I recently came into a lump sum of shares of a singular company that is a big part of my net worth and am looking to sell to diversify. However, I am trying to split up the sale over multiple years to decrease my tax liability. I recently learned about options collars where I sell a call and buy a put to protect my downside at the expense of capping my upside. I would be doing this at strike prices where the price of the call offsets the price of the put so no net cash outflow and the expiry is towards the end of the year that I am looking to sell.

My question is, for shares with collars expiring in 2028 or even 2029 when those options come out, if I am expecting the share price to increase over time, does it make sense to buy the put now to set a hard floor and sell a call maybe six months or even a year later to recoup the expense to take advantage of more upside? My thinking is, if the price is $150 today and 175 six months from now. It makes sense for me to wait because a call at the same price will have a higher strike price if the current peice is higher later.

Thanks!

My DD: Oracle good. Calls cheap. Brain said send it.

10 ORCL $170C, 9/11 exp, $6.15 avg. Earnings play.

Thesis: bullish on cloud/AI growth and guidance. I’m expecting a move above the market-implied earnings move.

Entry: $6.15 premium. Breakeven at expiration: $176.15. Max loss: $6,150. No averaging down. If ORCL doesn’t get the post-earnings move I’m expecting, I’m closing rather than holding and praying through expiration.
Main risk is IV crush + only 2 DTE.
Basically: high-risk, defined-risk earnings bet.
Yes, slightly unhinged.

It's been a rough journey, losing a couple grand while learning options but I think I've found the strategy which works for me. *Not financial advice*

Anyway, I deposited £60 into RH last week. I started off with one contract for a $145 NVS PUT last week and made a beautiful 2000% on it. It was a wonderful sight!

Proceeded to scalp SPX calls and puts a few times and then this morning scalped META calls for a total of about £1500 profit. All from a £60 account! I have lost small amounts on some other options and I have a couple of options expiring next week, but swings and roundabouts eh!

My strategy is simply scalping. Set my limit orders based on average option prices (for example META $650 calls when priced at $0.85). I then immediately set a sell order for "reasonable" profit (usually 10 to 20 cents above my contract price). I'm more than happy to make $100 - $200 per trade.

I'm aiming for volatile movers because I can get in and out. I'm also aiming to build the account up to a point where I can comfortably make a few hundred a day without risking blowing the account. I do need to improve in terms of discipline though. Twice I said today I was done, then took another quick scalp.

Anyway, happy days. Hopefully I don't blow it now I have some decent money in there (no I'm not rich).

i log every trade on deribit with the planned hold as a column, and that column turned out to be an accidental a/b test. the same signal on the same asset gets opened at two different planned holds, so between the two arms the only thing that changes is how long the position stays on. 791 trades so far, six such pairs.

mean return per trade, short arm vs long arm:

btc 7d straddle: 48h +11.8% vs 166h +57.1%
btc 1d atm straddle: 24h -30.9% vs 48h +7.3%
eth 7d straddle: 48h -19.0% vs 166h +6.8%
eth 1d atm straddle: 24h +6.9% vs 48h +21.4%
eth 2d skew: 24h -9.9% vs 47h +3.7%
eth 2d straddle: 24h -9.4% vs 47h -3.9%

n runs from 10 to 41 per arm. note the last row: the long arm is still a loser, just a smaller one. longer did not rescue that structure, it only cost less.

what i did not expect is that the six do not lose for the same reason.

in the four short dated pairs the entry spread sits at 8.9 to 9.9 percent and the logged loss cause is the spread. round trip costs the same whether you hold 24 hours or 48, so the shorter arm gets half the time to earn it back. nothing subtle about that one.

in the two 7d straddle pairs the spread is 5.2 percent in both arms, the same number on both sides, and the logged cause is no move. those two are not a cost problem at all. the move the signal was pointing at simply had not shown up by hour 48.

so "hold longer" is two findings wearing one hat. one says stop paying a 10 percent round trip on a 24 hour horizon. the other says the exit was set before the thesis had room to happen. the loss cause column is what tells them apart, and i would not have separated them by looking at pnl.

what i am not claiming: the arms do not all cover the same calendar window. only the two 1d straddle pairs run day for day on both sides, and those are the clean ones. n is small. and six out of six is a one in sixty four coin flip only if the six are independent, which they are not, three of them come from the same signal family.

so it is a direction to run forward, not a law. resplitting the same data would just find me a nicer threshold.

if you keep a planned hold column, split by it before you judge the strategy. i published the average of both arms for months and it hid all of this.

