MoneyByMath
Home Weekly Article Mortgage Calculator Coast FIRE Retirement Compound Interest DRIP Calculator Debt Payoff 401(k) Loan Rent vs Buy a House Can I Afford a House Budget Analysis Financial Health Check Learn Stocks Learn the Options Wheel New, Used, or Leased Car Kids Future What's my Tax Bracket
Compound Interest DRIP Calculator Debt Payoff 401(k) Loan Rent vs Buy a House Can I Afford a House Budget Analysis Financial Health Check Learn Stocks Learn the Options Wheel New, Used, or Lease Car Kids Future What's my Tax Bracket
Latest Article

5 Mistakes to Avoid When Starting the Wheel Strategy

5 min read • Apr 8, 2026

When I first started running the wheel strategy, I made several costly mistakes that ate into my returns. After two years of consistent execution, I've identified the five most common pitfalls that beginners face - and how to avoid them.

1. Choosing High IV Stocks Without Understanding Why

Yes, high implied volatility means juicy premiums. But there's usually a reason a stock has elevated IV - it's risky. I learned this the hard way with a biotech stock that tanked 40% overnight on failed trial results. Now I only wheel stocks I'd be genuinely happy to own long-term.

2. Not Leaving Room for the Unexpected

Using all your capital on a single position leaves zero flexibility. When a better opportunity arose, I couldn't take advantage because I was fully deployed. Keep at least 20-30% in cash reserves to handle assignments and capitalize on volatility spikes.

3. Going Too Far Out of the Money on Puts

Selling puts at super low strikes feels safe, but the premiums are tiny and your return on capital suffers. I found the sweet spot is typically 5-10% below current price - enough premium to make it worthwhile, while staying within range of quality stocks I want to own.

4. Panicking and Closing Early

When a trade goes against you, the temptation to close early and take the loss is strong. But remember, the wheel strategy assumes you'll sometimes get assigned - that's not failure, that's the system working. Unless the fundamental thesis has changed, let the strategy play out.

5. Ignoring Earnings and Ex-Dividend Dates

Selling options right before earnings is essentially gambling. The IV crush after earnings can work in your favor if you're selling, but the risk of a gap move isn't worth it. Similarly, be aware of ex-dividend dates that might trigger early assignment on short calls.

The wheel strategy is powerful, but it requires discipline and patience. Avoid these five mistakes and you'll be well on your way to consistent options income.

Discussion

Share This Article

Found this useful? Share it with someone!

More Tools

Not financial advice. Educational use only.

MoneyByMath

Free financial calculators and tools for new age to build wealth and make informed money decisions.

Resources

Newsletter Calculators Home

Community

Follow on X Contact Us Discussion

NOT FINANCIAL ADVICE:
This website is for informational and educational purposes only. Nothing on this site constitutes financial, investment, legal, or tax advice. All calculators and analysis tools produce estimates only - actual results will vary and may be materially different. Past performance is not indicative of future results. We are not registered investment advisors, brokers, or licensed financial professionals. Always consult a qualified financial advisor, accountant, or attorney before making any financial decisions. Some links on this site are referral links, meaning we may receive compensation or promotional rewards (such as free stock) if you sign up.

Mortgage rate data is sourced from the FRED® API (MORTGAGE30US series) and is not real-time. This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis. We make no representations or warranties as to the accuracy, completeness, or timeliness of any data displayed.

By using this site you agree to our Privacy Policy and the FRED® API Terms of Use. Use this site at your own risk.

© 2026 MoneyByMath. All rights reserved.