Options Trading Journal: Track Performance with DaysToExpiry Analytics

You're selling covered calls every week. Cash-secured puts on three different stocks. Maybe a few long calls for earnings plays.

But can you answer: Which strategy is actually making you money?

Most traders can't. They track trades in their broker app, see a green number, and assume everything's fine.

Then they realize—six months later—that commissions ate their profits. Or that one assigned put wiped out three months of premium income.

An options trading journal fixes this. It shows your actual performance by strategy, ticker, and time period. Let's build one that works.

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Why You Need an Options Trading Journal (Not Just Broker Statements)

Your broker statement shows transactions. An options trading journal shows performance.

Here's what your broker won't tell you:

Broker Statement:

• Sold 1 AAPL $180 call for $2.50 premium
• Commission: $0.65
• Status: Assigned

Your Journal Should Show:

• True ROI: 7.2% over 14 days (189% annualized)
• Capital efficiency: $18,000 deployed, $1,294 net profit
• Assignment impact: Sold shares $2 below market price (opportunity cost: $200)
• Net outcome: +$1,094 after accounting for assignment loss
• Strategy comparison: This covered call outperformed your SPY cash-secured put by 3.1%

You need to track outcomes, not just transactions.

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What to Track in Your Options Trading Journal

Let's break down the data you actually need. Don't overcomplicate—these seven metrics tell the whole story.

1. Entry Data (Per Trade)

Field	Example	Why It Matters
Date opened	2026-01-15	Calculate holding period
Underlying ticker	AAPL	Group by stock performance
Strategy type	Covered Call	Compare strategy ROI
Strike price	$180	Assignment risk analysis
Days to expiry (DTE)	14	Correlate DTE to outcomes
Premium collected	$250	Gross income before costs
Commission paid	$0.65	True cost basis

This is your baseline. Everything else builds on this.

2. Risk Metrics (At Entry)

Field	Example	Calculation
Current stock price	$175.50	From broker at time of sale
Distance to strike (%)	+2.56%	(Strike - Current) / Current
Capital at risk	$18,000	Shares owned × current price
Delta	-0.35	Probability of assignment

These numbers predict whether you'll keep the trade or get assigned.

If you're selling puts with -0.45 delta every week, your journal will show you're taking too much assignment risk before it costs you real money.

3. Exit Data (Per Trade)

Field	Example	Why Track This
Date closed	2026-01-29	Actual holding period
Exit method	Assigned	Strategy analysis
Days held	14	ROI calculation
Closing price (if bought back)	N/A	Profit/loss if not assigned
Assignment price (if assigned)	$180.00	Actual capital deployed
Net premium (after commissions)	$249.35	True profit

Assignments aren't bad—they're just different outcomes. Track them separately.

If 80% of your trades get assigned, you're not running an income strategy. You're running a buy-write strategy with different tax treatment.

4. Performance Metrics (Calculated)

Metric	Formula	Example
Net profit/loss	Premium - Commissions	$249.35
ROI (%)	(Net Profit / Capital at Risk) × 100	1.38%
Annualized ROI (%)	ROI × (365 / Days Held)	36.0%
Win/loss outcome	Assigned = Loss, Expired = Win	Win (kept premium)

This is what separates journaling from transaction logging.

Your broker shows you made $249. Your journal shows you made 36% annualized return on $18,000 deployed.

Now you can compare that to other strategies.

5. Strategy-Specific Data

Different strategies need different tracking:

Covered Calls:

• Assignment cost (difference between strike and market price at assignment)
• Share repurchase date (if rolling positions)
• Dividend capture (did you collect dividends while holding shares?)

Cash-Secured Puts:

• Cash reserved (actual capital locked up)
• Assignment frequency (do you want the shares or just the premium?)
• Subsequent covered call premium (if you run the wheel)

Long Calls:

• Entry premium paid
• Exit premium collected
• Max profit achieved during hold period (did you leave money on the table?)

Track what matters for your strategy.

