Reset

Regret Is an Unreliable Emotion

I have long believed that thinking about regret is a powerful motivator for action. When you're feeling indecisive, trying to figure out if a particular step is a good one, consider how you'll feel if you don't take the step. Often this leads you to what seems like the right direction.

But while mental models can be helpful, most of them also have limits. Lately I've realized there's a flaw in the logic of focusing your attention on the avoidance of regrets. Simply put, regret is an unreliable emotion.

Think about that for a moment—what does it mean?

It means, in short, that regret is both difficult to anticipate and even harder to characterize in retrospect. If you feel certain about your choices in either direction—either looking back or looking forward—you may be basing your interpretations on selectively chosen information.

Read More

The Greatest Story Ever Sold 💵

Two weeks ago, I wrote about how money mistakes are temporary. My main argument was that unlike other kinds of mistakes, money mistakes rarely have permanent consequences.

I'll return to that in this post, but first let's consider a few things that have happened this month:

  • We've all been hearing about NFTs, also known as "non-fungible tokens," also known as digital art that can be reproduced over and over but sells for a ton of money. The NBA has sold $230 million on these intangible "items." An artist sold one for $69 million the other day, and I'm sure that record will be broken soon.
  • The price of a single Bitcoin, another modern invention, has risen to more than $60,000. Like NFTs, Bitcoin is also completely digital. There is no such thing as "a Bitcoin" you can carry in your pocket or store in your safe deposit box at the bank. Everyone who trades Bitcoin or other digital currencies simply accepts that it exists.
  • The U.S. government has passed a law enacting a $1.9 trillion stimulus package. Put another way, the U.S. government has printed $1.9 trillion more dollars. This was on top of another $2 trillion they printed last March. And presumably there's more where that came from!

Read More

Money Mistakes Are Temporary

A common TV trope features someone who's down on their luck and forced to borrow from someone with questionable moral scruples: a loan shark, the Mafia, a representative from Wells Fargo.

As fate would have it, they fall further and further behind, until they're in an even greater bind. Soon they're being pursued by the loan shark, who threatens to break their legs, or by Wells Fargo, which forces them to remain on hold for hours. The rest of the story unfolds as the protagonist desperately tries to resolve their dilemma. What will they do? How will they get the money? 

"Getting the money" makes for a good plot foundation, since money is something that everyone wants. And when you don't have it, it becomes all that you think about.

But what if you didn't have to "get the money"? What if you just decided to not care?

Read More

The Real Imposter Is the Part of You That Hesitates

Hesitation What holds people back from making a bold choice or following a dream?

When you ask, often they’ll point to the lack of knowledge. They simply aren’t sure what to do, so they wait for someone to give them a step-by-step plan.

Other times, they mention a lack of resources or some kind of access—perhaps they need money, or maybe they're holding out on a specific connection or certification.

After writing and sharing online for more than a decade, however, I’m pretty sure that these cases are the minority. Instead, the thing that stops more people than anything else is internal resistance.

Read More

New Year, Same You

What if, instead of “New Year, New You,” you decided you were satisfied with the course you had already set?

What if you're already happy with who you are?

This doesn’t have to mean you have to stop improving. Change and growth are healthy. It just means: if you were already doing the right things in the “old” year—wouldn’t you want to keep doing them?

For me, challenge is one of my values. I want to set big goals and attempt hard things. But it's not a new value; it’s one I’ve had for a while. If I ever lose interest in challenging myself, I suppose that would be a new me. It’s just not a version of myself I’m remotely interested in.

Two years ago, I was in a dark place and feeling uncertain about a lot of things. Since then, I’ve made a number of changes in my life, both large and small. Many, many times in the months that have passed, I’ve looked up from whatever I’ve been doing with a sense of wonder.

I can’t believe I’m here, I think. I’m so glad I was willing to walk through that dark place.

Read More

The Three Conditions for Making Ordinary Magic

Magic is all around you. Maybe you’ve even made some magic of your own.

What you might not realize is that there’s a formula for such a thing. This formula requires three conditions to be met before magic can occur:

1. You have a crazy idea. 2. You can’t stop thinking about the crazy idea. 3. You decide to do something about it.

Note that all three conditions need to be met. Merely meeting one or two of them isn’t sufficient.

Read More

168 Hours: What I’ve Learned Tracking Every 15 Minutes of My Week

For the past two weeks I’ve been tracking every 15 minute interval of my life. I’ve borrowed this time-tracking practice from Laura Vanderkam, who writes helpful books including 168 Hours, which outlines the practice in a lot of detail.

