Some Advice for a 22-Year-Old Just Getting Started

Basically this is the blog post I wish I'd read in 2019.

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Earlier this summer, I had the pleasure of meeting my internet friend Kyla Scanlon in person for the first time. Meeting internet friends is always interesting, especially when you have interacted online for at least a year, because you feel like you know each other despite not really knowing each other.

I’m happy to say that Kyla exceeded all expectations (and if I could buy stock in anyone writing/creating on the internet right now, it would be her). We spent most of our time at our coffee shop hang-sesh discussing content: blog posts, newsletters, books, etc., and Kyla mentioned that her brother was a huge fan of my stuff (thank you, Ryan!).

After bringing up her brother, Kyla gave an interesting description of my writing style: you write about everything from financial markets to travel, but the best way I can describe your content is life advice for guys around our age.

The timing of her comment was ironic because just a few days earlier, I received an Instagram DM asking a question about this very theme:

Maybe Young Money is life advice for younger guys, or, at the very least, maybe younger guys do sometimes use my posts as life advice. I’m a 26-year-old dude trying to navigate my own life, and most of my content over the last two years has pulled from my experiences, so that makes sense.

But until today, I’ve never explicitly written a life advice post. Considering that I’m 26, I’m not married, and I don’t have any kids, I hardly felt qualified to tell people how to live. But looking back, I do have a few thoughts on how I would spend the next five years if I were a 21-year-old entering their senior year of college. Here they are:

Career Stuff

As a college senior (or even a recent graduate), you have no idea what you are going to want to do for a career. Even if you do think you know what you want to do, you actually don’t. That being said, there are three different viable paths that you can take early in your career. None of them is inherently better or worse than the other two, but they do each have unique advantages and disadvantages.

The first path is pursuing the highest-paying, most prestigious job possible. Think analyst at Goldman Sachs or the equivalent role in your chosen industry.

The second path is taking the most interesting job possible. Maybe this means working in a media publication’s London office instead of staying in the US. Maybe it means taking a chance with a startup. Maybe you are going to teach English in rural Ecuador.

The third path is working under the most impressive mentor possible, regardless of the role itself (though ideally, you would be working in an industry that you find at least somewhat interesting.)

Path 1 serves three purposes: you will make a lot of money in a short amount of time (~two years), you will have a permanent status signal on your resume that will open doors over the course of your life, and you will have a variety of lucrative exit opportunities that would otherwise be more difficult to access.

Path 2 serves two purposes: First, it will likely be the most fun path. Living in a foreign country, doing a “weird” job, and/or hitting the ground running with an exciting startup are all more fun experiences than grinding away in a cubicle for two years. Second, it will give you a unique perspective that can’t easily be replicated.

Path 3 serves one purpose: working under an elite mentor, whether they are an entrepreneur, writer, investor, craftsman, or anything else will accelerate your development 10x.

Path 1 will pay you the most money and/or provide you with the most status, Path 2 will provide the most fun and unique perspectives, Path 3 will most quickly develop and prepare you for whatever comes next.

These paths can be leveraged in different ways as you prepare for the next stage of your career.

Path 1 will provide you with the broadest optionality to pursue a variety of roles. Crushed two years at Goldman? You could stay in banking, pivot to private equity, apply for venture capital roles, work for a hedge fund, or handle finances for a startup. Path 1 is like a passport that gets you into any country without all of the extra visa work.

Path 2 provides you with a story that can be leveraged. Every interviewer will have dozens of applicants from the same run-of-the-mill jobs. But the person who taught English in a 3rd-world country? Well, that is interesting. If Path 1 rolls out the red carpet to the front door of the party, Path 2 opens the back door for you to enter without all of the fanfare. Whether you’re applying for grad school or a new job, Path 2 works if you know your story well.

Path 3 sets you up to take on a much larger responsibility than you would otherwise be capable of, especially if it is in the same field where you did your first job. Working under an elite mentor sets you up to be “the man” at a much younger age, because you likely weren’t part of some large development class that most early-stage employees are subject to.