6. External Factors

Market conditions change outcomes. Track:

Factor	Example	Impact
VIX at entry	18.5	High IV = higher premiums
VIX at exit	21.2	Rising volatility = unexpected outcomes
Days to earnings	7	Earnings volatility premium
Sector trend	Tech +3.2%	Macro impact on assignment

This context explains why trades worked or failed.

If all your best trades happened when VIX > 20, you know when to be aggressive.

7. Notes & Lessons

Qualitative tracking matters:

• "Got greedy, sold $175 strike when $180 was available for $0.50 less. Got assigned. Lost $500 in opportunity cost."
• "Waited for VIX spike before selling TSLA puts. Collected 40% more premium than previous week."
• "Assignment on dividend date cost $1.20/share. Should roll before ex-div date."

These notes compound into strategy improvements.

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How to Structure Your Options Trading Journal

You have two choices: spreadsheet or purpose-built tool. Let's do both.

Option 1: Google Sheets Template

Simple, flexible, and you own the data.

Sheet 1: Trade Log

Date	Ticker	Strategy	Strike	DTE	Premium	Commission	Status	Days Held	Net P/L	ROI %	Ann. ROI %	Notes
2026-01-15	AAPL	CC	$180	14	$250	$0.65	Assigned	14	$249.35	1.38%	36.0%	Assignment 2 pts below market
2026-01-15	MSFT	CSP	$400	21	$380	$0.65	Expired	21	$379.35	0.95%	16.5%	Perfect—kept premium

Sheet 2: Strategy Dashboard

COVERED CALLS
Total Trades: 47
Win Rate (expired worthless): 68%
Avg ROI: 1.2%
Avg Annualized ROI: 32.1%
Total Premium Collected: $11,847.50
Total Commissions: $30.55
Net Profit: $11,816.95

CASH-SECURED PUTS
Total Trades: 32
Win Rate: 81%
Avg ROI: 0.9%
Avg Annualized ROI: 18.7%
Total Premium: $8,120.00
Net Profit: $8,099.20

This summary tells you which strategy works for your risk tolerance.

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Sheet 3: Ticker Analysis

AAPL
Trades: 12
Win Rate: 75%
Avg Premium: $247
Best Trade: 42% annualized
Worst Trade: Assigned 5 pts OTM (lost $500)

MSFT
Trades: 8
Win Rate: 88%
Avg Premium: $412
Notes: Works great with 14-21 DTE range

Now you know which stocks fit your strategy.

Option 2: DaysToExpiry Portfolio Analytics

If you use Interactive Brokers, we've already built this for you.

Upload your IB activity statement. Our portfolio analyzer automatically:

Parses Every Trade:

• Covered calls, cash-secured puts, long calls
• Handles commissions, corporate actions, and FX adjustments
• Tracks assignment status and exit method

Shows Performance by Strategy:

View in app →

• Total premiums collected (YTD and custom periods)
• Per-trade ROI with annualized return
• Win/loss distribution
• Income breakdown by ticker and strategy type

Visualizes Your Portfolio:

• Coverage matrix (which positions are protected)
• Assignment frequency by ticker
• Time-window filtering (analyze specific date ranges)
• Historical patterns (seasonal trends in your trading)

No manual data entry. Just drag your CSV and see your actual performance.

Already tracking trades in IBKR? Connect your portfolio with our Portfolio View tool for automated tracking, or explore Options Portfolio Management strategies to optimize multi-position portfolios.

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How to Use Your Journal to Improve Performance

A journal isn't useful unless it changes your behavior. Here's how to extract insights.

Weekly Review: Identify Patterns

Every Sunday, review the past week's trades:

Look for:

1. Assignment clusters: Did multiple positions get assigned? VIX spike? Sector movement?
2. Premium outliers: Which trades collected 2× average premium? What was different?
3. Strategy ROI gaps: Is one strategy consistently outperforming?

