Options Portfolio Management: Complete Guide to Wheel Strategy Analytics

You're running 12 covered calls. Eight cash-secured puts. Three positions just got assigned.

Which ones are making money? Which stocks should you stop trading? Are you overexposed to one sector?

Most options traders have no idea.

They open positions when opportunities look good. They track individual trades. But they never step back to see the portfolio as a whole.

This is how you end up with five tech positions all moving together, or three underperforming tickers eating 40% of your capital.

Options portfolio management solves this. It's not about tracking individual trades—it's about optimizing your entire portfolio for consistent income. Let's build a system that works.

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Why Individual Trade Tracking Isn't Enough

Your options trading journal shows trade-by-trade performance. That's step one.

Portfolio management is step two: How do all your positions work together?

Here's what changes when you think portfolio-first:

Trade-Level View (What Most Traders Track):

• Sold AAPL $180 call for $2.50 → 36% annualized ROI
• Sold MSFT $400 put for $3.80 → 18% annualized ROI
• Sold NVDA $850 call for $7.20 → 42% annualized ROI

Looks great, right?

Portfolio-Level View (What You Actually Need):

Position	Capital Deployed	Annualized ROI	Sector	% of Portfolio
AAPL CC	$18,000	36%	Tech	24%
MSFT CSP	$40,000	18%	Tech	53%
NVDA CC	$17,000	42%	Tech	23%

Portfolio insight: You have 100% exposure to tech. If the sector drops 10%, every position gets assigned simultaneously.

Your individual trades are great. Your portfolio is fragile.

That's the difference.

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The 5 Core Metrics of Portfolio Management

Stop tracking trades. Start tracking these five portfolio-level metrics.

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1. Capital Allocation by Strategy

How much of your capital is deployed in each strategy?

Example Portfolio:

Total Capital Available: $150,000

STRATEGY ALLOCATION
Covered Calls: $75,000 (50%)
Cash-Secured Puts: $60,000 (40%)
Long Calls: $15,000 (10%)

Undeployed Cash: $0 (0%)

What this tells you:

• You're 90% in premium-selling strategies (covered calls + CSPs)
• Zero cash buffer for opportunistic plays
• Fully deployed = you can't add new positions without closing existing ones

Red flags:

• More than 70% in one strategy → Over-concentrated
• Less than 10% cash reserves → No flexibility for corrections
• Long calls above 20% → You're speculating, not generating income

Ideal allocation (for income-focused traders):

• Covered calls: 40-50%
• Cash-secured puts: 30-40%
• Cash reserves: 10-20%
• Speculative (long calls): 5-10%

Adjust based on your risk tolerance, but measure it.

2. Performance by Strategy

Which strategy is actually making you money?

Strategy	Trades (YTD)	Win Rate	Avg ROI	Annualized ROI	Total Profit
Covered Calls	47	68%	1.2%	32%	$11,817
Cash-Secured Puts	32	81%	0.9%	18%	$8,099
Long Calls	15	40%	-0.3%	-6%	-$1,240

Portfolio insight:

• Covered calls generate 58% of total profit despite being only 50% of capital
• Long calls are losing money consistently
• CSPs have higher win rate but lower ROI per trade

Action: Shift 5% of capital from long calls to covered calls. Expected annual increase: ~$2,400.

You can't optimize what you don't measure.

3. Sector & Ticker Concentration

How much risk is concentrated in one sector or ticker?

Example Portfolio:

SECTOR BREAKDOWN
Technology: 65%
Healthcare: 20%
Financials: 10%
Energy: 5%

TOP 5 TICKERS BY CAPITAL
AAPL: $35,000 (23%)
MSFT: $40,000 (27%)
NVDA: $25,000 (17%)
GOOGL: $20,000 (13%)
UNH: $15,000 (10%)

Red flags:

• Any sector above 50% → Sector risk (tech crashes = your portfolio crashes)
• Any single ticker above 25% → Stock-specific risk
• Top 3 tickers above 60% → Diversification illusion (you're betting on 3 stocks)

Ideal concentration:

• No sector above 40%
• No single ticker above 15%
• Top 5 tickers below 60% of portfolio

Diversification isn't about number of positions. It's about uncorrelated positions.

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4. Assignment Rate by Ticker & Strategy

Which stocks keep getting assigned? Is that what you want?

