Index Funds vs Individual Stock Investing: My Costly Mistake

Why pick stocks or index funds (ETFs and mutual funds)? The destruction of half my net worth in my 20s during the Great Recession offers up some lessons.

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What are the pros and cons of investing in index funds vs stocks? This article follows the end of my personal FIRE story with the start of the Great Recession in 2008-2009. For brevity: understand that this was a few years after undergrad, I had my first “real job” at 22 years old. I finally saved some money and invested in individual stocks after deciding boring index funds weren’t for me.

I read money magazines about investing in individual stocks, commodities, and precious metals. Occasionally, I purchased shares in company stocks I thought stood a good chance to rise in the future.

Deciding between broad stock market index funds vs individual stocks wasn’t a comparison I considered. I didn’t even have a clear understanding of the differences between ETFs and mutual funds or how they relate to index funds. Why bother? After all, you can’t be better than average and capture that sweet alpha if you just buy the index!

Do you have any guesses for what that did to my personal finances? Read on to witness the destruction of half my net worth and learn all about these mysterious financial instruments!

The Great Recession and Stock Market Collapse

I freaked out as half my life savings disappeared through late 2008 and into 2009. My individual stocks underperformed the market. Initially, these were just paper losses since I hadn’t sold my shares.

I’d returned from my stint in the Peace Corps to discover a dwindling net worth. I was in my mid-twenties and my nest egg wasn’t exactly huge, but it was all I had. Initially, I held strong but the world was sounding the alarm.

Headline companies were going bankrupt.

Capitalism was dead!

This time it was different.

The constant dread and fear got to me, and I sold.

I sold it all.

The end of capitalism and the markets

I took a capital loss of more than half my total investments. I moved the money into safer investment: treasuries, money market funds, savings.

Hell, I even put some money into leveraged inverse S&P500 tracking ETFs.

Oh, not familiar with those?

I’m not surprised, as leveraged funds are one of the riskiest types of investments. These ETFs carry significant expenses to leverage or multiply with debt, the change in the index they track. In my case, if the S&P500 went down 5%, I’d earn 15% (minus some leverage expense). If it went up 5%, I’d be down 15% (plus some leverage expense).

I’d really not learned my lesson it seems.

Fortunately, I’d already lost most of my investment so as the market recovered and my risky bet cratered, I only lost a little more.

Of the $34,015 I’d squirreled away and gambled over 2007, and some of 2008, I had less than half my net worth in 2009. Of the balance, I withdrew $3,300 in early 2009 to put into savings—nearly nailing the market bottom of the Great Recession.

I pulled another $3,617 out in May of 2010 as the recovery took a small stumble.

I didn’t make serious investments again until late 2010, missing out on a large amount of the recovery. The S&P 500 had bottomed at about 666 points near Spring 2009. By the beginning of 2011, it’d already nearly doubled. A similar whipsaw had occurred with the individual stocks I’d owned, with both the trough and peaks more extreme due to the volatility in the individual stocks.

ETFs vs Stocks: What’s the Difference?

A little learning sidebar: I mention exchange-traded funds (ETFs) a few times throughout this post.

ETFs are baskets of stocks, yet they trade on the stock exchanges like any other individual stock. They have unique ticker symbols and carry the same fees and trading options as regular shares.

ETFs are good choices when you want to invest in an industry that has rare, huge stars but many misses and failures. Think of something like biotech where one company has a breakout drug but many other companies’ drug research fails. A biotech ETF could make sense if you aren’t sure which company is going to be the big winner.

On the other hand, an industry like regulated utilities offers similar returns for the companies within the industry. An ETF can still be a good choice to diversify across the industry, but will probably have a return similar to the companies within the ETF since there’s not much deviation from the mean.

There’s a wide variety of ETFs: industry-focused, index-tracking, or more arcane ones like inverse ETFs.

Ultimately, it’s not really ETFs vs stocks since they’re both treated as stocks. It’s a question of index funds vs stocks, the individual companies vs broad groups of them.

Visiting Wall Street in 2008 to take a gander at where all my individual stock investments lived.
Visiting Wall Street in 2008 to take a gander at where all my individual stock investments lived.

I lost more than half my net worth

This was the moment I realized that maybe I wasn’t smarter than the average investor. Just like when we grow up thinking we’re physically invincible, we often think—and are reinforced with praise—that we’re above-average at many intellectual pursuits. It’s funny that a group that prides itself on math (personal finance generally), often has so much trouble identifying the mathematical likelihood that we’re a coinflip from being above average.