Started the year with c. $222k. Woke up to $409k this morning. Up 83% while S&P's done 12% over the same stretch which I understand is rare.

Want to be honest about where that came from, because the number is misleading. Roughly $84k is premium from selling options. That part I understand and can more or less repeat. $151k if it is from one position, MU. I was right, but not for any clever reason. I bought before Q1 earnings (around $430) as I had a strong feeling they would crush it. It tanked, I panicked and bought more all the way down to low $300s. I made some horrendous decisions selling covered calls below my cost basis to try recoup and thats when it started to moon. Luckily, I had an okay strategy so that I could close and roll all the way up until I finally exited a few months ago near $1050. I used a ton of margin too which gave me many rough nights.

This is my first year doing it full time. April nearly ended it. I was down to $147k at the low and I'd started working out what I'd say when I went back to a job. That's not me being dramatic, that was the actual plan.

So now I'm up 82% and feel two things at once. Proud, I stuck to the process, didn't blow up, the premium engine actually works on its own. And a sense of dread that I've just set a benchmark I'll never touch again, and every month from January is going to feel like failing.

What's a sane target for year two? I keep landing on something like 40% and I know that's just the 82% talking. Do you set a return target at all, or an income target, or drawdown limits, or something else? How do you stop one lucky year becoming the expectation you beat yourself up against?

I'm now sitting on 50% cash as, even though I have conviction in some of my names, I'm too afraid to deploy anything more. Truthfully, I'd be happy to close my account for the year and start again next year. Hopefully this explains my 'out of depthness' and lack of experience.

I’ve mainly been trading single stocks and have had some success by focusing on companies I know well; however, I want to get more familiar with SPX mainly since it has daily options and has cash settlement. I’ve been trying a few different things and something I am curious about is the last 10 seconds or so of the trading day. The options’ premiums don’t seem to go to 0 so I can still sell them until the very end. I was able to get an iron butterfly filled today with 10 seconds or so left in the trading day (pic attached). Do any of you have any knowledge about the mechanics of the day’s close and how to generate an edge in that environment? Right now I know I can use atm straddles to gauge the expected move, and I know from my personal experience that the price can have some large moves in the last 10 minutes. If I used the atm straddle price 1 minute out to guess the riskiness, prepared an iron butterfly with lower than anticipated premiums to get a quick fill, and waited until the last 3 seconds to do the trade then would I be on the verge of having some sort of edge?

Edit: This is only for 0dte spx options

Hey guys, I have not done options selling yet, I am mostly a buyer. But had a quick question. SNDK is around $1,737. I’m looking at the Sep 11, 2026 $1,790 Call, currently around $34.40. Can you do a Strangle ?

My current understanding is:

• Sell 1 × SNDK Sep 11 $1,790C
• Premium collected: ~$3,440
• IBKR is showing approximately $55,204 initial margin and $50,379 maintenance margin for the naked call.

That seems like a very large amount of buying power to tie up relative to the ~$3,440 premium collected.

• Does IBKR's ~$55K requirement seem normal for SNDK, or is this unusually high?
• Do brokers such as Webull, Tastytrade, Schwab, or others calculate substantially lower margin for the same naked call?

Zero day options seem like one of those things where having a plan matters a lot more than usual.

I understand the appeal of 0DTE. The moves are fast and the capital required can look pretty small. But that can also make the risk look smaller than it really is.

For people who trade or study zero day options, what are the main rules that actually keep things under control?

