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We all live with a certain level of regret. I know I do.

Mullets, Vanilla Ice, cheering for Lance Armstrong. We’ve all got our dirty little secrets of regret.

And when it comes to how I’ve handled my money, the list is long. Whether it’s investing in Iraqi Dinar, or buying cruises over the phone, I’ve heard myself say more than once, “If I knew then, what I know now, things would be different.”

It’s a common sentiment that almost everyone has felt, like those people who bought Bitcoin at $19,000 and thought it was headed to $100,000 and beyond.

If you’re anything like me, though, after taking the requisite time to beat myself up over my stupidity, I like to look at my mistakes and try to learn from them so that history doesn’t repeat itself at my expense.

This is one of those posts.


If you are looking for a way to learn how to get started investing your hard earned money, even as little as $100, this post could change your life.


Back to the Future

16 year old me wasn’t smart.

Sure, maybe for a 16 year old, there were kids who were dumber, but I wasn’t exactly the brightest bulb on the tree.


If you are looking for a way to learn how to get started investing your hard earned money, even as little as $100, this post could change your life.


When it came to money, I worked for it, spent it and saved what was leftover. And I had NO IDEA how to invest.

Not exactly a winning recipe for your finances.

But what if I knew then what I know now? What if I’d known how to invest? Would things have been different?

I decided to actually figure out if I knew at 16, what I know now about money, how much of a difference would it make to my finances?

How To Invest Like a Genius Teenager

In order for this back to the future voyage to happen in my imaginary Delorean, I need to make some assumptions:

When I was getting paid by the hour, I used the best estimates of my income based on my hourly wages. Once I started making a more regular wage or was salaried, I used my tax returns.

I assumed that when I learned how to invest, I started putting away 15% of my pre-tax income when I first started working. For the purposes of the calculations, I assumed I invested the 15% at the end of the year.

I used the actual S&P 500 annual returns for the past 21 years. Simple this is all about being stupid simple, 16 year old me would only be investing in index funds, in this case, one that tracked the S&P 500.

Using these numbers, I’d see, REALLY SEE, how much of a difference learning how to invest early on would’ve made.

Why would I want to do this?

Now some people may think this could be a pretty depressing experiment, a fruitless exercise in revisionist history.

Why would I want to put a number on how much my ignorance had cost me?

Well, there are a couple of reasons.

1. Those who ignore history, repeat it – Even though I’m not 16, and never will be again, I have two kids. I want them to know what I didn’t. I can’t guarantee that they’ll follow this advice, but that won’t be because they’re ignorant. Hopefully seeing the actual numbers will persuade them to be less dumb than their old man.

2. Studying past ignorance brings future wisdom – Think about the wisest person you know. Almost always, such people have gone through incredibly difficult experiences. But everyone goes through these circumstances, you say. Yes, but they don’t intentionally study them. Wisdom comes when people take the time and energy to reflect and dig through their experiences to pull out the valuable nuggets of knowledge that are life-changing. I’m hoping this will be a wisdom enhancing experience.


If you are looking for a way to learn how to get started investing your hard earned money, even as little as $100, this post could change your life.


3. This isn’t just for me – The process of self-reflection is hard. It’s time consuming, uncomfortable, and a pain. Because of this, most people don’t do it. So let me do it for you. I’ve taken the time to think about how my finances would be different if I’d started investing at 16. Using the self-reflection I’ve done, take the time to think about how your life might be different if you’d known then what you know now. Build wisdom. Change your life. And equally as important, use your newfound wisdom to change the lives of others.

The Results

You’ve hopped into your time machine and set the date for 1997. Steve Jobs has just returned to run Apple. Titanic is the most popular movie and Celine Dion is promising that our hearts will go on. The Backstreet Boys are begging everyone to Quit Playing Games with their hearts and Brett Favre and the Green Bay Packers are headed to Disney World as the Super Bowl champions. Oh, and Mike Tyson still has pieces of Evander Holyfield’s ear stuck in his teeth.

Be sure to keep a close eye on your mood ring as the next 21 years are going to be a roller coaster. (See the chart below to know how you’re feeling).


If you are looking for a way to learn how to get started investing your hard earned money, even as little as $100, this post could change your life.


Note, the stock market return in 1997 is N/A because the assumption is I didn’t invest the money until the end of the year.