A FIRE writer I respect, Dave, happened to write about his worst money mistake recently. I’m lucky my worst mistake didn’t lead me down a darker path.

To give you an idea of just how financially damaging the loss was during this time, here’s my Social Security Earnings history (by the way, you can obtain this official record from my Social Security if you’re in the U.S., we published our earnings history from 2006-2018):

2008: $26,597
2009: $12,645

The decision to sell in 2009 had turned a paper loss into a realized loss more than my entire earnings for the year.

The Recession of 2020

As we’ve come out of another V-shaped dive in the stock market, I didn’t actually think much about our investments. If anything, I was trying to find some more money to invest with when things were looking grim—partly by rebalancing our portfolio.

Rather than being fearful, I was greedy.

But is this simply because I’m older now? Is it because of that previous mistake in the Great Recession? After all, we became millionaires in 2018, so we had a lot more investment money to lose in 2020.

Dealing with losses in the stock market

Our paper losses during this recent market dive brought on by the pandemic equaled hundreds of thousands of dollars. Still, neither Jenni nor I really thought much about selling. I don’t think that’s necessarily simply because we’re “more experienced”, now.

I think it’s because we don’t really own individual stocks anymore (full disclosure: I have a very small amount of individual stock still held in old brokerage accounts that are stuck in pink sheets, they don’t represent a significant share of our portfolio).

During the Great Recession, several individual companies were going bankrupt—Lehman Brothers, AIG, Fannie & Freddie—I remember General Motors going under chapter eleven!

Seeing those big names going under left me to think that maybe my carefully handpicked stocks could also be bankrupt. After all, the one thing that enough time for stock values to recover won’t solve is an actual bankruptcy event.

I was fearful that one of my individual stocks would go to zero.

Reducing risk with diversification

The key difference in buying individual stocks vs a broad index fund like VTSAX for me is that I’m pinning my hopes on the entire US market instead of an individual stock.

Vanguard Total Stock Market Index Fund (VTSAX) is a well-known mutual fund that attempts to track the entire US stock market. It operates with incredibly low fees and has a very similar sister ETF with the tracker VTI. When comparing VTSAX vs VTI, the key difference is in the minimum investment amount (higher with VTSAX).

If VTSAX goes to zero, we’re all probably screwed anyway.

That’d mean capitalism in the U.S. has truly collapsed.

It really does help me sleep at night to know that the chance of our index fund investments going to zero is so much less likely even if there’s a huge hit to the economy like during a pandemic.

The world will eventually recover and so too will the broad market alongside your index funds.

Individual stocks and the companies they represent have a much higher chance of seeing bankruptcy during a bear market. Shareholders are often wiped out. Unless the industry or country your index fund represents collapses, it’s not going to zero.

Index Funds: ETFs or Mutual Funds

Another learning moment: index funds aren’t a specific type of investments that you can actually purchase (like a stock or bond).

We talked about ETFs earlier, and index funds can be an ETF like VTI which tracks the total US stock market. ETFs, if you recall, are traded like stock shares.

However, index funds can also be mutual funds like the much-loved VTSAX. Mutual funds are traded privately and less transparent than ETFs or stocks on the public markets. Brokerage accounts might have higher fees to trade mutual funds. Mutual funds are traded daily (rather than real time with ETFs) and settle on a single price that everyone pays that day at close.

Mutual funds can also be more tax-efficient than ETFs. You can learn a lot more about Vanguard’s incredibly popular US market index funds in another post: VTSAX (mutual fund) vs VTI (ETF).

Should You Invest in Stocks or Index Funds?

Not all investors feel that risk reduction through index fund diversification is worth reducing their upside investment potential. It is true that higher risk yields higher returns, on average, over time.

It’s one of the reasons that stocks tend to beat bonds in the longterm. It’s why lots of traders chase high beta (stocks with big swings up or down), as they think they can capitalize on the fast-moving changes better than others.

Jenni and I have been participating in the personal finance, FIRE, and investing Twitter-sphere since launching TicTocLife. Or at least, we’ve been trying to get the hang of it.

One of the threads I was following asked:

To my #dividend people: do you prefer dividend paying ETFs or picking individual stocks? Why?


Lots of the Twitterverse jumped on the individual stock bandwagon. While this is a question around dividends, the sentiment still applies to the general idea of handpicked individual stocks vs index funds.

