May 15, 2026

Millionaires Make These 4 Investing Mistakes Too — Here's What To Learn From Them

Written by Caitlyn Moorhead
|
Edited by Gary Dudak
Discover a man with a digital tablet reviews his current investments, conceptualizing stocks or dividends.

Wealth doesn't make you a better investor — sometimes it can make you a worse one.



Even millionaires with top financial advisors and sophisticated tools make costly mistakes, and according to those advisors, the same ones show up again and again. Surprisingly, most regrets don't stem from market crashes, but from emotional decisions, poorly timed moves and overconfidence.

Here are four investing mistakes even millionaires regret — and the lessons that can sharpen your strategy in 2026.

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Maybe timing is everything in showbiz, and while you can occasionally get lucky timing your investing around market trends, you don't want to consistently rely on it. That way lies madness in the short term, and fewer gains in the long term.

"Many millionaires fall into the trap of believing they can time the market," said Tyler Meyer, founder of Retire to Abundance. "Whether it stems from previous successes where high-risk bets paid off or the assumption that timing is the key to ongoing growth, this approach often backfires."

Anyone who has invested money understands there are certain assumed risks. And while everyone wants to rack up that compound interest, trying to time the market is one mistake that millionaires often regret -- because nobody has a crystal ball into the future.

Millionaires have a tendency to forget they have access to professional advice to guide them through financially stressful situations. "One advantage of reaching a certain level of wealth is the ability to afford services that were once out of reach, including professional financial advice," Meyer said.



Rich clients may also feel like they don't need professional advice because they've experienced a certain degree of success on their own. It's worth pointing out that just because someone makes money in one venture doesn't mean they're qualified for every other one.

"A skilled advisor can help you avoid many common pitfalls and provide strategies tailored to your unique situation. While no advisor is perfect, their experience with similar clients equips them to steer you clear of costly mistakes," Meyer said.

"For many millionaires, wealth is often concentrated in a single source, such as a business they own or stock options from their employer," Meyer said. "While these investments may have been instrumental in building their wealth, relying too heavily on one asset introduces significant risk."

Diversify, diversify, diversify. It can help mitigate potential losses and offer you a more balanced portfolio. Sometimes, a millionaire will build wealth through one asset class initially, and then feel that this is the best way to continue investing moving forward. However, as one's wealth builds, spreading the risks and looking into different investing options becomes more important. 

"Though diversification may not always be straightforward, taking steps to spread risk early on can prevent substantial financial setbacks," Meyer explained.

"Millionaires often make costly investing mistakes by overlooking tax-smart strategies," said Rachel Richards, head of product at Gelt. No one can escape the tax man, even if statistically higher-net-worth individuals are more apt to do so.

Even with investments that have done well, by not optimizing tax-wise strategies, millionaires could leave significant amounts of money on the table and spend more on taxes than they planned. According to Richards, one of the main regrets in this category is neglecting to sell underperforming investments before year-end, forfeiting opportunities to offset capital gains taxes.



Many millionaires also regret missing opportunities to leverage charitable giving and estate planning tools to provide immediate tax benefits and support long-term wealth preservation. "These missteps highlight the importance of aligning proactive tax planning with investment decisions to optimize your wealth," Richards said.

Martin Dasko contributed to the reporting for this article.

This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.

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Caitlyn Moorhead
Written by
Caitlyn Moorhead
Gary Dudak
Edited by
Gary Dudak