Hello friends, my name is Jack Raines. I will be writing on Alpha’s platform once a week. I also write a newsletter, Young Money, where I cover all things investing, finance, and careers. Hope you guys enjoy today’s piece!

It has been a weird year for everyone, but it’s been an especially weird one for me. I quit a stable job on a whim. I lived out of a backpack in 19 countries for four months. I lost $120,000 in a day. I started working for an anonymous meme page. I had articles read by tens of thousands of internet strangers. I was single for the first time in years. I battled demons that I never knew I had.

Here is some stuff that I’ve been thinking. Welcome to my brain.

Doing What You’re “Supposed to Do” Is Overrated

For 23 years or so, I was the king of doing what “I was supposed to do”.

4.0 with two majors, football team captain, good finance job out of college. Accepted to a top-5 business school. You know the drill. Everything was a steppingstone to the next thing. As a confident (arrogant?) 22-year-old with the world seemingly at my fingertips, there was no higher calling than climbing up the corporate ladder, earning a top five MBA, working for a cushy MBB consulting firm, landing a C-suite job with a Fortune 500 company, and becoming CEO.

Or put more eloquently, chasing money and clout. Talk about vanity, right?

Not that my priorities were atypical. There is an entire generation of intelligent-but-unsure college graduates who rush to investment banks and consulting firms because they offer high-paying prestigious jobs that serve as great steppingstones. Are you passionate about these fields? Of course not. But who cares?

Your decision-making matrix is simple: Will this help me “advance” my career. And life becomes a never-ending pursuit of the next level up.

And there’s this “Oh Shit” moment when you finally get that dream job, and it’s not all it’s cracked up to be. 

When you hit that “Oh Shit” moment, you have two options. You can ignore that “Oh Shit” moment, and double down on the job that you hate because a little more money or prestige will certainly solve your problems. Or you can embrace that “Oh Shit” moment and go figure out what you actually want to do with your life.

Both are difficult, but only the latter offers a chance at something better. Besides, if you win the rat race, you’re still a rat. Find a race worth competing in.

Perspective

“When we truly latch on to the fact that we are going to die at some point in time, we have more presence in this one.” – Matthew McConaughey

There are uncomfortable truths in life. The stuff that you want to hide from. This is one of those truths. You always kind of know it, but you don’t think about it. Until it hits you.  That moment hit me this year. And it changed everything. 

Life was a never-ending cycle: Wake up, work, go about my routine, go to sleep. And then I blink, and a week has gone by. A month. A year. And every day was the same damn thing. But I’m getting older. And people started advancing in their careers. Getting married. Having kids.

And I was just staring at numbers on screens. Trading stocks. Updating PowerPoints. Praying that 5 days go by fast so I could enjoy the last 2 each week. When you aren’t conscious of the sands of time slowly trickling down your hourglass, you can get trapped in this cycle of routine. Existing, but not living. Being a passenger in your own life, instead of the driver. 

And then one day, I woke up and thought, “What am I doing?”

The funny thing about realizing that this life will, at some point, end, is that you become acutely aware of how you are spending your time. And you’ll probably realize that you didn’t like how you were spending your time, which will lead to you making some difficult, but important changes in your life. Which brings me to another McConaughey quote: “I didn’t want to miss my twenties preparing for the rest of my life.”

I’m 24. There’s a lot of things you can do at 24 that you really can’t do later. Because at 24 I’m single with no house, no kids, and no major responsibilities. But at some point, I will (hopefully) have those things.

But the things that I want to do before I have those responsibilities? I figure I should do them now. After all, no 80-year-olds will be looking back fondly at the Excel model they built in their 20s. 

I knew I wasn’t particularly happy in my job, and I could afford to take risks right now. I knew I enjoyed writing, and the internet is a hell of an audience. And I knew there were a lot of cool places that I wanted to see.

So I started writing 24/7, and I quit my job to backpack Europe. Which brings me to my next point.

There is Never a Good Time to Do Anything

The number one thing I heard when I told people that I was going to Europe: “That sounds like so much fun. I wish I could do that, but I’ll go someday.”

Here’s another uncomfortable truth: someday isn’t a day. That country you want to visit? Business you want to start? Risk you want to take? There will never be a convenient time to do it. You can waste years “waiting”, or you can just go do that shit.

Most people won’t take that leap. Either they tell themselves that they will take that risk “one day” (a day that never comes), or they would rather exist in the fantasy realm of possibilities not attempted than the reality of attempts that could possibly fail.

