9 Biggest Investment Mistakes Users Regret

Back in early 2023 an old coworker told me to invest in SOXL. So I put $500 in for what was $15 a share at the time… then sold it like a month later to get the money back.

Now it’s trading at $277 a share… could’ve been pretty rich for my current age of 25 if I’d continually put money into the stock.

What’s your worst mistake 🙃trying to cope lol

The first time I ever panic sold and then saw the market recover without me will forever be seared into my brain.

Is being born too damn late to start investing…like damn I should have started investing out of womb with my chore money or something.

Jokes aside, this bull market is making me feel MASSIVE FOMO because I just got out of college and I can only invest so much with my limited income. I DCA ($50/week) in my personal brokerage account after my monthly Roth(etfs)/emergency fund allocations, so i choose to invest in riskier individual stocks with a go big and hopefully don’t go home mindset (moonshot hopefuls like NBIS/ASTS/ONDS/something with a lower share price bc buying fractional shares doesn’t hit the same if you know what I mean). But seeing some of these skyrocket in the past couple days meanwhile me over here, having only been able to DCA a meager $5-10/week per stock. Even if they were bought at big dips/lows, +100% of 5 is still only 10 and makes me nonstop think about the what-ifs like if I was born earlier and had more time to make money/invest. The only comfort I have is that the market isn’t normal rn or that I could have just as easily invested in something that crashes and burns too.

But I guess we all have to start from somewhere…Anyways hope everyone’s investing journey is full of wins and let’s all not retire at 75 if we can help it

Not the obvious ones, Not "I bought at the top" I mean the kind where you were wrong for months and genuinely thought you're fine.

I'll go first:

I bought Nike on the turnaround, brands still huge and were changing the product line and the strategy, and I figured I was in before everyone else believed it.

Before buying I wrote down what would make me wrong. Roughly, if the turnaround isn't showing up in the numbers after a few quarters, get out.

Then the quarters happened. Direct and digital kept sliding, digital is was down 10 quarters in a row, and direct down 6%. The turnaround kept getting pushed out further, and every time there was an excuse.

All of it sounded reasonable though

Then I reread what I'd written down before buying, and I'd already answered it, the exact situation I was explaining was on of my reasons to sell.

I hadn't changed my mind but I'd changed the rules for what counted as being wrong.

That stuck with me because I'd have done the same thing without noticing.

So now I lock the thesis before I buy, the claims, the rumors, and specific things that would prove me wrong. I set alerts on the levels that matter, and when earnings come out I check that transcript against my original claims which I have written down, what I get shown is what I write not what I remember writing.

I ended up losing on this position, but I'm happy that I realized sooner rather than later, I managed to sell at around 60, which is good because it now dropped to 40!

What's the mistake you only saw in hindsight, and what made you notice it?

Curious to know of stories where you made a costly mistake and how you overcome it. I can share my sad story to kick the ball rolling.

In 2020 when I was 29 years old, I invested in Tesla with all the money I had because I believed in the vision of the CEO which was to reduce reliance on oil and that EV will replace ICE cars eventually.

Each time the stock price went up, I bought more - to the point where I had 400 shares at a cost basis of $370 (around SGD200K) during its ATH.

When it dropped from the peak (from $370 to $123) my investment essentially more than halved and at the lowest point, I had only 80k in it. I was so mortified, I deleted the app and didn’t look at it for years.

It was only in 2024, when I chanced on a news article about Tesla reaching its ATH again. I reinstalled my app but this time I exited all my positions, making a loss of around 20-30K.

The real cost however was the opportunity cost. Had I invested in S&P500 during 2021-2024, I would have made around 60K.

So what’s your story?

Not necessarily your biggest loss, but a mistake that changed how you invest today.

Curious what lessons people here learned the hard way.

Don’t bet against the US. They might be some corrupt shitheads but they know how to pump capitalism.

My biggest mistake was to spend any time at all on Users, either soliciting or giving advice.

Worst investing mistake. Thinking I can outsmart index funds and pickin individual stocks, all my free money goes into index funds

Don't buy shares of companies that work in highly technical businesses that I don't understand (especially Biotech). I learned that I was the "dumb money" in those investments and I don't plan to go back to school to get a PhD in biology or medicine.

Believing the misconception that buying at all time highs is bad.

I’ve just started investing and as someone who’s being really careful what do I stay cautious of?

Buying spotify at a decent price, then it crashed and i baghold for damn long waiting for it to recover back to cost price. Once it did, i sold. Price continued skyrocketing to >2x my cost. Biggest L

My mistake as a conservative investor was not setting up a giro to buy vwra every month starting from when it was around 80dollars.

10k shares in pltr at $8. Sold at average price of $35 :(

At one point, I only owner Apple and Tesla. Bought 700 TSLA shares in 2010 @$15, after splits those now 10500 shares would be $4.2 Million. Same with Apple only had more shares and more splits, probably another $8 Million.

Trying to time the market.

Starting at 25 and not 18.

What is your biggest mistake that you experienced in investment / trading that we can learn from?

For me, many times I am easily affected by noises ( Be it news, convo with friends, analysts) and end up doubting my own thesis and making wrong decisions. Its still a work in process for me to learn to tune out all these noises and trust in myself.

I'e been thinking a lot about personal finance lately, and one question keeps coming to mind: What's the biggest financial mistake people make in their 20s?

Your 20s are often the first time you're earning a steady income, making independent financial decisions, and trying to figure out what kind of future you want. It's also a stage where mistakes can either become valuable lessons or create long-term financial stress.

Some people say the biggest mistake is not investing early, even if it's just a small amount each month. Others believe it's living beyond your means to impress people or keep up with social media. Many regret taking on unnecessary debt, while others wish they had built an emergency fund before spending on luxuries.

Then there are those who think the biggest mistake isn't about money at all—it's about not investing in yourself. Learning valuable skills, starting a business, improving your education, or building a professional network can often produce better long-term returns than any single investment.

I'm also curious about the role of financial education. Many of us leave school without learning how to budget, invest, understand taxes, build credit, or plan for retirement. Do you think schools should teach personal finance as a core subject, or is it something people should learn on their own?

For those who are already in their 30s, 40s, or beyond:

• What financial mistake did you make in your 20s that you still think about today?
• What would you have done differently if you could go back?
• What's one habit you started that had the biggest positive impact on your finances?

For those currently in their 20s:

• What's your biggest financial challenge right now?
• What are you doing to avoid common money mistakes?
• What financial goals are you working toward over the next five years?

Whether your experience involves investing, saving, debt, budgeting, entrepreneurship, real estate, cryptocurrency, career growth, or something completely different, I'd love to hear your story.

The best advice often comes from real-life experiences rather than textbooks. Hopefully, this discussion can help younger people avoid costly mistakes and make smarter financial decisions.

Looking forward to reading your insights!

Stocks I bought in Pandemic, didn't sold them their highs.

Not taking advantage of automatic withdrawal into company 401K with matching

Probably missed out on over $100K on the low end since I've been with the law firm for a very very long time now.

Should have started it in my 20s

Holding losers past 20% down