Example Analysis:

Ticker	Strategy	Trades	Assignment Rate	Avg Days to Assignment	Notes
AAPL	CC	12	75%	18	High volatility, assignments common
MSFT	CC	8	25%	N/A	Conservative strikes working
NVDA	CC	10	90%	12	Too aggressive, constant assignments
SPY	CSP	15	13%	N/A	Perfect for income, rarely assigned
TSLA	CSP	7	71%	15	High assignment = capital churn

Portfolio insights:

• NVDA covered calls: 90% assignment rate means you're constantly buying/selling shares (high transaction costs, tax inefficiency)
• SPY cash-secured puts: 13% assignment rate = ideal income generation
• TSLA: High assignment rate on puts means you're frequently taking ownership (is that your strategy or an accident?)

Actions:

• NVDA: Widen strike selection (push to 10% OTM instead of 5%)
• SPY: Keep strategy unchanged (working perfectly)
• TSLA: Decide if you want shares or just premium. If premium, increase DTE and widen strikes.

Assignment rate reveals intent vs. outcome.

5. Coverage & Exposure Matrix

For covered calls: What percentage of your shares are covered?
For cash-secured puts: How much cash is reserved vs. deployed?

Coverage Matrix Example:

Ticker	Shares Owned	Shares Covered	Coverage %	Naked Exposure
AAPL	200	200	100%	$0
MSFT	150	100	67%	$20,000 (50 shares)
NVDA	100	100	100%	$0
GOOGL	80	0	0%	$13,600 (80 shares)

Portfolio insight:

• GOOGL has zero coverage (you own shares but haven't sold any calls)
• MSFT is partially covered (opportunity to sell 50 more calls)
• AAPL and NVDA are fully covered (maximizing income from owned shares)

Cash-Secured Put Reserve:

Total Cash Available: $60,000
Reserved for Open Puts: $45,000
Undeployed Cash: $15,000

Deployment Rate: 75%

If deployment is above 90%, you have no cushion for new opportunities. Below 50%, you're leaving money on the table.

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The Wheel Strategy: Portfolio-Level Tracking

The wheel strategy (selling cash-secured puts → getting assigned → selling covered calls) is the most popular multi-step options strategy.

But most traders don't track it as a system. They track parts of it.

Here's how to track the wheel at the portfolio level:

Wheel Metrics Dashboard

WHEEL STRATEGY PERFORMANCE (YTD)

Total Wheel Cycles Completed: 8
Avg Cycle Duration: 67 days
Avg Profit per Cycle: $1,847
Annualized ROI (per cycle): 24.3%

CYCLE BREAKDOWN
Phase 1 (CSP → Assignment): 21 days avg
Phase 2 (Hold Shares): 12 days avg
Phase 3 (CC → Assignment): 34 days avg

WIN RATE BY PHASE
CSP Expired (no assignment): 38%
CC Expired (kept shares): 25%
Full Cycle Completion: 62%

What this tells you:

• 62% of wheels complete successfully (CSP assigned → shares sold via CC)
• 38% of CSPs expire worthless (you keep premium, don't get shares)
• Only 25% of covered calls expire worthless (you usually get assigned)

Portfolio decision: If you want to complete wheels, increase CSP delta (tighten strikes). If you prefer collecting premium without assignments, widen CSP strikes.

Ticker Performance in the Wheel

Ticker	Completed Wheels	Avg Profit/Wheel	Annualized ROI	Notes
AAPL	3	$2,140	28%	Excellent wheel candidate
MSFT	2	$1,620	18%	Slow but steady
NVDA	2	$3,200	42%	High profit but volatile
TSLA	1	-$480	-12%	Got assigned, stock dropped, sold at loss

Portfolio insight: TSLA lost money on the wheel because the stock dropped significantly after assignment. This reveals directional risk in the wheel strategy.

Action: Only run wheels on stocks you're bullish on long-term (or willing to hold through drawdowns).

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How to Structure Your Portfolio (Income vs. Growth)

Different goals require different portfolio structures.

Income-First Portfolio (Conservative)

Goal: Generate 15-25% annual return with minimal assignment risk.

Structure:

• Covered Calls (50%): Sell 0.30 delta calls at 21-35 DTE
• Cash-Secured Puts (30%): Sell 0.25 delta puts at 35-45 DTE
• Cash Reserves (20%): For opportunistic plays during volatility spikes

Target metrics:

• Assignment rate: 20-30%
• Win rate: 70-80%
• Avg annualized ROI: 18-25%

Best for: Retirees, conservative investors, portfolio sizes above $100K

Growth Portfolio (Moderate Risk)

Goal: 25-40% annual return with higher assignment rates and active position management.

