Knowing When To Sell Your Investments

Hi folks!  Unfortunately I’ve come down with a “summer cold” the last week and I don’t have the energy in me for a new post while I’m sick.  Sorry!  I’m doing my best to get well, but it’s taking time.

Instead, I’ve decided to clean-up and refresh one of my favorite older posts that covers a timeless investing topic — Selling.

Selling, is a topic many investors struggle with.  While there are countless internet articles on “when and how” to buy, there are comparatively few articles that intelligently cover the topic of selling your investments.

Why?  Perhaps it’s because knowing when to sell is often very similar to “market timing”.

But my view is a little different — It’s not about market timing.  Investing is actually a lot like rafting a river…


Rafting The River

Imagine for a moment you’re rafting down a scenic river.   This uncharted river has tons of twists, turns, rocks, waterfalls, and bends along its course.  We know eventually if we travel far enough, the river will reach its destination —  the ocean.  Sometimes the water moves slowly and sometimes it moves quickly, depending upon the terrain.

As we’re rafting down this river we have two choices:  We can either follow the river’s course through the twists and turns, or we get out and carry the raft to avoid hazards.

Now the most sensible thing to do is to hop-out of the raft when the river gets rough.  Unfortunately that’s not easy to predict.  With all the twists and turns in the river (and dense foliage) we can’t really see the rough spots coming until we’re right on top of them, with no time to get out safely.

If we get out of the river too early, we end up having to carry the boat and lose time on the way to our destination.

If we stay on the raft we have to ride through the waterfalls, the rocks and all the other hazards.  It’s possible the boat could be damaged or we could suffer injuries going through these hazards.  But sometimes the water is fastest near the hazards, and we make the most progress while passing through them.

Fortunately, there’s no rule that says we have to stay in the same boat all the way down the river.  We can hang out on the party boat when times are good.  Or, we can hop into the raft with the professional rafters….those with the most experience and best ability to survive the hazards that lay ahead.

If you haven’t guessed it yet, this rafting story is a metaphor about investing.  The destination is financial independence, and the river itself is the investment markets we traverse.  The rafts are the index funds, stocks, bonds, and businesses we choose to invest in.  Getting into or out of a raft equates to the buying or selling of an investment.


Timing Is Hard

As with any financial transaction, there are always two sides to the equation — The buying AND the selling.  The “getting in” or “getting out” of the raft, to use our metaphor.

I’ve already written about buying investments pretty extensively, but I haven’t written a post specifically about selling.

And selling is on a lot of people’s minds these days.  Among the personal finance bloggers I follow, selling is a common theme right now.

Some personal finance bloggers like Tawcan and the venerable RetireBy40 are thinking about hording cash.  Some are even outright selling like DividendHustler.

Lots of people worry the market is overvalued right now.  But who knows…instead of heading down, the market could keep rising for 2 more years.  We just never know!

So, how do we know when the river will finally take us over a dangerous waterfall?

Well, many investors try to “read the tea leaves” to divine the course of the market.  Some investors try to look at leading economic indicators like rail traffic, manufacturing activity, or even retail sales.  But those indicators aren’t perfect either…they can also contain a lot of noise that distorts the truth.

Being able to time the market is a very rare gift.  It certainly isn’t among my financial superpowers.  Hardly anyone can do it with any kind of proficiency.  The investors that appear to do it well, aren’t telling their secrets either.

Want my advice?  Don’t bother trying to time the market.  You’ll make yourself crazy trying.  You’re just as likely to miss “the good parts” of the investing river as you are to avoid the hazards.

It’s not timing the market that matters most, it’s time in the market that matters.  I recommend focusing on the ‘why’ to sell instead of the ‘when’.


Long Term Compounders

First off, let’s start the discussion on selling by talking about compounders.

Normally when investing, my favorite kind of stock is called a “long term compounder”.  I try to find them at a fair price.  This is my ideal kind of investment, but they’re very hard to find at good prices.

In our rafting metaphor, the long term compounders are the professionals rafters — The guys with the sturdy boat, the big arms, and serious expressions.  They might go a little slower than the party boat when times are good, but these guys will survive the hazards.

Hazards in investing
Avoiding hazards when the water gets rough is key to making winning long term investments.  Good rafters know how to do this.  Of course, identifying the best rafters is the hard part.

Compounders are businesses that consistently produce more than $1 in value for every $1 invested in the business.  Even better, if these companies can compound value a rate that exceeds the S & P 500, then you’re golden.

If the business can continue to compound value like that, I would probably never sell.  Are they all superb businesses?  Not necessarily, sometimes compounders are actually poor businesses!  But they create incredible value for shareholders.

