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. 

2026 direction for the portfolio - What am I adding, strategies for portfolio growth and where I want it to be at the end of 2026

2025 was quite a good year for the portfolio, it went up in value with my contributions and also the volatility of it provided such excitement for me. Hoping to reduce the risky factor in the portfolio by diversifying more into index funds but at the same time to make calculated bets into what I believe will grow in the coming years. 

2026 continues on the AI momentum as we see IREN, NIBS, uranium stocks as well as copper (commodity) gain interest, I do not know where to put my money in but am observing them as I feel I need to know more so that if any black swan event happens, I have the conviction to hold and not sell out. 

Tesla and Bitcoin (both quite substantial positions in my portfolio) performed not as well as expected towards the end of 2025 and I don't intend to add more Tesla but for bitcoin I will add more positions slowly. I will be receiving some money from a savings plan that I started when I was 21 so after 10 years, the money will be back in my pocket. I think I would have done better investing it or maybe I would have just lost it all so it is a good addition. When I started the savings plan at that time, I just started working and my mum wanted me to get into the habit of forced savings so it was a save 5 years and locked in for another 5 years. Turns out, time passes really fast!

Read: Savings plan - Yes or No

Since it will be a sum of about low 5 digit, I might start doing some cash secured puts on it before deciding where to deploy the money in. No concrete plans for now but holding on to it and doing cash secured puts is the current plan. 

Other than that, IREN seems to be a counter that I like to have a position in. I understand that they used to be a Bitcoin miner company but have since pivoted to doing data centers for AI using 100% renewable energy with Bitcoin mining still around. I haven't done much research into it. There seems to be a momentum for its analyst are setting a pretty high buy price for it as it recently had a contract awarded by Microsoft. I am not really knowledgeable in AI, chips and data centers but I can see the rise in excitement as well as more people talking about the relevant industries. Will initiate a small position before their earnings on 11 Feb 2026 and see how it goes. 

Besides that, CSPX monthly position is still going on and so that is my plan so far, looking at uranium shares but I don't want to be investing into so many counters that I am not familiar with so that is just something I am looking at now and not initiating any positions. 

2026 portfolio expectations

I think it will be a volatile year and the portfolio value is not something that I can control over time as it depends on many factors however, I want to make sure that I am adding in consistently and that is the plan. Of course, building a cash position is also part of the plan as I think the stock market might face some downturn although no one knows but having a cash position will allow me to take some opportunities if there is a downturn. 

Reflections on 2025 and entering 2026, wishes, plans and a letter to myself

2026 has arrived and we are now in the middle of January, I had a trip to HK just recently and it was great with amazing weather, I realised that Hong Kong does not have heaters or warmers so they go back to a cold home everyday but the coldness is bearable for a trip but if I were to stay there for long, I would get a heater. It has been tough getting back into the momentum of working as the December celebration and start of new year festive season is still strong making me lazy to get back into full working mode. I think it will take me till end of CNY to get back into it hahaha. 

Going on a trip at the beginning of the year was nice, it seemed like places weren't as crowded as compared to November and December where people were winding down for the year. I might try to make it a yearly thing if I can. 

Work 

On my work side, my job role has been transferred to the parent company where the company I worked at was bought over 6 years ago and now all corporate functions is being brought over to the parent company, the benefits are horrible where annual leave has been reduced and flexible benefits removed, even insurance coverage has been reduced.

Well, I guess jobs are not as secure as they wrecked before, happy to still have a job as I have to admit that AI is coming fast for my job role and if I lose my job, I don't think I can find one easily as the role is really easily automated. 

Not really preparing or up-skilling myself although the government and my parents are telling me to, it just seems like the AI wave is coming for everything, so what if I make the effort to upskill, would that save me? I don't know. 

I will work in this job as long as it goes and see where it brings me, lazy to go through the multiple rounds of interviews for what I think is not necessary for such an entry role job. 

Health

I guess I want to pay more attention to my mental health, I do get anxious easily and am an over thinker and worrier. I also do not have many social interactions as I work from home, hoping to improve on that in 2026 although it really takes a lot of effort on both me and my friends. 

My friends are all busier as they find their significant other and we tend to spend lesser time together and in Singapore where most relationships are transactional, it does take a lot of effort to find someone genuine and part of it is that I have got so used to being alone that sometimes, it takes a lot to let someone enter my life. 

So I want to push myself to open up and expand my social network at least for 2026, nothing too ambitious just say yes to more events and spontaneous meet ups. 

Finances

As mentioned above about my job, I think I need to really build up a more substantial emergency fund as the reality of being laid off is so real. The retrenchment benefit/package in Singapore is not even guaranteed so having a more robust liquid cash position is important for me at the moment. I actually hold really little cash as I prefer being invested but looking at the stock market, I do think that this is quite a good time to accumulate cash. Will write up another article on my plans for the portfolio in 2026. Overall finances is not a huge concern for me at the moment *touchwood* since I have no children or mortgage and health is still all right. 

2025 was not a huge year for me rather it was an autopilot kinda year, I let things happen on it's own and didn't work hard or much to achieve as it was the year I turned 30 but felt that I wanted to take a break, slow down in life and not work so hard like previous years. 

My family sure felt that as they saw me lazing around most of the time and was at one point questioning me on what I want to do with my life, I guess it is really weird in Singapore to not think about work or money or life although the younger generation is trying to change that. I think my friends could also feel the carefree attitude I had because when we met, they would talk about their work, colleagues and I would just be not talking about work as there really is nothing much going on for me on that end. 

I think I have done well in the year, it was a kinda year where I compared myself to others a lot, as I wasn't doing much in my life, it was easy to open social media and see everyone else living an amazing life but I know social media breeds negativity as comparison arises. I am hoping to reduce doomscrolling and usage on social media, hopefully get back more into putting my thoughts into words. Hoping that 2026 will be smooth and that some excitement can happen in my life too!