Here’s a selection of comments:

  • “For those just starting, a broad market index fund is often a good idea considering most investors can’t beat the S&P500. Then once you have that base, you can start picking individual stocks as they generally offer more upside + higher yields.”
  • “Indiviudals. More opportunity to gain advantages. You’ll pick some losers, but if you do it right, the winners will outshine the losers better than an ETF can track.”
  • “Individual stocks. I can analyse balance sheets. I choose what I want. Not what someone else picks for me.”
  • “Picking my own individual stocks. I like to make my own mistakes Especially when the economy is strong, I feel better taking on riskier stocks with higher dividends Also avoids management fees…”
  • “World class, blue chip, perpetual dividend increasing individual stocks. I can target undervalued companies, I can strategically reallocate the dividends, I can shift strategy and optimize my portfolio in response to current world events.”
  • “Stocks. I like to know what I’m holding and have control. I like to know at what sort of valuation I’m buying the stock and don’t feel like it warrants an annual fee.”
  • “Leaning individual stocks for now because a lot of them are still on a nice discount and have great growth upside.”
  • “Individual stocks due to the tracking error some etfs have as well as the stable growth potential of one really solid company.”

Do you see a common theme here?

People want to have control.

People think they’re better than average at picking stocks.

Even as the first comment I highlighted mentioned that most investors can’t beat the S&P500 by picking individual stocks, they proceed to recommend them.

Index Funds vs Stocks FAQ

It’s fun to tell a story, but let’s clear up some frequently asked questions about index funds vs stocks.

Can you lose all your money in an index fund?

It’s incredibly unlikely, but if all companies represented in an index fund were to enter bankruptcy, it’s possible.

Are index funds still a good investment?

Vanguard popularized index funds in the 1970s as a low cost way to own tiny slices of lots of companies the index represents without involving active money managers with high fees. Yes, they’re still a good investment but require due diligence like any other investment.

Can you get rich with index funds?

Yes. Our index fund investments have appreciated hundreds of thousands of dollars on our path to financial independence and reaching $1.2M in 2018. In the decade between July 2010 and 2020, a $10,000 investment in VTSAX would have grown to about $37,000. That’s a 370% jump!

What are the disadvantages of index funds?

Index funds follow specific policies and strategies to match their underlying index. Even if it seems clear to the investing world that a company is cratering, an index fund may continue to have to hold it right up until they’re delisted from the index. This was a hot topic with GM during the 08-09 Great Recession as GM reached bankruptcy. Index mutual funds can’t be traded as quickly as stocks though index ETFs can.

What is the difference between an index fund and an ETF?

Index funds aren’t a specific asset type you can purchase. They come in two flavors: a mutual fund and an exchange-traded fund (ETF) which trades like a stock. Either one can reflect an underlying index of companies. Check out the sidebar above to learn about the differences between ETFs and mutual funds.

Got a question about index funds vs stocks we didn’t answer? Post a comment at the end of the article!

Passive vs. Active Investing

The common wisdom is that most people can’t beat the S&P500. I wanted to understand just how uncommon it was.

There’s a primary source many financial outlets cite to suggest that most investors can’t beat the market. It is an analysis performed by none other than the company behind the DOW itself: S&P Global. They publish a scorecard multiple times per year for different regions and industries around the world pitting active investors against passive indexes.

Per their 2019 year-end analysis, 70% of domestic equity funds lagged the S&P 1500 composite they track for the year. A similar result occurs internationally.

That means that the professionals, most of the time, can’t beat the market. These are the companies dedicated to financial analysis with all the research and tools available to beat individual investors into oblivion.

What chance do we amateur investor gals and guys have?

Some amateurs and some professional money managers will beat the market, but it’s luck and by extension—a very rare skill.

I know what some of you are thinking: “but I am that skilled!”

I’m making the assertion that it’s more luck than skill, not only from the 70% figure already discussed but also because the chances of beating broad market index funds with individual stock picks gets worse over longer periods.

Risk-adjusted Stock Return

S&P Global releases a risk-adjusted scorecard, that among other things we’ll discuss, tracks the active versus passive investing approach over a longer timeframe. Once the comparison is held over 10 or 15 year periods, the odds of passive indexes beating their active counterparts reach upwards of 90% in many different sectors.

As time passes, the chance a stock picker will beat index funds, decreases. With time, more chance is removed from the equation.

