Should You Invest At Market Highs?

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A reader, “Joe,” recently wrote:

I’ve been a traditional saver my whole life (55 yr old). Meaning I never informed myself on investing and put my savings directly into the bank. About a year ago I started to feel like leaving my job (I haven’t) and wondered how long I could live on my savings. . .

Market top?

My dilemma is now after a year of researching investing- it seems most asset valuations are very high.

I keep reading that the Fed and central banks around the world are doing (and will continue to do) everything they can to prop up asset prices. At the same time I’m reading people saying there is only so much juice you can squeeze from a lemon and the market is going to drop big. I don’t know who/what to believe.

My question: Is there a safe way to invest into the market without losing my shirt?

We get different versions of this question frequently. Some, like this one, come from people who put off investing until another day that turned into 20-30 years. Other people are just getting out of debt and ready to start investing. Some were working with an advisor and decided to become DIY investors. Others inherited money, received a lump sum payout from a pension, or had a large portion of their money tied up in homes or businesses which they sold.

Regardless of how you get there, many people reach the same destination. You now have money. You want to invest. Markets are near record highs. 

Investing your money is scary. So what should you do?

Embracing Uncertainty

Every time I receive a version of this question, there is a similar theme: a desire for certainty. I understand that desire. I would love nothing more than to be able to provide certainty.

This desire for certainty is the reason my wife and I initially invested with an advisor. We needed an “expert” to tell us what to do.

The desire for certainty is why we were so hesitant to take control of our own investments. Even after figuring out how bad the advice that “expert” provided was. Even after figuring out that all financial advice comes with conflicts of interest.

That desire for certainty is why Joe, after spending a “year of researching investing,” reached out to me to assure him he wouldn’t “lose his shirt.”

I don’t write this in a flippant or disrespectful way. I write it because it is important to understand we all desire certainty. Unfortunately, certainty doesn’t exist in complex financial markets.

Recently, I wrote about the idea of making decisions with incomplete information. This requires focusing on the decision process, which is completely under your control, as opposed to the outcome, which is ultimately out of your control.

An excellent resource to help make better decisions in the face of uncertainty is Annie Duke’s book Thinking in Bets. David Stein’s new book Money For the Rest of Us covers this topic well from an investing specific perspective.

Still, there is no substitute for experience. At some point, you have to stop researching and start making decisions with skin in the game. 

 Understanding history can help make better decisions.

Recent History Lesson

After a decade investing with a financial advisor, my wife and I started to manage our own portfolio in 2013. The concerns Joe expressed in his email to me were the same concerns we had then as well. 

In May of 2013, JL Collins addressed a similar question from a reader of his blog. If you are struggling with this topic, I encourage you to read his entire blog post Investing in a Raging Bull.

Here is a direct quote from his reader from Spring 2013:

“If I’m am going to start investing for the very first time, is NOW a good time, right before a possible stock market crash?

I have read about us being in a boom and a lot of people seem to think a stock market crash is just around the corner.”

Sound familiar?

Here is a quote from Collins’ response:

“As I sit here typing this afternoon the S&P 500 is trading at 1670, up 14% since the beginning of the year. 27% over the last 12 months. The very definition of a raging Bull Market. Add to this the fact that it has more than doubled since the Spring of 2009.

Whether you are considering investing a new chunk of cash that has come your way or whether to sell and sit on the sidelines for a while, it is times like these that test your core investing principles and beliefs.”

More Recent History

Many of us share the concern about markets that are near all time highs. It’s easy to forget that the market was very turbulent at this time just last year. The S&P 500, Dow and Nasdaq all dropped at least 8.7% in December 2018 alone. Many experts thought the prolonged bull market was coming to an end.

As I sit here typing this, the S&P 500 is trading at 3033. That is 82% higher than it was when JL Collins typed that sentence 6 years ago. It’s about 16% higher than it was at the start of 2019.

Despite warnings that had the writer to Collins’ blog so fearful. Despite Joe reading that “there is only so much juice you can squeeze from a lemon and the market is going to drop big”. And despite warnings in between like this one from financial guru Robert Kiyosaki in 2016:

This is not to imply that markets won’t crash (they will), or that it couldn’t happen tomorrow (it may). It just reinforces the idea that no one knows with certainty when it will happen or what it will look like when it does. 

