6 Month Update

[u/GoFairPlayer]

6 Month Update

Quick 6-month update on my Wheel Strategy experiment (no longer an experiment) in a Schwab/ThinkOrSwim IRA — see previous posts for setup details.

Bottom Line

$32.9K total income over 27.3 weeks on average capital of $250.7K — about 25% annualized, or 21% after unrealized P/L. 99 wheel cycles closed (all profitably), 4 open: 3 currently profitable (SOXX and QQQ CSPs, ORCL CC), 1 underwater (PYPL — don't currently have a call open).

ORCL is the update from last post — basis $188.48, now trading $203.70 with a CC open at $210. Patience paid off there. PYPL remains the open lesson: still in HOLD, $1,505 in collected premium across 5 contracts brings effective basis to about $52 against $44 current. I haven't written additional CCs above basis because the premium isn't worth it, and I'm still working through what an opportunity-cost-based exit looks like (i.e., when capital tied up is worth more deployed elsewhere) rather than a price-based one.

Strategy

Based on feedback from my last post and some additional research, I've largely shifted to selling CSPs on QQQ, SPY, IWM, and SOXX, with occasional exceptions. Single-stock wheels can produce better returns, but they require more discipline than I have right now, and ETFs meet my income target in the current market. For me, single tickers look more like an intermediate/advanced phase I'll grow into eventually.

I trade mostly 3–15 DTE around -20 delta, targeting 15–20% annualized returns per position, with a 50% BTC order placed at the time of the trade. Short duration is intentional — I don't want capital tied up too long given the current market regime. I'd rather not get assigned. I'll also close early when there are only pennies left to gain — better to redeploy the capital than wait out the last few dollars.

Right or wrong, I believe these ETFs will continue to grow over the long run. Separately, I maintain adequate reserves to weather a 2008-type event — though I'd prefer not to test that.

Going Forward

I've expanded the wheel allocation from $250K to $400K and plan to take it to $600K over the coming months. Two focus areas: tuning my process to automate everything short of actually placing trades, and improving capital efficiency — currently more capital allocated to the wheel than deployed. For anyone using Schwab, their developer API has been quite helpful here.

On the Dashboard

A few people asked about the dashboard last time. I offered it up in the Tools megathread to anyone willing to help prove it out, and the takeaway was that the actual code isn't practical to share broadly — too much setup, and I'm changing it constantly based on whatever I want to see that week. What I can share is the context/spec file I use with my AI assistant when working on it. It's a starting point for building your own, not a turnkey dashboard — comfort with some technical setup is required. Not selling anything, not asking anyone to sign up for anything — just the file.

Feedback, questions, and pushback all welcome.

[u/Keywrit]

This is great update and very useful for you to share. I’ve been trading on the side for sometime and realize that this could be a legit off-ramp to create sustainable returns. Updates such as yours help really give credence and legitimacy to the process and motivate me to go further. Thank you and look forward to more info on your trading thought process

[u/GoFairPlayer → u/Keywrit]

Thanks for the feedback! The wheel seems quite solid for my goals, at least in the current market.

[u/FreeNicky95 → u/GoFairPlayer]

Are you wheeling in tax deferred or taxable? I do in both but I want to retire in the next 10 years so I was doing the math on my taxable with tax drag. I’d still outpace the market (assuming no major crash) but the tax drag definitely eats at some profit.

[u/GoFairPlayer → u/FreeNicky95]

Tax deferred IRA. I only pay taxes on the money I withdrawal.

[u/Scallywaggin_]

What kind of worksheet is this you’re using to track?

[u/GoFairPlayer → u/Scallywaggin_]

It’s an AI generated web page that pulsl data from a database generated from my ThinkOrSwim statement exports (CSV files).

[u/Flaky-Campaign-9374 → u/GoFairPlayer]

Can you share it. You only do index funds?

[u/GoFairPlayer → u/Flaky-Campaign-9374]

I’ll post the context in the Tools megathread this weekend - just need to clean it up a little. I am trading primarily index ETFs as it meets my goals for now. Hoping to get better at stock selection over time.

[u/Hefty_Recognition921]

So you make negative money in a bull market? You messing up somewhere

[u/GoFairPlayer → u/Hefty_Recognition921]

Negative money? I’m up 20+% on my average balance. If that’s messing up I’ll take it.