My worst investing mistakes, EVER

investing mistakes

The following is a post about real investing mistakes I’ve made. It is my own opinions on investing. You are responsible for your own investment and financial decisions. This post is not investment advice or a recommendation to purchase any particular security. This post may contain affiliate links. You can read my disclosure/about page for more information.


Since I’ve been out of my twenties, I’ve been noticing myself reflecting a lot more about my past.

What’s strange is that your past doesn’t seem that far off while you’re in your twenties. But the moment you crossover into your thirties, it starts to hit you that your past happened decades ago.

Summer tends to make me think about having time off to enjoy the weather with friends. After that moment passes and reality sets in, though, it’s alarmingly apparent how much has changed.

On the other hand, the same type of reflection occurs with investing once you build up enough experience. Now that I’ve built up experience with investing over the past 6 years, I’ve been able to develop the proper investment strategy to fit my goals.

Though, I haven’t experienced a catastrophic market correction on the level of 2008 or 1929, if a market correction did occur, my intention would be to buy as much high quality dividend paying stocks as I could afford.

Market corrections are often how Intelligent Investors are able to create enormous wealth.

However, even the best investors of all time don’t hit 10 for 10 on their selections.

Though I’ve made many mistakes with investing, I’ve actually done quite well with my individual investment selections overall.

With the exception of my positions in Walmart and IBM, I’ve made money on pretty much every single long term equity I’ve ever purchased.

But, I’ve also made a few investment mistakes that literally cost me thousands of dollars.

Here are the 5 biggest investment mistakes that come to mind:

My 5 worst investing mistakes, EVER #SMH #investing #blogging Click To Tweet

Selling Corning (GLW)

Corning Incorporated is engaged in manufacturing glass and ceramics. More specifically, it produces display technologies for electronics.

I originally purchased approximately $2,000 worth of GLW shares in 2011 at $13.80 per share.

The reason for my purchase was based on the company profiting longterm off their cellphone display segment.

In addition, I made the purchase based 100% on the rules recommended by Ben Graham in The Intelligent Investor. I thought the company was grossly undervalued. In fact, I found it through a stock screener while searching for undervalued equities.

With that said, I ended up selling the stock at a loss (between $11 to $12 per share) in early 2012. I sold it because I didn’t think I knew enough about the business and because it was a lower dividend (around 2%).

Nowadays, Corning Incorporated is trading at $27.88 per share #SMH! My evaluation was completely right, and the company has doubled its value while paying dividends along the way #SMH! 🤦‍♂️

Trading before the Crude oil inventory report was released

For the readers that don’t know, I took a year off to have more time, to day-trade and blog.

During my day-trading stint from March 2016 to July 2016, I had a few successful trades and even went on a few impressive winning streaks.

But I also made some major mistakes. Fortunately, none of them were life altering because I used stop limits and proportionate amounts of money to trade with.

But I also saw good chunks of money disappear in seconds.

The worst time this ever occurred was on Wednesday April 27, 2016. As I wrote in my post covering it

On Wednesday, I got smoked out of the market with my worst trade to date.”

You can read the entire post, Trade Notes: Results After 55 & Revisions for May, by clicking here. However, the numbers for the trade are included below.

Since I made a similar, successful trade the prior Wednesday, my plan for the trading day was to attempt to predict the direction of crude before the inventory report was released.

My trading plan for that day was to wake up early, read all the early crude oil reports, analyze volume and U.S. dollar, and pick a direction before the inventory report was released.

Here’s how the trade went down:

I bought 200 shares of UWTI at $29.98 for $6,006.03 in anticipation that the inventory report would push oil higher for the day.

I was wrong and the price of oil dropped sharply. In fact, it dropped through my stop limit so fast it didn’t sell. Based on my strategy at the time, I got out immediately at the best available price. I sold 200 shares of UWTI at $28.06 giving me a final amount of $5,612.02. I lost $394.01 in matter of minutes SMH! 🤦‍♂️

Selling Apple shares, EVER

Since I worked in retail selling iPhones at the time, I originally purchased AAPL shares in 2011 around $375 per share, pre-split.