Bold predictions get people to spend money on books, seminars and advice. These predictions draw eyeballs to TVs and get people to click sensational headlines. Advertising dollars follow those eyeballs and clicks.

Just don’t forget to check if the person who “correctly predicted” the last market crash also predicted 14 of the last 2 crashes. (Extreme sarcasm and skepticism intended.)

Understanding Market History

Let’s get to the heart of what concerns all investors. We work hard for our money. No one wants to take that money, invest it and see the value drop in the ensuing days, weeks or months. 

It’s possible that might happen, and of course that would hurt. So it is rational to do whatever possible to be as certain as we can that won’t happen when investing our money.

Ben Carlson recently examined the relationship between the twelve recessions between 1945 and 2007-2009 and the performance of the stock market around those events. He concluded:

“The problem with trying to time the stock market by calling a recession is that I could give you the exact start and end date of the next economic contraction and you still may not be able to profit from that information. The stock market is simultaneously forward-looking, backward-looking and maybe even sideways-looking so the fall in GDP is never going to line up perfectly with the decline in stocks.”

We tend to fear a big drop immediately after investing our money. This is natural recency bias, given the magnitude of the last market crash in 2008, and even the smaller correction last fall.

But a large drop followed by a rapid recovery is no big deal if you don’t sell at the bottom, whether out of panic or out of need to produce income.

Understanding longer term history of bear markets is helpful. Check out Darrow’s coverage of bear markets in this blog post or get a more detailed take on planning for them in his second book. Karsten Jeske also recently covered this topic in great detail in this blog post at Early Retirement Now.

What to Do?

The reason I decided to turn this reader email into a full blog post is that this topic is too complex to address each time I receive it.

It is not lost on me that I’m over 1,200 words into this blog post, and I’ve given no actionable advice to address the original question — yet.

So what can we do?

Reframe Risk

Returning to our original problem, Joe wrote seeking certainty while dealing with fear. We need to minimize these powerful emotions to accurately assess risk, thus enabling logical decisions.

Stock market investors often use the terms volatility and risk interchangeably. This is the wrong way to approach risk, because it doesn’t factor in how volatility would affect your personal situation.

Investing expert David Stein gave a different perspective on framing risk in our recent Q&A. He said, “… individuals should focus on the personal financial harm a bad outcome, such as a major stock market loss, can cause. In other words, how would your lifestyle be changed if stocks fell 60%.”

Joe has a desire to invest his money without the risk of “losing his shirt.” This requires incorporating an investment plan into a larger overall financial plan.

Investing plan ≠ financial plan

Volatility in the stock market is normal. That volatility becomes a real risk when you sell assets after they’ve dropped in value. One reason you may sell is your need to produce income.

Before putting any money into the stock market, it’s important to assess your needs. Your investment plan should be part of a bigger financial plan.

Do you have other sources of reliable income that would cover your basic needs (social security, pension, an annuity, rental income, royalties, income from consulting or part-time work) or will you be relying solely on investments? 

How much income do you need from your investments and how will you produce that income? Do you need to sell shares to produce income or will the dividends and interest meet your income needs? 

How much of your spending is discretionary? What would it look like to cut your spending by 10% to 20%? Would that mean skipping a few restaurant meals and taking more modest vacations or does it mean you can’t make the rent or mortgage payment?

Two people can have the exact same asset allocation and portfolio size, but completely different risk profiles based on the answers to these questions.

Managing Behavior

The other reason people sell after the market drops is fear. Just like no one knows when the market has peaked until it drops, no one knows when we’re at the bottom until it starts going back up. We need to have systems in place to take emotion out of our decisions.

Writing an investment policy statement (IPS) can be extremely valuable. Here is ours. This is not to suggest that our plan is right for you. 

Creating the IPS creates an opportunity to explicitly state your personal investment principles and rules when you are calm and thinking rationally. You can then refer back to this document and use it to direct your actions when emotions are running high.

When investing a lump sum, it is also important to understand the psychological benefits as well as the potential risks of dollar cost averaging into the market vs. investing the whole sum at once.

