Life Is a Stage-Specific Endeavor.
An excerpt from my new book, Young Money. Pre-order your copy today, book goes live August 4th!
This blog is an excerpt from my first book: Young Money: A Field Guide to Wealth and Purpose in Your Twenties. I wrote 270 pages on status games, opportunity costs, and the stage-specificity of life; topics that I think are particularly timely today. To read the rest of the chapter (and the full book!), order your copy below:
Also, I’ll be live with Scott Galloway on Substack at 3:15 ET today! Come tune in.
In late September 2021, I fell asleep in the back row of a FlixBus in Sevilla, Spain, and woke up four hours later in Lagos, Portugal.
Sitting above a cliff just outside the mouth of the Mediterranean, Lagos could be mistaken for a Greek island town with its whitewashed limestone buildings, scents of fresh scallops and crabs wafting through the air, and congregation of drunken British twenty-somethings swarming the area in their hopeless attempts to tan their pale complexions in the Iberian sun.
Being the budget-conscious twenty-four-year-old that I was, I had booked five nights at the Rising Cock hostel for a total of $100.
A classy establishment, the Rising Cock’s amenities included fresh sheets and towels every three days, Wi- Fi that worked 85 percent of the time, and a fifty-year-old Portuguese woman named “Mama” who brewed lemon-tea hangover cures and cooked homemade crepes each morning.
Although hostel amenities can be lackluster, hostel culture is second to none. When you’re staying at a hostel, it doesn’t matter what you, or your parents, do for a living. It doesn’t matter if you’re a trust-fund nepo baby with a nine-figure net worth or a broke university student from Madrid who scraped together enough money for two train tickets and ten nights in a bunk bed. At the Rising Cock, you are just another twentysomething traveler living out of a backpack who wants to party with his new friends.
A few of my favorite characters from the Rising Cock:
My roommates Elliot and Chris: two late-twenties British playboys who loved to rave, surf, and participate in any other activities that didn’t require them to wear shirts.
James: a twenty-eight-year-old Australian who, after getting stuck in France during the pandemic, decided that spending $5,000 to fly back to Australia wasn’t worth it and opted for a new life in Europe. (His girlfriend, who still lived in Melbourne, proceeded to dump him. He proceeded to indulge in exactly the type of lifestyle you’d expect from a hot, single, twenty-eight-year-old Australian nomad.)
Mike, a twenty-four-year-old Canadian working remotely from Lisbon, with whom I would, four months later, travel to Argentina for three months.
Anna, a smokeshow of a Norwegian girl whose high volume of travel-centric Instagram posts in the months following Lagos gave me serious doubts about her claim that she was in “law school.”
But no one made a stronger impression on me than another American, named Simon.
On Friday evening, after donning my go-to bar-fit for this trip (sneakers, sweatshirt, jeans), I headed to the Irish pub nearby for stop one of God-knows-how-many stops on our hostel’s bar crawl around town. This bar matched every other “Irish pub” in tourist hot spots. It was a dimly lit establishment with sticky wooden floors and posters of Liverpool FC plastered across the walls. The bartender, who could have been anywhere from twenty-two to thirty-seven, was sporting a man bun, a couple of ear piercings, and a Hawaiian shirt unbuttoned to his navel. He was preoccupied with giving free shots to girls who could have been anywhere from seventeen to twenty-seven. And, of course, “Mr. Brightside” by the Killers was blasting through the speakers.
While hunched over the bar trying (unsuccessfully) to make eye contact with the ambiguously aged bartender, who was far more interested in an ambiguously aged Dutch girl, I started chatting with Simon. Every travel/hostel conversation starts off the same:
“Where are you from?”
“How long are you in town?”
“We should go kayaking/explore a museum/other ____ thing tomorrow.”
“What’s your WhatsApp?”
“Oh, sorry, I forgot that you’re American too. Thank God; let’s use iMessage.”
I told Simon that I was twenty-four, from Atlanta, and planning to travel for roughly a year before moving to New York for business school. Simon was in his early thirties, living in Chicago, and taking a few months off between jobs to see the world.
I finally caught the bartender’s attention and ordered two Guinnesses, and Simon and I grabbed a table in the back of the bar. Then we ordered two more Guinnesses. Then two more, at which point we reached my favorite part of the night: a heart-to-heart conversation with a stranger I’d just met two hours ago.
There’s this implicit, shared trust between individuals who willingly book a five-night stay in bunk beds in a Portuguese beach town when both parties are aware that you have, at most, a week to hang out before you go your separate ways, never to see each other again.
As a result, the typical multi-month friendship-development cycle that exists in the real world is condensed into a three-day sprint where, within seventy-two hours of meeting a stranger, you learn some of their life’s most intimate details. There’s something cathartic about sharing your life’s regrets, tales of heartbreak, and worries about the future with another American who wanted to get drunk in southern Portugal at the end of the summer.
Between drinks three and four, Simon asked what I was doing in Lagos, and I explained how a few months earlier, I came to the realization that I was wasting my twenties answering Zoom calls and editing Excel and PowerPoint documents from my living room. I wanted to spend a year traveling and seeing as much of the world as possible while I was young.