Structure:

• Covered Calls (40%): Sell 0.35 delta calls at 14-21 DTE
• Cash-Secured Puts (35%): Sell 0.30 delta puts at 21-35 DTE
• Wheel Positions (15%): Active wheel cycles on 3-5 core tickers
• Cash Reserves (10%): Smaller buffer, higher deployment

Target metrics:

• Assignment rate: 40-50%
• Win rate: 60-70%
• Avg annualized ROI: 28-40%

Best for: Active traders, portfolio sizes $50K-$200K, moderate risk tolerance

Aggressive Portfolio (High Risk)

Goal: 40%+ annual return, high assignment rates, frequent trading.

Structure:

• Covered Calls (35%): Sell 0.40 delta calls at 7-14 DTE
• Cash-Secured Puts (30%): Sell 0.35 delta puts at 14-21 DTE
• Wheel Positions (25%): Aggressive wheel on volatile stocks
• Long Calls (10%): Directional plays on earnings or catalysts

Target metrics:

• Assignment rate: 60%+
• Win rate: 50-60%
• Avg annualized ROI: 40%+
• Higher transaction costs and tax implications

Best for: Experienced traders, full-time focus, strong risk tolerance

Choose your structure based on time commitment and risk tolerance, not just return goals.

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Portfolio Rebalancing: When and How

Your portfolio drifts over time. Positions close, assignments happen, new opportunities emerge.

Rebalancing keeps you aligned with your strategy.

Monthly Rebalancing Checklist

Step 1: Calculate Current Allocation

CURRENT STATE (End of Month)
Covered Calls: $85,000 (57%) [Target: 50%]
Cash-Secured Puts: $35,000 (23%) [Target: 40%]
Cash Reserves: $30,000 (20%) [Target: 10%]

VARIANCE FROM TARGET
CC: +7% (overweight)
CSP: -17% (underweight)
Cash: +10% (too much idle capital)

Step 2: Identify Adjustments

• Close 2 covered call positions (free up $18,000)
• Deploy $48,000 into new cash-secured puts
• Keep $15,000 in cash reserves (instead of $30,000)

Step 3: Execute Rebalancing Trades

Prioritize:

1. Close losing or underperforming positions first
2. Redeploy capital into highest ROI opportunities
3. Maintain sector diversification while rebalancing

Step 4: Document Changes

"Rebalanced 2026-01-31: Closed GOOGL and TSLA covered calls (underperforming). Opened 3 new CSP positions (SPY, MSFT, AAPL). Reduced cash reserves by $15K."

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Tracking Portfolio Greeks (Advanced)

If you want to get serious about portfolio risk, track aggregate Greeks.

What Portfolio Greeks Tell You

Greek	What It Measures	Ideal Range (Income Portfolio)
Delta	Directional exposure	0 to +30 (slight bullish)
Theta	Daily time decay income	+$50 to +$150/day
Gamma	Delta change risk	-100 to 0 (short gamma)
Vega	Volatility exposure	-50 to +50 (neutral to slight short)

Example Portfolio Greeks:

PORTFOLIO GREEKS (Total)
Delta: +22 (slight bullish bias)
Theta: +$87/day (collecting $2,610/month in time decay)
Gamma: -45 (short gamma, typical for premium sellers)
Vega: -30 (slight negative volatility exposure)

What this means:

• Your portfolio benefits from time passing (positive theta)
• You're slightly bullish (positive delta)
• You lose money if volatility spikes (negative vega)
• If the market moves sharply, delta will accelerate against you (negative gamma)

Portfolio decision: If VIX is low and you expect volatility to increase, consider reducing positions or widening strikes to reduce vega exposure.

Most brokers (including Interactive Brokers) show portfolio Greeks. Use them.

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DaysToExpiry Portfolio Analyzer: Automated Portfolio Management

If you use Interactive Brokers, we've built portfolio analytics into DaysToExpiry.

Upload your IB activity statement and instantly see:

Portfolio Dashboard

View in app →

Strategy Breakdown:

• Total capital deployed by strategy
• Premium collected per strategy (YTD, monthly, custom periods)
• Win rate and annualized ROI by strategy
• Assignment rates by strategy and ticker

Sector & Ticker Concentration:

• Visual allocation breakdown
• Exposure warnings (>50% sector, >20% single ticker)
• Correlation analysis (which positions move together)

Coverage Matrix:

• See which covered call positions are fully/partially covered
• Identify naked exposure
• Calculate undeployed capital available for new positions

Wheel Tracking:

• Automatic detection of wheel cycles
• Profit/loss per completed wheel
• Avg cycle duration and ROI
• Phase-by-phase breakdown (CSP → Hold → CC)

Time-Window Filtering:

• Analyze Q1 vs Q2 performance
• Compare high volatility periods vs low volatility periods
• Seasonal pattern detection

No manual tracking. Just upload your statement and see your entire portfolio performance.

