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Turning 26 tomorrow so it's time for your annual reflection post.
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I’ve always been a big fan of “lessons learned” pieces, such as Kevin Kelly’s 68 Bits of Unsolicited Advice and Ryan Holiday’s 2 Years of Lessons from Running My Own Book Store. So last year, on the eve of my 25th birthday, I published a piece on some thoughts I’d been having as I crossed the quarter-century mark.
Well here we are one year later, and on the eve of my 26th birthday, I’m sharing 26 ideas I’ve had over the last year. I guess this is now an annual tradition?
Long piece inbound, and yes I was born on April Fool’s Day.
Let’s get started.
1) The range of possible outcomes is larger than you can possibly imagine.
Every single day, we experience dozens of unplanned occurrences that then open the door for dozens more to unfold. An accidental encounter opens the door to an unknown set of opportunities which invites more novel encounters, and the cycle continues.
Compound this for months and years, and our lives look drastically different from what we originally forecasted.
You never really know what you’re going to do and who you’re going to meet, but that’s part of the fun, isn’t it?
2) There actually isn’t a convenient time to make a drastic change in your life.
The most dangerous phrase in the English language is “I’ll do that someday” because it allows us to transfer our sense of urgency to a future version of us who will likely never exist.
The truth is that the hypothetical “someday” will always sound alluring because drastic changes, by their very nature, will literally never be convenient. You can’t ‘get ready’ to turn your life upside down, whether that means moving to a new city, ending or beginning a relationship, or making a career pivot.
You just have to dive in. Or, you know, you can always take solace in the realm of infinite “what could have been’s.”
3) Conversing in someone else’s native tongue gives you a newfound appreciation for non-native English speakers in the US.
We (meaning native English speakers) won the linguistic lottery by being natural-born speakers of the world’s most prevalent language, and we often take for granted the efforts that immigrants have to make to learn English just to access the opportunities that we have by default.
If you’ve never tried to learn another language, let me tell you what it’s like:
You have visualized a fully formed thought in your head, and you know 90% of the words needed to turn that thought into a coherent sentence, but when you open your mouth to speak, your tongue gets twisted, you misconjugate a verb, and you vomit a poorly construed string of words that sounds more like sleep-talking six-year-old than a grown 25-year-old man.
And then your conversation partner flawlessly rattles off prose that you wish you could replay at 80% speed, you attempt to digest their way-too-fast (but actually slower than your typical English) Spanish, you try to reply, and the whole cycle continues.
It’s embarrassing and frustrating but you do it over and over again because every once in a while you have that small breakthrough that keeps you hooked.
I have mad respect for my multilingual friends reading this. It’s not easy.
4) There’s no better way to bond with someone from another country than by speaking in their native tongue.
There has been a silver lining to the trials and tribulations of my language-learning struggles: people genuinely appreciate when you try to connect in their native tongue. I had a haircut the other day, and after exchanging a few pleasantries, my barber stayed quiet until, hearing her accent, I asked, “De dónde eres?”
Suddenly, we were talking all about my trip to the Dominican Republic (she was Dominican) last fall, some of my funniest language mishaps, and what I’ve thought about life in New York City. From introvert to extrovert, all because I switched languages.
Some of my closest friends in business school are from Colombia and Argentina, and one reason that we bonded so early was that I was willing to (somewhat unsuccessfully) converse in their language.
I imagine that having to speak English every single day as a non-native speaker is an exhaustive exercise. Switching roles every once in a while is always an appreciated gesture.
5) Taking care of yourself physically becomes more and more important as you hit your mid-20s and beyond.
There is a beautiful time between the ages of 18 and 21 when you can drink four nights a week, live and die by Waffle House and Taco Bell, hit some light cardio and a few pushups every week, and still maintain a phenomenal physique.
And then one day, you can’t.
For me, an interesting aspect of getting older is that it becomes obvious who takes care of themselves, and this effect only grows more pronounced with time.
6) Pretty much every career path sucks to some capacity, but we do get to pick our suck.
Writing sucks.
Staring at a page and rewriting the same sentence for 30+ minutes, just to delete the whole paragraph and start from scratch? It’s a soul-sucking experience that I subject myself to every single day.
But I embrace it because it’s the suck I chose.
Every job has aspects that suck. Sometimes that suck is long hours, unfulfilling work, horrible bosses, a terrible commute, or any number of things. We do get to pick which sucks we tolerate though.
