Finances,  Investing

The Unlucky Long Term Investor Still Makes Money

It’s sometimes hard to be a long term investor. The stock market moves up slowly but can drop quickly.

The pain of loss has more impact than the elation of gain.

Right now, we’re in a spot where a long term investor has had a great run. Those who entered the market after the crash of 2008 have seen great returns without any huge pauses.

That’s why days when the market drops a few % feel so foreign and scary.

However, the long term investor must be aware that things can and likely will get worse. It might not happen this week or this year but eventually, this bull run will come to an end. The sting of loss will be felt at some point.

However, the long term investor, should also know that might not be so bad in the long run.

It takes a strong stomach to sit through those times and stay invested. However, that’s the best way to make money in this market.

The worst enemy to long term returns is selling at the wrong time. Many people think that buying at the wrong time is the problem. However, that’s rarely the case.

The Case for Being a Long Term Investor

Let’s imagine an unlucky investor. She had some money to invest and saw that the market in 2007 was rising.

Ms. Unlucky heard all about the great returns from the market and wanted to set herself up for a good future. She didn’t have a lot of knowledge about the market. However, a colleague told her that an S&P 500 index fund would give her stock market exposure and she could set it and forget it.

She even spoke to Mr. Risk Averse who said the stock market was a fool’s game and that everything was going to crash. He had been mostly out of the market for years. Yes, he’d missed all the gains but he’d catch up when it crashed. He wasn’t about to get in now. He still held a few stocks but nothing big. It was too risky and overpriced!

He recommended putting her money under a mattress. Perhaps a bond fund if she wanted to get crazy. In either case, the market was at an all time high, it was not the time to buy!

After these discussions, she read some books and learned about the risks involved with stocks. Ms. Unlucky decided she was comfortable with those risk and put a part of her money she didn’t need for the next decade in the market. She was young, had a long term horizon and had some cash on the side in bonds and savings accounts already.

It was time to dive into the world of stocks.

Ms. Unlucky took $100,000 and put it in the market on October 9th, 2007.

You know what happened next. October 9th, 2007 was the day the stock market peaked. That began a long term decline that didn’t end until March 9th, 2009.

The graph below shows what happened to Ms. Unlucky and her investment of $100,000. The green is her investment and the blue is a simple bond fund.

stock market crash

Including all dividends, the peak to bottom drop was 55.2% meaning Mrs. Unlucky’s $100,000 quickly became $45,000.

Mr. Risk Averse was the first to point out how smart he was. “I told you so,” he said as his bond fund grew a little bit and he sold off all his remaining stocks at a big loss vowing to never get back in.

Ms. Unlucky shrugged. It took an iron stomach to deal with the big drop. However, she knew what she was getting into when she invested. This was money she didn’t need and after reading all those books, she knew this was a possibility.

It sure was bad timing to get in at what seemed like the top but this had happened many times before. And after all, the stock market has a long term trend and that trend is up.

“This time is different, things are still overpriced” said Mr. Risk Averse. He was even more confident about his decision to never invest in stocks.

In a way, Mr. Risk Averse had been right in the short term. The stock market did move south but this wasn’t a short term game, it was a long term decision.

There might have been an inkling of doubt in Ms. Unlucky but she pushed it down and carried on. When she made the decision to invest, she had at least a 10 year timeline and what had changed? Nothing, in fact, stock prices were lower now. She vowed to carry on and her 401k contributions continued to go in the market. She even started a new Roth IRA account with some extra money she had.

The fact that her initial $100,000 had shrunk didn’t change much in her life.

She was lucky enough to keep her job and kept moving on. She didn’t pay much attention to financial news and concentrated on her hobbies instead.

March 9th, 2009 passed. Things looked bleak. Worst of all, people said it was going to get worse. Ms. Unlucky just decided to stop paying attention to the financial news. The talking heads there just screamed and yelled. It wasn’t all that interesting to her because who cared what happened to the stock market in the short term.

