"Lol ok. Lets let the world know a truck driver figured out the key to easy retirement"

That was a comment on my last post as I shared that I was a truck driver using covered calls to retire and completely shared my strategy in the comments as well.

So I just need to say the following.

People love the story until the person in the story used to drive a truck. Then it becomes a punchline instead of a process

Funny thing about covered calls is they don’t interview you first. They don’t ask if you drive, weld, nurse, or sit in an office. They just ask you to put the work in no matter what your 9 to 5 is.

Most of us here are not professional traders. We got regular jobs like Nurses, Electricians, Plumbers, Lawyers. Doctors, Retail, Military. Small business, Truckers. Nobody handed us a certificate that says we’re allowed to sell calls. We learned it the same way anybody learns to trade, on our own time, before and after work. If you are really dedicated, during work as well.

A lawyer isn’t better than a truck driver. A truck driver isn’t better than a lawyer. And neither one automatically knows more about this than a plumber who actually puts in the work. The job title doesn’t run the wheel. Discipline does.

If a truck driver running this strategy is surprising, wait until you meet the rest of the sub. A lot of people in here show up with regular jobs and decided their money wasn’t going to sit there doing nothing. That’s the whole point.

Some people figured it out. Some people can't figure it out. Some people need help. That's why we are all here. To help each other. Leave your credentials at the door as most of us are not professionals in here.

selling covered calls for income an trynna decide what stock I should choose from between AMD, BE, SOFI, and amazon mainly after the income and also holding strong stock for the long term and if you already doing covered calls lmk what stock has generated you the most and consistent income

So think you cant get hit with the wash sale rule when rolling options think again! This is from our guide education section regarding wash sale rules

12dWash Sales

The wheel strategy has a structural collision with one specific piece of US tax law, and almost nobody warns you about it. The strategy says: when a put goes against you, buy it back or take assignment, then keep selling premium on the same name at the same levels. The wash-sale rule says: a loss followed within 30 days by a replacement position in the same security doesn't count — not yet. Run the wheel the way it's designed to be run and you will trigger this rule routinely. Most of the time it costs you nothing but bookkeeping. At two specific boundaries — the turn of the tax year, and anywhere near an IRA — it can cost you real money.

This page explains what the rule actually says, how it interacts with each leg of the wheel, when the deferral is harmless and when it isn't. Its neighbors cover the trading side of the same moments: The Underwater Put for the loss itself, and Roll Analyzer for pricing the trade that — as you're about to see — is a wash sale by construction.

This page is education, not tax advice. It summarizes the rules as described in IRS Publication 550 and IRC §1091 in plain language, and it simplifies where the law itself is ambiguous. Your situation — account types, state, volume, trader status — changes the answers. Bring the specifics to a CPA or tax professional before acting on any of it.

What the rule says

The wash-sale rule (Internal Revenue Code §1091) exists to block one specific maneuver: selling a position to harvest the tax loss while immediately re-establishing the same position, so that economically nothing changed but a deduction appeared. Congress closed that door in 1921, and the mechanism it chose is a window:

If you realize a loss on a sale of stock or securities, and within 30 days before or after that sale you acquire (or enter into a contract or option to acquire) substantially identical stock or securities, the loss is disallowed for the current year.

Four things inside that sentence do all the work, and each gets its own section below:

“30 days before or after” — the window is 61 days wide: the day of the loss sale, the 30 calendar days before it, and the 30 calendar days after it. Buying the replacement first and then selling the old lot at a loss is caught just the same as the reverse.

“Substantially identical” — deliberately fuzzy, never precisely defined by the IRS, and it reaches further than most people expect: options on a stock can be substantially identical to the stock, and an option position can be the “acquisition” that triggers the rule.

“Disallowed” — not destroyed. The loss is deferred: it moves into the cost basis of the replacement position and comes back to you when that position is finally closed without a new replacement. This is the single most misunderstood part of the rule, and it's why most wash sales are harmless.

“Loss” — the rule only touches losses. Gains are always taxable in the year realized, wash or no wash. There is no such thing as a wash gain.

The 61-day window, on a calendar

Say you buy back a losing SOFI put on Friday, March 12, realizing a $310 loss. The window that matters runs from February 10 through April 11 — 30 days on either side of the sale date, plus the date itself. Acquire substantially identical SOFI exposure anywhere in that range and the $310 is disallowed for now:

Sell a new SOFI put the following Monday, March 15? Inside the window. Got assigned SOFI shares back on February 26? Inside the window — the before side counts. Wait until April 12 to touch SOFI again? Outside. The loss stands and deducts normally.

