Investing as Your Own Devil's Advocate

September 12, 2022
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We all have at least one argumentative friend or family member.

Or two. Or ten.

These are the ones you go out to dinner with, and they always have an argument for something. Turns out it’s usually the opposite of your beliefs.

Every time.

Some people love to do this.

They get a kick out of being on the other side of anything. Whether it’s COVID policies, the economy, politics, your favorite sports team, or where to go for dinner.

They delight in playing the devil’s advocate.

Ok. Be honest. This cantankerous person might just be you. Ha!

Even if it’s not, we should all learn to play the part of our own devil’s advocate occasionally.

What are you convinced is going to happen in the stock market, bond market, or overall economy right now? You might have a truckload of evidence that supports your theses, or you might just have a gut feeling that you cannot shake.

What would convince you of the other side of that opinion and outlook? Anything?

Political change. Lifestyle upgrade. New technology. Scientific breakthrough. Social shifts. War. Peace.

Play the devil’s advocate with yourself.

  • List any reason that you can think of that would flip your opinion.
  • Ask that friend, family member, or professional who you know will not agree with you what they think. Let them do their best to blow apart your financial opinion.


There is a sense in which playing the devil’s advocate in portfolio construction goes by the name diversification.

Portfolios usually need investments that work when other investments in the portfolio aren’t working.

The riskiest among us may need to get safer. The safest may need to get riskier.

Do you need help seeing the holes in your strategy?

Don’t worry. We won’t intentionally play the part of devil’s advocate. Instead, we want to be a financial advocate for you and your future.

Take our free portfolio risk analysis and set up a meeting with us.

Or send a friend.

(Just don’t send us *that* friend ;)