When should you sell your stocks?

When should you sell your stocks?

In a perfect investing world, maybe you don’t ever sell any stocks. You could make a case in your asset accumulation years that a pure index investor just keeps buying for decades on end since the best price is the market price of the day.

That said, there are certainly other (successful) ways to invest and your mix of stocks, bonds and real estate can matter to your overall returns…

There are also a few guaranteed ways to lose money too. For example, if you’re doing high-cost anything related to money management fees (paying a costly advisor), paying too much taxes, or using excessive leverage via borrowing costs – that can be a loser’s game.

Consider another Warren Buffett quote when he said:

“Over the years, a number of very smart people have learned the hard way that a long string of impressive numbers multiplied by a single zero always equals zero.”
― Mark Gavagan, Gems from Warren Buffett – Wit and Wisdom from 34 Years of Letters to Shareholders.

While the notion of just keep buying is one part of my investing thesis there are some instances in this post whereby I have sold some stocks over the last 15 years or so – in favour of other decisions. I’ll link to those in a bit. Only in hindsight, will I know if those decisions turn out to be much better than the alternatives!

For today’s post, I thought I would explore when should you sell your stocks and the considerations that are involved. I look forward to your comments and your decision-making as well!

Stocks for the long run at your peril?

In a recent Weekend Reading edition, I questionned some investing advice from a notable U.S. financial expert here.

I argued instead of worrying about stock market corrections, how long any stock market correction might last, and more…I’m more inclined to worry about some things within my control and influence since I believe stocks for the long-run can work wonders for most retail investors. I/we focus on:

  1. Our sustained savings rate for investing.
  2. The ability to remain/stick with my hybrid investing plan of stocks and low-cost ETFs.
  3. Keeping some cash handy, and
  4. Avoiding fearmongering market news.

So, I’m aligned with this:

“I see the stock market, as a tool, for average people/average investors to be long-term business owners.” – Larry Bates, Beat the Bank.

Any sensible investment plan must be tailored to the investor’s tolerance for risk (including losses) including the need for any equity drawdowns – since “avoiding zeros” in your portfolio is more critically important in your asset decumulation years vs. asset accumulation years given you have less time/runway to financially recover.

For every investor, knowing when to sell shares (or not) can be important to your investing success.

Here are some key reasons below that might prompt you to consider selling your stocks…

1. To rebalance your portfolio

Over time, your investment portfolio can drift from your initial allocation of money – namely your mix of stocks and bonds. Your portfolio could also drift away from your desired geographical allocation as well: your desired mix of domestic and international stocks. Rebalancing is the process of realigning the weightings of your portfolio by selling off shares from over-performing categories and reallocating the funds to other opportunities.

Ultimately, rebalancing helps maintain the level of risk you’re comfortable with.

2. To meet income needs

Life can be unpredictable. We keep some cash on hand for those reasons and maybe you do too.

However, one good reason to sell your shares as you age is because you need the assets sold to pay for living expenses. That timing however may be critical due to sequence of returns risks. In fact, those risks are just a few key factors in any decision to retire.

5 Important Factors to Consider in Your Decision to Retire

Selling at the wrong time, you could incur losses. Selling at a good time, could yield capital gains. 

3. To take profits

I know many investors that have some rules-based approaches – when they sell stock shares after any stock realizes a huge profit goal in their portfolio. I know others that simply let their winners run. 

Securing your capital gains can be a challenge since you’ll only know in hindsight whether the broader market has peaked or the stock in question has topped out in price.

4. To reduce systematic stock risk

As you approach major life milestones, such as semi-retirement or retirement, I’ve seen, heard and listened to hundreds of retirees – most tend to reduce the level of equity risk in their investment portfolio before they cross this milestone or least hold a modest cash wedge.

The Cash Wedge – Managing market volatility

To help manage systematic risk, recall that investors should ensure that their portfolios include a variety of asset classes: fixed income, cash/cash equivalents and some real estate – all of the above that can react differently in the event of a major systemic change like a sudden spike or decrease in interest rates (ahem, as an example)! In the event of an interest rate rise, as experienced in recent years, you might want to ensure your portfolio incorporates ample income-generating securities that should mitigate the loss of value in equities in some sectors.