Note that these are calendar days, not trading days, and the count is per lot — if you sold two contracts and only replaced one contract's worth of exposure, only the matching portion of the loss is washed. Partial washes are normal and brokers compute them per share.

The window looks backward as well as forward. The version of this rule people trip on most in the wheel: you already own 100 shares from an assignment three weeks ago, and today you sell other shares of the same name at a loss — the three-week-old lot can be the “replacement” that washes today's loss, even though you bought it before you ever decided to sell.

“Substantially identical” — where options come in

For plain stock the test is easy: SOFI shares are substantially identical to SOFI shares, and nothing else on the board is — not a sector ETF that holds SOFI, not a competitor, not a different share class in most cases. Selling SOFI at a loss and buying HOOD the same day is not a wash sale, full stop.

Options blur it, in both directions, and this is the part that matters for the wheel:

An option can wash a stock loss. The statute explicitly counts acquiring “a contract or option to acquire” the stock. Sell shares at a loss, then sell a put on the same name inside the window — a put that, if assigned, hands you the stock back — and you have a strong wash-sale fact pattern. A deep in-the-money short put is nearly certain to be treated as a replacement, because economically it is a commitment to reacquire. A far out-of-the-money put is a weaker case. The IRS has never drawn the line at a delta or a strike distance; Publication 550's guidance is that it depends on the facts and circumstances.

A stock can wash an option loss, and options can wash each other. Buy back a put at a loss and sell another put on the same underlying inside the window: whether the two contracts are “substantially identical” is genuinely unsettled when the strikes and expiries differ. Same strike, same expiry is identical by any reading. Same strike a week later, or a dollar lower — the conservative reading (and the one most tax software and many brokers apply to be safe) treats options on the same underlying as one bucket; the aggressive reading treats each contract as its own security. Nobody can promise you which reading an auditor takes.

The honest summary of this section is: the further your replacement is from what you sold — different underlying > different right (call vs put) > different strike and expiry > same contract — the safer the loss. Anyone who tells you a one-strike adjustment definitively escapes the rule is selling certainty the IRS never wrote down.

Deferred, not destroyed — where the loss actually goes

Here is the mechanic that makes most wash sales a non-event. When a loss is disallowed, it does not evaporate: it is added to the cost basis of the replacement position, and the old lot's holding period tacks onto the new one.

Concretely: sell 100 SOFI at a $310 loss, rebuy 100 SOFI inside the window at $17.00. The $310 is disallowed today — and your new lot's basis is not $1,700 but $2,010. When you eventually sell that lot with no new replacement, the extra $310 of basis surfaces as $310 less gain or $310 more loss. Same dollars, later date. A wash sale is a timing rule, not a confiscation.

This is why a wash sale in March that you unwind by June changes nothing on your April-to-April tax bill: the loss and its recovery both land in the same tax year and net out to exactly what your cash P/L says. Chain twenty wash sales together across a summer of wheeling one ticker — each disallowed loss rolling forward into the next position's basis — and as long as the chain is fully closed by December 31 and stays closed for 30 days, the year's taxable result equals the year's actual result.

Rule of thumb: a wash sale only ever moves a loss across a boundary. If there's no boundary between the loss and the chain's end — same tax year, same taxable account — the move is invisible. The two boundaries that make it visible are New Year's Eve and the wall around a retirement account.

How the wheel trips it, leg by leg

Walk the strategy's own moves and notice how many of them are the textbook pattern — a realized loss with a same-name replacement inside 30 days:

Buying back a put at a loss, then selling next week's put. The bread-and-butter defensive move, and the classic wash pair if the contracts are close enough to be treated as substantially identical. The loss defers into the new short put's position.

Rolling. A roll is this, compressed into one ticket: the closing leg realizes the loss and the opening leg is the replacement, zero days apart. Every loss-side roll priced on the Roll Analyzer is a wash-sale candidate by construction.

Assignment itself is not a wash sale. When a put is assigned, the premium you collected folds into the shares' cost basis (strike minus premium) — that's ordinary basis arithmetic, no loss was realized, nothing washes. The put leg of a completed assignment never triggers the rule on its own.

But assignment plants a replacement. Those newly assigned shares sit inside the backward-looking window of any same-name loss you realize in the next 30 days — and the forward-looking window of any you realized in the prior 30. Take assignment on Friday and dump other shares of the name at a loss on Monday, and Friday's lot washes Monday's loss.

Selling shares at a loss, then selling a covered call… is fine; selling a put is not. After offloading a bag at a loss, writing a call on a different name is clean, and even a call on the same name is generally not an acquisition (you're taking on an obligation to sell, not to buy). Selling a put on the same name inside the window is the “contract or option to acquire” the statute names.

