Just Dump It In
Why waiting for the perfect moment can be its own expensive decision.
"When the money lands, don't wait for the perfect day to invest it. Just dump it in and get on with your life."
Meet Jeff. He sold his financial services company in 2025 for life-changing money, and then waited for the right day to invest it in the market.
After we sold our company, I went looking for the right day to put the money in the market.
Here's the embarrassing part. I've spent my entire career in the financial industry, and read every study on lump sum investing (investing all at once) versus dollar cost averaging (investing a set amount on a preset timeline), and the research isn't ambiguous. Lump sum wins. I knew all of this. I could have taught a class on it.
The money should have gone straight into the market when I received it. But the market was choppy that day, so I waited. The next day the market was up, so I kept waiting. A week later it was down, so I invested a little, saving the majority for another dip. There was no science to it. No rhyme or reason. The market drops 2 percent, okay, let's drop in a hundred grand. Then wait. Watch the news. Wait some more. I checked the market every single day, hunting for my moment. It took almost twelve months to get it all invested.
The waiting cost me six figures in missed gains, and to rub salt in the wound, if all my money had been in the market from day one, tax loss harvesting would have saved me another $100,000.
The mistake wasn't ignorance. I knew the right answer and didn't act on it. So now I tell people: if you're lucky enough to become an overnight millionaire like we were, invest it the day it arrives. Don't wait and watch. Don't wait for the dip. Just dump it in, and get on with your life.
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