I finished Jack Raines’s Young Money in a week. He is a borderline Gen Zer (cusper?) but I think his book was a good insight into many of the challenges as well as the opportunities his generation will face. Somehow he traveled without a plan, got into day trading, went to business school, and blew up his life several times in his 20s. He published this book as he was turning 30. It is an impressive arc.
But also, Jack is a fun writer. He does a good job of telling his story and sharing his own failures, questions, and decisions along the way. I found it fascinating because he very much went through the same waking-up experience I did in my early thirties, but he did it in his early 20s. I’ve been noticing that many of my readers of The Pathless Path are making bigger shifts earlier in life, and this book will be a good addition for them.
At 23, he looked ahead at his career path (literally the path I followed mindlessly for ten years) and said, hmm, maybe that isn’t the best use of my time right now.
He took a step back, realized that when he was older he might actually wish to work more, and decided that, as Kevin Kelly urges, it was time to “goof off.”
I honestly wish I had a book like this in my twenties, because it would have helped me realize:
- The kind of adventures you can go on in your twenties expire because you just don’t want to do the kind of bare-bones travel later in life
- There are costs to narrowly pursuing success at work as your core quest
- There are many more possibilities for a modern career and being without a job may actually enable you to be more ambitious over the long term because you can quickly try new kinds of work that don’t require being employed first.
I did wake up to many of these things, but it took me quite a bit longer than Jack.
I’ve also loved watching Jack share his book and have so much fun with it. I’ve always been saddened by how little fun people have with their books.
His chapter on apathy was one of my favorites, and when I texted him about this, he told me that he had to rewrite it several times because he was disappointed with his writing and felt it wasn’t honest.
The final book was well done. It was honest, clear, and fun to read. If you are in your 20s or 30s and like memoirish non-fiction, you’ll enjoy this book.
Highlights
The “Oh, shit” moment
Once you have that realization that time is flying by, it’s impossible to “go back” to when the passage of time wasn’t a concern. The more you try to push it out of your mind, the more it forces itself to the forefront of your consciousness. You can’t re-create an ignorance you previously experienced, because choosing to ignore the reality of your finite existence still acknowledges that finiteness.
Life before your Oh, shit moment is simple: You’re so busy living that you pay no heed to what you’re doing with your life. But after experiencing your Oh, shit moment, you become hyperaware of how you’re spending every moment and how you spent the moments that you’ll never get back.
Truthfully, however, this was the most well-thought-out, calculated decision of twenty-four-year-old Jack’s life. Although I didn’t realize it at the moment, this marked the first time I had considered the opportunity cost of how I was spending my time, and I adjusted my life accordingly.
Spending money while you’re young
Money, on its own, is inherently worthless. Its value comes from what you eventually exchange it for, and a retirement calculator can’t tell you if you would experience more joy spending that $10,000 at twenty-four than you would spending $220,000 at sixty-four. There’s an opportunity cost associated with not spending that money: the experiences forgone as a result of your thrift. Think about it this way: Would you, at sixty-four, spend $220,000 to have the opportunity to once again spend that $10,000 as a twenty-four-year-old? If so, that money would have been better spent when you were young.
Life in stages
The deal that I struck with myself before quitting my job in 2021 was that I would live it up over the next three years, knowing that, when it came time to shift my priorities, I could do so with no regrets: “Yes! I took the trip. I lived the adventure. I have the stories. Now, I can move on to the next stage.”
There are no “good” jobs and “bad” jobs, there are simply jobs that match your lifestyle goals and jobs that don’t. I was in a stage of life where “fun” was more important than “finances,” so I needed a job that offered flexibility.
Sooner or later, everyone has to grow up. The only question is will you determine what that growing up looks like, or will growing up simply happen to you? At twenty-seven, I felt like I was running out of time to make that choice.
The issue was that I got particularly good at a thing, writing, in my previous stage of life, where it served nicely as my primary form of compensation when I wanted flexibility. After writing for three years, my writing got momentum, and it became easier and easier for me to continue being a “writer” as I approached a new life stage.
Think about it this way: “Future you” will never regret “current you” making the most of your current stage of life, even after your desires or circumstances change.
Performative work and apathy
And many of these white-collar jobs are mind-numbingly simple. During my first job, there were weeks in which I “worked” five to ten hours but I was always pretending to “work,” either by moving my mouse to look active or tinkering with files, models, and decks that didn’t really need tinkering. From talking to friends and acquaintances, my experience was more the norm than the exception. Performative work is the backbone of the modern educated labor force.
The antidote to apathy is replacing optionality with necessity by defining “the only things that matter” in each phase of your life. The key to figuring out “what matters” in each stage is working backward from death.
The problem with chasing status for status’s sake is that you spend all of your time optimizing for outcomes that, upon achieving them, you just might realize you never cared about in the first place.
Experiments and infinite games
The nice thing about experiments is that they don’t have to be “jobs” to be valuable. Experiments are just differentiated experiences that reveal truths to you about yourself. I would argue that most of your valuable experiments during this period of life shouldn’t be jobs. If you spend an average of two years at each job after graduating from college, you experience three, maybe four, jobs before you’re thirty. That’s not a lot of data points to determine “what matters” to you. By stacking jobs and nonjob experiments, however, you can more readily paint a full picture of what works for you and what doesn’t.
When thousands of equally competitive and talented individuals are competing on the same field, the finite players who pursued this game only for status or money or some other extrinsic reward will flame out years before the infinite players. Extrinsic motivation lacks the duration of playing for the love of the game.
Infinite games are simply the pursuits that allow you to be your most authentic self. If you find a job where you are encouraged to express, rather than repress, the innate things that make you “you,” then you’re on the right track. But it’s only through experimentation that you can understand who the “real you” actually is.
This trip was formative because it marked the first time that I realized that it was my responsibility, and mine alone, to pursue the life that I desired, even if those desires contradicted what I felt like I was “supposed to do.”