How to invest for higher inflation

Back to the milestones, smart retirees/investors may also sell shares in any volatile stocks they have owned in favour of more stable investments, like bonds or dividend-yielding companies including those in defensive sectors which can safeguard your retirement nest egg to a degree.

Some readers might also be aware of an equity glide path – a risk reduction approach – there are three (3) main ones that I know of:

4a. A declining equity glide path is where you slowly reduce your exposure to equities as you get older, like the “100 minus your age” rule of thumb for your bond allocation. This means as you age, you would reduce your equities portion by 1% and increase your bonds by 1% weight over time.

4b. A static glide path is where where you maintain a specific strategic asset allocation, such as 60% stocks and 40% bonds and if you were taking money out of your portfolio, you would take enough from each asset class to keep that balancing act.

4c. A rising equity glide path is the opposite of the declining glide path (4a). As you age, your equities portion would slowly increase…which seems counterintuitive – but it works. In fact, U.S. retirement experts Michael Kitces and Wade Pfau have found that a rising glide path, in retirement, such as one starting with 30% in equities and going up to 70% over 30 years, yields better outcomes than a static or declining glide path.

From Kitces:

“Instead, the optimal glidepath for asset allocation appears to be a V-shaped equity exposure, that starts out high in the early working years, gets lower as retirement approaches, and then rebuilds again through the first half of retirement. Or viewed another way, the prospective retiree builds a reserve of bonds in the final decade leading up to retirement, and then spends down that bond reserve in the early years of retirement itself (allowing equity exposure to return to normal).”

5. To avoid individual stock risk – deteriorating company fundamentals

We’re seeing this a bit, with some Canadian stocks – right?

Too much debt coupled with existing shareholder expectations (e.g., Bell (BCE) to pay a dividend) tend to punish stock prices now and then. Certainly, as a DIY investor, if you feel the fundamentals of any company you’ve invested in start to deteriorate—like increased debt, poor strategic decisions, or other management issues—it may be time to sell (some) of your shares to reduce individual stock risk. 

6. To participate in tax loss harvesting

This is not an issue with your registered accounts like RRSPs/RRIFs or TFSAs, etc. but tax-loss harvesting can be helpful to offset capital gains on other investments held in taxable accounts – this way – you can lower or nullify any taxes owed as a result of a capital gain by simply selling an investment that has an unrealized loss to offset the gain. This allows you to achieve a certain amount of tax savings.

Factors to consider with this:

6a. Superficial Loss: When employing tax-loss harvesting, make sure to consider the CRA’s “superficial loss” rule. According to this rule, investors claiming a capital loss on the sale of an investment cannot buy the same investment within 30 days of the sale. For example, disposing of capital property for a loss, and repurchasing the same property within a 30-day period following its sale, the CRA’s “superficial loss” rule will come into effect. This means a capital loss cannot be deducted from your income for the year. The “superficial loss” 30-day rule is specifically designed to prevent investors from playing the system to lower their income tax payments.

6b. Portfolio Rebalancing: Tax-loss harvesting can be used to rebalance a portfolio – see above. Just make sure in a taxable account you maintain your adjusted cost base.

6c. Your investment type: Not all assets are created equal – the nature of what you own in a taxable account will impact how easy or difficult tax-loss harvesting actually is. For a portfolio that consists of individual stocks or exchange-traded funds (ETFs), tax-loss harvesting can be easier to employ. Investing only in mutual funds can be more challenging as mutual funds sometimes make annual capital gains distributions regardless of whether investors continue to hold the fund units or not. 

6d. Eligibility: A reminder tax loss harvesting only applies to investments sold in non-registered accounts.  Capital gains inside registered accounts, such as an RRSP/RRIF or TFSA, are tax exempt. The CRA does not allow the use of capital losses within registered accounts to offset gains in other accounts.  

When considering selling your shares, it’s essential to avoid making decisions based solely on emotional reactions to market fluctuations – stocks go up and down all the time and in fact: every market day!

Instead, focus on your long-term investment strategy, personal financial goals, and whether selling aligns with these objectives or updated objectives. 

Which Stocks Should You Sell First?

Good question!