Simon nodded his head knowingly while I shared my story, and as he finished Guinness number four, I reversed the question:
“So what are you doing in Lagos?”
His answer stuck with me for months.
“When I graduated from college, I was worried about one thing and one thing only: making money. I didn’t grow up rich, and for the last ten years, the only thing in my life that really mattered was financial stability. I figured that once I had saved enough money, I could take my foot off the gas and live a little.
Well, guess what? I made the money, I took my foot off the gas, and now I’m spending a few months traveling before I start my next thing. But all I can think is where did the last ten years go?
It feels like I missed an opportunity to live a little. This hostel thing is fun, but man, it would have been more fun five years ago. It feels like I missed the window to make the most out of spontaneous stuff like this. And I wanted some of my friends to travel with me, but my friends don’t have the flexibility to ‘live a little.’ They’re married, they have kids, they can’t take a spontaneous trip. And that’s fine. I get it. I just wish I’d done this trip sooner. It’s still fun, it’s really fun, but I would have enjoyed this so much more a few years earlier.”
The conversation soon reverted back to more pressing topics, such as “Have you said ‘hey’ to the Norwegian girl from our hostel?,” but the next morning, I couldn’t stop thinking about Simon’s story. Simon had described the stage-specificity of life, and his regrets confirmed my decision to make the leap and take the trip now, before the opportunity slipped away.
To read the full chapter (and book!), order your copy below:
When you’re young, you have several advantages over your older counterparts: You are the hottest you’ll ever be, you have a kick-ass metabolism, you don’t yet have real responsibilities like a mortgage or your child’s tuition, you still view life as an adventure full of unknown possibilities, living frugally isn’t seen as a sign of failure, you can travel cheaply, and your required cash flow is the price of rent for your room in a three-bedroom, one-bathroom apartment with two of your best friends.
But the biggest advantage the young person has is optionality.
Thanks to a low burn rate and lack of real responsibilities, you have the freedom to live anywhere, do anything, and change where you’re living and what you’re doing on a whim. Your one disadvantage, however, is your lack of money. When you are optionality rich and cash poor, the idea of trading that optionality for money is quite seductive.
I have a few friends who are, or who used to be, investment bankers in New York. Why does one become a banker? Because it’s one of few predictable occupations that will pay a young person a guaranteed $200,000+ income in their twenties.
Investment banking is, obviously, a popular career choice for MBA students, but one of the more interesting things I noticed during business school was that my classmates who joined investment banks out of undergrad would commit seppuku before ever returning to a bank.
As a naive kid from the South who had never heard of “investment banking” until he got into business school, I asked my buddy Antonio, who had spent his first two years out of undergrad as a banking analyst at Goldman Sachs, why he was so dismissive of the job. His answer was bleak:
“I remember, probably eighteen months into my job, we were going on two weeks straight of late-nighters in the office. Like, staying until at least two a.m. each night for client demands. We had this VP on our team, a German guy. He was probably thirty, and he had been at Goldman for eight years at that point. It was, I don’t know, one thirty in the morning. The rest of the analysts and I were revising our model for the tenth time when we heard something across the room shatter as our VP screamed, ‘What’s the point! I’ve been here for eight years! What’s the point?’ “And then, the next morning, all of us, including the VP, were all back in the office at ten a.m. as if nothing had happened.
This guy spent a decade with Goldman, and there he was, at thirty, still in the office with all of us at one thirty in the morning. After that, I knew that I was going to bounce after I hit my two years. No amount of money could convince me to live like that.”
How does one end up in such a position that at thirty, they find themselves screaming in an office filled with startled twenty-three-year-olds? By selling eight years of your life for a check.
The Goldman banker likely told himself that he was simply postponing his other desires for a “few years” for the sake of a steady income, implying that after a lucrative bonus or four, he would have enough money to “buy back” the years he lost to the firm. But sacrificing time for money is a Faustian bargain, especially during one’s youth. Sure, perhaps it could work. Perhaps you could, with meticulous budgeting, spend a few years in a high-pay/higher stress job and come out on the other side with hundreds of thousands of dollars in the bank and a bit of optionality.
But what if you aren’t meticulous about your budgeting? What if your apartment costs $4,000 a month, oh, and your post-tax bonus isn’t quite as grandiose as you thought it would be? And, well, if you wait two more years, your pay will jump another 60 percent, so maybe it’s worth sticking around a bit longer?
You wanted to leave the bank at twenty-five, but then twenty-five turns into twenty-six, and twenty-six turns into twenty-seven. What you don’t realize, with each passing year, is that the opportunity to act on the desires of your youth is coming closer and closer to expiration.
- Jack
This blog is an excerpt from my first book: Young Money: A Field Guide to Wealth and Purpose in Your Twenties. I wrote 270 pages on status games, opportunity costs, and the stage-specificity of life; topics that I think are particularly timely today. To read the rest of the chapter (and the full book!), order your copy below:
Also, I’ll be live with Scott Galloway on Substack at 3:15 ET today! Come tune in.



Banger. There’s also something a bit sad seeing someone in their 30s still living the early 20s lifestyle
Spot on. Your priorities are in the right place. Great interview with Scott Galloway, by the way!