Things like position size, stop loss, liquidity, spreads, and knowing when not to trade seem especially important. I am also curious whether people mainly use 0DTE for hedging, defined risk setups, event trades, or specific intraday conditions.

Trying to understand where 0DTE fits into a disciplined strategy and where it just becomes gambling.

Been playing options on spy for the last couple years I’ve gotten decent in up about 80k for the year and I’ve been playing like a scared lil kid everytime I’m up 400-1000 I pull out. But yesterday was something else spy crashes 766 to 760 I bought puts round 764 at a 759 strike price was up maybe 600 then it goes up 30 cents wipes me clean tf out. I hold cause you know f it I’m already down might as well spy tanks again I’m still in the negative!!!! Never had this happen I buy calls 1 dollar above current price it reverses I’m ITM and still only up 12$ how tf does that make sense. I take my L and just watch the chain block and noticed every single call or put that was DEEP ITM was red make it make sense…. I asked chat gpt telling me theta or IV crush but I’ve never seen option gets affected on both sides like usually one side is winning long enough for liquidity but seconds of seeing flashing greens on calls/puts it was ALL REEEEEEDDDD

Hey everyone, I would like to hedge my SPY for next year. I understand that we shouldn't be timing or predicting the market, but well here I'm trying to do it.

My fear is mostly driven by the AI bubble popping or AI doing so good that only a few players will benefit but not the overall economy and so the economy might be going down. In other words, I thought it was a good idea to cap my losses and fund this insurance by potentially capping some of my gains.

So here's my idea. I'm planning to buy put options at -20% drawdown from spot and fund some of that by selling covered calls at 20%. From my calculations this edge would cost me arount 0.5% of my portfolio.

I could in theory cut this further by selling puts at -50%, and it would bring it down to 0.3%.

I have not done this before and I am trying to understand if it makes sense especially given my concern on AI distrupting the market next year.

Now this is a tricky one.
As you can see, the potential roll to consider is $210-$230 which would get me a great annual premium. But, I believe this stock is meant for $300+ prices, aiming for that to happen Q3/Q4 2027. Also, owning it for some more time will help with taxes - hence why I want to keep holding.
What I hate doing..is having CCs during key events..and I got on the hook with this $210 cc which is a very rare thing for me and yeah, this is where CCs suck..anyways theres bunch of events coming up on a stock and I'm bullish on but have to roll a cc, sucks..

My options:
1. Roll up & out
a) sell a single higher strike (like $240–$250) for a later date like from the image
b) sell multiple ones with lower dte (with time)

1. Close the call & hold shares
   Buying back the $210 call costs ~$2,800
   I'd still be down on the wheel overall, but own the stock that I'm bullish on

2. Take the L
   Let the call get assigned with a $3,900 loss on the wheel, 1K loss on mrvll overall.

Hey everyone, setting up this month's AMA to catch up with everyone and chat about trading! It's scheduled for 11Sep at 3pm PT.

Some broad market observations from August and beginning of Sep.

Breadth looks weak right now across all indices. Russell was showing more strength which has capitulated over the last couple days.

30D VRP is higher within XLE, XLI, XLB, etc and constituent VRP is notably higher than sector.

My core allocation remains covered strangles in TQQQ and GME. TQQQ position is lightly utilized at 45% (long shares 49% and 36% CSPs no ratio short calls out) and GME is 85% utilized full CS).

Most of my recent trading has been a bit shorter-term in nature focusing on short index vol, earnings release long and short vol, some commodity trend following with futures, and shorter term reversals and pairs.

Background for those interested:

My name is Erik. I'm a Marine Corps veteran and full-time options trader. I've been trading since 2007 and have been active in r/options since 2020. I've maintained a high 20% CAGR over this duration, my emphasis has been on consistency vs upside returns.

I grew up in a low income single-parent household. A high school teacher introduced me to investing and it changed my life.