Before I share what I’ve sold over the years and why, I will remind readers why I am a hybrid investor:

  1. I like optionality – with my ownership in many Canadian stocks (and a few U.S. stocks) I can reinvest the dividends and/or distributions as we wish or just take the cash related to #2. 
  2. I aspire to “live off dividends” – for me/us, I worry about when to sell equities in the future so I believe I can reduce my fears about when to sell shares, including sequence of returns risks (during any market downturn of 10% or 20%) if I remain invested and simply spend the cash dividends or distributions as I please. I hope to do this a bit in the early years/semi-retirement years in my 50s while working part-time. 
  3. Earning dividends is a great complement to my low-cost ETF investing approach that focuses on growth. I have little intention of selling any low-cost ETFs in the early retirement years. 

So, with my “hybrid investing” approach I feel I get the best of both worlds:

  • Dividend income, earned today, to deliver cash or I can reinvest the money as I please and,
  • Low-cost, global growth, beyond Canadian borders. 

Your mileage may vary. 

When it comes to which stocks should you sell first, well, I will confess I believe that answer depends on where you hold such stocks and some of the factors above. 

In our portfolio, we have stocks/equities in all three major accounts:

  • Non-registered
  • RRSP
  • TFSA

In recent years, I’ve avoided selling any stocks in our non-registered accounts but I have sold stocks inside our RRSPs and TFSAs for some or a combination of the reasons above. 

In my post a few years ago with the guys at StockTrades we discussed if you should sell a stock after a dividend cut. I believe that may or may not make sense!

When to sell a stock after a dividend cut

In some cases, I’ve sold stocks because of a dividend cut and in other cases, not at all. 

Here is a list of key stock sales I’ve made over the years:

I sold H&R REIT here.

I sold a bit of AQN after they cut their dividend here.

And more recently, I sold every stock share of JNJ even without any dividend cut.

In favour of those decisions:

  • I bought other stocks with the proceeds to stabilize my portfolio more, and
  • I bought more low-cost ETFs like XAW to diversify the portfolio more. 

When should you sell your stocks?

At the end of the day, unless you’re a pure index investor in an all-in-one fund, you might not sell any stocks for some time to come. Even then, at some point as you age, you might need to sell some of your all-in-one equities to fund your living expenses and fund the cash wedge portion of your portfolio.

Selling shares can sometimes be a knee-jerk reaction to market events or personal biases. Here are some reasons that should not immediately dictate your decision to sell:

  1. You see the stock price is falling: Stock prices fluctuate ALL THE TIME. 🙂 Selling just because a stock drops in price can prevent you from benefiting from potential recoveries. Selling shares due to short-term underperformance can be counterproductive…
  2. You read, hear or watch some bad stock news: The financial media is great at selling drama. They need to put food on the table too! Most companies are frequently hit with setbacks, for many quarters in some cases, that can cause stock prices to drop and remain down for prolonged periods. So, selling your stocks on one piece of bad news can negate the company’s long-term returns and give in to the financial noise.
  3. You are trying to time the market: Trying to time the market is incredibly challenging and likely a fool’s game. It is therefore far more effective to have a long-term investment strategy (hybrid investing strategy or other) rather than selling your stocks in an attempt to buy back shares later at a lower price.
  4. You feel pressure from others: Ignore what other people are doing – just because other investors may be selling their stock shares doesn’t mean you should do the same thing. Your investment objectives should be tailored to you alone.
  5. You’re only thinking about tax: Yes, see above, there are some tax considerations in taxable accounts but that shouldn’t be your primary decision IMO. 
  6. You feel emotional: Investing can be an emotional journey. Usually, financial decisions made out of fear, anxiety, or excitement are not part of a well-planned investment strategy. So, it’s OK to keep some BCE stock but you might need to suffer some lower BCE stock prices for some time to come… 🙂 

Established readers will know I own many Canadian individual stocks and a few U.S. stocks at this time – part of the approach I’ve always had – along with a few low-cost ETFs for extra diversification. 

At the end of the day, I think if most investors can invest regularly, continue to keep their money management costs lowdiversifyavoid tinkering with their investments, and hold more equities than bonds, chances are they will be rewarded many, many years from now – and they may avoid selling stocks at the wrong times for the wrong reasons. 