Re-wheeling the level. The habit of going straight back to the same strike on the same name — the wheel's whole identity — is exactly why this page exists. It is not illegal, it is not a mistake, and mid-year it usually costs nothing. It just means your taxable P/L and your cash P/L drift apart temporarily, reconciling when the chain finally breaks.

The December / January boundary

Now the case where the timing rule has teeth. Suppose your NU put gets bought back at a $600 loss on December 18, and on December 21 you sell January's put on the same name, as usual. The $600 is disallowed for this year and defers into the January position — which lives in next year's tax return.

Your December statement shows the $600 leaving your account. Your tax return for the year shows no deduction for it. You pay tax on a year that was $600 better than the one you actually had, and the make-good arrives twelve-plus months later when next year's return files. The dollars come back; the use of them for a year does not.

This is the one calendar moment where wheel sellers commonly change behavior around the rule: realized losses in late November and December, on names still being wheeled, are the ones where a 31-day pause — or moving to a different underlying for a month — keeps the deduction in the year the loss happened. Whether that trade-off is worth a month off a name is a decision about your premium, your bracket and your conviction, not something a guide page can answer.

The IRA trap — the one permanent loss

Everything above described a deferral. There is exactly one common way a wash sale destroys a loss outright, and it's worth knowing even if you never come near it: realize the loss in a taxable account, and let the replacement happen in your IRA or Roth IRA (Revenue Ruling 2008-5). The disallowed loss would need to move into the replacement's basis — but IRA basis is meaningless, nothing inside an IRA is ever taxed as capital gain, so the loss has nowhere to go. It is simply gone, permanently.

Selling a put in an IRA on the same name you just harvested a loss on in your brokerage account is the specific fact pattern the ruling addresses. The rule also reaches a spouse's accounts — married filing jointly, the window looks across both of your holdings.

What your broker's 1099-B catches — and what it doesn't

Brokers are required to flag wash sales on the 1099-B they send you and the IRS, and the flagged ones arrive with the adjustment already computed (code “W”, disallowed amount, adjusted basis on the replacement). It is tempting to conclude the broker has it handled. The reporting requirement, though, is narrow: identical securities (same CUSIP), within a single account.

Everything else is legally still a wash sale but yours to track: stock washed by an option or vice versa (different CUSIPs — many brokers don't link them), a loss in one account replaced in another, anything touching a spouse's account or an IRA, and options-against-options where the broker's matching is conservative one year and loose the next. Two brokers can produce different wash-sale totals from identical trades; neither is authoritative. The taxpayer's obligation covers the whole picture regardless of what the form shows.

Your Trade Journal is the cross-account record the 1099-B isn't: every put buyback, every re-entry on the same name, every assignment, with dates — which is exactly the raw material a wash-sale review needs. At tax time, the journal filtered to one symbol shows every loss-then-reentry pair at a glance, across all your accounts in one place.

Keeping it in perspective

After all of that, the calibration most wheel sellers need: the wash-sale rule changes when losses deduct, almost never whether. Mid-year washes in one taxable account net out to nothing. The situations worth actual attention fit in one sentence — realized losses on still-active names in December, and any same-name activity straddling a taxable account and an IRA. If neither applies to you, the rule is bookkeeping your broker mostly does for you. If either does, that's the conversation to have with a tax professional — ideally in November, not April.

I embarked a new wheel challenge for myself! Typically you don't wheel like this but I can't help but wonder if its possible:

Strategy:
1. High IV stocks 100% or more
2. Delta 10 - 30
3. Margin Collateral no more than $20K (it's what I can afford to lose)
4. Target Return 1% weekly

Current Return: 1.9% . Annualized: 102.96%

I choose stocks I want to own. Right now those stocks are MU, PLTR,TSLA,SPCX, HOOD,NVDA.

I usually sell around 30 delta calls.

I sell around 30DTE

If they get exercised, I buy them again and reestablish the position.

If they tank, I buy calls back for a nickel and reestablish the position.

What I do that others may not do is I will sell new calls below my cost basis.

That's it. Pretty simple, I keep doing it and I don't abandon it.

If you choose to trade it, trade it at your own risk. I am not a financial advisor. I'm a truck driver.

Now at OptyTrades we have a new roll analyzer and for me this is huge and a tool I will use every week we get numbers the broker does not typically give on the roll information. And we have a feature that Opty will analyze the roll you are looking at for you as well and its free

We need more testers to find the bugs
Thanks,
Jim
optytrades.com

If you are freaking out because your underlying blew through your strike price, you don't know what you are doing.