The stock continued to rise up to $700 before coming back down for a while. I sold some shares at around $680 for a very nice return.

Again before the split, the shares bounced around from approximately $418 to $460 for a while. I bought a couple times at $420 and $428—I later sold them around $456 and $460 for decent profits again.

Since then, the shares rose to nearly $800 as talk of the company becoming the first trillion dollar market capped company surrounded them. Furthermore, the company announced a dividend payment and 7 for 1 stock split.

If I remember correctly, the price of the stock was just under $100 post-split, now it’s on the rise again—it’s priced at $157.50 as of last Friday, post-split.

To be honest, I’ve even made the same mistake post-split! With the cash AAPL has on their balance sheet, dividend policy, brand name and how good they’ve been to shareholders—I will never sell an AAPL share again SMH! 🤦‍♂️

Holding off or not investing into an employer share program

I worked for two big Canadian companies prior to the company I work at now. I’m not going to mention them by name, but they’re both publicly listed equities that offer stock sharing plans.

I spent nearly 2 years employed by one of them and didn’t participate in their share plan at all.

Furthermore, I spent nearly 4 years at the second company but didn’t start participating in their stock sharing plan until my last year there.

By not participating, not only did I end up missing out on investing thousands of dollars into a quality dividend stock, I didn’t even get to keep their matching contributions when I resigned SMH! The shares have to be vested in order to be released—company matched shares are usually locked in for a certain number of years to encourage employees to stay with the company.

Nevertheless, not enrolling into employer share plans can cause you to miss out on thousands of dollars #SMH! 🤦‍♂️

Selling Shoppers Drug Mart (SC) before Loblaws purchased them

Again, I completed a Ben Graham style analysis and Shoppers Drug Mart kept back in early 2013.

Over and over, it kept coming up as a great value stock to buy.

I bought it around the start of 2013 close to the time that Drakes “Started from the bottom” came out. The music video for Drakes song was shot in a Shoppers Drug Mart—everything seemed to fit.

I liked the store as a customer, and I anticipated that the business would grow with the aging baby boomer demographic in need of pharmacy products and services.

With that said, I purchased roughly $2,500 worth at around $41 per share (not exact numbers). After becoming worried that larger competitors like Walmart and Amazon would eat into their business, I sold around the middle of 2013.

Though I sold for roughly $44 per share, which earned me a small profit, an announcement was made within a short period of time stating: Lobalws was acquiring Shoppers Drug Mart for 12.4 billion SMH!

The following is a quote from the above linked article:

“Shoppers shareholders will be able to choose either $61.54 in cash or 1.29417 Loblaw shares, plus one cent in cash for each Shoppers Drug Mart share held, on a pro rationed basis.”

$61.54 per share!—SMH! 🤦‍♂️


investing mistakes

Conclusion | Errors of omission

Though I’m probably missing a few other investing mistakes, those are the biggest ones that come to mind.

Besides what’s mentioned above, I can only think about the errors of omission I’ve made.

Frankly, I go on to name a lot of stocks that I should’ve bought. Stocks that I should’ve trusted my analysis on and taken on the risk on. However, for whatever reason, I either purchased another equity or missed the opportunity.

In conclusion, mistakes, slippages and failures help you become better equipped to deal with the future the next time a difficult time comes around.

Once you learn how to listen to your intuition, it becomes much easier to tell the difference between something that is good and something that is not.

Questions for the readers: Have you made any big investment mistakes? Were you able to learn from your mistakes?