My name is Mark Seed - the founder, editor and owner of My Own Advisor. As my own DIY financial advisor, I'm looking to start semi-retirement soon, sooner than most. Find out how, what I did, and what you can learn to tailor your own financial independence path. Join the newsletter read by thousands each day, always FREE.

26 Responses to "When should you sell your stocks?"

  1. I dumped AQN stock. They have had no forward guidance the last few times I have read their earnings and only appointed a CEO recently it seemed, because their majority shareholder forced two board of directors on them. I see them as trying to continue with the renewables as they are starting to present these as profitable and their regulated energy (Liberty) as unprofitable. Management seems stuck in an old culture. For them to succeed – I believe they need a whole new management team. The one they have is dithering around considering renewables sale – as they have been for the last year. Perhaps they are waiting for an attractive sale price, but considering wind and solar are variable and depend on how much sun and wind are present – I can’t really see it being a solid investment long term unless they start making and installing solar and wind capacity in a much more efficient manner. The big banks don’t seem to really want to fund renewables at favourable interest rates. Favourable rates are given to oil and gas in my opinion. The old mentality continues. – Christopher.

      1. I would like to buy american V:US (visa) stock, but also want to sell some of my excess EQB stock once it rises again. I bought Starbucks and ADP a little while ago – American stocks. The Canadian to US $ conversion kills me sometimes. I know about Norbert’s gambit, but have used just direct quest trade purchase of American stocks too. Until I get the extra cash from selling some EQB I’m considering buying the US: TBIL ETF -> supposed to give monthly dividends in US $. I would also like to buy Microsoft but right now that’s out of my price range in cost per share.
        – Christopher

        1. Ya, I hear ya on the Gambit. Need to have enough worth your while. I have used RY and other stocks over the years for the Gambit.


          I’m really not bothering with any Gambits now since we’re just letting CDN and US cash accummulate for future RRSP withdrawals in the coming years to avoid selling any stocks or ETFs. MSFT is very expensive it seems, as are most tech stocks. I hold QQQ for a tech proxy.

          Happy investing, keep me posted on your decisions!

  2. I sold some WCN in the last few months. I am now mostly leaning toward letting the fliers fly except if they are very volatile in price. An example of this would EQB. At some point in the future when I feel it has gone about as high as I anticipate – I will sell some of it. But since it is killing it overall I won’t sell all of it. When selling it is important to find another good stock to buy at a good price. I sold some CP in the past but bought BNS at too high a price – lowering my current – capital gain in the stocks I hold based on market prices. That was a bad move. Still contemplating selling AQN. They seem to be taking forever to sell off their renewables and appoint a new CEO. At some point I will lose patience and ditch them. – Christopher

    1. Hard to know when to sell…to be honest, since you’re making so many assumptions about an unknown future.

      I will continue to own WCN and WM myself. Small % of my portfolio about 1-2% each.

      I also like and own EQB – likely a growth story for years to come.

      Ya, AQN is struggling and once they get the focus back, the stock price should come back but when I don’t know…but it should rise over time, slowly, is my guess. That one is <1% of my portfolio. Not worried.

      Nice to hear from you!

  3. Thank you, Mark, for the article and your work in general with this blog. I found the idea of a ‘rising equity glide path’ during the retirement period very interesting, especially as I am considering implementing a similar strategy (50% of portfolio as 10-year GIC/bond ladder, with rest in equity) myself as I am nearing the R-day – while I also did not know this was a strategy out there. The conditions of the markets today – expensive stocks, higher interest rates – might in my opinion make this strategy even more interesting than it was back in 2016 (refering to the article by Michael Kitces). My own cursory modeling / simulation convinced me this strategy would be very efficient at protecting a portfolio should major corrections occur late in pre-retirement or early in retirement. Always good to know there is also research backing our intuitions!

    1. I appreciate the comment, AB.

      Regardless of the financial jargon used, it seems to make sense, right? The rising equity glide path?

      Nobody wants to invest in “a zero” as Warren Buffett puts it and we all want income security as we enter retirement. I find the challenge is, everyone has a different income security number. Some need $5k per month. Others need $6k per month. Still others need and want $9k per month. Etc.

