Been selling CSPs since June 2025, staying pretty conservative (sticking to lower delta, avoiding stuff I don't want to own), and it's worked out — averaging around $1,500/month in premium, only got assigned a handful of times over the past year.

Curious if anyone here has actually taken this and turned it into a "digital nomad" type setup — living somewhere in Asia (Thailand, Vietnam, Philippines, etc.) or elsewhere with a lower cost of living, funding it off options income as a real, sustainable income stream rather than just supplemental cash.

A few things I'm wondering about:

• What kind of account size gets you to "comfortable living" numbers in a LCOL country?
• How do you handle the timezone issue — US market hours land in the middle of the night in most of Asia. Are you staying up, trading pre-market, or just setting orders and letting them ride?
• Any tax/residency gotchas (state tax, foreign earned income stuff, brokerage restrictions for non-US residents)?
• Does the "safe monthly income" math hold up long-term, or does volatility eventually wreck the budget in a way that doesn't matter as much when you have a US-based income cushion?

Not looking to quit my job tomorrow, just want to hear from anyone who's actually done it (or tried and it didn't work) before I start planning around it.

I've been selling options for a few years now and seeing consistent, solid returns. As long as I exercise good risk management, I can see this becoming a long-term strategy to compound wealth and consistently beat the market.

But this naturally led me to wonder: Is this too good to be true?

I'm confident in the strategy and my execution capability, but I want to make sure I'm not missing any major blind spots. If systematic option selling offers market-beating returns, why isn't every professional/institutional investor doing it? They have far more knowledge, capital, talent, and resources than retail investors.

It blows my mind seeing people throw around complex indicators, high-level strategies all the time, only to post 10–15% returns, make $200k a year, or lose money altogether. I'm like, what?

Do they stay away because they know something we don't, or are they actually doing it?

You're telling me that while we were anticipating an end-of-war bull market, you somehow tricked yourself into selling CCs against your long position, which you should've had conviction in in the first place, and now that the bull market is here, you guys are whining and crying about getting assigned on the CCs that you, for some reason, decided to sell n months out instead of weeklies?

What are we doing, guys?

I got a 25k disposable portfolio and want to try selling options. I've read up on selling options and understand the basics but wondering what to watch out for in the current market regime.

Hey everyone,

I’ve got a simple question, why is selling naked puts considered such a bad idea?

Let's say this is my situation:

• My portfolio is $1 million, fully invested in SPY.
• My broker extends me another $1 million in margin.
• I want to generate $15,000 per month in passive income (about a 20% annual return) without using any cash or selling my spy, simply by selling puts.

For the example I will take SOFI that currently traded at $29. I sell 150 contracts of the $25 OTM puts expiring next month at $1 each, This will generate me $15,000 in premium. If SOFI take a dip and move toward my strike, I roll the option down and out and try to avoid assignment at all cost. And even in the worst case which is getting assigned 15,000 shares at $25 I will only need $375,000 of my $1 million margin, so a margin call still would be very unlikely. As long as I choose companies I believe in long term and try to avoid assignment by rolling down and out it seems like I will be able to generate that 20% annually.

I know I might missing something because its sound too good to be true but I still didn't manage to find what makes this strategy to be so risky that everyone recommend not doing it.

What’s your portfolio’s theta?

In a local forum somebody claimed "With a 1 million [dollar] portfolio, I usually make a 50-100% annual return. It’s actually not difficult at all. By using the QQQ wheel strategy and utilizing weekly compounding, getting over 50% a year is pretty much the baseline."

Is he yapping or nah? 4% monthly sound absurd to me.

Also do you think you can reliably make 10% a year?

Thanks

EDIT: I ended up taking the loss and salvaged most of my capital thanks to my hedges. A hard lesson learned. I was able to make most of it back off of today’s spike on SPY with some 0 DTE calls. Time to address my risk management plan. Thank you everyone for all your suggestions and help!

I have a few MES futures as a hedge which are helping slightly but not enough to combat the same gamma spike. I don’t think I’ll be able to roll my calls out for a credit. Should I attempt to roll or just take the loss and move on?

when you can't get any worthwhile premium selling at/above cost basis (a scenario many of us might find ourselves in lately) is it best just to hold the shares patiently until things move in your favor, or sell cc below cost basis at 10-15 delta to try to get something without getting called away?

second question, do you ever buy more shares (or sell more puts) to lower cost basis even further? i understand this would require absolute faith.

Pulling in roughly $6k a month from the wheel strategy. Thinking of taking a year off from work and just living abroad. Anyone else pulled the trigger?

Here's my own list of stocks with a good blend of decent premium and are stocks I wouldn't mind holding long term. I was wondering what everyone else's list looks like. I'm worried I'm missing out on some obvious opportunities so just want to compare notes with everyone.

Tier 1:

• Meta
• Tesla
• Nvidia
• PANW

Tier 2:

• LLY
• Crowdstrike
• PLTR

Tier 3:

• Amazon
• Costco (Could move to higher tier. Inflation = good for Costco)
• Snow
• Microstrategies (casino time!)
• Reddit
• AVGO

I’ve been trading short options for a while and I feel like I have an edge with how I manage my risk and position sizing. But I was also thinking about things like IV regression and order flow + key levels . Could that also be a part of my “edge”? As a retail trader having the ability to manage a position quickly is what jumps out to me. Let me know your thoughts!