One of Laura’s principles is that “you have more time than you think.” Through her research, she’s found that most people who claim to work more than 50 hours a week tend to over report their work hours, sometimes dramatically so. In other words, a lot of the time they think they’re working, they’re not. It’s not just that their priorities are out of order; they also waste a lot of time.

Read More

The Truth Is a Terrible Thing, But Not Compared to Falsehood

Reality isn’t just what someone tells you. They could be lying to you, or they just might be speaking from their own limited perspective. We know this, right? We can't just accept at face value everything we hear.

But reality also isn’t just what you tell yourself, at least not if you're trying to avoid something. You too have a limited perspective. You have weaknesses, insecurities, and fears that can be surprisingly resilient in their pursuit of a false narrative.

Reality is at least somewhat objective, at least when it comes to basic facts. Sure, you can interpret those facts as you’d like, but facts are facts.

When you choose to persistently believe something that you know, deep down, might not actually be true, you’re lying to the most important person in your life: yourself.

Read More

To Win the Lottery, Buy a Ticket and Never Check the Numbers

I recently bought my first lottery ticket in something like 15 years. The purchase happened on a whim, as I was walking down the street in California. When I passed by a minimart, I thought, “I should go inside and buy a lottery ticket.” And so I did.

To a lottery novice such as myself, the process was a little confusing. Apparently there’s not just one lottery... there are many! Not being familiar with the pros and cons of various options, I asked the clerk for the cheapest one.

I bought the ticket on a lark and didn’t really have a plan at first. But then, before I left the store, I knew what I would do next: nothing at all. I’d hold on to the ticket but never check the numbers to see if I’d won.

Read More

Don’t Feel Pressured To Find Your Life’s Purpose At Age 21

I don't think you're supposed to know your true passion or purpose right away. It tends to emerge as you embark on different paths.

It's good that you're frustrated—it shows that you understand the importance of the search. But I think the best thing you can do is be open and explore different paths. The truest one tends to appear as you go along, not before you start.

At least that's how it was for me. From a young age I felt exactly what you describe: the idea that I was just pushing my life along with no north star.

Read More

The Importance of Having a Breakdown, AKA “What Happened to the Annual Review”

What can I say about the Annual Review process that I’ve completed without fail for more than a decade?

This year, I gave up on it and walked away.

Well, not quite—that would be an exaggeration. But to be fully honest (and we shall return to this phrase again), I had a hard time facing it. Eventually I was able to make some progress, which I’ll note below, but the overall sense was one of sadness.

Last year was hard, too. And there have been other hard years. This time, however, felt nearly insurmountable.

A challenge became a struggle. The struggle became a crisis, and the crisis became, well, something that approaches a total breakdown.

Read More

2017 Annual Review: How to Evaluate Your Life Even When You’re Feeling Sad

Last year I resisted my Annual Review for the first time in 10 years. This year, what can I say... I guess it’s the second wave of resistance.

Over the past month I’ve entered a season of wandering in the wilderness. I don’t want to sound overly-mopey, so I’ll spare you the details. I know I’ll get through it at some point; it’s just hard to celebrate accomplishments or feel festive at the moment.

There are still several reasons why I’m going to proceed with the review...

Read More

Feeling sad on the holidays? Me too. Here’s all I know how to do.

clem-onojeghuo-178228 Maybe you like hearing Christmas music in September. Maybe you can’t get enough of Rudolph's story of triumph over reindeer bullying. And let's all pour another glass of egg nog!

If you’re wearing matching sweaters while stringing lights and singing carols with your family, good for you. I really do mean it. Take joy whenever and however you can.

The thing is, not everyone feels joyful this season. In fact, not everyone likes the holidays in general. Some of us actively dread this season, because it tends to correspond with seasons of sadness.

Sometimes these seasons of sadness are connected to specific events, and sometimes they aren’t.

Read More

When You’re Stuck in a Hole, Look for Someone to Join You: A Lesson in Empathy

A man is walking down a street when he falls in a hole. The walls are so steep he can’t get out.

A doctor passes by and the man shouts up, “Hey you! Can you help me out?” The doctor writes a prescription, throws it down in the hole, and moves on.

Then a priest comes along and the man shouts up, “Father, I’m down in this hole. Can you help me out?” The priest writes out a prayer, throws it down in the hole, and moves on.

Then a friend walks by. “Hey, it’s me," the man calls out. "Can you help?” And then the friend jumps in the hole...

Read More