      I’ve learned cashflow is king – the ability to earn meaningful income from your portfolio, heck or high water, is critically important in the first 5 years or so in any retirement plan since broad equity markets (i.e., 100% broad market ETFs) may or may not cooperate. I hope to guard against that via owning cash, cash equivalent ETFs, potentially some GICs long-term and some dividend stocks beyond growth ETFs.


  4. Lloyd (63, retired at 55) · Edit

    That article about The Retirement Danger Zone with the rising equity glide path was quite interesting. It’s kinda what I did/am doing even though I wasn’t aware it had an actual name or was a possible plan. Granted it isn’t *exactly* the same.

    When I retired at 55, I started considering having what I termed a safety net. A bunch of GIC ladders that could provide an annual amount over an extended period of time if necessary, not subjected to the whims of a market. Using no analysis or study, I arbitrarily chose $40K per year for 30 years as a target. This, in addition to the DB pensions, CPP and future OAS, seemed like a reasonable amount and time frame. As I was accidentally making money on the farm post-retirement from work, there was no rush and I built up these ladders over a few years (beginning around age 57).

    Jump to today. Given that keeping a 30 year time frame in perpetuity would be silly, I’ll begin reducing that safety net time frame by rebalancing some maturing GICs back into equities beginning in a couple of years. Again, wasn’t planned but that will also be around when we will have definitive numbers on all the pensions and the wife’s disability income replacement ceases. If the numbers aren’t what I hope they will be, or the markets and/or geo-political situation is in a kerfuffle, we can make adjustments.

    I’ll admit this was in no way a thought out financial “plan”, it just seemed reasonable and logical at the time. As a bonus, this maneuver got the gold seal stamp of approval from she who must be obeyed. 😉

    1. Well, to your defense, the financial industry/community has a lot of fun terms to make things sound complex. 🙂

      In my 30s, I didn’t really care too much about any cash wedge, cash buffer, whatever you want to call it cushions.
      In my 40s, as I started thinking more about semi-retirement/part-time work in the coming decades, I realized it was pretty important.
      Now in my very early 50s, while I believe cashflow is king, cash/cash equivalents are pretty important too.

      The ability to fund your life, and expenses, without touching your portfolio at least for a few years if the market doesn’t cooperate (grow at 5-6-7%) has always made sense to me.

      So, I think it’s very important whatever age you consider retirement or semi-retirement to consider where your money is going to come from.

      I know folks that “live off dividends” just fine but few folks at age 55 have a $2M portfolio that churns out tens of thousands per year. So, the rest of us might need to consider cash, bonds, FI, GICs, etc. as buffers since we will and want to draw down equities at some point.

      Regardless of following any financial jargon, you’ve done well Lloyd. 🙂


  5. Hi Mark,
    The primary reason I am selling stocks now is to reinvest the money into my/our TFSA i.e. from the taxable account to my/our TFSA. I try to manage the capital gains by selling the big winners with the not so big winners. I have had most of the stocks for a while so not really any losers. We are retired so we will continue this process until the taxable account is 0.
    I have sold some ETF’s in my TFSA as I decided that I would get rid of my Canadian dividend ETF’s and only buy individual Canadian stocks for dividends as my TFSA was fairly diversified. I still own AQN and have considered selling.

    1. That’s another good/subtle reason I should have added, I will amend for an updated post. I see this with many retirees as part of their plan to move stocks from taxable to TFSA every year and/or those still saving for retirement to move non-reg. funds to TFSAs every year to reduce taxable income.

      I wrote about that here too, re: transferring stocks to the TFSA:


      “We are retired so we will continue this process until the taxable account is 0.”

      Nice – I can appreciate the joy of having thousands of dollars to spend from the TFSA, tax-free. I hope I get there too. 🙂

      I still have a bit of AQN but only in taxable, makes up <1% of the portfolio. No big deal for me.

  6. Reasons to sell include rumours about impending crash, especially from those so called experts!!! You make decisions based on pure emotions and fear. One anecdote I heard before comes from investors who consulted fortune tellers if you believe in them!!! For some reasons, there are still believers in those fortune tellers…so funny…

    Great article as usual, Mark.