Even though no one knew it at the time, that day was the bottom.

Ms. Unlucky concentrated on her job, her life, she met a great guy and worked on herself as a person.

The days passed and Ms. Unlucky was happy enough to ignore the financial news until she spotted a news article in the paper. The Dow had “crashed” 800 points, a whole 3% and everyone was panicking again.

She thought back to those days 10 years ago and wondered how that $100,000 she had invested was doing. You know that same, $100,000 that she invested at the market top that fell to $45,000 just a year later?

Well, it was doing pretty well.

Long Term Investor

She now had more than $250,000 in that account. That’s without adding any additional dollars beyond her initial $100,000 contribution.

Despite dropping 55% from peak to bottom, that account had still yielded an annual return of 8.0%.

The S&P 500 was now above $3000. That was a big jump over that the 1565 she bought at during the “peak” in 2007.

She smiled; much time had passed since then. Her name had changed too after marriage.

The $250,000 wasn’t all the money she had but it was a good reminder of where it started. There was a 401k too and a Roth IRA she started years ago. Contributions had been flowing into those accounts during the drop in 2008 and the subsequent rise after 2009. She was older now and her risk appetite had changed. She added more bonds to her allocation. After all, the stock market can sometimes take longer to recover than it did in 2008 and she might need the money sooner now. However, she knew that if the stock market dropped, she’d be OK.

Even recently in December of 2018, there was a small fall. However, just like the other time, the market recovered and she didn’t panic.

She told this to Mr. Risk Averse whose bond account trailed hers quite a bit despite her buying when things were “overpriced” at the very peak in 2007.

He could never get back into stocks after 2008. He always thought they were bound to crash. After all, they were always at all-time highs!

“Maybe it’s time to get back in,” he said to her. She smiled and walked away to go have dinner with her husband and new namesake, Mr. Lucky.

Sometimes, you don’t have to have good timing. Even unlucky investors who buy at the top can get pretty lucky and have good returns. All it takes is patience and a long term mindset.

market timing


  • Financial Pilgrimage

    It’s all about the long game! I feel terrible for everyone who pulled their money out of the market in 2008-09. Such a rough ride down but the ride back up has been awesome. I hope people hear this message so they are encouraged to hold strong during the next downturn!

  • Stephen

    I started my career in 2006 and began investing at the same time. I was able to continue investing through the great bull run and have done really well. Would I feel the same if I had started my career in the year 2000? I’m not sure. How about those that start investing in 2018? They may not do as well, but in any of these situations, like you mention, it’s time in the market that’s the big factor.

    Thanks for the article!

  • Simple Money Man

    The key I see here is to NOT pay attention. It’s easier said than done. And in her contributing account, she could cope by knowing that she is at least buying at low prices when the market is dropping.

    • TimeintheMarket

      That’s definitely a big part of being a winning investor – ignore the downturn and keep chugging along. If your timeline is long enough then it’s hard to lose. If your timeline is short then you probably shouldn’t be fully in the market with that money.

  • That Charles Life

    Lovely story, and very needed at the moment with the volatility we are experiencing. I personally can only hope we are on the verge of another 2008 so I can take advantage of the buying opportunity you did 10 years ago!

    All the best,
    Colby from That Charles Life

  • The long term investor

    Hi TITM,

    Great story, I do more or less the same. I buy stocks and don’t look back. I only monitor their results to see if the company is still doing well. And as long that they do well and send some (growing) dividend my way I couldn’t care less about the stock price.


  • Dividend Diplomats

    Time –

    Always love a good “story” and to show that the financial noise can really play a big part – either from news or from someone who has no idea. Great perspective, especially at a time where we are currently in.


  • juststartinvesting

    Great example shown here. Would be interesting to map out every 40 year time period since 1950 and see is there any scenario where bonds beat the S&P500?

    I’m thinking out loud here, but I would be surprised if there were very many (if any)!

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