No more monthly paycheck. A portfolio worth less than USD 500,000. And an ambitious goal of generating USD 10,000 a month in investment income. Here’s where I’m starting.

For most of my adult life, I never really had to wonder where my next paycheck was coming from.

Every month, money would arrive in my bank account.

It didn’t matter whether the stock market was going up or down, whether my investments were doing well, or whether I had made any good financial decisions that month.

As long as I had my job, I had a salary.

That changed at the end of September 2026.

At 45, I walked away from a well-paying job without another one lined up.

And for the first time in years, I don’t have a regular paycheck to rely on.

Instead, I’m going to see how far my investment portfolio can take me.

My goal?

To generate USD 10,000 a month from my investments.

It sounds ambitious. Perhaps a little unrealistic, especially considering my portfolio hasn’t even reached USD 500,000 yet.

But I’ve been working towards this for several years, and now I’m finally putting the plan to the test.

I don’t know whether I’ll reach that number.

What I do know is that September brought in about USD 4,884 in investment income.

That’s where this experiment begins.

How I Ended Up Here

I’ve always believed in saving and investing.

But about three years ago, I started taking income investing much more seriously.

Until then, much of my investing had been focused on growing my wealth.

Buy good investments, hold them, and hopefully watch the portfolio grow over time.

That was fine while I was working.

I didn’t need my portfolio to pay my bills. My salary took care of that.

But as I started thinking about what life might look like without full-time employment, my priorities began to change.

I didn’t just want investments that could grow in value.

I wanted investments that could provide money I could actually use.

Money that could help cover my expenses without requiring me to sell shares every month.

That led me to explore dividend stocks, covered call ETFs, and eventually selling options myself.

I spent the next few years building up these sources of income.

At the same time, I made sure I wasn’t depending entirely on the stock market.

Before leaving work, I had accumulated at least two years of emergency savings in liquid funds, with additional money in short-term government bonds.

That buffer was important to me.

Because the last thing I wanted was to leave my job, experience a market downturn, and then be forced to sell investments at a loss just to cover everyday expenses.

I wanted to give myself some breathing room.

By September, I felt ready to try.

Not because my investments could already replace my paycheck consistently.

But because I finally had enough of a cushion to find out whether they could.

Where My Investment Income Comes From

When people hear about living off investments, they often think of dividend stocks.

Buy shares, collect dividends, and enjoy the passive income.

That was where I started too.

But over time, my income strategy evolved into three main parts.

1. Dividend stocks: The foundation

I own dividend-paying stocks. Mainly from my Singapore Bank Stocks.

These provide cash distributions throughout the year.

Some of my holdings pay only a few times annually, so the income isn’t evenly spread across every month.

And because I’m based in Singapore, there’s another consideration when investing in US dividend stocks.

For the US dividends I receive that are subject to the standard withholding rate, 30% is deducted before the money reaches my account.

So a USD 100 dividend may leave me with just USD 70.

It’s something that matters when you’re trying to build income you can actually spend.

I still like dividend stocks, especially businesses that can maintain and grow their payouts over time.

But dividends alone weren’t going to get me to my income goal quickly.

Which brings me to the next part.

2. Covered call ETFs: More income, but with trade-offs

I started adding covered call ETFs to my portfolio because they offered the possibility of more frequent distributions.

I hold funds such as BTCI, along with covered call ETFs listed in other markets, including Hong Kong-listed 3419.

The attraction is understandable.

Instead of waiting for dividends a few times a year, some of these funds make distributions every month.

For someone trying to replace a salary, monthly income is appealing.

But I’ve learned that a high distribution doesn’t necessarily mean a good investment.

Take BTCI, for example.

As of early October, its market price was about 21% below my average purchase price.

Yes, it has been paying distributions.

But the value of my investment has also fallen.

And that’s something I think is important to talk about.

Receiving USD 1,000 in distributions doesn’t automatically mean you’ve become USD 1,000 wealthier.