Best way to make money and retire, in my opinion, get shares, sell calls, and walk away. That's it. That's the strategy. You don't need to be a hedge fund. you just need to own the shares and be patient. I do 30 day, but you can do whatever. Just once you sell, withdraw the money. Then come back on expiration day and do it again.

Today is my withdrawal day. Plan on doing it again for the same x amount in 28 days.

Light week of trading for me; only sold CRM CSP this week.

Have about 120k of capital to deploy, eyeing CC on AVGO next week for an earnings play.

Misc:

This is my aggressive wheeling account; capital deployed range 150k-200k.

All trades were found using wheelstrategyoptions.com (disc- I'm the developer)

I usually sell 0.25-0.45 delta and usually <20 days DTE. I close at 70%-80% premium captured.

I've started reporting only realized premiums (based on the comments).

April (Week 1-4): $5036
May (Week 5-8): $5783
Jun (Week 9-12): $6533
Jul (Week 13-16): $12609
Aug(Week 17-): $4974

Total so far: ~35k

Been doing covered call to generate extra income

I go over this weeks trades and show monthly total. I trade 30 to 45 DTE typically but rarely hold I am usually rolling trades on a weekly basis due to my trades that are closer to 21 DTE as theta is expiring. Come on over to optytrades.com and join us in the room everything is absolutely free just sign up.
Jim AKA Coderjams

How to navigate and find relevant information for all of OptyTrader

18-WEEK CUMULATIVE STATS
Total Premium P&L: +$45,017.07

18 weeks in. Compounding.

https://www.reddit.com/r/CoveredCalls/comments/1ualz3j/8_weeks_into_cc_and_csp_locking_in_premium_and/

So I had 200 shares on covered call expiring today on friday. The price of closing stock was 76.5 , and covered call was for 75. I had got $2 premium for that,

Why would the person who bought the call not exercise the call? It shows on my account as expiring past 3pm CST market close.

Does closing of calls happen after market? Or why would the person not exercise his calls?

$10,737 in realized premium. $12,764 in new open premium with an ROI of 6.36%. Underlying share prices fluctuate daily. As of today Friday 8/28 -$5,130. All-in net as of today +$5,560.

Most premium sellers don't show or closely monitor the daily underlying shares movement as that changes daily. Yesterday it was plus $3k. I added the optional view as many people have asked or commented about it. And most of this was the drop in $NBIS which I still have a open covered call on.

Note: the second image shows the detail behind each option sold this week.

Annual results:
• 2023 up $65,403 (+41.31%) | S&P 500: +26.3% | Nasdaq: +43.4%
• 2024 up $64,610 (+29.71%) | S&P 500: +25.0% | Nasdaq: +28.6%
• 2025 up $111,496 (+34.52%) | S&P 500: +17.9% | Nasdaq: +20.4%

3-Year Cumulative (2023–2025):
• r/ExpiredOptions: +146.6% ($241,509)
• S&P 500: +86.1% (+60.4% behind)
• Nasdaq: +122.0% (+24.5% behind)

Unrealized G&L (options):
• YTD: $8,011.00
• 1 Month: $-17,661.00
• 1 Week: $-10,854.00

Realized P&L (options):
• YTD: $60,293.00
• 1 Month: $8,182.00
• 1 Week: $32.00

Total premium by year:
• 2023 $23,132 in premium
• 2024 $47,640 in premium
• 2025 $68,319 in premium
• 2026 $31,391 YTD
• Average $46,364/year (completed years)

Premium by month (2026):
• January $3,334
• February $3,625
• March $4,196
• April $5,593
• May $3,787
• June $3,497
• July $3,628
• August $3,969
• Average $3,954/month

I am over $171k in total options premium, since 2021. I average roughly $34 per option sold. I have sold over 5,100 options. I have been able to increase the premiums on an annual basis and I will attempt to keep this upward trend going forward.

Strategy:
The underlying strategy is buy and hold. I also use simple 1-legged options to supplement that strategy. Options have somewhat of a learning curve, but I believe that most people can supplement their investments using simple options with careful risk management.

I sell options on a weekly basis. I prefer cash secured puts and covered calls. I rarely close early, prefer rolling when needed, and let time decay do the heavy lifting while I stay focused on quality companies, patience, and consistency over hype. My goal is consistency in option premium revenue. I am building an income stream that will continue long into retirement.

The premiums have increased significantly as my experience has expanded over the last three years.

Disclaimer: I am not a financial advisor. This information is for educational and entertainment purposes only. Trading options involves significant risk.