Berkshire Hathaway would be a prime example of this kind of company.  Before Warren Buffet took over the company, Berkshire Hathaway was a failing textile businesses.  After Buffett took the reins, he redirected capital into better businesses where it would compound at better rates of return.  It ended-up working out extremely well for shareholders.

Imagine how bad you’d be kicking yourself today if you were a early owner of Berkshire Hathaway and then sold for some reason like “the market was expensive”.  Yeah, you’d definitely be kicking yourself for that mistake, wishing you held on.

So, my rule is:  Don’t sell long term compounders if you can help it.  As long as they keep compounding, stick with ’em!


Your Investment Hypothesis No Longer Holds True

Of course, sometimes even long-term compounders stop being compounders.  Like stones in the river, time has a way of wearing away at every company.  Eventually good leaders retire, new products are invented, and industries change.

For better or worse, anyone who’s invested in stocks should be watching for the day when your investment hypothesis ceases to be true.

Take for example, the sale of my Telus shares.  When I first invested in Telus, the valuation was cheap, business was healthy, dividends were growing, and compounding at reasonable rates looked possible.

Unfortunately all that changed over the years.  I suffered through declining cash flows, growing debt levels, and poor returns on capital.  Given the poor state of the business (with little chance of compounding possible), I threw in the towel and sold at $33/share.

The investment was profitable, but it was time to move on.  My original investment hypothesis no longer proved to be accurate, so I sold the business at a fair valuation.

Now, nearly two years later (in mid-2018) those same Telus shares sell at around $35 per share, making my move look fairly prescient.  But I assure you I have no ability to predict the future. I merely saw a business that couldn’t compound easily.

When the rocks, waterfalls, and other hazards finally do appear, we want to be in the rafts that are going to survive with few injuries.  Financial strength should definitely be a category you consider in your investment hypotheses.  Plain and simple.


Undervalued Investments Reach or Exceeds Fair Value

Not all investments are going to be long-term compounders.  Sometimes I purchase investments for valuation reasons alone.  These are your Ben Graham style cigarette-butt investments — Bonds or preferred shares under par value, stocks so undervalued they’re likely to see a higher valuation once the proverbial dust has settled.

Strange rafts
Some rafts may look strange, but they can also hold significant value.  Don’t underestimate the power of the ‘Undervalued’ investment category.

These kinds of investments may be terrible businesses, so the intention isn’t to hold them long term.  But how do we know when to sell a stock in the “Undervalued” category?

Frankly, when it’s no longer undervalued.  If you did your analysis correctly (before you purchased) you’ll already know what a fair valuation is.  Usually there’s historical valuations and industry valuations to compare against with premiums or discounts applied for quality.

To put this in extremely simple terms:  When a can of beans goes on sale, you buy the beans at $0.50 on the dollar.  When the price of beans goes back up to $1, you sell.  You don’t hold onto your mountain of beans hoping they’ll somehow get to $2.   That’s just unrealistic. You sell when they’re fairly valued.


Better Investment Opportunities Exist

One of the best reasons to sell an investment is because there’s an even better investment out there.  An investment with more moats, better management, higher returns on capital, and any other factor you can think of.

It doesn’t mean your old investment was a bad one, it’s just that they are better places for you to allocated capital…and this distinction is key:  Whenever shifting out assets for better assets, start with the assets that have the lowest projected long-term rate of return.   Usually this is going to be cash with a near 0% rate of return.  Next up would be something like U.S. treasuries at 1.5%, and so on.

It’s a simple strategy to maximize returns, but we also have to be cognisant of taxes.  If you hold business for long periods of time like I do, sometimes this means paying big taxes when you shift investments.  It goes without saying, the new investment better be worth paying all those taxes.

If the new investment only has a 1% improvement in the long-term rate of return….well, it’s going to take a LONG time for the new investment to be worth paying the 15-20% you might pay in taxes.


You Need The Money

Last, but not least is the best and final reason why you should sell an investment:  You need the money for something else.

Life isn’t just about piling up the biggest portfolio possible.  There are other things worth spending money on — like experiences, buying a comfortable home, education, or maintaining your health.  Maybe you even want to spend money on frivolous things like nice cars or a boat.  Whatever the case, it’s your life and completely up to you.

But PLEASE don’t be dumb about how you fund your spending.  Just like we did when swapping out investments for even better investments, start by selling investments with the lowest long-term returns, and then working your way up.

In simple terms: Let the winners keep on winning, and only sell the laggards.

More often than not, investors end up doing the opposite of this.  They sell the winners because they’re ‘up’, and hold on to the laggards in the hope of avoiding losses.

I’ve made this mistake myself, and it’s completely wrong headed.  The winners are winning for a reason.

For someone who wants to reach the end of the river, you need to keep the long term compounders.  What should get sold is the investments that run into trouble, or were merely undervalued situations from the start.