Once you’ve worked two years in your specific path, you can re-evaluate and pivot as needed. There aren’t any rules to any of this, and everything is malleable. Pick a path, give it a try, and adapt on the fly.

How do you figure out what you want to do? First, find someone, or, even better, 2-5 someones, 10 or so years ahead of you that you think has the coolest job/life ever. Figure out how to do what they do.

My personal example of this, which I’ve mentioned before, is Morgan Housel. He wrote for The Motley Fool for a decade before becoming a partner at Collaborative Fund. Why was he hired? To write his blog, the only difference is that it’s now hosted on their website. He is a best-selling author and venture partner with a very popular finance blog, and he speaks at different conferences around the world.

Can I perfectly emulate that career? Probably not. But if I write enough good content (as he did for 10 years) and take my opportunities as they come, it will probably work out. And so far, things have been working out pretty well. Find your Morgan Housel, and figure out how to build your version of their career.

What if you can’t think of anyone with the “perfect” job? Then find someone who has the opposite of that. Someone 10 years ahead of you that seems miserable and generally unhappy with their career prospects. And if that person, or even worse, those people, are above you in your current line of work? Quit as soon as possible, because one day that will be you.

Also, if you can get into a top business school, go. A professionally acceptable excuse to have the most fun two years of your life, and the base level outcome is a high-paying job, a collection of incredible folks to call friends, and a network that will pay dividends for years after? I mean, come on. (Plus, it’s the perfect chance for a career pivot.)

Non-Career Stuff

Being young, and especially being young and single (or at least young and without kids), is a unique time that shouldn’t be taken for granted for two reasons: 1) the stakes will never be lower for you to take a risk and 2) you will never be able to survive on less money. Keeping that in mind, I have a few pieces of advice.

First, you have two windows where you can travel extensively: right after you graduate from college and after you have worked for a couple of years and you’re considering a career pivot.

Realistically, you will be 21-23 and 24-25 years old during these two windows. I cannot emphasize this enough: you need to take advantage of at least one, if not both, of these windows and see the world for at least six weeks. It doesn’t matter where exactly you go or what exactly you do while you’re there, but traveling as a young adult is one of the few things that no one ever, ever regrets doing.

Maybe you and a friend choose 1-2 locations abroad to live in for one to two months. Maybe you buy a Eurail Pass and zip from city to city around Europe, hitting the beaches of Barcelona and the highlands of Scotland. You could work in a hostel in Buenos Aires for a month, or rent a car and surf your way down the coast of Australia.

You would be shocked by how cheaply you can travel at this stage of your life. You can rent a bed in a shared hostel room for $20 a night (or $5, in Southeast Asia), or, if you have a bit more money saved up, you can get a private room instead, but either way, I would recommend staying in hostels for a bit. The reason is that hostels facilitate interactions between young people from all over the world. Few environments are better for sparking camaraderie between rednecks from South Georgia and socialists from Berlin (I’m speaking from personal experience here.)

There is a way-too-short window of time when you both 1) have disposable income and 2) find this reckless, gritty form of travel to be fun. Take advantage of it now and laugh about it later. Don’t stay in resorts and five-star hotels. This should be a cheap, borderline-reckless form of travel. The type of travel that inspires stories that you’ll enjoy retelling for decades. Miss a flight, get lost once or twice, sample some foreign cuisine, get drunk on a Tuesday, and mix and mingle with the locals.

Second, learn a foreign language. And if you’re still in college, start today, and treat it like another class. Seriously, even my vastly mediocre Spanish has paid dividends while I’ve been abroad. You can reach functional proficiency in a language much, much quicker than you would think. It’s just a matter of getting the reps.

(Read this for more details on how to actually learn a foreign language.)

Third, stay physically active. This is, without a doubt, the most important thing that you’ll read in this blog post. If you don’t continue to run, work out, play sports, or otherwise engage in something active, your body will start to fall apart. You bounce back quickly in college, and you’ll bounce back quickly for the first few years after. But if you don’t develop early adulthood fitness habits in your 20s, you will pay the price in your 30s and 40s. I’ve seen 50-year-olds that look 35 and 50-year-olds that look 70. It all comes down to how you treat your body.