Take control of your portfolio: Use our Interactive Brokers Portfolio Analysis tool to automatically parse your trades and track multi-strategy performance, or explore Options Risk Management to set position sizing rules.

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Common Portfolio Management Mistakes

Mistake 1: Tracking Trades Instead of Strategy Performance

Bad: "I made $2,400 this month from options trading!"

Good: "Covered calls generated $1,600 (67% of profit) with 50% of capital. CSPs generated $800 (33% of profit) with 40% of capital. Long calls lost $200. Should shift 5% from CSPs to CCs."

Always compare strategy performance as ROI per dollar deployed.

Mistake 2: Ignoring Sector Concentration

Bad: "I have 10 positions, so I'm diversified."

Reality: All 10 positions are tech stocks. You're not diversified—you're leveraged to one sector.

Fix: Limit any sector to 40% of portfolio. If tech is your edge, fine—but measure it and accept the risk consciously.

Mistake 3: No Cash Reserves

Bad: "I deploy 100% of my capital at all times to maximize returns."

Reality: When VIX spikes 50% and premiums double, you have no capital to take advantage.

Fix: Keep 10-20% in cash reserves. This isn't idle money—it's optionality.

Mistake 4: Treating Wheel as Passive Income

Bad: "I just run the wheel on autopilot. It's a passive strategy."

Reality: The wheel requires active management. If you get assigned on a stock that's dropping, you'll either:

• Hold shares at a loss (capital trapped)
• Sell covered calls below your cost basis (locking in losses)
• Exit the position at a loss (failed wheel)

Fix: Only run wheels on stocks you're bullish on long-term. Set maximum position sizes per ticker (10-15% max).

Mistake 5: Not Adjusting for Market Conditions

Bad: "I sell 0.30 delta calls every week regardless of market conditions."

Reality:

• Low VIX (12-15): Premiums are terrible, selling 0.30 delta barely pays commissions
• High VIX (25-35): Premiums are rich, you can sell 0.25 delta and collect more than usual 0.30 delta

Fix: Adjust strike selection based on VIX. When VIX < 15, consider 0.35 delta or reduce position sizes. When VIX > 25, widen strikes to 0.25 delta.

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Your Portfolio Management Workflow (Step-by-Step)

Here's how to implement portfolio-level tracking:

Daily (5 minutes)

1. Check open positions for upcoming expirations (within 7 days)
2. Identify positions with >50% max profit (consider closing early)
3. Log any new positions opened or closed

Weekly (15 minutes)

1. Calculate portfolio allocation by strategy (should match targets ±5%)
2. Review sector concentration (any sector >50%? Flag it)
3. Identify underperforming tickers (should you stop trading them?)

Monthly (30 minutes)

1. Run full portfolio analysis:
   • Total ROI by strategy
   • Win rate by strategy and ticker
   • Assignment rates by ticker
   • Capital allocation vs. targets
2. Rebalance if any strategy is >10% off target
3. Document one change for next month (strike adjustment, new ticker, exit underperformer)

Quarterly (1 hour)

1. Review portfolio Greeks (if applicable)
2. Calculate full-year projections based on current performance
3. Evaluate whether current strategy mix aligns with goals
4. Make major adjustments (shift from growth to income, increase/decrease risk)

Consistency beats complexity. Even a simple monthly review is 10× better than no portfolio-level analysis.

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The Bottom Line

Trade tracking shows individual performance. Portfolio management shows system performance.

Most traders can't answer:

• Which strategy makes the most money per dollar deployed?
• Are they overexposed to one sector?
• What's their actual assignment rate vs. what they think it is?
• Should they rebalance based on current performance?

If you're running more than 5 open positions at a time, you need portfolio-level tracking.

Track your allocation. Measure strategy performance. Rebalance monthly.

And watch your portfolio become more consistent, more profitable, and easier to manage.

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Automate your portfolio tracking: Upload your Interactive Brokers statement to DaysToExpiry Portfolio Analyzer and see strategy breakdowns, sector concentration, and wheel analytics—automatically. No spreadsheets. No manual calculations.

For detailed trade-by-trade tracking before aggregating into portfolio analytics, read Options Trading Journal: Track Performance with DaysToExpiry Analytics. To learn how to set up position sizing rules within your portfolio, check out Options Risk Management: Position Sizing & Loss Controls.

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