A Final Word

I’m going to end this post with a final word of caution to everyone:  Don’t use market movements to determine if you should buy or sell.  In most cases, that’s like looking at random swirls in the water (from our raft) and making big decisions based upon little eddies.  It’s nonsensical.

Instead, look at business returns or metrics like return on capital or other measures of business efficiency.

The market can do a lot of crazy things on any given day.  Don’t let crazy old Mr. Market make your decisions for you.


[Image Credit: Flickr1, Flickr2, Flickr3]

30 thoughts on “Knowing When To Sell Your Investments

  • October 7, 2016 at 4:39 PM

    I’m with you when it comes to timing the market. It’s too difficult to figure out the top and bottom. If I listened to the pundits I would have sold every year since 2011 because the unsustainable gains in the market.

    I have a friend that hasn’t put in any new money in the market since 2009 because he’s still waiting for a “pull back.” In the meantime I’ve watched my portfolio increase by more than 150%.

  • October 7, 2016 at 6:18 PM

    The rapids in the river is a great investing analogy. I hope to keep on the river as long as possible as the ocean is more an analogy of leaving the world. I plan to keep a portfolio going until the end of my life.


  • October 7, 2016 at 6:24 PM

    Great article Mr. Tako! Given that selling your investment is appropriate when it’s reached or exceeded its fair value, calculating this value is crucial. Describing how you come up with the fair value is probably a post in itself, but how do you go about it?

  • October 8, 2016 at 3:10 AM

    I love the analogy, very fitting! I’m definitely a long term investor and always have been. I may endure another crash like 2008 but even then the market showed resilience by bouncing back quickly in the years to follow.

    • October 10, 2016 at 9:14 AM

      Thanks Green Swan! Haven’t seen you around these parts in awhile! Welcome back!

  • October 8, 2016 at 7:26 AM

    Channeling your inner Benjamin Graham I see. Ultimately studies show that the biggest determinant of your returns is not your investment choices but rather the psychology driving you to time the market. Make a plan including an exit plan for any individual stocks and stick to it. That is how to ensure your long term succes. Great analogy and reminder.

  • October 8, 2016 at 10:02 AM

    Not really considering selling but I suppose holding cash more rather than deploying cash right away. As you mentioned, market timing is extremely difficult. I have done a few courses on analyzing charts to time your purchases and sells. I have to say, life is a lot easier if you just kept executing your investment strategy and only sell if the said stock no longer meets your investment hypothesis.

    Great write up.

    • October 8, 2016 at 11:14 AM

      Thanks for the correction — I’ll do a quick stealth edit!

  • October 8, 2016 at 11:17 AM

    Excellent analogy! I tried my hand at trading and timing the market when I was younger. Now I know better and try to stay out of the loop. While I do still hold a few individual stocks, most of them I liquidated long ago in exchange for index funds. These manage themselves and are kept on the river through the good and the bad.

    • October 10, 2016 at 10:03 AM

      The vast majority of what large index funds invest in are going to be long term compounders, the index managers take care of that. So I totally agree with your strategy!

  • October 8, 2016 at 11:55 AM

    Great article! You make complex things easy to understand with this analogy. But I guess once people understand it, they just start to realise how complex investment is. At the same time this gives the beauty of it…

  • October 8, 2016 at 6:28 PM

    so so true Mr. Tako. I keep advocating for the disciplined and patient approach. I see the comment from one reader who gained 150% while others were on the sidelines. This is what happens when you stay disciplined and keep at it. This the reason so few make money in stocks.

    I advocate making steady investments in the stock market every week, month, or quarter. When you make purchases at steady intervals you shave off much of the market gyrations and are able to participate in the upward trend. During a downward trend you are averaging a lower cost so when the trend goes back up you make a sizable return. When will people learn?

    I wrote a post about how to make 4.7% when the market returns nothing – it basically shows an example of dollar cost averaging during a period where the stock market looked like a “V.” By getting the average of the prices the cost basis was lower than the ending value – a 4.7% return. Genius!

  • October 10, 2016 at 9:07 AM

    Thanks for the mention! We are hoarding our cash, but it is just a tiny percentage of our net worth. I’m willing to forgo a little dividend income for a year or so. We are still contributing to our 401k and Roth IRA regularly so we’re not missing out that much.
    I agree that timing the market is very difficult. You have to sell and the right time and buy in again at the right time. It’s rare to get one of these right, let alone two.

  • October 10, 2016 at 11:12 PM

    Totally agree, the basics should govern over speculation. However, deploying some hoarded cash after a crash like 2008-2009 is never a bad idea 😉 But timing it is indeed very, very difficult if not even impossible.

    Like the river analogy, very fitting.

  • October 11, 2016 at 2:15 AM

    Loved the article Mr. Tako. So much wisdom in one place from someone who’s achieved what most of us are still working on.

