How to Avoid Losing Everything You Have

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

I have three short announcements before we dive in:

1. I created a referral program that gives you free access to Foundations (my digital library of book notes) if you refer 7 new people to Life Reimagined. You can find your shareable link at the bottom of the email.

2. I added a poll at the end of the newsletter so that you can let me know what you think about the content every week. Your feedback is anonymous.

3. I’m experimenting with a Q&A section of the newsletter where I answer reader questions in an advice-column style. You can find out more info below and submit any questions you have here.

My hope is that these changes will make the newsletter more relevant and interesting for you every week.

🙋‍♂️ I. Get Your Questions Answered

I answer hundreds of questions from readers every year. These questions range from navigating relationship problems to making career decisions to all the fun and not-so-fun stuff that comes with living in this world.

While I enjoy these interactions, most of the exchanges happen in private over email. And recently, a friend pointed out that other readers may have similar questions and benefit from hearing the answers.

I think he’s right, so as an experimental newsletter section, I’m going to answer reader questions.

My idea is to make it like an old-school magazine advice column. Something with stories and style (not a prescriptive to-do list) about how to deal with situations that many of us encounter.

To get things rolling, I’ve created this Life Reimagined Reader Q&A form in the event you have something on your mind that you want to be answered. Moving forward, I’ll include a link to the Q&A form at the bottom of the newsletter.

And as a sneak peek for next week, I’ll be answering the following question from a long-time reader:

📉 II. Losing it All

I saw a story about a guy who put his life savings into a short position on NVIDIA ahead of their earnings call this week. NVIDIA’s stock soared on better-than-expected results, and this guy lost half a million dollars in 24 hours.

A lot of people commenting on the story said some version of, “That guy is an idiot. He deserves to lose money for being so stupid.”

I had a different response. I thought, “Damn, that could have been me. I hope he’s alright and understood the game he was playing.”

As I’ve shared in the past, I got swept up in a costly, 2-year effort to try to beat the market. And as part of my “strategy”, I shorted companies that I thought were overvalued.

Despite being “correct” about many of those companies being overvalued — most now trade 75% below where they were — I lost money on most of my shorts. It turns out that making money with shorts is not so easy.

I never put more than a small fraction of my money into short positions, but I can understand why someone would bet the farm in this way.

If you’re right, you make a lot of money and look like a genius. If Nvidia’s stock had moved the same amount in the other direction, for example, this guy may have never had to work again. That would be nice, right?

But the problem with these types of all-in gambles is that if you get mesmerized by the dream of experiencing the upside case, you can overlook the risk that you’re taking. And with a single click of a button, you can end up in a financial and emotional hellscape.

Unless you have an iron stomach and really know what you’re getting into, it’s possible that you never recover from such a blunder. And these types of blunders, the ones that destroy you internally and externally, are what you must avoid in life.

Because while you can pick yourself up after thousands of small mistakes, there are some mistakes so costly and pernicious that they can alter your sense of self and the trajectory of your life forever.

Of course, I can’t say that the NVIDIA short trader made such a mistake. I have no idea who he is, why he did it, or how this decision will impact his life. He may have a trust fund and be feeling just fine about the loss. Or he may be in the darkest period of his life and not sure how to hang on. I don’t know.

But what I do know is that we all have moments in our lives where we are at risk of making decisions that can sink us. And often, we don’t always know or appreciate that we’re in such a situation.

Consider a decision that thousands of people face every day: being a little tipsy and deciding whether or not to drive home.

You may have driven home safely in a similar state of tipsiness dozens of times before. Perhaps those experiences make you believe that you’re “okay to drive.” You’ve done it many times before, so what’s one more time?

Or maybe your risk sensors are firing today, and you consider for a moment that you could get a DUI, pay a fine, and lose your license. That seems bad, but not that likely. You live 5 miles away and rarely see police in the area, so why pay $20 for an Uber and have to deal with getting the car tomorrow? You decide that it’s best to drive home and take your chances.

And as you’re driving, everything is fine. You’re in control and wondering why you were ever worried. But then you lose focus for a moment and drift into the other lane. Before you know what’s happening, your car is spinning out of control. It eventually comes to a stop and you realize that you hit another car, sending it into a ditch.

You exit the car in shock and a little bruised. But you’re alive and no bones are broken. You walk over to the other car to make sure everyone else is okay and figure out what to do next.

You discover a woman in the driver’s seat who is crying hysterically. Her husband, who was sitting in the passenger seat, is dead.

You get charged, convicted, and sentenced to life in prison for vehicular homicide. For the next 50 years, you’re separated from everyone you love. You replay the events of that night in your head thousands of times.

And you dwell on every detail that led you — a sensible person who tried his best to be a good person — to take an innocent life and end up in prison.

While this scene may seem like something out of a bad movie, it happens to people every day. It happens because people do not take seriously the possibility that something like this could happen to someone like them.

The truth is that these types of nightmare scenarios are seconds away from happening to many of us.

Every time you drive after a few drinks or send a quick text while driving, you’re at risk of such a fate. But how many people do these things all the time without batting an eye? Too many, of course.

A small number of these people suffer consequences that change the trajectory of their lives. And when we hear the stories of these people, we often wonder how they could be so stupid or selfish or whatever we want to call them.

We ignore the fact that we have made similar choices and have simply been lucky to come away unscathed. It never occurs to us to think deeply about how we are just as susceptible to making a bad, seemingly harmless decision that sinks us.

Of course, you can’t spend your life worrying about everything bad that can happen to you. That’s no way to live. And it’s a fool’s errand to think that you can prevent all bad things from happening in your life.

However, for this particularly pernicious class of mistakes that ruins lives, you can at least mitigate the risk of experiencing the worst outcome.

You can decide to never drink or text and drive. You can choose to avoid bets that can bankrupt you. You can decide to wear a helmet while skiing.

These are easy decisions once you’ve accepted that you are just as fallible as the next person and learn to take risks seriously.

But even when we do these things, we are still susceptible. We may be momentarily overcome by exhaustion, anger, or greed that causes us to lower our guard right at the moment that we need it most. It can happen to anyone.

So the next time you hear a story about someone who has ruined his life in some way, remember that in some world not so different from the one you’ve experienced, you could be that person.

🚕 III. Niche Granola Bar I’m Enjoying

If you have never had a Lenka granola bar, you are missing out. I’ve fallen in love with these surprisingly tasty granola bars over the last three months.

I don’t know what Lenka does differently, but their bars taste far better than the dozens of other brands I’ve tried. And one thing I really respect about the company is that they do not try to dupe you into thinking they’re healthy.

They are not healthy. They are guilty, delicious pleasures that deserve to be savored fully in the moment and regretted later if you must badger yourself.

The Peanut Butter & Sea Salt and Peanut Butter & Chocolate are my favorites. Lenka is not widely available at the moment, but I’d be surprised if they weren’t top sellers in major stores in the next few years.

🧠 IV. Something I’m Thinking About

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.