There’s something seductive about timing the market.
Waiting for the perfect dip. Holding cash for the “inevitable crash.” Believing you’ll buy right before the rebound. I used to think that way. In fact, I managed to pull it off more than once, scoring some great deals that I continue to hold till this day, and which have compounded tremendously over the months and years since. But I have also missed on some great ones, thanks to my insistence on timing the market and the exact entry price. One famous example is Bank of Montreal (BMO) . Around August 2024, it was hovering around $110-115, and I set a price of $112 which I missed by mere cents, and then the transaction didn’t materialize, and watched the share skyrocket to almost $230 now!
That is 65% price appreciation that I missed due to my thinking I could time the market. That one will continue to hurt for years to come, but a big lesson learnt!
Over time, I realized something simple: I don’t need to outsmart the market. I need to simply out-discipline myself. Enter bi-weekly investments!
Here’s why I invest biweekly instead of trying to time it.
I Don’t Believe I’m Smarter Than the Market
The market isn’t one person making emotional decisions. It’s millions of investors. Institutions. Algorithms. Pension funds. People with more information, more capital, and more resources than I’ll ever have. Best analogy would be for me to think I can predict the winning lottery numbers.
If professionals struggle to time the market consistently, why would I assume I can? It is a wishful thinking at best, so why even bother? Trying to time it requires two perfect moves:
- Selling at the top
- Buying at the bottom
Most people can’t even get one right. Imagine the odds of getting both of them. So instead of pretending I can predict the future, I focus on what I can control: consistency.
Biweekly Investing Removes Emotion
My income comes in every two weeks. So my investing goes out every two weeks.
No debates. No headlines. No “maybe I’ll wait a little longer.”
It’s all automatic.
When markets are high, I invest. When markets are crashing, I invest. When everyone is panicking, I invest. That rhythm removes fear and greed from the equation. And in investing, emotion is usually the most expensive mistake you can make. Automation protects me from myself. Volatility Becomes an advantage, not a threat. Most people see a market drop and feel anxiety. I see a market drop and see shares on sale.
If I’m investing biweekly no matter what, downturns actually help me accumulate more. My fixed dollar amount buys more units when prices fall.
Over time, that averaging effect works quietly in the background.
I don’t need to predict when the bottom is. I just need to keep showing up. And the best way to do that is to automate and forget.
My Goal Is Freedom, Not Excitement
Timing the market is exciting. It gives you a rush. It makes you feel strategic.
But building wealth? It’s boring. And boring works. It is the the classic answer to those who ask the question “if it is so simple, why don’t more people do it”. Well, because most people are not excited to chase what they consider boring or requires patience. Not me: I have read and experienced enough to realize that ‘boring’ does it for me.
I’m not investing for next month or next quarter. I’m investing for long-term passive income. For financial freedom. For the ability to choose how I spend my time.
Biweekly investing aligns with that goal. It’s steady. Repeatable. Scalable.
I don’t need brilliance.
I need decades of consistency.
At the end of the day, I don’t try to predict the market. I participate in it. And I let discipline do the heavy lifting. Over the long term, I will have achieved financial freedom with not much effort, emotion or stress.