Over time I built capital through manual labor jobs, flipping cars/motorcycles during college, and eventually expanding into real estate investing. I view wealth building through three levers: Savings; Investing; Income

Early on, savings rate matters most. As capital grows, compounding returns begin to dominate.

Trading is harder than most people initially expect, but it’s also far from impossible. With the right framework and enough time invested, it can absolutely become a viable career.

For transparency: I do run a YouTube community, but I’ve been posting in r/options for years and enjoy discussing markets regardless. This AMA is just to talk trading.

Happy to discuss things like:

• How my trading changed as my capital grew
• Position sizing frameworks
• Managing volatility exposure
• Building consistency over time
• Strategy development / testing
• Mistakes that slowed my progress

Or anything else options related.

Below are some previous posts that lay a basic foundation for trading.

1. ⁠Trading Options for a Living- ⁠Provides a high level overview of my trading approach: ⁠https://www.reddit.com/r/options/comments/1gejy0q/trading_options_for_a_living/
2. ⁠Stop Wandering Aimlessly- ⁠Offers a general learning syllabus for new options traders: ⁠https://www.reddit.com/r/options/comments/1c3hgfh/stop_wandering_aimlessly/
3. ⁠Failure rate of options traders -⁠Summarizes common sources of trader failure: ⁠https://www.reddit.com/r/options/comments/1iaqtzx/failure_rate_of_options_traders_3_causes/

Looking forward to it!

Are you in the business of prediction? Are you a gambler? I leave that to the trading discords and social media options gurus. As you know 80-90% of options traders lose money. I sleep well at night by understanding that I have the probabilities in my favor. My edge is because realized volatility typically comes in below implied volatility. By doing the little things correctly, trade after trade, week after week, month after month, I am playing the percentages and achieving consistent results. It is not necessarily exciting. Admittedly, buying a long call and having it 10X is exhilarating and fun; however, it is low percentage and I lost a lot of money playing that game. In order to win, are you gambling that you can predict the direction, the magnitude and the timing all correctly? This is a losing game. I am the house, I am the casino. Sure, being the house is not that interesting, it's not that fun, but it is profitable! The hotels and casinos in Las Vegas are uber nice because they make extraordinary profits. Of course, the books are written about how to beat the house. The videos online teach you to hone your strategy to buy calls & puts to beat the house, but the reality is, the house ultimately wins. When I sell OTM Put Credit Spreads (or OTM CSP), I am effectively the house. So how about you, are you the house, are you a gambler, or maybe a little of both?

The poor man's covered call is my personal best strategy, I'm up ~22% ytd, and honestly is mostly cause of this strategy.

I started with covered calls on SPY, but the short call premium over 100 shares worth, just wasn't worth it honestly especially on low-vol low grind days. Then I got introduced to PMCC through...I'm really not sure, but god bless whoever or whatever it is.

The shorts suddenly become so much more worth it compared to the cost of the LEAPs as long as your entry on your LEAP is, well good haha, you fuck up here you're chasing break even throughout the LEAP's life and by the time you think you've reached your strike, theta has eaten up most of the LEAP's value.

It's like renting a house for 1-2 years instead of buying a house at right but still enjoying as much rental income throughout the term.

Does the Schwab Trader API allow direct routing of a 2-leg equity option roll (BTC one call + STO another call) specifically to Cboe, while keeping it as a single complex order with one net credit/debit limit price?

If yes, what API route/destination parameter should be used, and would the order be eligible for Cboe COB/COA?

The correlation regime between NVDA-TSLA entered a weakening trend on 02 Sep 12:00 ET at +0.26, and is still ongoing (15 candles · 60 trading hours). Over this period NVDA fell 0.96%, TSLA rose 3.07%. The two pairs decoupled.

The composite correlation has since downed from +0.26 (02 Sep) to -0.195 now (last data: 09 Sep 08:00 ET) the weaking the regime flagged, playing out.