    1. Thanks, Ken! Analyst and expert predictions are interesting but I’ve learned they cannot predict the future accurately at all better than anyone else. So, devise a plan, try and stick to it, and adjust as you wish along the way. 🙂


  7. I read this and was hoping for a magic formula or fool proof method for “When to sell”. You pointed out the factors and considerations well, but still feels like I fell for a click bait title!

    I guess if there was a magic formula or fool proof method you wouldn’t be sharing it to the masses for free. Just another reason why I became a pure index investor no need to know what or when to sell just hold it all in the index. My plans for selling will only to for rebalancing (yearly on my birthday or if allocations move more than 5%) and also for retirement income.

    1. Well, I wish I had the perfect answer for everyone, Tech – but I’m not sure that exists. 🙂

      I’ve sold stocks because of dividend cuts (for sure, a couple of examples are included) and I’ve sold a dependable dividend payer in my stock because I felt there were opportunities elsewhere – so far, I’ve been correct. We’ll see long-term!

      As a pure indexer, are you using an all-in-one fund or a mix of ETFs in various accounts? Beyond that, are you keeping some cash/dry powder handy?

      1. I have a mix of Vanguard ETF’s the all-in one funds were not around when I first started. The separate funds work well for me even though Its take more time and effort to manage. I have the added bonus of being able to holding certain funds in certain accounts like VCN in my taxable account to take advantage of Canada dividend credits and VTI in my RRSP for lower MER and no withholding tax.

        USA 50% VTI, VUN
        Canada 20% VCN
        Emerging 15% VEE
        Developed ex North America 15% VIU

        I am still working in the accumulation phase so cash/dry powder is coming in every two weeks. I do hold cash in a high interest account making 4.5%. In retirement I think a bigger cash wedge (maybe a year of expenses) is the way to smooth out the ride and give some flexibility when to sell/make withdrawals from the portfolio.

        1. Nice stuff, Tech.

          Certainly a few geographical locations have lagged (e.g., emerging = VEE) but we can’t know that in advance! Same with individual stocks.

          Super smart (I’m biased) around the cash position since I’m building mine/ours for 2025 for eventual withdrawals/spending.

          Yes, good on VCN. I personally like XIU for DTC for taxable accounts since little worries about phantom distributions but both are excellent as you well know.

          Also earning 4.5%+ on our cash now although we keep some liquid beyond just ISA/HISAs as spending is variable.


  8. Chuck – you say “minimal capital gains” – but in fact for donations to a charity (or donor-advised fund), it’s ZERO capital gains – ie. a 0% inclusion rate!

  9. Another reason to sell might be related to the possibility that an stock sector/sub sector becomes unpopular. I am speaking of the energy sector/Oil and Gas. I don’t want to start any climate change debates, but if we see more climate related disasters in the next few years I predict that this sector could fall out of favor. Maybe be replaced in popularity by renewable energy providers. I will definitely be watching my oil and gas stocks and pipeline stocks closely over the next 5 years.

    1. That’s true…thinking about O&G stocks a few years ago = totally unloved. Now, everyone wants them 🙂

      Yes, ignoring the climate change debate for now, O&G will be needed for at least as long as I am alive = another 40 years.

      I own renewables just in case (BEPC) but that’s been VERY beaten up but it could very well rise again and likely will…I figure everything has a cycle. 🙂


  10. Lloyd (63, retired at 55) · Edit

    Similar to Chuck I’ve utilized the gifting of shares for endowment purposes with local Foundations. I *was* using ETFs in the non-reg equity account solely for that purpose. But then the pseudo distributions bit me in the butt so I sold them all, ate the capital gains and bought BAM. Now I hold only BAM in that account and intend to donate these shares over the next five or so years.

  11. Hello,

    I suggest a comment/topic that is another good option. When stocks have appreciated significantly, consider donating shares (without selling stocks). This will both lock in minimal taxable capital gains, generate significant donation tax credit, and make a real difference to the essential & needy health, food bank, arts, education, research, culture, etc programs. I did this last year through a donor-advised fund and am enjoying the tax refund, sense of giving and feeling part of something beyond capital growth.

    1. Excellent points and I just added that as part of my newsletter re: gifting shares. Kudos to you and the opportunity to do so/give back.


Post Comment