First month of Options selling: Cash Secured Puts - Earned

In my previous post, I mentioned that I received a low 5 digit figure, from a savings plan bought 10 years ago when I first started working and I am planning to generate some cash flow from it. It is not a huge sum of money and is about 8% of my investment portfolio so I want to see how much cash can be generated from it and if it hits the strike price and then I have to cover the positions. 

I did do this before previously but chose stocks that were very volatile like Tesla and in turn, it really kept me up all night and was like struggling to not panic when I got exercised. I think sticking to positions that you are comfortable with and not touching the base portfolio helps as I sold covered calls on my base Tesla positions and when it got exercised, I struggled to quickly get back in. So doing CSP helps as it is separate from my base portfolio and can be done separately with the wheel strategy eg if it is exercised then I will sell covered calls. Of course, it might drop to a price that is below my original cash position but at least it is separate from my base portfolio. 

I have a few stocks in mind for this as I am not able to do cash secured puts on QQQ or SPY as they are too high for my budget although I would love to do cash secured puts on them. I will list down the stocks that I am currently looking at, ok to have them in my portfolio and also low enough for me to do cash secured puts. They are not in any order and *Please note that I am not providing financial advice and that the counters below are just as a reference for myself. 

- NBIS

- MSTR

- CRCL

- RBLX

- HOOD

- PLTR

Heard that SOXL, TQQQ are also great stocks to sell CSP on as they provide juicy premiums but they are leverage ETFs so I do have second thoughts if I really do want them in my portfolio if I get exercised. 

Of course, I don't have enough capital to do it on all but I might do it on rotation, avoiding earnings season and see how it goes, I will probably take the cash generated and re-invest it back into the market or slowly accumulate and buy LEAPs (long term calls usually a year or more out). 

So far on my first month from March 2026 to April 2026, I generated about $700 and nothing much to scream about but it seems to be pretty substantial for me. It can cover my gym subscription, phone bills and even the wifi bill. I know that the market has been on a sideway trend where it goes up when Trump says the war has ended and downward when Iran says no, or when new attacks have been launched. So usually ending pretty flat. 

Great month for CSP and shall see how the following months go, might eventually use the money to initiate positions but I hope to grow it enough to a point to do CSP or covered calls on QQQ just as a separate bucket to generate income while also have my base investments as a priority and majority. Don't think it will happen that fast but slowly accumulating. Nice to have a lump sum coming in although I might have done better if I invested it instead of having it in a savings plan but since it was 10 years ago when I started, if I had the money, I would have busted it somewhere else or lost it all originally. 

There are pros and cons to a savings plan but I think the liquidity is an issue especially as you grow older since more commitments might arise. I am not planning to start another savings plan but might do a SSB (Singapore saving bonds) or have some  in IB01 as I build up the cash position. 

My Cash Secured Put for IBIT, Bitcoin ETF got exercised

In a previous post, I wrote about selling 3 cash secured puts on IBIT and using the premium to buy more well, that happened when IBIT was at $66 USD, crazy, how it dropped to around the $30 area I bought it pretty far out about 9 months (for the one expiring March 2026) and 12 months out (expiring in June 2026). 

Read: Leverage can double your gains but wipe you out too, what "dangerous" positions am I holding currently?

For the March 2026 cash secured put, I set the strike price at $49 and I had to buy 100 shares at $49 when it was trading at around $40 so I am still in the red since the current price at the moment is also around $40. I have 2 more upcoming expiring on 18 June 2026 with strike price of $40 and $45, not too sure if they will be exercised but I do have the funds and don't mind adding on. 

It has been volatile so I cannot guarantee if they will be exercised of course, I don't wish to buy them at a higher price than the market rate so hoping that Bitcoin stage a recovery and stays above the strike price or at least pretty close so that I don't lose too much. But in the long term, I believe Bitcoin is going up and no harm in adding more positions.  

In the meantime, I received a low 5 figure sum recently and started selling some cash secured puts with them since it can allow me to choose a strike price lower than the market price but with the volatility, it can mean that it goes lower than expected. In terms of the broader market, I think sticking with my DCA-ing of index funds have been good, with 50% of my portfolio in broad index funds (namely QQQ and CSPX), the crazy news hasn't brought it down as much as crypto or Tesla. 

Thoughts on cash secured puts

When I first sold this 3 puts, I didn't think that they would have a chance to be exercised but I think that definitely after doing CSP for some time, you learn. I sold them pretty far out and thought bitcoin would be well above $100,000 by now but well, we are far from that. 

I now usually sell CSP on monthly basis with 28 days to 30 days expiration dates. I tend to sell them on red days and definitely on shares that I don't mind getting if it ever hits the strike price. It is fun seeing the premiums coming in but I need to restrain myself from getting too greedy eg to sell without holding the necessary cash to cover. 

Overall, I am slowly learning and not overstretching myself so hoping to see where it brings me for this year and if I will still be continuing to sell puts after 2026. I use about 8% of my total portfolio to do this CSP system as I want to still be invested in the market. As the portfolio grows, it might also mean that this cash set aside might grow but nothing is fixed in stone.Happy to generate some income on the side in this sideway/volatile market but in a bull market, it will definitely be better to be invested so it depends.