I’m Investing $750,000 After Losing $1 Million in Cash—Will I Avoid My Past Mistakes This Time?

Investing in the stock market is one of the hardest financial decisions anyone can make. It can very much feel like you are gambling with your money, and while the stock market has continuously risen over time, it still feels like you are taking a huge risk and could lose it all. 

Well, one Redditor is considering all of the risks very carefully and is looking to invest upward of $1 million into the market. The hope is that after already deploying $250,000 and losing 10%, they will take the remaining $750,000, be as thoughtful and rational as possible, and begin to invest without emotion. 

It’s worth emphasizing again that investing in the market is a personal decision, and there are risks, but it’s also one of the best ways to make enough money to have a comfortable retirement.

The Decision 

While there are several different things this Redditor could do with $1 million, their decision to leap back into the stock market isn’t without risks. According to the original poster’s post in r/ChubbyFIRE, they already missed one of the biggest downturns in 2020 when they panicked, didn’t buy, and kept a good chunk of cash on the “sidelines.” 

Now, they realize that the market may be in another downturn, so they want to take advantage, pick up some stocks on a dip, and do some tax-loss harvesting to balance everything out at the end of the year. 

The good news is that they plan to be more methodical this time and not let emotion get in the way as they did in 2020. This said, they are concerned that with $250,000 already invested and down, they have reason to be nervous and freeze up again. However, they want to try and push through, slowly invest the remaining $750,000, and avoid their past mistakes. 

Is this the right move? 

The Smart Move

While it will be among the most challenging moves, the best scenario is for the original poster to invest in the market and not look for a while. Looking at the market daily can be an emotional rollercoaster if you intend to invest for the long haul. I think we can all speak from experience on this one. 

If you read the comments on this post, the most common advice is to invest without looking. However, tax harvesting with potential losses can help wipe out any taxes due to capital gains, so it should work out in the end. 

Another strong piece of advice being echoed by multiple Redditors here is that this investor should consider diversifying their investments. If they are stuck on going into the market, don’t just invest in tech or healthcare, but diversify so you can ride the ups and downs as best as possible. The market will rise and fall, so the more diversification you have with your stocks, the better the chance is that you don’t feel the worst impacts. 

Don’t Time The Market

The last and final advice for this Redditor is that trying to time the market is a fool’s errand. It’s just impossible and something even the smartest and best-performing investors know. They might offer quality advice that helps you believe you know the best time to get in, but all it takes is a piece of tariff news or a natural disaster, and all bets are off.

In other words, this Redditor posts in the comments about how they regret missing the downturn in 2020, but there is no telling what the downturn in 2025 will look like in the end. This tariff news could be gone in a day or a week, so they realistically have to pick a day, buy what they want, and hope for the best and prepare for the worst.

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