Take Action

I’m now approaching 2,000 words, and I’m afraid I still haven’t provided any information that, “after a year of researching investing,” hasn’t already been seen or heard by Joe. Here lies the real problem for most people who write with a variation of this question.

Knowledge is power, but only if you act on that knowledge. At some point, every investor needs to take action with incomplete information.

Darrow and I are DIY investors and planners. This site focuses on helping other DIY investors and planners. 

But not everyone has the interest, ability or psychology to do everything themselves. Some people need individualized financial help

That’s perfectly OK. You’re welcome here too. It is important to be an educated consumer.

When you need help, your best bet is to find a fee-only advisor, preferably one who is paid for advice only. An advisor with Certified Financial Planner (CFP) credentials who works under the fiduciary standard shift the odds of getting good advice further in your favor. 

A good place to start is the National Association of Personal Financial Advisors. If finding good help is overwhelming, Advice-Only Financial can assist you with finding an advisor for a nominal fee.

Providing Certainty

So can Joe start investing in today’s markets without “losing his shirt.” Should any of us be investing when markets are at all time highs?

I don’t know any secret optimal asset allocation. No one can tell you with certainty whether it is better to invest all your money at once or to dollar cost average into the market.

I have no idea what the market will do next week, month or year. I can’t predict what any individual’s behavior will be if investments are performing better or worse than they anticipated.

What I can tell you with certainty is that investing requires making decisions and taking action. Sitting on the sidelines and not making a decision is actually a decision in and of itself.

It is a decision that provides certainty. You are guaranteed to not experience market risk if you are not in the market. This decision also guarantees that you will remain stuck on the sidelines where you won’t experience any upside of being a long-term investor.

So I’ll answer the original question in the headline with another question. Is it ultimately more risky to invest or to stay on the sidelines?

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[Chris Mamula used principles of traditional retirement planning, combined with creative lifestyle design, to retire from a career as a physical therapist at age 41. After poor experiences with the financial industry early in his professional life, he educated himself on investing and tax planning. After achieving financial independence, Chris began writing about wealth building, DIY investing, financial planning, early retirement, and lifestyle design at Can I Retire Yet? He is also the primary author of the book Choose FI: Your Blueprint to Financial Independence. Chris also does financial planning with individuals and couples at Abundo Wealth, a low-cost, advice-only financial planning firm with the mission of making quality financial advice available to populations for whom it was previously inaccessible. Chris has been featured on MarketWatch, Morningstar, U.S. News & World Report, and Business Insider. He has spoken at events including the Bogleheads and the American Institute of Certified Public Accountants annual conferences. Blog inquiries can be sent to Financial planning inquiries can be sent to]

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  1. This is a difficult issue. I think that the vast majority of people will be better off investing as soon as possible and staying invested, provided that they have the fortitude to stay invested through a sharp market decline.

    That said, the market appears to be significantly overvalued by numerous measures (e.g. stock market capitalization to GDP, Shiller PE, Price-to-Sales, dividend yield, and on and on). At current valuations, investors are not likely to do much better than break even in nominal terms over the next 10 to 12 years, and investors are likely to experience a very sharp decline during that time, if history is any guide.

    Personally, I think that there is a huge asymmetry with potential for a large downside risk with a small upside potential at current valuations. Still, I’m reticent to encourage people to stay in cash, because most people would probably stay in cash until *after* the market has recovered significantly. In other words, I don’t think that they would benefit much, if at all, from moving to cash.

    1. I don’t disagree with anything you write Mark. Very tough decision, with no easy one size fits all answers.

  2. The worst fear I have for a robust market is the political chicanery being used to manipulate valuations. This is the highest risk I see and the most unpredictable given the non linear thinking coming from D.C.

    1. Markets are complex. Do you think those things which are concerns for many people are already factored into valuations?

  3. When confronted with the “lump sum” windfall question, I tend to fall back to 1) Do I have enough “safety” cash? For some that’s 6 months of expenses; for others it’s a percentage of assets in the whole portfolio firmly in cash or cash equivalents 2) After resolving #1, I put a portion of the windfall immediately in stocks (say 1/3), 1/3 in income producing investments (bonds, REITs), and the remaining 1/3 I dollar cost average into investments over 12-15 mos with my portfolio allocation in mind. I think really focus on having #1 covered, it takes the long term risk of investing out of the equation, as you have stated.