If the value of the underlying investment falls significantly, those distributions may not be enough to make up for the loss.

Some funds also distribute amounts that include a return of capital.

That’s why I’ve become more interested in looking at total returns rather than just the yield advertised by a fund.

Income matters to me.

But so does keeping enough capital invested to generate income in the future.

3. Selling options: My biggest income contributor right now

The third part of my strategy is selling options, mainly cash-secured puts and covered calls.

This has become a significant contributor to my monthly investment income.

The basic idea is fairly simple.

When I sell a put option, I receive a premium in exchange for agreeing to buy shares at a certain price if I’m assigned.

When I sell a covered call, I receive a premium in exchange for potentially having to sell shares I already own at an agreed price.

The premiums can be attractive.

But there are risks.

A stock can fall far below my put strike price, leaving me holding shares worth much less than what I paid.

And selling covered calls can limit how much I benefit if a stock rises sharply.

It’s also not completely passive.

I have to monitor positions, decide when to close trades, manage assignments, and think carefully about how much risk I’m taking.

Some weeks involve more work than others.

Still, this is the strategy that has contributed the most to my investment income recently.

In September alone, my completed options trades generated USD 3,110.30 in net trading income.

That’s a meaningful amount of money.

But one good month doesn’t mean I can expect the same result every month.

And that uncertainty is something I’ll have to get used to.

My First Financial Snapshot: September 2026

Now for the numbers.

September was my strongest month of 2026 so far in terms of the investment income I’ve been tracking.

Income source	September 2026
Completed options trades, net	USD 3,110.30
Dividends and fund distributions, after tax	~USD 1,773
Total tracked income	USD 4,883.69

That works out to roughly 49% of my USD 10,000 monthly target.

I was pleased with the result.

Not because I’d reached financial independence through some magical investment strategy.

But because the income was starting to become meaningful enough to test whether it could support a life without a salary.

Still, I have to be careful about what these numbers represent.

This is the income I’m tracking from completed options trades and cash distributions. It isn’t the same as my portfolio’s total investment return.

It doesn’t fully capture unrealised losses, changes in the market value of my holdings, or how much capital I’m putting at risk to generate that income.

And those differences matter.

The Income Is Growing. But It’s Not a Straight Line.

One thing that has encouraged me is seeing how my investment income has developed during the year.

Back in January, my tracked income was only about USD 1,559.

By July, it had increased to around USD 4,130.

August came in at approximately USD 4,281.

And then September reached USD 4,884.

Month	Tracked investment income
January 2026	~USD 1,559
July 2026	~USD 4,130
August 2026	~USD 4,281
September 2026	~USD 4,884

Selected months shown. Figures include completed options trading results and after-tax distributions.

From January through September, the total was approximately USD 24,587.

Part of the increase came from selling more options starting in July.

Which means the improvement wasn’t simply my portfolio producing more income on its own.

I was taking a more active role in generating that income.

And with that comes additional risk.

It’s tempting to look at the last three months and assume the income will keep growing.

But markets don’t work that way.

I could have a month with fewer opportunities.

I could take a loss on an options position.

Or the market could fall sharply and reduce the value of my holdings.

So while I’m encouraged by the progress, I’m trying not to get too carried away.

The Part That Doesn’t Look So Good

It’s easy to share an income screenshot showing nearly USD 5,000 in a month.

It feels good to see money coming in.

But that isn’t the whole picture.

For example, some put options I sold resulted in shares being assigned to me.

One of those positions was VST.

By the end of September, those shares were sitting on an unrealised loss of about USD 1,394.

And as I mentioned earlier, my BTCI holdings were trading roughly 21% below my average purchase price in early October.

Those losses don’t disappear simply because I collected premiums or received distributions.

They are part of the investment results.

This is something I’ve been thinking about more as I move from accumulating wealth to depending on my portfolio for income.

When you’re still earning a salary, a market downturn can be uncomfortable, but you may have the luxury of waiting for your investments to recover.