Fourth, find a hobby that you enjoy that has nothing to do with your job. This could be a sport (related to the last point), a musical instrument, standup comedy, writing, film-making, whatever. Everyone needs their thing that they identify with outside of work, and no one likes talking to the guy at a cocktail party who has nothing interesting to say that isn’t related to his job.

Fifth, take a risk. Now, this could be career advice as well. A few years out of school is an excellent time to join a startup, experiment with an unorthodox job role, or move to an unknown city for work, because the stakes are lower. You aren’t that far from rock bottom, so it won’t be that hard to reset. But this applies to a lot more than just job stuff. Move to a new country for a bit, test out new clothing styles, start a podcast or blog or YouTube channel, do something that seems off. The perceived risk of pretty much anything at this point in life is much higher than the actual risk.

Sixth, be interesting. No further comment needed. Literally, just be anything but boring.

Seventh, Don’t force yourself to grow up too fast, but also realize that the decisions you make now, both professionally and personally, will, in fact, dictate the direction of your life. No one likes the hard-ass 22-year-old, but no one likes the 29-year-old who refuses to get their life together either. Have fun, but get your work done as well.

Relationship Stuff

Don’t make your post-college decisions (where you live, what jobs you consider) based on your significant other unless you know beyond the shadow of a doubt that you’ll marry that person.

And there is a 99% chance that you don’t know beyond the shadow of a doubt that you’ll marry that person. Seriously, we change so much between the ages of 18 and ~26 (this is as far as I’ve made it so far, can’t speak for anyone older) that there’s a very good chance that 26-year-old you will grow out of 20-year-old you’s relationship.

If you do make a large personal sacrifice for your college significant other, like, say, moving to San Francisco because they got a job there, even though your career prospects are better in NYC and you would prefer to live there instead, it’s very likely that you’ll end up unfairly resenting someone that you loved for a choice that ~you~ made. And if the relationship doesn’t work out? Then it all would have been for nothing.

This doesn’t mean you have to break up post-college or that you should intentionally live as far as possible from your college girlfriend, but you should make your own independent choices about what you’re doing after school. If those choices align, great! The relationship will be stronger because of it. If not, that sucks, but you’ll be alright. A tough breakup at 22 is infinitely better than four years of regret or resentment at 26.

One more thing on the relationship front: don’t get married just because inertia is pushing you that way. I’ve seen too many relationships that progress to marriage not because of love or compatibility or mutual respect or aligned values, but because staying together was easier than breaking up. Seriously, if at 22, you’re already thinking, “I don’t know if they’re the one, but…” then they’re not the one. Too many of those relationships end in marriage, and then those marriages end in divorce. Complacency is a cancer. Don’t marry it.

Talk to your parents and grandparents often if you’re lucky enough to have them. When we’re young, we often take family relationships for granted, and that’s honestly just ridiculous. Is it really that hard to pick up the phone a few times a week and call mom, dad, grandma, and grandpa? No. And yes, you need to take the initiative to call them. They likely don’t want to interrupt your “super busy” adult life, but no job, happy hour, or Netflix series is more important than your family.

Similarly, be intentional about maintaining your friendships after school. College is a unique bubble where friendships are easy because you’re living 5 minutes away from thousands of people your age, and you don’t have real responsibilities. The natural state of existence is a saturation of friendship. That dynamic inverts when you graduate. People move, jobs take up a lot of time, and it’s easy to just “eat, work, sleep,” and ignore anyone not actively in your current stage of life.

Call your friends each week to catch up, especially if they live in a different city. Plan 1-2 trips per year. Don’t be the reason that relationships with your friends stagnate.

If you move to a separate city from most of your college friends, actively put yourself out there to find new friends. Reach out to your network and see if anyone knows anyone in your new city. Join a local sports league. Do something to find people your age to do things with.

That’s all I’ve got, good luck with the rest of your life, kid.

- Jack

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