Bonus Points: Contemplating the Cliff


There’s no denying that the world is in an anxious place right now. No matter whether you look outside the window to war and politics or inside your home to increasing prices and shrinking account balances, there are frightening situations all around. Everyone has a pressure point, and it’s enough to make even the most stoic person flinch and start to feel as though they’re standing on the precipice of a bad situation.

An important thing to understand, however, is that while many of the things going on around us are not pleasant they are also not particularly new. Ask your grandfather about the stressful times when he was your age, and you’ll probably gasp at what he experienced. But I bet he also enjoys the time sharing with his grandkids more than you imagine.

That’s in no way meant to diminish the seriousness of the things we’re seeing today, but simply to put the world around us in proper historical context. Life isn’t always easy, yet it goes on. And our overall happiness is largely determined not by how we coast through the good days without worry but by how we productively deal with the hard times.

That’s easier said than done, of course. And I certainly don’t have all of the answers. But to contribute towards that goal in my own small way, here’s a collection of links to articles I’ve been thinking more about lately.

Expertise Does Not Shield You From Failure

Psychology, Beginner

My news feed recently contained a trio of interesting articles that had little to do with finance but shared a theme that is quite universal — the failure of the best of us. But rather than the typical stories of deliberate fraud and tragic mistakes that are sadly all too common, these are a more nuanced grouping that taken as a whole offer an interesting perspective on something many of us take for granted.


So if you think you have everything figured out or have hired the smartest minds to do it for you, read on. You may learn something new about risk and adjust your expectations in the process.

Remembering Harry Markowitz

Psychology, Beginner, Theory

The world lost a true investing legend recently when Harry Markowitz passed away at the wise old age of 95. Markowitz is widely known as the father of modern portfolio theory, and it’s impossible to overstate his significance not only to my own outlook on investing but also to the entire modern industry of portfolio management. He was a good man and a brilliant thinker, and his unique insights will continue to influence us for a very long time.

How Investing Personality Types Frame Your Money Perspective


It’s interesting how the simplest question can sometimes cut straight to a complex reality that is deceptively difficult to explain. For example, I recently received a nice email from a new Portfolio Charts visitor that went something like this:

“I’m new to stocks, kind of. I know crypto decently. I’d love to know in layman’s terms what this site is about exactly? To buy stocks that are historically low and going to go back to its high someday?”

While that may seem like a softball on the surface, the thing that tripped me up is the phrasing. I recognize that the reference to buying stocks low is an important social cue that provides insight into the investing mindset of the writer. And I know from experience that it’s not good enough to reply with just any boilerplate summary, as presenting new information in terms people can relate to is critical to effective communication.

So we’ll need to go deeper. How deep? Lean back, relax, and let’s talk about the concept of investing personality types.

Bonus Points: Failing Early And Often


Today SpaceX launched its new and massive Starship rocket on its first test flight, and the event ended with a flourish. By “flourish” I mean it exploded in spectacular fashion.

One of the more confusing things that seems to be tripping up people unfamiliar with such tests is the reaction of SpaceX employees on the live feed. At the moment when the rocket experienced its “rapid unscheduled disassembly”, rather than hanging their heads in failure the entire team erupted in applause. It’s easy to wonder what world they’re living in.

But engineers watching the event understood. The greatest design achievements are never achieved flawlessly in a single step. If they were, they wouldn’t be such great achievements! So rather than planning forever for a reality full of unknown variables that we’ll never truly understand until we finally hit the launch button, we celebrate failures for what we learn. And we press on creating something even better.

If you’ve ever found yourself evaluating portfolio ideas for the thousandth time without making a decision, stop for a moment to think about the flight crew cheering their work going up in flames. I’m not saying you should make hasty financial decisions. Be smart about it and start small. But at the same time, don’t be afraid to try or regretful when things don’t go as planned. Embrace each small failure as a required educational step towards your long-term success, and before you know it you’ll be enjoying the view from orbit.

Learning the Hard Way: 2022 Portfolio Rankings

Psychology, Portfolio Talk

Now that we’ve had a few weeks to recover from the holidays and start planning for the new year to come, it seems like an appropriate time to revisit the events that made 2022 such a uniquely memorable year in the investing world. It ended up one of the worst years on record and I imagine most people are ready to move on. But before we all pick ourselves up and start anew after the carnage, I think it’s important to put what we all experienced into proper historical context.

Sometimes the hardest lessons are the most educational.

How did each portfolio option fare in a truly tough time to invest? How does this past year compare to other bad years that came before? And what can we learn to affect our path forward?

I’ve got the data for all of the 2022 portfolio rankings. So let’s find out.

Bonus Points: A Time to be Thankful


The whole world is watching the ongoing financial carnage resulting from the FTX collapse, and every revelation is truly a sight to behold. I’m definitely working on my own article discussing the situation, but an extended writeup about greed, corruption, and downright stupidity just seems painfully out of place during the week of Thanksgiving. To highlight the worst in the world completely misses the point.

So in honor of my favorite holiday, let’s take a moment to turn off the inflammatory news and appreciate the good things in life. You only get one, so don’t waste it being angry or disappointed.

Happy Thanksgiving!

Bonus Points: Election Hangover Edition


The Tuesday after the first Monday in November seems arbitrarily ordinary when you write it out like that, but for US investors it carries a unique importance. It’s election day. That day came and went on Tuesday to much stress and fanfare depending on whether your favorite candidates or ballot measures won or lost. I don’t know about you, but I could use a break.

The beauty of asset allocation is that it transcends party affiliation. Sure, politics affects markets. But diversification is there to help no matter who is in charge, and the sovereign law of compound interest doesn’t care who the nightly news is talking about today. Wise portfolio construction is the level head that steadies the ship in both calm and stormy seas.

So as you detox from the political bender affecting all of us, maybe take a moment to appreciate the stable things in life. Find the right portfolio, turn off the news, and take a walk outside. In both politics and money, the quiet voice of calm clarity requires focus to hear over the din of loud, attention-seeking voices. But it’s worth the effort.

Moving Forward One Step at a Time


I’m moving next week, and even though I still have a few days to go I’m already pretty spent. From the decision to find a new place to the painfully long search and ultimately to the final move, it consumes so much physical and mental energy that at some point you inevitably wonder if it’s really all worth it. As I think past the near-term pain and anxiety to the post-move future with more space, a nice view, and significantly lower rent, I know things will eventually work out and we’ll look back fondly on our good choice. But that still doesn’t diminish the reality that moving is hard.

In a moment of brief silence lost in a day full of errands, it struck me that I’ve felt this way before. And it wasn’t even in another physical move like the one I’m caught up in now. Now that I think about it, making a big financial decision can bring out a lot of the same emotions as changing the place you call home.