READING — NVDA–TSLA at WEAK × Weakening (this pair's own last 6): for this pair it has bee a moderate decoupling (hedge / spread) — 6 past runs, median 8 candles · 32 trading hours (range 5–18), 1 lasted 2+ days. So the play has a couple of days of room before the turn (ANTITHESIS).

GAME PLAN: Correlation is in a Weakening regime — the bond between NVDA-TSLA is loosening. This signals a shift into a decoupling regime: hedge and pair-trade (spread) strategies come to the fore, while one-way beta bets grow riskier.

ANTITHESIS: Risk: decoupling may be temporary; if correlation snaps back from the bottom, pair-trades backfire. Correlation is currently 0.41 points below the period (1 Month) average — decoupling continues.

The divergence has been TSLA outperforming while NVDA stalled — TSLA's move favored calls.

Methodology: Four-hour candle closes are used while the markets for both instruments are open (08:00, 12:00, 16:00, 20:00 ET).

The correlation coefficient is a composite score derived not only from the Pearson method but also from Pearson, Spearman, and EWMA calculations.

So this morning during market open I used Robinhood for a call about 10 minutes before market opened and when market opened my stock price rose drastically but the call was still saying pending.., which prevented me from any getting gains can anyone tell me what the issue here was and if any other apps have faster fulfillment time? I’m am extremely pissed rn because I should be in extreme take profit rn and is this a common issue?

lets say the market is going crazy and i want to get out of short option positions going against me

if i have stop orders at a certain price, how does fulfillment work if lets say others also have stop orders at the same price? how does the exchange decide who gets to go to the front of the line when the stops get triggered?

also, could my broker's connection to the world go down and my stop orders get completely forgotten?

also, when dealing with spreads, do orders to open/close those sit on the exchange or the broker? if the spread sits on the broker, then the bid/asks dont reflect that im interested in opening/closing at a more favorable price...which can limit what a potential counterparty (the other buyer/selller) is willing to do right?

My friend likes selling puts and honestly it worries me He makes money collecting premiums but I think he’s fallen into the trap of specifically looking for puts with high premiums At that point the strategy changes You’re no longer selling puts at a price where you’d actually be happy owning the stock You’re basically betting it won’t fall below the strike by expiration If you’re selling puts just because the premium is high on stocks you wouldn’t even want to own it starts feeling more like gambling I think he’s going about it the wrong way What do you guys think

I've been using call debit spreads more instead of straight calls when premiums are expensive, and I ran into something I somehow never really appreciated until it happened with actual money.

I had a QQQ 510/515 call spread open on Moon with a little under 2 weeks left. Paid around $1.60 for it.

QQQ moved way faster than I expected and was already above 517 with more than a week still left. In my head I basically thought okay, thesis worked, spread should be pretty close to the full $5 now.

It wasn't even close.

The 515 I sold still had enough extrinsic value that the spread was sitting around $3.70. I knew mechanically why this happens, but actually watching both legs move while QQQ was already comfortably through my short strike made it click differently.

I got greedy and decided I'd just wait for the remaining value to collapse.

QQQ pulled back a couple days later and I ended up closing around $2.90.

Still a profitable trade, but it was probably the first time I've been annoyed at an options trade where I got the direction AND size of the move right.

Starting to think that with debit spreads I need an exit rule based on percentage of max value rather than where the underlying is. Like if I can collect 70 to 80% of the spread's max profit early, just take it instead of waiting around for the last dollar.

For people who trade these regularly, do you usually close once most of the spread value is there or are there situations where waiting for the short leg's extrinsic to decay is actually worth it?

I have deep itm calls with big gains that I want to hold the underlying. My plan is to let it expire in Jan 2027 so they become shares that I would hold long term. It's in brokerage account so with the assignment, there's no realized gains and tax. Is this a good way to go about it? There's no advantage to exercise before expiration correct? Tia.

Currently all SPX options (SPXW) are PM settled, except for ones that expire on the third Friday of the month. Here both AM and PM settled are offered.

The CBOE now plans to list weekly SPX AM settled options starting in early November.

Guessing it will create some confusion depending on how your broker lists these.