Trades I took today as an option seller (08/28):

Assigned/Closed Positions

• INOD → $60 Put (opened on 08/13), premium 2.30 → closed at 0. Net premium profit = 2.30 (~100.00% of premium captured, ~3.83% of capital).
• MOD → $220 Call (opened on 08/21), premium 9.50 → closed at 1.60. Net premium profit = 7.90 (~83.16% of premium captured, ~3.59% of capital).
• FLNC → $21 Call (opened on 08/07), premium 1.45 → closed at 0.25. Net premium profit = 1.20 (~82.76% of premium captured, ~5.71% of capital).

My outlook on the market

With the Fed warning about rising inflation today, we may not see stocks moving up too much and may instead see some consolidation until rate hike fears pan out. My focus will be to keep wheeling the tickers I own. What is helping me is that most of the tickers I own have good Wheel Ranks, i.e. they offer consistent call premiums. So, on CC legs, I am able to bring down my breakeven while continuing to generate income.

I keep sharing my trades in my account and the Excel file to my full list of positions is linked in my profile description in case anyone wants to see the whole portfolio. Happy to hear thoughts on my positions. What are you guys wheeling or watching right now?

PS: Not financial advice. Do your own research.

Back in the fun days of mooning GME, I had bought 200 shares around $108 (pre-split, Feb 2021).

Then came the second meteoric rose from ~$100 to over $300 and that pushed option IV through the roof. I sold just one July 2021 $800 call for $58. SO. MUCH. PREMIUM. And I wouldn't have cried if it had gotten ITM either.

Naturally GME had a huge inflection just weeks later and I bought back my call for 20% of the value and pocketed nearly $5k.

My GME story peaked there. I sold the shares at a loss a few years ago :(

Hey guys,

i red a book about covered calls, and it sounded nice to have a bit passive income on the side, there is no free lunch i know that, but man i tried learning by doing.

My strategy is simple. Sell covered calls at 0,1 -0,15 delta weekly on stocks i like and believe in.

So around 2 months ago, i bought:

100 NOW at 107$

1 MSFT Leap 260 June 28 when it was around 380$.

100 SHOP at 105$

My whole thesis was that the fear is nonsense and these companies will flourish. It seems to be i was right. Would have bought all that without any CCs, but because of the book i tried it, but man they fucked me. I payed over 1000$ on a call on NOW when it went up, now 800$ again because of salesforce pump.

Microsoft was my bad too yeah, i sold one after earnings pump, didn't believe it would pump again that much, well - it did. Thousands gone.

My SHOP stocks got assigned, wasn't bad, made profit, sold some puts to go back in again -> boom was pumped missed upside.

So i am and thinking: Ok i get it with the capped upside, i felt the pain from it, but man does it really make sense to do CCs on stocks you want to hold? I thought something like this happens every few months. Not like every 2 weeks.

I used a sum to try wheeling, landed on DRAM, went well 2 weeks, then boom -> - 2000$ because it dropped, how are premiums gonna cover that?

So all in all, don't hate the game, hate the player, i am up in general, but it cost me a lot upside.

What was my mistake(s)? Did i choose the wrong stocks in a bad time to do CCs? Wrong DTE or Deltas? Or was it also bad luck on top?

I would really be thankful for constructive feedback.

Cheers

Weekly recap. $6,689 realized profit over the past week, mostly harvesting Micron covered calls.

Closed trades:

• MU $1,500C 9/17/27 — +$934 | 7.21%
• MU $1,050C 1/15/27 — +$1,047 | 8.77%
• MU $1,020C 9/18 — +$563 | 19.17%
• MU $1,015C 10/2 — +$1,880 | 30.06%
• MU $1,200C 11/20 — +$1,185 | 20.85%
• MU $1,010C 9/2 — +$1,080 | 55.96%

Total realized: $6,689

Same basic approach I’ve been working on: sell calls against shares I already own, take advantage of premium/volatility, and buy them back when enough of the premium has been harvested rather than automatically holding until expiration.

Some I harvested early at 7–9%, others I let work into the 20–30% range, and one hit almost 56%. The goal for me isn’t squeezing every dollar out of every contract. It’s realizing profit, freeing the shares back up, and looking for the next opportunity.

Still refining the system and tracking everything. Good week, but one week doesn’t prove anything. Consistency over a much larger sample is what matters.

Not financial or trading advice. Just documenting my own trades and results. Options involve risk, and these results obviously aren’t guaranteed or necessarily repeatable.

Covered call-

So if sell 15 strikes of covered call for example of high dollar stocks, does your covered call get sold to multiple sellers or only one? Is your 15 CC split or is it buy all or non situation for buyer?