    1. I don’t think there is necessarily any one “right” way of doing things, but I do think you provide a clear example of having figured out a way that works for you, that you understand fully, and that is simple enough to stick to. Thanks for sharing.


      1. Another way that may work for some (me!), which yes, involves a level of market timing, but clearly based on history of 10-year periods, is the following:
        Continue to invest at your desired asset allocation level (stocks vs bonds), but regarding the US Schiller Cape10, realize the graph of Cape10 levels vs 1-year follow-up returns is basically an uncorrelated circle graph (anything could happen in the next year), BUT the same Schiller Cape10 level graphed against following 10-year US market returns IS a fairly linear, direct correlation where the present Cape10 levels suggest barely positive 10-year returns. I am going where the 10-year sectors are expected to clearly outperform: emerging markets, especially EM value, which has the highest expected return over 10 years, and foreign markets in general which have underperformed the US market for almost 9 consecutive years now. And bonds (and for me, commercial passive real estate for uncorrelated cash flow) to your ‘comfortable’ asset allocation level. Yes this is market timing, but I feel over 10 years is much less risky. Hey, staying in all or mostly US index funds is timing (vs the world) too.

        1. I agree with holding a widely diversified portfolio. Mine includes international developed and emerging markets as well as domestic small, value and REIT funds. (See link in post)

          It’s slightly more expensive and it has underperformed a more basic approach of buying a domestic total market fund, but I’m comfortable that over time it will even out and provide less volatility, so I have no problem sticking with it.

          I’m just not convinced that I can improve my performance by having a more dynamic allocation, shifting it to asset classes with more favorable valuations. If you haven’t, check out my recent Q&A with David Stein (linked in the article above as well). This is what he does with his portfolio, but he was cautious at best in recommending others to do it.

  4. Even though I’ve been investing in equities and bonds for over 20 years…I still struggle with the whole market timing issue primarily because 1/2 my compensation is paid out annually in a lump sum bonus( In Sept). I faced this same issue in Sept 2018 when the market was somewhat peaked, I wanted to invest that lump sum but was concerned about the hot market. I finally decided to hedge and put 10k in per week over the course of 2 months. As we all know the bottom dropped out in Q4…and I was kicking myself for not waiting, but what I did was to put more in at the bottom…which in the end actually lowered my average cost per share for my 2018 buys. looking back at those buys…Im now above for most of them. Timing the market is always a losing proposition but if we’re in for the long haul…it will eventually even out.

    1. It is definitely easier when you don’t have a decision and DCA into investments out of necessity when investing a paycheck regularly vs. getting a lump sum which requires a decision. One thing to think about, as your case shows, is that while DCA is often viewed as an alternative to market timing, it is in reality just a different market timing strategy that comes with its own risks.

    1. I’m also a big fan of his writing and I linked his recent Bear market article. David Stein’s new book is also excellent, though like ERN it is not always an easy read and requires some effort and interest to get the most value from it.

  5. Totally agree…essentially my 6 buys in 2nd half of 2018 were each in themselves a market timing play…for me it was all about piece of mind and understanding the trade off in my decision. I could put the whole amount in all at once in Sept, or hedge and spread it out over 6 weeks. In the end the latter allowed me to sleep better. With nearly a year past all those purchases they are ALL above water some more than others…even my most expensive shares (in Sept 2018). The hedge decision worked out for me by lowering my average cost per share, but I fully know it could have gone the exact opposite. To your point, there is no Right answer when it comes to lump sum purchases…I think we all have to do what makes the most sense in the context of our IPS.

  6. Chris, I want to engage with a CFP that can help my wife and I through a transition to retirement over the next few years. My problem is, I am not sure how to select the CFP. Are there any sites that rate planners, have customer feedback, etc. and are there some good questions to ask? We want someone who can coach us through deciding on a safe retirement #, consult and advise on tax efficiency and the best means of generating income from savings and how to adjust our portfolio for the transition. Do you have any advice or sources we can use to select the right CFP for us?
    Thank you!

    1. Dave,

      I don’t have a better answer than the suggestions and resources I provided in this post. A fee only CFP is not cheap, but considering the stakes, it may well be worth the cost of meeting with 2-3 to get different perspectives before pulling the trigger on this decision. Hopefully that will give you more confidence that you’re making the right decision or alert you to any blind spots you may have been missing. Best of luck!