7) Broadly speaking, there are three levels of financial wealth. At the bottom level, every additional dollar can meaningfully improve your life. Maybe you’re living paycheck to paycheck, and an extra $1,000 would give you breathing room, or maybe you’re one medical emergency away from catastrophe. Money is literally an existential issue.
At the second level, you don’t really have to think about money at all. You have enough money to both support your lifestyle and build a strong safety net. No, you can’t buy everything, but you can buy everything you need. Your kids have college funds, you can take your family skiing every winter, and you don’t have to double-check a restaurant’s prices before ordering steak and wine.
At the top level, no amount of money will ever be enough. At this level, ambition overpowers logic as money is no longer a means to an end, but a measuring stick that always comes up a little bit short when we meet someone with more.
The first and last groups share one trait: both are slaves to the pursuit of more.
8) Friends are the family that you get to choose.
The thing I struggled with most when I moved to New York was leaving behind an unbelievable group of friends in Atlanta. To quote one of my pieces from August:
I have been incredibly fortunate to live within 10 minutes of my best friends for the last seven years. How cool is that? Forming a great group of friends as a freshman in college, and the gang sticking together through 25? Most people don't get that lucky.
Of course, my best friends will still be my best friends. But the convenience of walking down the hall and knocking on their door or driving five minutes down the road to surprise them at home won't be there anymore.
So yeah, I'll miss that.
But it's a good thing that I'll miss that. If you miss something, it means that you enjoyed and cherished that experience. Struggling to move on to the next stage of anything doesn't mean that you're making a mistake, it just means that you did the last stage right.
Jack Raines
It turns out that Atlanta, GA didn’t have a monopoly on high-quality people, and New York City has provided me with the thing I was most worried about leaving behind.
There’s an “Alpha” stereotype that guys shouldn’t be worried about petty issues such as “friendship.”
Respectfully, that idea is total bullshit. There are few experiences better than having a group of guys that you just click with. As we get older and move on with our lives, there’s this tendency for men to lose touch with their friends due to a variety of reasons: living in different cities, family commitments, and career obligations, to name a few.
But, like, that can’t be healthy, right? I may have taken friendships for granted in college when we all lived together, but I cherish them more and more as I get older. Friendships don’t have to be a casualty of growing up, ya know?
9) Knowing how to make money and how to spend money are two entirely different skills.
We have turned the art of “getting rich” into a science. If you let ___% of your earnings compound in the market over ____ years, you will one day have a multi-million dollar portfolio. That’s personal finance 101.
But once you are rich, figuring out how to spend that money is an entirely different beast. After decades of “save, save, save,” you can’t just flip that switch and begin to spend, spend, spend.
Spending feels wrong. It arouses a sense of guilt. Besides, you might not even know what you want to spend your money on in the first place. Knowing how to get rich is important, but it’s only part of the equation.
10) You would be better off delaying any impulsive decision by 24 hours.
I’ve always had a bad habit of reacting instantly to fire drills and bad news, mainly because the initial shock leads me to believe that the world is ending and we’re all gonna die. Yet, despite my fears, the world hasn’t ended and I’m still here.
Anything worth getting upset over is also worth waiting 24 hours before making a careful response.
11) We are surrounded by an abundance of distractions and a dearth of authenticity.
Attention is an increasingly valuable asset in our internet-native world, and the TikTok-ification of everything has created a culture of hot takes and clickbait headlines designed to capture this attention by any means necessary.
When you do find a rare source of authenticity in this sea of noise, latch on and don’t let go.
12) Money is a seductive scoreboard because it’s so easy to quantify.
What was your salary last year? How much did your home cost? What’s your net worth? Every single one of these questions can be quantified. There’s a number. And a number means that you can keep score. Of course, when you ask someone about their physical health or marriage or relationship with their friends and family, the answer gets blurred.
We can give detailed, precise answers to the former, but we respond to the latter with nonchalant, binary “goods” or “bads.”
Of course, the irony of this is that money is largely a binary variable (do you make enough money to comfortably support your ideal lifestyle? Yes or no), while all of the other questions should elicit replies with some depth.
Money is a seductive scoreboard, but just because you can keep score doesn’t mean that you should. Knowing the difference between “can” and “should” goes a long way.
13) Optionality is only as valuable as the things that it allows you to commit to.
I spent most of 2019 through 2022 chasing optionality for optionality’s sake.