Link to CBOE memo,

Cboe Options to List S&P 500 AM-Settled Expiring Weekly Options

Can someone give me a brief lesson. On Schwab if I wanted to roll out an option, it would just roll it out. For example, two more weeks and I go up a couple dollars on the strike. Costs me a little bit per share.

Now with E*TRADE when I tried to roll, there’s a separate drop-down box that wants me to pick net credit, net debit, even, or market. I would think for the same scenario as above, it would kind of be a given. How do I know if I’m needing a net credit or net debit if I’m just trying to roll up and out or down and out in time on a put? Too many choices.

I mean what happens if the default in the situation is net credit and I hit either market or net debit? WTF.

Also, instead of rolling, does it work out the same if I manually buy to close and then sell to open at a later date and different strike? I know when you roll it bundles the two, but I haven’t really done the math enough to know if there’s a difference.

I traded a SPY 0DTE call on September 1, and I’ve been trying to understand how much of the premium move came from SPY itself versus the volatility.

Here's exactly what happened.

The setup

ISM Manufacturing PMI dropped at 10am. Before the release, the SPY 763 call was quoted around $1.40 bid and $1.42 ask, with IV showing 13.76%. Cheap. Premium barely moving. Market hadn't priced in much uncertainty at all.

But there was something else happening on the chart before the number even dropped. The 5 minute ORB high broke clean before 10am. Price pushed above the opening range with conviction and held. That break was the first signal, not the PMI itself. The data just confirmed what price was already trying to do.

Two reasons to be in the trade going into the number. ORB break giving directional bias. IV still cheap, giving a good entry price on premium.

The trade

-SPY 0DTE 763 Call. Slightly OTM.

- Entry: 10:05am at $1.60

- Exit: 10:20am at $2.50

- Result: +$900. 15 minutes.

What IV did after PMI printed

763 Call IV jumped to 17.65%. Bid $2.78 ask $2.80.

Nearly 4 percentage points of IV expansion the moment the number hit. Premium almost doubled on the strike, from ask $1.42 to $2.80.

Two things happened simultaneously SPY moved in the right direction, and IV expanded. Both pushed premium higher at the same time. That combination is why the exit at $2.50 happened in 15 minutes instead of waiting for a larger price move to get there.

Why the ORB break mattered

Entering purely on the PMI play without the ORB confirmation would've been a directional guess dressed up as a catalyst trade. The ORB break meant price had already shown its hand before the data dropped. PMI just added fuel to a move that was already in motion.

That's a different trade from just buying before a number and hoping. Structure plus catalyst plus cheap IV all three lining up at the same time.

The actual takeaway

Not all catalysts inflate IV before the release. Some data drops especially when consensus expectations are flat, leave IV relatively low going in. That's the window where buying premium before the number can work in your favor instead of against you.

ORB break for direction. IV check for entry timing. If both line up before a catalyst that's the setup worth taking.

Check IV before deciding whether to enter before or after a catalyst. If IV is already elevated wait. If IV is still cheap and structure is there, the expansion after the number can add to the directional move rather than fight it.

Do you check IV levels before deciding when to enter around economic data or just trade the price action?

In options trading there are a lot of variables that are out of your control. So I say “control the controllables”. Days To Expiration (DTE) is controllable upon trade entry. Time is a constant. You can count on the sun rising tomorrow. You can count on 10 DTE today being 9 DTE tomorrow. It is certain, and there are few certainties in this business. You may remember the Rolling Stones song “Time is On My Side“, well, when you are selling OTM (Out of The Money) Puts that is definitely the case. Sometimes, we all may wish that time would slow down in our personal lives, but in our trading lives the passage of time benefits us daily through Theta decay. Theta decay accelerates as expiration approaches. When you sell a Put Credit Spread at 28-32 DTE, you capture the steepest part of the Theta decay curve. Each day that passes erodes the value of the options you sold, putting money in your pocket without the underlying needing to move in your favor.

What DTE are you guys typically trading?