When should you invest? How to time the market.
- Ben Clarke
- Oct 27
- 3 min read
Updated: Oct 29
*Not personalized financial advice - your money, your choice*
That’s how much cash Americans are sitting on right now, parked in money market funds - all waiting for the “right time” to invest.
The problem? There is never a “right time”.
Every day, the market goes up for some and down for others. Headlines tell us that a recession is imminent or that the AI bubble is about to pop. These headlines may be true but the trillion dollar question is “when?”. As soon as you ask that, no one knows.
The fear that a recession is “about to happen” or that the “AI bubble is surely going to pop soon” is enough to paralyze many of us in fear. It makes keeping our money in a savings account seem like the risk-free option even though doing that would have lost you 30% of your buying power to inflation over the last 5 years.
Lets assume there are 2 people, Lily and Jeff.
Lily decides it’s best to put dollar-cost-average (DCA) into the market - for her this means investing $100/mo.
Jeff is a saver. He also has $100/mo to spare but, he instead puts it into a checking account with no interest.
If Lily were to invest $100/mo starting in Jan of 2015 through December of 2018 (48mo) she would have invested $4,800. If she didn’t invest a dollar more, by the end of 2025 she would have a whopping $20,419.
In Jeff’s case, he wouldn’t have done so well. If he invested the full $4,800 at the bottom of the market in December of 2018, then stopped; by the end of 2025 he would be left with just $14,852.

In this scenario, Lily crushes Jeff (DCA vs perfect timing) because of time invested and compounding interest.
Not only that, but if fear had been what was causing Jeff to wait to invest, then it’s likely he would have continued to be afraid. There would be the fear that it wasn’t actually the bottom yet and, if he were ever to get the courage to invest, he’d likely do so when the market was well on its way back to all time highs.
Trying to time the market can feel smart, but when you look back to when you could’ve invested, even when there is a market crash, most of the time, the market bottoms above where it would’ve been 10 years prior to the crash.
That’s where the saying “Time in the market beats timing the market,” comes from.
Fidelity and Bloomberg also did the math on how much in gains you would miss out on if you didn’t invest during the best days of returns in the S&P 500.

If you just missed the 4 best days when investing $10,000 between Jan of 1988 through Dec of 2024, you would miss out on nearly $200,000 in gains. Big L.
If you weren't in the market for just the best 30 days of market returns then you’d be down a whopping $433,786. Almost half a million dollars! That's a lot of avocado toasts.
If you learned something, subscribe to my YouTube channel or newsletter. Timing the market doesn’t have to break ankles when it jukes.