I originally applied to business school when I was graduating from college because, like any other 22-year-old with their whole life in front of them, I had no idea what I wanted to do, but I figured that an MBA from an Ivy League school would provide a better, wider variety of options than anything else at the time.
Then, in March 2021, I broke up with a girl I’d been dating for almost two years because my 24th birthday was coming up, and I was experiencing that “Oh shit I haven’t been single for a day of my post-college life and I don’t actually know if this is the proverbial ‘one’ and I can’t commit my life to someone else right now ” sensation that precedes pretty much every 20-something’s breakup.
This quarter-life crisis was followed by another quarter-life crisis when I flew to Europe for four months, bouncing from city to city every five days because I felt like I had to visit every single place on the map for fear of missing something cool.
And then I moved to New York City where there are quite literally a million things to do every single second of every single day making it damn-near impossible to commit to anything or anyone.
The whole journey has been fun and exciting and I wouldn’t trade it for the world, but the biggest benefit of this optionality marathon is that it’s made the importance of commitment that much more clear.
Optionality is important, especially when you’re young. You don’t really know what you want to do, who you want to date, where you want to live, or anything else. But optionality isn’t supposed to be a means unto itself. It’s supposed to be a means to finding the end of itself. Optionality is only as valuable as the things that it allows you to commit to. These things might be a partner, friends, a home, a career, or something else, but once you find your thing, you have to be willing to go all-in.
I haven’t found all of my things yet, but I’m getting there. I found a city that feels like home, a career that doesn’t feel like a job, and some friends that feel like family.
I think the other stuff will work itself out.
14) Serendipity has been the driving force behind some of the most important parts of my life.
The idea of a 20-year plan is nice, but more often than not it’s small, unplanned events that have outsized impacts on my life. The last-minute invitations that I’ve accepted and random acquaintances that I’ve made at parties tend to be far more consequential than some blueprint of where I think my life should go.
15) We weren’t meant to handle this much dopamine.
I get a lot of phone notifications.
I’m in a million WhatsApp groups, I have four emails, I quite literally live and die by my ability to go viral on Linkedin and Twitter, I love keeping up with folks on Instagram, and I dabble in the Hinge game.
We weren’t designed to handle this constant tsunami of positive feedback.
The late biologist and Harvard professor Edward Wilson once said, “The real problem of humanity is the following: We have Paleolithic emotions, medieval institutions, and godlike technology.”
Ain’t that the truth?
We have built smartphones and social media sites that are designed to keep us scrolling for every minute of every day, and the only way to avoid the dopamine loop is to disengage entirely.
Deleting Twitter and Linkedin from my phone has been a life cheat code for me over the last month, I highly recommend giving it a shot.
16) Every piece of content seeks to either inject or extract value. The difference between promoting and shilling lies in the creator’s intentions.
An issue I often hear from other writers/creators is that they don’t want to be “overly-promotional.” I get it, no one wants to be the narcissist with a megaphone screaming “READ MY FREE NEWSLETTER!”
But this is the wrong approach. If you have created something informative, entertaining, beautiful, enticing, funny, or thought-provoking, you owe it to the world to “promote” it.
Promotion is only nefarious when it becomes a means of deception, to sell someone something they otherwise wouldn’t buy.
If your intentions are authentic, the world needs to hear you.
17) Always book the private room in the hostel.
Maybe as a 26-year-old, the better advice would be to not book the hostel at all at this point. But hostels can be a blast, especially if you meet a fun crew in the downstairs bar. So I’m not going to say never stay in a hostel.
I will say, however, that if you have any level of expendable income, nothing justifies reserving a bed in a 12-person dorm in Barcelona. I don’t care if it’s $13 a night. I don’t care if your bunk has a reading light, plug outlets, and fresh sheets every morning.
Strangers coming and going and turning on the lights at all hours, alarms going off at five in the morning, crescendos of congested snoring, and the occasional Parisian who decides to turn his top bunk into a personal love shack will have you willing to pay $1200 for a little privacy and peace.
And yes, it’s always the French, and occasionally the Germans, who are willing to two-man tango in hostel bunks. That’s not a stereotype, it’s the truth.
18) Sincere compliments offer fantastic ROI.
Telling someone that you like their shoes or you appreciate how hard they’ve been working on a project costs you nothing more than 10 seconds of your time, but it can make their entire day. That’s an insane return on investment, but we’re often so caught up in our own heads that we forget to be kind to those around us.
