Richer, Wiser, Happier by William Green Changed How I Think About Investing

Richer, Wiser, Happier is blurbed as being about how “the key insights for building wealth apply to life as well.”

For me, though, the book provided the vice-versa insight:

It opened my eyes that the key insights for building a rich life apply to investing as well.

And, as over-the-top as this may sound, it may have changed my life.


Nearly Broke, Wiser, and Happy

For the past couple of years, my “professional” focus has been The Unconventional Route, my blog about staying curious, questioning the status quo, and living on your own terms. There, I explore a broad range of topics from fasting to shifting identities to fitness to peeing sitting down.

It’s fun!

It’s rewarding!

But it’s not lucrative.

You could say my blog floats my boat, but doesn’t generate enough buoyancy to keep my wife, son, and I financially above water. The extra cushion that keeps us from sinking, and protects me from having to get a real job, are my “pretirement” savings—my stash from a 4.5-year career at Procter & Gamble. Thanks to some lucky stock picks, those savings have ballooned enough to support us. Barely.

So if we dissect the Richer, Wiser, Happier title, you could say I have the third (happiness) and am slowly progressing toward the second (wisdom), but, in pursuing them, I’ve been sacrificing the first (getting richer).

But the book has me thinking that maybe I can have all three.

Trading Ties for Tampons

Fifteen years ago, if you’d have asked me what I wanted to do for a career, my best guess would have been investing.

I took courses on it at the University of Toronto. That intrigued me enough to read many of the classic investing books during my free time. Then, after graduating, I interned at Deans Knight Capital Management in Vancouver and passed my CFA Level 1. They subsequently offered to take me on full-time.

My runway was clear and ready for takeoff.

But I got off that plane. Helping rich people get richer felt hollow to me. I wanted to work on something that “made the world a better place.” Also, I hated having to wear suits to work.

So instead of playing with Excel in a suit and tie, I took off backpacking in Southeast Asia. Then I detoxed back home in Canada, fired out resumes for five months, and eventually landed a khaki and collared shirt corporate job in Switzerland, helping Procter & Gamble supply the world with diapers, razors, dish soap, and tampons.

I blame my independent streak for where I went from there.

My complete “pretirement” story.

Too Independent?

I did ok in corporate, but didn’t have the single-minded determination and butt-kissing dexterity it took to kick the other crabs aside and climb higher up in the corporate bucket.

So I quit.

Then I attempted to unleash my brilliance by becoming a world-denting starting CEO. I exported blueberries to Mexico, turned maggot fat into cooking oil, took on Uber, and started a hostel. Those (misad-)ventures mostly failed largely due to my lack of understanding of how to market to the masses.

So I settled into blogging about off-the-beaten-path places, actions, and ideas. It only attracts a trickle of attention from fellow free-thinking weirdos. But I don’t mind. The upside of being independent-minded is it prevents me from caring too much about what other people think about me. And it gives me the freedom to follow my curiosity.

Which led me to Richer, Wiser, Happier—and, in a way, back to where I started.

My Type of People

In Richer, Wiser, Happier, William Green writes about the peculiar methods and mindsets of mega-millionaire money managers like Nick Sleep, Mohnish Pabrai, and Joel Greenblatt. I’d never heard of these guys before, but a lot of how Green describes them sounded familiar.

One chapter after the other describes how they:

“…are not like other people. They are iconoclasts, mavericks and misfits who see the world differently and follow their own peculiar path.”

“…are not afraid to question and defy conventional wisdom.”

“…don’t have that tribal gene so they don’t feel the urge to follow a tribe.”

“…willing to be ‘short’ social acceptance and stand apart from the herd.”

And I could go on.

So I will!

The investors Green profiles:

  • exhibit unusual amounts of patience
  • live according to their own inner scorecards
  • love learning
  • seem unusually immune to emotion
  • don’t chase fads, and
  • “are not always endowed with an abundance of social skills.”

I felt like I was reading my horoscope or something. Aside from my deficiency in intelligence compared to these super investors, all these profiles fit me eerily well.

What made this feel less astrological and more scientific was that I had just resurfaced from a deep dive into the psychology of personality. My biggest takeaway was this:

You can’t change how you’re wired, so you’re better off understanding and working with what you’ve got.

“Well,” I figured, “it seems these investors are wired like me. And they’d found a way to get rich off it. Maybe I could, too?”

My Type Of Game

One of the grand poobahs of investing, Charlie Munger, hammered this home into my head with his advice to Green in the book:

“You have to play in a game where you’ve got some unusual talent. If you’re five foot one, you don’t want to play basketball against some guy who’s eight foot three. It’s just too hard. So you’ve got to figure out a game where you have an advantage, and it has to be something that you’re deeply interested in.”

Charlie Munger

While I’m no genetic Giannis Antetokounmpo of investing, I don’t think I’m some five-foot-one schlub either. I’m confident that I have enough of Munger’s requirements—talent and interest—to go semi-pro at the very least.

In any case, I have no desire to become a hall of fame-worthy level billionaire investor who gets profiled in Green’s Richer, Wiser, Happier sequel. A cool ten million would suffice.

This Time Is Different

Yes, I’m aware that “this time is different” are the four most dangerous words in investing.

But from a life trajectory standpoint, “this time is different” seems like an ok motto to live by. It’s optimistic and open-minded. And in this case the difference between me now and my early Deans Knight days is that focusing on investing won’t make me feel hollow anymore.

That’s because:

  1. My blog offsets it. Millions of people have read my posts and thousands subscribe to my Consider This newsletter, so I like to think I’m doing some small part to help them find their own unconventional routes.
  2. I have a wife and son. They aren’t as content to live off of 2 kg bricks of Costco cheddar cheese as I am.

Also, for what little it’s worth, I plan to continue sharing with you my story and lessons here on HowI’mInvesting.com.

It’s a win-win. Or at least a can’t-lose for me. Writing about my investing research and actions improves my thinking, which ought to improve my performance eventually. And if I attract a bit of an audience, that opens up opportunities for more revenue streams.

So I’m confident that focusing more on investing, and writing about it, will make me even richer, wiser, and happier.

And that’s thanks in large part to picking up William Green’s book.

Subscribe to see if I’m still thanking him a few years from now:

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