18 Comment

  1. It is funny to look back on the mistakes we made, especially within the early days of trading. Wither it be chasing yields or IPOs for the next big thing. I got burned a few times on IPOs myself. Picked up a few shares of Fitbit as soon as they went public. It rose like 30% in the opening day/ week. Then proceeded to fall. Never rebounded and kept falling more and more. I did get out for a loss eventually. But today, they are selling at around $5 a share when they started in the $20s. Sad.
    Dividend Daze recently posted…Recent Buy – LTC Properties (LTC)My Profile

    1. Graham says: Reply

      Hey Dividend Daze,
      Thanks for sharing your IPO mistake. I nearly made similar mistake with Facebook, Twitter and Snapchat more recently. I didn’t end up buying any of them though.

      Facebook’s IPO was priced around $40 and I almost placed an order but decided against it. Though it dropped quickly to about half its value, it has since made a very big comeback and is one of the most successful stocks over the past few years – I guess buying and holding the FB wouldn’t have been a bad move.

      In regards to your experience with Fitbit – that’s surprising that the shares never made a comeback. Perhaps it was because of competitors like Apple Watch.

      With that said, I think the only thing we can do is learn from our investing mistakes. Through making mistakes, I’ve been better able to understand what type of investor I am and the type of risk I’m willing to take. I learned that trading makes me uncomfortable, even after winning trades. All my mistakes led me straight to dividend investing. Thanks for reading and commenting. Have a great day! 🙂

  2. Hi Graham
    Thank you for sharing your investment experiences. I think I made several mistakes from your list as well (or at least some quite similar ones). But as you write, these experiences served you well, you became a dividend growth investor with a long term view. Time and the compound effect are your powerful allies now.
    Looking back, I wish I had started investing much earlier and focused on rock-solid businesses such as Johnson & Johnson, P&G, Coca Cola, Pepsi etc.
    But anyway, I am very happy with my portfolio I have been building since 2009 and just love watching the dividends growing each year.
    Take care!
    Cheers

    1. Graham says: Reply

      Hi Financial Shaper,
      Thanks for reading and commenting! My past investing mistakes have definitely helped me form a longer term, more goal orientated view. Time and compound interest are certainly my most powerful allies now – every dollar I put away is working for me.

      I wish I started investing in high quality dividend stocks like the names you mentioned earlier too. It would’ve been great to know about the concept of dividend investing while in College or even high school. If I had known, I would’ve started immediately at 18.

      On the other hand, like you mentioned, it’s fun to watch your dividends grow. It’s a fun process to put a dividend income portfolio together. Glad to hear that you’re happy with the progress of your portfolio. I’m looking forward to future updates! Take care!

  3. Thanks for sharing! Since I’ve just started I’ve most likely made a few mistakes. For now it only seems to be resulting in total capital value loss and not dividend cuts or something.

  4. Graham says: Reply

    Hi Mr. Robot,
    Thanks for reading and commenting! I hope you were able to find some value through learning about my investment mistakes. As long as you’re able to stay consistent with your investing strategy and learn from your own mistakes, I think you’ll end up in a better position than most. I haven’t experienced a dividend cut either. Thanks again. Hope you’re having a great week! 🙂

  5. I have plenty of investing mistakes myself. Isn’t it just the tuition that learning the market costs? Good thing the costs were low for me. Just a few thousand dollars.

    Making mistakes is the best way to learn. Agree or no? 😀
    MrDoublingDollars recently posted…Guest Post: How to Live Like You’re Rich for Pennies on the DollarMy Profile

    1. Graham says: Reply

      Hey Mr Doubling Dollars,
      I agree 100% that making mistakes is the best way to learn! In fact, it’s the only way I learn. I really never fully understand something unless I trial and error my way through it. I also view mistakes as a tuition to the market – as long as you don’t repeatedly make the same mistakes. Fortunately, the majority of my mistakes have been opportunity costs. I’m glad to hear that your investment mistakes were not overly costly either. Thanks for commenting! Have a great week!

