BECOMING BOSS OF MY TIME (BOMT)

How a regular 9-to-5 employee earns passive income for financial independence

Why Time in the market beats timing it: How Dividends and patience build real wealth

After 20 years in the 9-to-5 world, I had done everything “right.” I climbed the corporate ladder, chased promotions, and worked harder every year. But by 2015—at the age of 40—I realized something unsettling:

I wasn’t building a life. I was just busy surviving.

That year, I made a commitment to walk away from the rat race—not by quitting my job overnight, but by understanding how money really works. I studied investing, built a portfolio of passive income, and turned consistent habits into long-term freedom.

 

Today, I can walk away if I want to. Not because I got lucky, but because I embraced time, dividends, and discipline—not gambling on the next hot stock or timing the market.

Why Time in the Market Beats Timing the Market

One of the biggest myths in personal finance is that smart investors “time” the market—buy low, sell high, and dance around every dip.

 

But the truth? Most people who try to time the market end up missing its best days.

 

Look at this chart:

time in the market vs timing the market, S&P 500 investing, dividend stocks, long-term investing, passive income, financial independence Asia, dividend growth strategy, retire early, FIRE movement

From 2003 to 2022, if you had simply invested $10,000 in the S&P 500 and left it alone, it would have grown to $64,844.

 

But if you missed just the 10 best days? Your return drops to $29,708.

 

Miss the 20 best days? You’re left with only $17,826.

 

This stat says it all:

 

Investment returns are 93% lower if you miss the 60 best days in the market.

And here’s the kicker: 7 of the 10 best days happened during bear markets—when most people are too scared to stay invested. Timing the market isn’t just hard—it’s nearly impossible.

Time Smooths Out the Risk

Let’s zoom out even further. Over the past two centuries, market data shows the longer you stay invested, the more predictable and positive your returns become:

time in the market vs timing the market, S&P 500 investing, dividend stocks, long-term investing, passive income, financial independence Asia, dividend growth strategy, retire early, FIRE movement

Source: Chapter 2 Risk, Return, and Portfolio Allocation of Jeremy J. Siegel ().  Stocks for the Long Run. McGraw Hill. DOI: 10.1036/007/1494707

  • In a 1-year holding period, stocks can swing wildly from +66.6% to -38.6%.
  • But over 30 years? Even the worst case is a +2.6% return per year.

This is why I always say: volatility is the price of admission for long-term growth.

Dividends: The Hidden Superpower of Wealth Building

Not all stocks are created equal. Some dazzle for a while, but fade. Others quietly compound wealth in the background.

Here’s what happens when you invest in dividend-paying stocks over time:

 

time in the market vs timing the market, S&P 500 investing, dividend stocks, long-term investing, passive income, financial independence Asia, dividend growth strategy, retire early, FIRE movement

Source: Ned Davis Research and Hartford Funds

From 1973 to 2020:

 

  1. Dividend Growers & Initiators turned $100 into $11,346
  2. Dividend Payers grew to $6,946
  3. Meanwhile, Dividend Non-Payers ended with just $844
  4. And Dividend Cutters dropped to $56

 

The takeaway? Reliable, growing dividends beat flashy stock tips.

 

Dividend-paying companies tend to be more financially healthy, less volatile, and more focused on long-term results. They reward shareholders consistently—especially during downturns.

My Personal Journey: From Paycheck Cycle to Financial Clarity

I started investing seriously in 2015—not with a windfall, but with a decision. I committed to consistently saving and investing, even when the market dipped or headlines screamed doom.

Along the way, I made mistakes. But I learned that failures are feedback, not final stops.

Today, my passive income portfolio gives me peace of mind and optionality. I can choose how I work, not just if I work.

This blog is part journal, part message-in-a-bottle—for anyone feeling trapped in the paycheck-to-paycheck life, and for my two sons. I want them to learn what school doesn’t teach:

  1. How money really works
  2. Why your mistakes matter less than your persistence
  3. And how to build a life full of purpose—not just paychecks

Final Thoughts: Invest with Intention, Not Emotion

If you’re serious about breaking free from the rat race, here’s what truly works:

 

  1. Stay invested for the long haul
  2. Focus on dividend-paying stocks
  3. Ignore short-term noise
  4. Let compounding do its job
  5. Choose simplicity over speed

 

Financial freedom isn’t about quitting your job tomorrow. It’s about creating the clarity and space to ask deeper questions:

 

What truly matters to me?

How do I want to spend my limited time here?

 

Thanks for stopping by.

If this helped, feel free to share it with someone who needs to hear it.

 

— Boss Of My Time

Have you tried market timing before and changed your strategy?

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