  7. This is a great post Chris, covering the very same questions on my mind. I’m semi retired and moved some funds into cash during the summer and rolled over a 401K into an IRA money market. I’m hoping to jump back into the market. I agree with Mike Cancellieri’s post and will watch from the sidelines until the next substantial drop. At my age, I can’t afford to get back in and take the chance.

    1. Donna,

      I understand your sentiments, but let me play devil’s advocate here.

      If you are choosing to sit on the sidelines until the next substantial drop, how will you know when to jump back in? Will you wait for the market to bottom out? If so, how will you know when we’ve hit the bottom?

      Will you wait until it drops X%? If so, X% from what point? And why stop there? And what if it takes another 5 years until the markets correct to your target? Or if they never drop to that level?

      This is what makes that approach so challenging in my mind.


  8. Unfortunately, fear of market risk and the desire for certainty makes one a likely victim for about the worst financial charlatans out there; the variable annuity salesmen.

    I think a step “Joe” could undertake would be to cultivate a relationship (e.g., open an account.) with a reputable brokerage (Fidelity, Charles Schwab, E*Trade, TD Ameritrade, Vanguard, etc), and dip a toe in the water.

    You don’t have to necessarily have an advisory relationship with them; just have an open account so you can transfer funds to a sweep account and frome there, make investments in mutual funds or ETF’s.

    Spend some time browsing the brokerage’s web site reading about investments and retirement planning fundamentals.

    Perhaps start with a good quality balanced fund (there are many).

    I think it would be best to keep your job for a time, while accumulating some experience with investing.

    1. It is tricky. There is an element of real risk. And there is an element of behavior involved.

      On the behavioral side, I think this is where an advisor can be worthwhile, but as you state there are many people who present themselves as advisors who will not look out for your best interest. Following the steps I outline should allow people to avoid the landmine of annuity salesmen, but it still doesn’t guarantee an advisor is a good fit for your needs or that they are competent.

      Thanks for your feedback.

  9. Dollar cost averaging is your friend. Start investing now and make regular investments of X amount each month or quarter. When the market dips you end up buying more shares, and over time this strategy ensures you buy more when low than when high and over time I really believe you will be ahead.

    1. Dave,

      For a new investor, or even a seasoned investor with a lump sum, DCA can be comforting as compared to investing the whole amount at once. If that gets you to take the action you deem appropriate for your situation, them I’m all for it.

      That said, it isn’t a no brainer. In fact, more often than not, DCA is not the optimal decision. This year is a perfect example. Imagine someone starting on Jan 1 of this year utilizing a strategy to DCA in an equal $ amount on the first of each month. Each purchase would buy you progressively less shares than the month before.

  10. Annie Duke is brilliant. In addition to thinking of what would happen if you invested in the stock market, also consider what would happen if you DON”T invest.

    And an interesting site to assess asset allocation is

    1. I really loved Duke’s book and I obviously agree with your conclusion.

      Thanks also for sharing the resource. I know several readers love that site. That said, I’m not sure a lack of information that holds people back nearly as much as the idea that it is intimidating to take that first step.

  11. Great post Chris…

    …and thanks for linking to mine.

    Wow. Was that back in 2013? Yikes.

    Of course, when I wrote it, I had no idea how robust the next six years would be. I only knew those predicting the market “had” to go down from there also had no idea. Just more hubris.

    Same is true today. I have no idea what is coming in the next six years. No one does.

    Of course since someone is predicting every possibly, someone will be right. And, oh my, but how they will crow about it. And silly people, as always, will believe they have (finally!) found someone who can see the future. 🙂

    1. I greatly appreciate your humility in admitting you have no idea what will happen in any period of time. That insight led me to develop a strategy I can live with no matter what happens. That in turn gave me the confidence to implement the strategy knowing that I don’t have to be right to succeed. There is a lot of power in admitting that you don’t know.

      Thanks for reading and taking the time to comment, and thanks for all you’ve done to help me and other investors like me with your work!