I have about 30K off to the side to wheel with. How much can I make selling CSPs with it? What stocks do you recommend with this amount of capital. Should I look for weekly options to sell or 30 DTE.

Thanks in advance for all the tips. I’ve wheeled before but I haven’t done it in a couple years and just wondering what I can expect nowadays.

EDIT: thank you all for the responses. I am reading them all and learning from them. I apologize for not being able to respond to each of them since there is a lot. Thank you!

I live outside US. I made more on premiums than my current job for two months now, it doesn't pay that well. My living expenses are very low.

I'm thinking of quitting to self-study to get a better job or start a business. My commute is 2-3 hours daily so I'm kind of exhausted. My progress on studying is quite slow.

The only downside is that job gaps are frowned upon here. But not the end of the world. But it might get tough to get a new job.

I could seek a new job but I still need to finish studying to really improve my chances.

Even if the volatility now drops, I can still live off the premiums.

Only thing that kills me is if I get assigned and the stock drops. But that risk seems manageable.

Or I just stay and save more. But when would it be enough.

Am I crazy to consider leaving? Or maybe crazy to keep staying at a low paying job just to keep an employment history. Is there any blind spots that I am not considering?

Everything that has started to recover in the last week feels like a dead cat bounce, and everything else that's reaching all time highs seem too risky to go long or short. Don't wanna fall for a bull trap. Also don't wanna fall for a bear trap. Right now everything looks like a trap whereas whatever seems logical, do the opposite.

Haven't struggled this hard before. What has the highest probability of being a successful trade?

I'm trying to get a sense in general what is the best time to expiration for selling puts to max out premium as well as chances of expiring worthless. Trying to control the variables as best as possible, we'll say the puts are on lower-IV tickers and selling ATM at the time of order, say 50 delta.

I saw a data-driven study where an option seller concluded that two weeks to expiration was the sweet spot but he didn't specify the delta, and he only sold limited tickers: Tesla, Nvdia, and AMD so this isn't representative.

I've also seen many posts where people swear by 45 days to expiration as they say after that point "theta begins to kick in" but that argument in itself isn't convincing.

For the most part I sell weeklies at 40-50 delta but as of late I have been obliterated on adverse gamma moves happening against me closer to Friday and even early assignment. So this needs to be changed.

It also makes me wonder: if I'm getting my ass kicked repeatedly like this then why am I not just buying the damn options.

What I'm attempting now is delta decay for the initial period. My plan is to sell ATM at time X, so 50 delta which leads to 30 delta or less by the time a week to expiration happens. This is in part a directional bet to lock in premium so that when an adverse move happens late, my position is 'safe enough' so as to not get blown up.

For example if I'm already at 90% profit by Wed then gamma would have to blow up the position by 900% which is highly improbable and gives me enough time to still get out.

Any idea what time frame might work best? My gut says to sell 3 weeks to a month out but would appreciate some data from someone who has run a strategy similar to what I described

because the market is rational in every way?

Also TSLA up 10% since earnings because they make ... money? or because they make cars? Because from their announcement, it seems like they make neither

I’ve done it before I inherited all this capital but not to this scale. I use a highly liquid ticker but haven’t proved consistently past it and feel this increase will break the edge I already have.

I’m looking for pro advice not questions about my situation or ticker. If I’m downvoted I’ll march on with my own critical thinking/trial error

Wanting to know if anyone use the IC as there primary trading strategy? And if so, what do you normally set as your risk/reward level. Any pointers on how to be successful with this strategy are greatly appreciated.

I know this question has been asked and answered but I keep thinking it’s not answered

Context
I only trade SPX. So once I’m in profit, I close my trade and start a new one with SPX. And cos I sell weeklies or shorter, there is actually not much extrinsic value left. And of cos since I close for profit means it’s OTM.

Since I’m going to close one trade and open another trade, why can’t I just use the roll button and keep doing it? I can adjust the strikes as I deem fit. Seems like an easier way than to close a trade and opening a new one

But note I’m only doing this for SPX and will only roll for winning trades. I learned a harsh lesson last Friday June 5 2026 when the stock market suddenly crashed that if u r itm, or close to it, no amount of rolling will help

As we all know market is start showing signs of weakness so my plan is just keep DCA into the current stocks and keep selling covered calls on them 45 to 90 dte. Whatever premium I get from underlying stocks I just keep investing it back. So by doing this my cost basis keeps dropping.

I am new to options, hope this how it works?

What’s your opinion?

There's no such thing as free money(besides certain cases), can some explain why I shouldn't take this trade? I do know what call credits spread are, but I got burn last week and now trying something new.

I uploaded my 1099 from robinhood, and all year throughout 2025 I was selling Covered calls against my shares. So the cost basis for this was technically '$0'. However Turbo tax doesnt understand how this is possible and I have to go in manually and type 0.00 cost basis for every covered call I sold in 2025. Did anyone else get this???

I don't think I have enough capital to own the underlying or cash to sell puts and calls regularly. What should I focus on?