  6. Mr ATM says: Reply

    Thanks for sharing. One can learn so much from their mistakes, especially in investments. I keep a log book of all my investment mistakes and review them quite often.
    Mr ATM recently posted…A Lesson From History: Market Does Not Go Down In A Straight LineMy Profile

    1. Graham says: Reply

      👋🏻 Hi Mr. ATM.
      Thanks for commenting! I think learning from mistakes is the best way to learn. It is for myself at least. I keep a log of all my trades and investments too. I use excel to track any portfolio changes and review transactions. Not only is it good for learning from your mistakes, it’s a great way to find ideas for posts too. Thanks again🙏🏻 Have a great weekend!🌞

  7. Ah yes, investing mistakes. We all have them. No use kidding ourselves. I’ve learned so much since I have started investing. I’m glad my mistakes weren’t too terribly costly. Although I suppose you could consider not investing in Apple or Facebook 5 years ago costly! It’s just like life, we learn as we go and get wiser with time. Thanks for sharing my man!

  8. Graham says: Reply

    Hi Mr. Defined Sight,
    Appreciate the comment! It’s true that investing mistakes are inevitable. But like you said, it’s just life and at least it provides a learning opportunity. I’m glad that I haven’t made overly costly investment mistakes either. The missed opportunity costs do hurt though! I nearly bought FB during the week after its IPO. However, to be honest, I’m glad I didn’t because I probably would have sold too early. Since I’m not personally a fan of FB, I more than likely would’ve become uncomfortable holding it. I think it’s best to stick to what you know. If you don’t know an industry or sector, index funds are the way to go. Thanks again for commenting! I hope you’re having a great weekend! 🙂

  9. DivHut says: Reply

    Everyone has those “doh!” moments when we realize an investing mistake we made. It’s interesting to read that most of your mistakes was actually selling a stock well before its time or ever. As a long term dividend growth investor I really loath selling even if a stock is over valued, etc. Often, over the long haul, we regret our selling decisions as quality assets tend to gain value over time. Thanks for sharing!
    DivHut recently posted…September 2017 Stock ConsiderationsMy Profile

    1. Thanks for taking the time to comment, Keith! Much appreciated. I came to the same conclusion about most of the mistakes being about selling. There’s even more selling mistakes that I didn’t mention in this post. I really loathe selling quality assets too! I sold a few other U.S. equities that I strongly regret selling now with the exchange rate making it so difficult to acquire quality positions. Thanks again for stopping by! 🙂

  10. Thanks for sharing your experience! When I started investment, I made mistakes and lost my money, because that time I had no experience. I learned a lot from that and now working only for results with planning and strategy. If you publish more information about investment tips, tricks etc, that will more helpful.

    1. Hey 👋🏻,
      Thanks for taking the time to read and comment! I think the best way to learn is by failing and making mistakes. It’s good that you were able to learn from the money you lost. Fortunately, I’ve never really lost that much money because I was lucky to read a few good books prior to putting money in the markets. I take things I read very literally, so I guess the principles from the books stuck with me.
      Also, thanks for your request to include more Investing posts. I’ve got a few saving/investment post in the works. Take care! 🌞

  11. Thanks for sharing! I especially agree about the Apple stock, I just recently arrived at the same conclusion after learning some lessons myself 😉 I think my biggest mistake is not getting into investing sooner and especially not getting into investing in solid, dividend paying companies like Coca-Cola sooner. I try not to think of how much money I could have now if I started investing even a couple years earlier than when I actually did!! But you live and you learn!

    1. Hi Millennial Spirit,

      Thanks for taking the time to read and comment! It’s too bad that we both didn’t hold onto Apple shares. I’m afraid it’s becoming a once in a lifetime dividend stock opportunity now. I agree about getting into dividend investing sooner in life. That’s a noteworthy mistake that I should’ve mentioned! I can only dream about where I’d be if I saved and dividend invested even 10% of my income from 18 on… I understand the pain lol But like you said, it’s the way you learn. Have a great week!

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