S&P 500 Returns with dividends reinvested (invested at year end)

Year                      Stock Market


Income                         $ added

(15% total income)           

Value before

$ added           

Total Value at

end of the year                     

What’s My Mood


1997 N/A 6120 918 0 918 N/A
1998 28.6 2832 425 1,181 1,605 Violet
1999 21.0 2832 425 1,942 2,367 Violet
2000 -9.1 1800 270 2152 2422 Amber
2001 -11.9 12,000 1,800 2,134 3,934 Amber
2002 -22.1 1920 288 3065 3353 Black
2003 28.7 3840 576 4315 4891 Violet
2004 10.9 10,880 1632 5424 7056 Blue
2005 4.9 21,000 3150 7402 10,552 Green
2006 15.8 40,000 6000 12,219 18,219 Blue
2007 5.5 52,000 7800 19,221 27,021 Green
2008 -37.0 58,500 8775 17,023 25,798 Black
2009 26.5 65,000 9750 32,634 42,384 Violet
2010 15.1 75,000 11,250 48,784 60,034 Blue
2011 2.1 81,000 12,150 61,295 73,445 Green
2012 16.0 89,000 13,350 85,196 98,546 Blue
2013 32.4 107,000 16,050 130,475 146,524 Violet
2014 13.7 111,000 16,650 166,598 183,248 Blue
2015 1.4 115,000 17,250 185,813 203,063 Green
2016 11.9 120,000 18,000 227,228 245,228 Blue
2017 21.8 120,000 18,000 298,687 316,687 Violet


When I graduated, I would’ve had $7056 socked away. If I’d let that ride in the stock market, it would be worth $20,439 today.

If I’d invested that $20,439 for the next 18 years until I’m 55 (my planned retirement date), at a 7% rate of return, it would be worth $71,793.

Not too bad for a kid just learning how to invest and graduating from university.

So the difference between investing at 16 and investing when I graduated is almost $72,000!!

That’s A LOT of MONEY!!!

In this case, beginning to invest at 16 is a $72,000 decision.

In total, 16 year old me invested $6334 to gain $72,000.

Now earlier I said that 16 year old me was…intellectually challenged (I blame it on a lack of a fully developed prefrontal cortex).  

But they aren’t many 16 year olds I know (actually none) who would turn down a trade of $6334 for $72,000.


If you are looking for a way to learn how to get started investing your hard earned money, even as little as $100, this post could change your life.


It’s a big bang for a small buck, especially when I consider how much money I wasted on stupid purchases.

I really wouldn’t have missed 15% of my income. It wouldn’t have been a big deal, especially when thinking about the potential payoff.

Bringing It All Together

While it’s healthy to reflect on our past experiences, a person can fall into the trap of trying to navigate through life while simultaneously staring at the rear-view mirror and the front windshield.

It doesn’t work well.

This isn’t an exercise in regret for me. I don’t live staring at the rearview mirror.

Like any good driver, you take periodic glances in the mirror at what’s behind you, but the lion’s share of your attention is focused ahead.

Which is what I’m doing.

This glance behind me has reemphasized just how important it is to teach my kids how to invest at a young age and the power of compounding coupled with time.

How else can you turn $9 an hour into $72,000?

You can’t.

It’s a lesson that I’m going to be introducing to my kids very early, in the hopes that they’ll be a bit smarter (but not too much smarter) than their old man.


How old were you when you started investing? When are you planning to start with your kids? Add to the conversation in the comments below or on Twitter @method_money or my Facebook page Method To Your Money.  You can also find me on Pinterest.  Want more great ideas for mastering your money? Sign up to receive my weekly emails detailing how to keep more of your hard earned cash!

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  1. Simple isn’t easy. Especially for smart and well-educated people. We tend to think we can outperform “the average” with just a little thought, research, and effort.
    Readers, learn from those who futilely tried to outperform and failed. Invest in low-cost passive index funds. A teenager can do it. But can an intelligent adult?

    1. Couldn’t agree more Wealthy Doc. We think we’re smarter than we really are and that gets us into all sorts of trouble. The first and most important step in investing wisely is understanding your limitations. Then, and only then, can you take what the market gives you without being greedy. Those who are greedy for too long always end up being humbled.

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