    I’ve dabbled in buying undervalued stocks which are not the kind of “long-term compounder” that I like to have in my portfolio, to seize the opportunity and make some quick profit. However, I don’t enjoy the stress that comes with it – I keep checking the share price several times a day and hope it reaches a fair valuation soon!

    I much prefer the peace of mind that comes with more stable, blue-chip companies with long records of dividend hikes. Much easier to sleep well at night! 🙂 At the same time though, I have my own criteria for selling them – if once day they don’t meet that, they’re gonna go!

  • October 11, 2016 at 10:10 AM

    If you can time it right, it would be amazing! For my own portfolio, I simply look at the math and see that 7 out of 10 years are up therefore, might as well stay invested…

  • October 12, 2016 at 3:01 AM

    I ended up with a bunch of company stock from my last workplace. It pays dividends which is nice, but I am feeling ‘eggs in one basket ‘. My current job is in the same industry and I am doing the employee stock purchase plan too. I put in my sell order last night to pick up some different dividend stocks. My first time really selling, so nervous excitement about making improvement. 🙂

  • October 31, 2016 at 11:40 AM

    I love this analogy. Sometimes anchoring in the river makes sense until you can get a good coxswain back on board.

  • July 4, 2018 at 9:04 AM

    Guessing this was sitting in your queue for a long time, since DividendHustler shut down his site in 2016 😉

    Anyway, agreed timing is hard. A few people like the ones you mentioned (Tawcan, RetireBy40) were all talking about hoarding cash back then, and all ended up being spectacularly wrong. If I had gone to cash, I’m guessing I’d have missed out on multiple 6 figures gains.

    • July 4, 2018 at 12:52 PM

      Ah, your right DH shutdown. I removed the link. 😉

  • July 4, 2018 at 11:38 AM

    Surprised you don’t mention technical analysis. For years now, the major stock averages have been trending up and to the right on charts over longer term periods. Do you not use any form of TA?


    • July 4, 2018 at 12:51 PM

      That’s correct, I don’t use TA. Technical analysis charts don’t contain useful information.

      • July 4, 2018 at 1:28 PM

        Wow. Quite an extreme statement. Many entire divisions of major financial firms and untold numbers of traders would disagree.

        • July 4, 2018 at 7:48 PM

          And they’re absolutely welcome to disagree. Reading tea leaves from squiggly lines and trying to predict the future isn’t for me however.

  • July 5, 2018 at 8:15 AM

    I sold GE late last year and it looks like an okay move now. It’s going to take them quite a bit of time to turn it around. They might never recover at all. I generally don’t sell our dividend stocks unless I’m very pessimistic about the company.
    It’s another story with our index funds. I don’t mind selling and holding some cash while an economic recession is looming. Market timing a bit is okay with index funds.
    Also, hoarding cash is relative. I didn’t sell everything and moved to all cash. I just increased my cash/bond percentage to 20% over the last few years. This year I’m trying to increase to 30%. It’s just hedging. I’m still invested.
    Thanks for the mention!

  • July 5, 2018 at 1:49 PM

    I’ve sold a number of stocks over the years. Even taking some loss, glad I did then rather than wait. For example Corus Entertainment and GE. But that really depends on the stocks, I held onto Intact Financial and Manulife during the financial crisis and 9 years after both stock prices have recovered and went higher.

    Like you said, market timing is HARD! That’s why I typically just end up holding on and collect dividends. We usually have some cash reserve on the side so we can deploy when the opportunity is right.

  • July 7, 2018 at 2:54 AM

    “Don’t use market movements to determine if you should buy or sell. ”

    Preach it, Mr. Tako! This is why we don’t bother market timing. Having a cash cushion and a yield shield helps. I don’t bother freaking out whenever there’s another article about “trade wars” in the news. Live on the yield, fall to cash cash cushion if dividends get cut, and finally “if shit hits the fan, we’re going to Thailand!” As a result, I’m losing zero sleep.

  • July 12, 2018 at 2:02 PM

    Hello mr Tako!
    I was interested in the reasons for wanting to sell investments and found the undervalued part quite interesting, I did not consider those type of investment : buy at a discount and sell when reached fair price. For the rest going with the flow on my raft here, the start was rocky trying to time the markets though. After 2 months of playing around I just started to invest in european/local “blue chips” and some index funds and have never lost one night of sleep thinking of my stocks (ok maybe some nerdy compounding calculations kept me up at night but I like numbers and knowing where the investments are headed).
    When the Dow dropped in February of this year it felt like the boat hit a stone along the river, and nothing more :). Timing the market for the average retail investor is difficult and if successful it indeed makes for exciting talks at cocktail parties but it is arriving at safe heaven that is more important to me.


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