Are You Worried About Investing at an All-Time Market High?

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Maybe folks are worried about the yield curve, maybe it’s the political drama, or maybe they just feel it in their bones – I’ve been getting more questions about if I think now is still a good time to invest.

Well, here are some articles that may help you feel better:

What if You Only Invested at Market Peaks? by Ben Carlson. What if you were so unlucky as to invest only at the following market peaks (and suffering the subsequent drops)? As long as you kept on saving your money (putting it in cash when not at a market peak), and not selling at all, you would have actually done fine.

Meet Bob.
Bob is the world’s worst market timer.
What follows is Bob’s tale of terrible timing of his stock purchases.

Should You Invest (Or Wait) When The Stock Market Is At An All-Time-High? at Here is another interesting interactive tool that lets you pick any subsequent time period and see how the distribution of future returns compared if you invested at an all-time high (ATH) during that period. The market tends to spend a lot of time near all-time highs.

The key takeaway is that in the past several generations of investing, the market has done well and most of the time, the market is within 5% of its ATH. If you waited for a large dip to invest, you could be waiting for a long time and you would have missed out on a large amount of the gains.

Finally, here’s an older post to consider: The Only Two States of Your Portfolio: Happy All-Time High or Sad Drawdown.

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  1. Direct from former Governor Eliot Spitzer: Can’t win…..Don’t Play.

    I’ll take my cue from the ancient Greeks, Odysseus specifically. I choose not to drink the poison and be suckered in by the sweet songs and enticements of the Sirens of Scylla.

  2. Steve Kohn says

    I’m not convinced. It assumes the market will always rebound. Ask the Japanese about their Nikkei 225, at almost 40,000 in 1990, then dropping to near 10,000 three times since then, and now “up” to about 22,000. So 28 years later, and half your investment is gone.

    Not saying we should be day traders, but buy ’em and hold ’em just isn’t realistic.

    Also not saying America is Japan. In some ways, unfortunately, we’re worse. Trillions of dollars in unfunded state and local pensions; a trillion more in student loans that will never be repaid; “just” millions for disability abuse; baby boomers in the millions to draw Social Security; unfunded Medicare and Medicaid; and a national debt in the trillions that our grandchildren will curse us for leaving them.

    I’ll inch my way back in the market at the next crash. Until then inflation will kill me, but not as much as buying at a high and seeing my lower balance month after month after month.

  3. Oh the good old market with it’s ups and downs.. I remember looking at NVDA crossing the $40 mark back in 2016 thinking to myself “I cannot invest in this now. It’s at it’s all time highs, I missed the train.”

    Truth is, nobody knows where the market is going and history is not always an indicator of future performance. I’m happy that I found a way to generate a monthly cash flow without investing in the stock market.

  4. Focus on buying undervalued companies – they’re undervalued regardless of what the wider market is doing. If there’s a wider market drop that drags down your investment then c’est la vie – I will recover.

  5. Jason Boxman says

    That’s the premise of Dividends Still Don’t Lie which I’ve been reading lately.

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