A life deficient in risks is a dangerous way to live, because as time goes on, you’ll find yourself regretting missed opportunities far more than failures. But it’s difficult to realize that in the present moment. It’s only down the road, when you realize that you’re out of time to do all of the things that you wanted to do, when the weight of your reality comes crashing down on you.

I want a life full of failures. And struggles. And stories. Because it’s not going to be perfect. And often it will be terrifying. But It’s certainly better than a life spent wondering, “What if?”

Opportunity Cost Is Everything

Productivity consultant David Allen once said, “You can do anything, but not everything.” That’s the damn truth. I had never really thought about that until I went to Europe. This is most definitely a first-world problem, but I was overwhelmed by choice. When you can get anywhere within three hours, how the hell do you decide where to go? Because you can’t see every part of Europe in a few months. And if you try to, you won’t stay anywhere long enough to actually experience it.

And that’s life. A decision to do anything is inherently a decision not to do some other thing. 

Choosing one career path is not choosing 100 others.

Choosing a partner is not choosing a billion others.

100 hours spent working this week is time not spent with friends and family.

We all face these choices every day, and the choices we make shape our lives. However, not making a choice is, in itself, a choice too. Choosing not to do anything because you don’t know the right path is the worst choice of all, because your opportunity cost becomes everything. The longer you spend “undecided”, the more that cost grows.

Choose wisely, but choose quickly.

Counting Dollars Is a Vain Game

Lawrence Yeo wrote the best article that I’ve read all year: The Nothingness of Money. Go read that article. Then read it again a few more times (and while you’re at it, read everything that he’s written).

This graphic came from that article.

Money is dangerous, because it makes such an attractive scoreboard. It is easy to track. A simple tool to compare ourselves with others. But there is no upper limit to money. And if money is your way of keeping score with the world, you will find yourself in a game that you can’t win.

And you’ll want to quit. To step out of the “money game”.

But that’s not going to happen. A nicotine addict will keep smoking. An alcoholic will keep drinking. An adulterer will keep cheating. When money has been the scoreboard for your entire career, money is all you know. And you won’t be able to escape this infinite game.

But time isn’t infinite. It’s quite finite. Unfortunately, most people don’t realize just how finite time is, and how little that vast sum of money actually means, until their time is almost up. That graph that Lawrence created? It speaks volumes.

Inertia

I started writing online because no one would pay me to write for them. I applied to 14 writing-related jobs. I received 14 rejections. So I wrote my own articles and posted about them on Twitter, Instagram, and LinkedIn. And maybe I would gain a subscriber or 2. But that was it. For 3.5 months, I was throwing words into the void, and receiving nothing in return.

But I kept writing, and writing, and writing. And then one day in early November, one piece gained traction. And I gained more than 100 subscribers. Then another, and 250 subscribers. And then the momentum really got moving.

And then opportunities began materializing. And my network started growing. And hundreds of thousands of people have now read stuff that I’ve written online. And I see how this might just be a viable career path for me. And it’s only been six months. I’m just getting started.

Inertia is frustrating because it takes so much energy to get moving. And for a long time, your efforts will feel useless. You won’t see anything happening. But those reps are quietly compounding. And the longer that you can compound, the higher the likelihood that you’ll start seeing success. Inertia means that objects at rest tend to stay at rest. But objects in motion tend to stay in motion. If you can stay in the game long enough, inertia flips from being your biggest obstacle to your best friend.

On Writing

Writing gives me a medium for making sense of the chaotic, jumbled thoughts in my head. It gives me an opportunity to create something new, and share it with the world. It gives me timestamps of what I was thinking at different points in my life.

I write the things that I simply can’t not write. I write about things that anger me. And excite me. And set my soul on fire. I write to make sense of chaotic markets. To help me understand my own impulses with money and people. To hopefully warn others of perils that they may not see. To share stories of my life with others.

Writing has been a highlight of my life in 2021, and I look forward to seeing where it takes me in 2022.

Closing

Making changes is hard. Remaining unhappy with your current situation is hard. Luckily, we get to choose our hard.

All of those things that you want to do “someday”? Those changes you wanted to make in 2021? No one is going to do it for you. The timing isn’t going to be right. But it doesn’t have to be right. You can change your life tomorrow. The only thing stopping you is the fifth word of this sentence. 

Everything that I write online is written for myself. This is no different. My biggest fear is being a passenger in my own life, watching the world go by out the window. So here’s to more risks. More failures. And more stories. Because in 60 years, those risks and failures and stories will be worth infinitely more than any amount of money anyway.

-Jack

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