Invest like a Roman general

Humility is something to be cultivated in all walks of life.

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According to some accounts, after a successful battle, the victorious Roman general would be paraded through the streets of the city.

And, behind him, a slave would repeat the phrase 'Memento mori'.

Translated, it means: 'You are mortal'; a reminder to the general not to let success go to his head.

It's good advice.

Humility is something to be cultivated in all walks of life, I reckon.

(And when you've done that, you can be proud of yourself. Which… means you're back to square one!)

But seriously, humility is a very, very handy trait, particularly for investors.

We all know the stock market is volatile. Certainly the last few years have been a case in point.

Starting in February 2020, we had the fastest bear market in history, followed by the fastest recovery.

In 2022, the technology sector lost around one-third of its value. Then in 2023, it gained about 30%.

And those examples are nothing compared to the rises and falls of some individual companies' shares, often in much shorter timeframes.

Now, no-one needs to be reminded of their mortality when shares fall. That one's easy, unfortunately.

But it's when they rise that we need to remain sober in our assessments.

It's also really hard.

We want to believe that rising share prices are justified: because we like getting richer.

And we like the feeling of having our judgement validated. "See, I was right!" is a powerful emotion.

But, dear reader, memento mori.

The problem is that our instinct is to take the gains for granted, but that same instinct causes us to suffer the losses greatly.

Again, it's only natural.

They're just not very helpful instincts.

They blind us to the fact that sometimes our gains are pure luck. A fluke.

That sometimes the investment case is justified, but the gains get out of all proportion.

A great example of that last instance is Microsoft, currently the world's second-largest listed company (by market capitalisation).

In early 2000, before the tech crash, Microsoft's shares sold for almost US$52 per share.

Then, dot com became dot bomb.

Microsoft shares wouldn't reach those heights again for more than 15 years, not crossing the US$52 mark until October 2015!

Imagine how good you felt, in 2000: the shares had tripled in less than three years.

Imagine how tough the next 15 years were.

And since 2015? The shares are up almost 8-fold in price, to US$404 as of this writing.

What's next for Microsoft? I don't know.

Maybe the shares go straight to $1,000.

Maybe they fall to $200.

No, I don't want to rob you of the joy (relief?) of rising share prices.

Because, here's the thing: if you can be equanimous when shares rise, you'll also be more philosophical when they fall.

But, if you let your emotions get the better of you in the good times… they'll probably get the better of you during the unavoidable falls, too.

Yes, those of us who have been battered over the past few years can be excused for wanting to enjoy it when shares rise.

Yes, I'm being a killjoy. Sort of.

But I'm doing it because I want you to be prepared for both the ups and the downs.

I want you to be prepared – financially, mentally and emotionally – so you can see this investing thing through to the end.

If you're still nursing some losses, remember that a diversified portfolio of well-chosen shares is very, very likely to go up, over time.

And if you're ahead? Memento mori.

Fool on!

Motley Fool contributor Scott Phillips has positions in Microsoft. The Motley Fool Australia's parent company Motley Fool Holdings Inc. has positions in and has recommended Microsoft. The Motley Fool Australia's parent company Motley Fool Holdings Inc. has recommended the following options: long January 2026 $395 calls on Microsoft and short January 2026 $405 calls on Microsoft. The Motley Fool Australia has no position in any of the stocks mentioned. The Motley Fool has a disclosure policy. This article contains general investment advice only (under AFSL 400691). Authorised by Scott Phillips.

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