When your portfolio is expected to help fund your living expenses, the situation feels different.

You need cash flow.

But you also need your capital to survive.

And sometimes those two goals can pull in different directions.

I don’t want to build an impressive-looking monthly income at the expense of slowly destroying the portfolio that produces it.

That’s the balance I’m trying to figure out.

Is USD 10,000 a Month Even Realistic?

This is where the maths gets uncomfortable.

My goal is to generate USD 10,000 a month.

That’s USD 120,000 a year.

And my portfolio is still worth less than USD 500,000.

Even if I had a full USD 500,000 invested, generating USD 120,000 a year would require a 24% annual cash-income rate.

With a smaller portfolio, the required rate would be even higher.

That’s a lot to ask of any investment strategy.

Goal	Amount
Monthly income target	USD 10,000
Annual income target	USD 120,000
September income	USD 4,884
Monthly gap	~USD 5,116
Required annual income rate on USD 500K	24%

And that calculation doesn’t even address whether the portfolio could maintain its value while producing that much income.

There’s a big difference between receiving a 24% cash payout and earning a sustainable 24% total return.

High distributions can sometimes come with falling capital values, limited upside, or significant exposure to market risk.

So I know the goal is aggressive.

To get there, I’ll probably need some combination of portfolio growth, reinvesting income, improving my options strategy, and accepting that some months will fall short.

What I don’t want to do is blindly chase higher yields just to make the monthly numbers look better.

A strategy that produces USD 10,000 a month but leaves me with a much smaller portfolio after a few years wouldn’t be the success I’m looking for.

Why I’m Doing This Anyway

Here’s the thing.

I don’t actually need to hit USD 10,000 next month.

Or even next year.

I’ve deliberately avoided setting a deadline.

Right now, I have a financial buffer, a portfolio generating income, and the freedom to take a break from full-time work.

That gives me some room to experiment.

To learn which strategies work for me.

To make mistakes, hopefully ones I can afford.

And to find out how much income my portfolio can realistically generate without taking risks I’m uncomfortable with.

There will probably be months when my income falls.

There may be periods when I have to reduce my options activity or rethink my allocations.

And it’s entirely possible that I’ll discover USD 10,000 a month isn’t sustainable with the amount of capital I have.

If that happens, I’ll have to adjust.

I’m not trying to prove that everyone can leave their job at 45 and live off investments.

Everyone starts from a different financial position, and my circumstances won’t be the same as someone else’s.

I’m simply documenting my own attempt.

The Real Test Starts Now

For years, I built my investment portfolio while receiving a steady salary.

I could reinvest my income, add new money regularly, and give my investments time to grow.

Now I’m entering a different phase.

Instead of asking only how much my portfolio can grow, I’m asking how much income it can produce and how long it can keep doing that.

That’s a much harder question.

September’s USD 4,884 was a promising start.

But it’s just one month.

What matters more is what happens over the next year or two.

Can I generate reasonably consistent income?

Can I manage the bad months?

Can I avoid taking excessive risks just because I want to reach a certain number?

And, most importantly, can I do all that without seriously damaging my long-term wealth?

I don’t have those answers yet.

But that’s what makes this next chapter interesting to me.

I’m 45, I no longer have a regular paycheck, and I’m going to see whether my investments can eventually pay me USD 10,000 a month.

Maybe I’ll get there.

Maybe I’ll have to lower the target.

Maybe I’ll discover an entirely different approach along the way.

For now, I’m starting with USD 4,884.

And I’m going to see where it takes me.

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If you’re building an investment portfolio for income, I’d love to know how you’re approaching it. Are you focused on dividends, selling options, capital growth, or a combination?

Disclaimer: This article documents my personal investment experience and is not financial advice. I’m not a licensed financial adviser. Options trading and income-focused investments involve significant risks, including assignment, capital losses and distributions that may not be sustainable. Past performance does not guarantee future results.