  12. I’m convinced the purpose of the stock market has less to do with financial reward than to teach us humility. God knows it’s humbled and humiliated me many times. I experienced exhilarating highs from market wins and (once) deep depression during a terrible correction. I have learned the hard way, more than once, what comes innately to the likes of Jack Bogle and Warren Buffett: set a reasonable allocation, diversify your investments and invest in broad based funds/etfs . Ignore the talking heads and try not to check your portfolio balances.

    In my 30s I owned nearly 50 stocks, traded most every day, and held no bonds and no cash. Today, at over 60, I am comfortable with my allocation and I DO NOT stray from it. I have no emotional tie to the stock market.

    My “humble” advice for your reader is to take heed of what I (and many others) have learned the hard way. I also suggest setting overall allocations (ex: 40% bond/ 50% stock/10% REIT, or whatever is right for you) and dollar cost average into them. Invest a set amount or percentage of your savings during a timeframe you pre-determine until all your savings are invested. And don’t be afraid to take two or three years to accomplish this.

    Finally, Chris, I think your articles have been excellent and often thought-provoking.

  13. Whenever someone asks me this question it just indicates that they do not have the right asset allocation which would help them be comfortable with their stock portfolio. The talking heads on TV do not make it easier to eliminate emotions from investing.

    1. In this case, the allocation is all cash. Many people are in this position or hold a high percentage of their portfolio in cash waiting for the right time to deploy it.

      I agree that it would be a lot easier to invest if so much attention wasn’t given to the squeakiest wheels, but that is life.

  14. What to think of the astounding record of historical growth of S&P 500? Buffet has been quoted saying bonds are stupid investment such as what he said to A Rod once. He told his wife upon his demise to put investment in the S&P 500, but keep 10% in cash. I read some Bogleheads are doing just that with intermediate bonds as the cash. I look at this historical chart and scratch my head. It looks like one could just buy the market and enjoy higher returns. Returns that over a few years will outpace any bond combination. Meaning if the market did dip 50% you still will be better off with 100% stocks. There is more money in the stock pile even with a large draw down. Does this make sense?

    Also, the logic of investing in EM or foreign markets escapes me. I’ve heard financial people discuss this. The U.S. is the market. What happens here will greatly effect foreign market and usually more severe. The U.S. has way to many advantages. Our transparency, laws, regulations, competitiveness, open markets, creativity, business acumen. I’ve heard our financial workings are relatively young. We have a mature economy that is battle hardened. I do think we are honing a better economy. Think of our energy supplies and avoidance of quick solutions that have turned out to be not so cost effective. I just witness so much invention within our shores. We are entering into a golden age of transformation thanks to technology. I follow farming and forestry as a person with production engineering background and will say basic economic sectors such as these are on a fast track of cost efficient improvements. What if the markets and economy just continue to grow and expand? Would the U.S. stock market be the best bet? If so, why have these diverse portfolio’s that may only work to lower returns? I don’t know the answers to these questions, but have often thought of why no financial adviser ever broaches the subject? Could the discussion hurt their industry?

  15. I got started by reading columnists whose opinion I valued. One was Humberto Cruz who wrote a column for the Florida Sentinel called The Savings Game which was carried by my local newspaper. My employer’s pre-tax savings program was another incentive to read about the stock market. I survived the 2009/10 stock market meltdown with minimal losses, again, by reading. Read, learn, explore, invest. Don’t invest in anything that makes you feel uncomfortable. The point is to watch your money grow. That’s where the fun comes in.

  16. I do my own investing but not sure I got the right mix.. any books you recommend.. I’m hoping to retire in 10 more years on my current track.. eventually I’m guessing I’ll have to talk to a financial professional to make best tax choices. If you had a fee only advisor that also helped wth tax info in our area would appreciate contact info.

    I read ur blog often and love it! One of Johnstown’s 94’ finest! 😉

    1. Hey Alice. Thanks for reading and taking the time to comment.

      I’ve read countless books and narrowed it down to the 4 that most helped me. Depending where you are starting from, you may not need to read all of them, but this is what really shaped my investing philosophy. They are:

      There are many others that are good including anything by the Bogleheads, John Bogle and William Bernstein, but most are pretty repetitive if you’ve read those 4 that build upon one another. One exception is David Stein’s new book that I recently read and reviewed.

      Hope that helps.


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