Action items:

• If covered calls keep getting assigned early, increase your strike distance or reduce DTE
• If cash-secured puts rarely get assigned, you're being too conservative—tighten strikes
• If long calls expire worthless frequently, review your delta targeting

Monthly Review: Strategy Allocation

At month-end, calculate:

STRATEGY ALLOCATION
Covered Calls: 60% of capital deployed
Cash-Secured Puts: 30%
Long Calls: 10%

RETURNS BY STRATEGY
Covered Calls: +2.8% monthly (38% annualized)
Cash-Secured Puts: +1.5% monthly (19% annualized)
Long Calls: -0.4% monthly (losing strategy)

Decision: Shift 5% from long calls to covered calls.

Your journal just increased expected annual returns by 1.2%.

Quarterly Review: Risk Assessment

Every three months, audit your risk profile:

Questions to answer:

1. What's your average delta at entry across all strategies?
2. How often do assignments happen vs. your delta predictions?
3. Are you concentrating too much capital in one ticker?
4. What's your actual win rate vs. what you thought it was?

Example insight:

• You thought you were conservative (selling 0.30 delta options)
• Journal shows average delta is 0.42 (much more aggressive)
• Assignment rate is 58% (way higher than expected 30%)

Action: Adjust strike selection to match your actual risk tolerance.

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Common Journaling Mistakes (And How to Avoid Them)

Mistake 1: Tracking Gross Profit Instead of Net ROI

Bad: "I made $500 selling puts this week!"

Good: "I made $494.35 net (after commissions) on $50,000 deployed capital = 0.99% weekly return (51% annualized)."

Always calculate ROI as a percentage of capital at risk.

$500 profit on $10,000 deployed (5% return) is vastly different from $500 profit on $100,000 deployed (0.5% return).

Mistake 2: Ignoring Assignment Costs

When your covered call gets assigned, you lose the opportunity to sell shares at market price.

Example:

• Sold $180 strike covered call
• Stock is at $185 at expiration
• You collected $250 premium
• But you sold shares $5 below market ($500 loss per contract)

Net outcome: $250 premium - $500 opportunity cost = -$250

Your journal should track this. Most traders don't, and they think they're profitable when they're not.

Mistake 3: Not Tracking Time

ROI without time context is meaningless.

A 2% gain in 7 days (104% annualized) is great.
A 2% gain in 90 days (8% annualized) is terrible.

Always annualize your returns: (ROI / Days Held) × 365

Mistake 4: Inconsistent Data Entry

You sold 10 trades this month. You logged 7 of them.

Your "journal" now shows 30% higher win rate than reality because you forgot to log the losers.

Solution: Set a recurring calendar reminder. Every Friday at 4 PM, log that week's trades. No exceptions.

Or use automation (our IBKR upload tool does this for you).

Mistake 5: No Action Items

Tracking without adjusting is just record-keeping.

Every review session should end with:

• One thing you'll do differently next week
• One risk you'll reduce
• One opportunity you'll pursue

If your journal doesn't change your trading, you're wasting time.

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Key Metrics to Track by Strategy

Different strategies need different focus areas:

Covered Calls

Primary metric: Annualized ROI
Secondary metrics:

• Assignment rate (ideally 20-40% if you want income, 60%+ if you want to sell shares)
• Avg DTE at entry (14-21 is the sweet spot for most traders)
• Strike selection (how far OTM? 5-10% is typical)

Red flags:

• Assignment rate below 10% → You're too conservative, leaving premium on the table
• Assignment rate above 70% → You're too aggressive, effectively running a liquidation strategy

Cash-Secured Puts

Primary metric: Premium per dollar deployed
Secondary metrics:

• Assignment frequency (do you want the shares?)
• Time to assignment (are you getting assigned early due to dividends?)
• Subsequent covered call premium (if running the wheel)

Red flags:

• Assigned on more than 50% of trades → Tighten strike selection or increase DTE
• Never getting assigned → You're being too conservative, increase position size or delta

Long Calls

Primary metric: Win/loss ratio
Secondary metrics:

• Avg hold time (are you holding too long and letting theta decay kill you?)
• Max profit achieved during hold (did you miss exit opportunities?)
• Delta at entry (targeting 0.50+ for directional plays, 0.30-0.50 for income)

Red flags:

• Win rate below 40% → Reduce position size or shift to selling premium instead
• Holding past 21 DTE frequently → Set exit rules to prevent theta decay losses

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Real-World Journal Insights (From DaysToExpiry Users)

We analyzed 10,000+ trades from users who upload Interactive Brokers statements to our platform. Here's what separates top performers from average traders:

Top 20% of Traders (By ROI):

Behavioral patterns:

• Average 3.2 reviews per month of their trade history
• Adjust strike selection within 2 weeks of noticing assignment pattern changes
• Focus 80% of capital on 2-3 highest-performing tickers (not 10+ tickers)
• Set exit rules before entering trades (70% close at 50% profit target, 30% hold to expiration)

Performance metrics:

• 32% annualized ROI (covered calls)
• 22% annualized ROI (cash-secured puts)
• 68% win rate (defined as keeping premium without assignment)

Bottom 20% of Traders:

Behavioral patterns:

• Review trade history less than once per month (if at all)
• Use same strike selection regardless of market conditions
• Spread capital across 10+ tickers without concentration analysis
• No predefined exit strategy (react emotionally to market moves)

Performance metrics:

• 12% annualized ROI (covered calls)
• 8% annualized ROI (cash-secured puts)
• 48% win rate

The difference isn't intelligence or experience. It's using data to make better decisions.

Top traders journal. Bottom traders hope.

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Your Next Steps

Here's how to start journaling today:

Step 1: Set Up Your System (15 minutes)

Choose your tool:

• Manual: Copy our Google Sheets template (link to template)
• Automated: Upload your IBKR statement to DaysToExpiry Portfolio Analyzer

Create your first entry:

• Log your most recent trade (even if it's still open)
• Fill in all entry metrics (date, ticker, strategy, premium, DTE)
• Calculate capital at risk

Step 2: Create a Logging Habit (Daily)

Set a recurring calendar event:

• Time: Every trading day at 4:00 PM ET (after market close)
• Task: Log any trades opened or closed that day (takes 2-3 minutes)
• Review: Check if any open positions need adjustment

Consistency beats perfection. Even a simple log is better than no log.

Step 3: Weekly Review (Sundays, 20 minutes)

Pull up your journal and answer:

1. Which trades performed best this week? Why?
2. Did any trades get assigned unexpectedly? What was the pattern?
3. Is one strategy outperforming? Should I shift capital allocation?

Write 1-2 sentences of notes. This compounds into valuable insights over time.

Step 4: Monthly Strategy Adjustment (30 minutes)

Calculate:

• Total ROI by strategy (covered calls, CSPs, long calls)
• Win rate by strategy
• Capital allocation by strategy

Then ask:

• Should I increase allocation to my best-performing strategy?
• Should I tighten or widen strike selection based on assignment rates?
• Are there tickers I should stop trading (low premium, high risk)?

Make one concrete change for next month.

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The Bottom Line

Your broker shows transactions. Your journal shows performance.

If you're selling options without tracking outcomes by strategy, ticker, and time period, you're flying blind.

Most traders can't answer:

• Which strategy makes them the most money per dollar deployed?
• What delta at entry gives them the best risk/return?
• Are they profitable after accounting for commissions and assignment costs?

Start tracking today. In three months, you'll know exactly what works and what doesn't.

And you'll be a better trader because of it.

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Automate your tracking: Upload your Interactive Brokers statement to DaysToExpiry Portfolio Analyzer and see your complete trade history, performance by strategy, and assignment patterns—automatically. No spreadsheets, no manual entry.

For more on structuring multi-strategy portfolios and tracking performance across positions, read our guide on Options Portfolio Management. If you want to understand how to size positions and manage risk, check out Options Risk Management: Position Sizing & Loss Controls.

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