The risk-adjusted scorecard also accounts for, well, risk—it’s a common thought that though passive indexes may beat active managers, they often won’t do so during downturns. The rationale is that active managers will move funds into safer assets during a downtown, protecting the principal. Passive index funds will continue to match their index along with underlying businesses, right into bankruptcy.

The scorecard develops a clear methodology for how they ascertain risk-adjustment, but ultimately the result is:

Actively managed domestic and international equity funds across almost all categories did not outperform the benchmarks on a risk-adjusted basis

Risk-Adjusted SPIVA® Scorecard

It’s important to note that this is even when the scorecard works from a gross-of-fee basis. This means that even where the analysis ignores the fees active managers charge they still lose to passive index funds. This is even where the comparison is risk-adjusted which active managers are supposed to be better!

My Most Expensive Mistake

I dumped hours into learning how to evaluate company balance sheets, researching different industries, understanding commodity trades, and so much more during 2007-2008. Hundreds of hours that could have gone to improve my career skills, or hell, just having fun in my twenties!

I could have been working to build the life I wanted to save for.

I sold stock into the bottom of one of the worst bear markets in the last century, taking a realized loss larger than my earnings for that year. The experience delayed my return to the market for over a year, causing me to lose out on much of the recovery. The opportunity cost mixed with the realized losses easily beats out my terrible experience with lifestyle inflation.

Had I simply kept the money in the market in an index fund, I could have been in a stronger financial position today and avoided the time sunk learning detailed investment theory.

Early retirement and freedom could have come even sooner.

That’s one expensive lesson.

What do you think about investing in index funds vs stocks?
What about passive versus active funds?
What’ve you learned from my mistakes?

Let us know in the comments!

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By Chris

Chris began his financial independence pursuit in 2007 as he learned basic personal finance from Get Rich Slowly as an aspiring web designer and novice investor. After several missteps, he learned the secrets of financial independence and began his pursuit of freedom.

He reached financial independence in 2018 with $1.2M and two businesses. He began the process of transitioning to early retirement in 2020.

Learn more: Meet Chris.

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3 months ago

OMG, I cringed while reading your story about pulling out during the 08-09 recession. Ah, but – hey – it sounds like you learned your (costly) lesson. And I couldn’t agree more with all of this!

When I saw those responses to my tweet (thanks for including me, by the way!) I was shocked at how many people preferred to own and invest in individual stocks! Then again, this is the Twitter world we’re talking about.

If someone was truly curious about how the stock market functions on a more intimate level and wants to get their hands dirty, then I can empathize with the desire to spend, let’s say, $5K for stock market ‘play’ money where you pick a few individual stocks and try to learn/understand it. But I couldn’t see wanting to do more. Not only is it financially not in your best interest, but you will lose so much time trying to understand the individual company and when to sell/buy.

Like you said, just buy and hold in a broad based index fund like VTSAX (my personal favorite too!) and you will not only do just fine, you’ll fare far better than those actively playing the game. The only hard part will be stomaching the drops. When that happens just don’t look at your investments! 🙂 Of course, easier said than done.

Great post – really engaging writing. Loved this!

Backpack Finance
3 months ago

Excellent. In the beginning I was invested in a few weird active funds which had ridiculous fees. I even remember how clueless I was sitting with the bank’s advisor. I cringe when I think about it now.

You know, this quote for me is the key to successfully “surviving” the volatility of the equity markets.

“If VTSAX goes to zero, we’re all probably screwed anyway. That’d mean capitalism in the U.S. has truly collapsed.”

I always tell myself that if everything goes to 0 then I’ll have bigger things to worry about.

2 months ago

Just recently found your blog – writing some great stuff. Reminds me of the early MMM days. Excited to keep reading.

freddy smidlap
2 months ago

funny thing here is that even though we’re older than y’all we started really investing around 05 or 06 but did not sell at the bottom and kept buying. that was a big help in getting where we are today. i used to own some bad individual stocks like mining companies, oil drillers, etc. i got better at investing and we now own around 35 individual stocks that make up 57% of our non-housing assets. last year we were up 58% and this year it’s 54% to date compared to -3 for the vtsax. i don’t know how long it will last but we are not traders but buy and hold strong growth companies. i write about it monthly in the malevolent missy investment series and put out all our own holdings once a month. all that being said most people should index but consider a little qqq.

all things being equal we don’t care what the rest of the world does as it’s their hard earned money. those when the pie was smaller was the equivalent of an MBA from the school of life. salud.