wheel strategy or regularly selling cash-secured puts, purpose-built tracking tools provide significant advantages over spreadsheets or brokerage reporting.
Most brokerage platforms track your purchase price but don't automatically adjust cost basis for collected option premium. This creates reporting problems and tax complications down the line.
Consider what would happen if this BBWI put had been assigned instead of expiring worthless:
| Scenario | Brokerage Reporting | True Cost Basis (MyATMM) |
|---|---|---|
| Shares Acquired | 100 @ $42.00 | 100 @ $42.00 |
| Premium Collected | Not tracked in cost basis | $64.33 (reduces cost basis) |
| Reported Cost Basis | $42.00 per share | $41.36 per share ($42 - $0.64) |
| Break-Even Price | $42.00 | $41.36 |
This $0.64 per share difference might seem small, but it represents the true economic reality of your position. When you later sell covered calls or eventually exit the position, accurate cost basis determines whether you're actually profitable.
MyATMM maintains running totals of all premium collected on each ticker. If you've been selling weekly cash-secured puts on BBWI for months, the system shows cumulative premium across all transactions. This becomes essential for understanding which tickers generate the most consistent income and which strategies provide the best risk-adjusted returns over time.
The platform offers a free account that allows tracking up to 3 tickers forever—perfect for traders focused on a core set of underlying stocks or those wanting to test the platform before upgrading. As demonstrated in this walkthrough, even tracking a single ticker like BBWI with weekly positions provides substantial value in cost basis accuracy and performance visibility.
While this particular BBWI trade resulted in the ideal scenario—full premium capture with no assignment—it's critical to understand the alternative outcomes and how to manage them when they occur.
What Happens: Stock closes above strike price at expiration
Result: Option expires worthless, full premium retained
Collateral: Released immediately for redeployment
Action Required: Remove position from tracking, analyze next week's opportunity
What Happens: Stock closes below strike price at expiration
Result: You purchase 100 shares at strike price, premium retained
Cost Basis: Strike price minus collected premium per share
Action Required: Begin selling covered calls above your adjusted cost basis, potentially collect dividends
What Happens: Stock moves toward strike mid-week, extrinsic value approaches zero
Result: Buy-to-close current position, sell-to-open new position at later expiration or lower strike
Cost: Difference between buy and sell premiums (can be net credit or debit)
Action Required: Record both transactions in MyATMM, update position tracking
Experienced cash-secured put sellers follow several guidelines to manage risk effectively:
This complete trade walkthrough from execution to expiration demonstrates the practical reality of selling weekly cash-secured puts as an income generation strategy. While this particular trade resulted in optimal outcome, the workflow remains consistent regardless of whether positions expire worthless or result in assignment.
The 1.53% weekly return captured on this trade represents the income potential available to disciplined cash-secured put sellers. While no strategy produces identical results every week, maintaining systematic position selection, accurate tracking, and consistent execution creates a framework for generating option premium income over the long term.
Options trading involves substantial risk and is not suitable for all investors. Selling cash-secured puts obligates you to purchase shares at the strike price regardless of how far the stock price declines. The 1.53% weekly ROI demonstrated in this example represents a single trade outcome and does not guarantee future performance.
This content is for educational purposes only and should not be considered personalized investment advice. Before engaging in options trading, carefully consider your financial situation, investment objectives, and risk tolerance. Consult with a qualified financial advisor regarding your specific circumstances.
Past performance does not guarantee future results. Market conditions, volatility levels, and individual stock movements will cause actual results to vary significantly from any single example. Always understand the complete risk profile of any options strategy before committing capital.
MyATMM provides purpose-built cost basis tracking for option sellers. Record every transaction, track cumulative premium, and maintain accurate cost basis across all your positions.
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