Compliment folks more, it goes a long way.
19) It’s actually financially irresponsible to delay personal spending to some hypothetical later time in your life.
Let me explain how this whole money thing works: When you graduate from college, you probably don’t have much money, and you probably won’t be making much money, initially. 20 years into your career, assuming that you’re a competent, contributing member of society, you will probably both have and make a decent amount of money.
There is a tradeoff: your remaining time goes down, and your net worth goes up. The thing they don’t tell you about money is that you can’t just "buy back” experiences from your youth with the savings of your old age. Many experiences are age-dependent, and you have a narrow window to take advantage.
So if you are confident that your income will outpace your expenses over time, it actually makes sense to spend your lower income on the fun stuff now, knowing that your future earning power will have you covered financially.
Like, seriously, why are you worried about saving every dime of a $50,000 salary when you will realistically make $200,000 a few years from now? Live a little, your life isn’t a spreadsheet.
That’s the problem with most “financial advice,” it teaches you how to save and invest your money, but not how to spend it.
20) If you’re going to be an entrepreneur, get a good accountant.
Going back and trying to categorize a year and a half of “business expenses” has been the biggest headache of my young adult life. Seriously, if you’re going to do your own thing, set up some business accounts early, take bookkeeping seriously from day 1, and don’t get stuck diving through thousands of transactions across five bank accounts and credit cards to figure out which hostel from March 2022 can be written off as a business expense.
21) Monotonous consistency generates exponential outcomes.
Exactly one year ago, I had 4,625 subscribers. Today, that number has grown to 35,408 readers and counting:
The secret to the number on the top left is the number on the bottom right: 185 posts, at an average of ~2,000 words per piece, is 370,000 words published over the last 20 months.
It’s really hard to be bad at pretty much anything if you do spend thousands of hours doing it 185 times.
It’s boring. It’s supposed to be boring. That’s a feature, not a flaw of this whole thing. Simply being able to work on something longer than most other people is an insane competitive advantage, especially in the world we live in today.
22) There aren’t actually any rules to any of this.
We all have a set of norms that we abide by in our daily lives largely driven by a combination of societal norms and a fear of the unknown, but it’s important to remind ourselves that we don’t actually have to do anything.
You get to pick the game that you want to play, and if you haven’t picked your game, well, that kind of makes you an NPC. Please don’t be an NPC.
23) There’s no better way to “find yourself” than by traveling alone for an extended period of time.
To clarify, no, I don’t mean that you will “find yourself” in an Eastern European nightclub at 4 AM. Though you will certainly find something there, I’m sure.
If you live in the same place around the same group of people for long enough, you start to identify more with your role within that group than with who 'you’ are as an individual. It’s only by stripping away those outside influences that you can figure out which parts of ‘you’ were actually ‘you.’
When you’re in a new environment, removed from any expectations of what you’re supposed to be, all that’s left is the real, raw ‘you.’
24) Similarly, the strongest bonds are made on trips with your friends.
The best inside jokes are the byproducts of cold beers with good people in a new city.
There’s something special about going on a trip, whether that’s a road trip through the Rockies or a two-week voyage to Japan, with a small group of close friends. Some combination of adventure and camaraderie makes the conversations a little bit deeper, the jokes a little bit funnier, and the friendships a little bit stronger.
And those bonds ensue long after the trips end.
25) Past a certain point, reading about “how to do _____” has an inverse relationship with your likelihood of accomplishing _______.
Productivity porn is rampant online. Everyone wants a mental model for success, a 1-2-3 guide to achieve your goals and desires. While there’s nothing wrong with seeking occasional advice, preparation beyond a certain point is often antithetical to success because it provides you with dopamine that you didn’t earn.
Pornography and brainstorming are pretty similar in that they both leave you feeling like you have accomplished something, while you’re really just sitting there staring at a screen. Hence, productivity porn.
26) If you’re not having fun with it, then what’s the point?
No further commentary needed. Let’s have a weekend, shall we?
- Jack
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Jack's Picks
Rosie Gray published a fantastic piece on Nassim Taleb in The Spectator.
Phil Bak hosted “Doomberg” on his podcast for a detailed conversation about the business of content creation.
Sasha Chapin wrote a good piece for any writer who has “writer’s block.”
The beehiiv (my newsletter platform) team has been crushing it, shipping new features every single week. If you’re looking to launch a newsletter or move over from Substack or ConvertKit, check out my preferred platform here.