Advice to My 20-Year-Old Self

There is probably no decade more formative, or so often under-appreciated, as our 20s. For most of us, we are starting our first “real” job, leaving the security blanket of childhood homes, paying all of our own bills, and making lifelong commitments to a spouse (and perhaps to raising children).

I am fortunate that I do not look at my 20s as a time that I wasted. I finished college, worked hard, got good job experience, married the love of my life, received a graduate degree, took a six-month coding bootcamp, traveled a bit, and even had my first kid.

But I failed to grow in important ways that I now wish I would have. Ways that do give me pause. Ways that might give me regrets if I were to get lazy, or simply more susceptible to that temptation.

Hindsight is always 20/20, so I’m not beating myself up. But I figure that some of my readers are in their 20s right now, and the rest of you all know people in their 20s that might benefit from my thoughts.

So please do me a favor. If you think anything I have to say here is valuable, please send it to any 20-year-olds in your life with the comment, “This guy is a genius (and incredibly handsome and witty). You should subscribe to his newsletter…”. 

Without further ado, my advice for the college and post-collegiate crowd.

Education is greater than entertainment

One thing you may have noticed as a young person in 2022 is that there are approximately 11,291 ways to keep yourself amused from dawn until dusk. Smartphones, social media, online gaming, partying, more social media, and also those pesky smartphones that I probably forgot to mention.

While there are constructive ways to use, for example, smartphones and social media, that probably isn’t what you are currently doing. Right now, you have the opportunity to decide if you are a learner or a consumer. Learners grow, consumers don’t. There are books I didn’t read, advice I didn’t take, and educational rabbit holes I never wandered that I now regret.

Get off the drug of entertainment and focus your time on self-education.

Get really curious about everything

Don’t be the person that is blinded by a single, all-consuming passion. Even if your favorite thing in the world is creating your own oil on canvas masterpieces, that should still be only one part of your life. When you hear that interest rates might be “raised by five basis points,” don’t just shrug your shoulders and assume only finance people need to know that – go look it up. Everything you don’t know is an opportunity to learn.

Many of our culture’s heroes are incredibly well-rounded beyond what you’d suspect. LeBron James is invested in many businesses, beyond his basketball career. Elon Musk isn’t just sending rockets into space and making electric cars – he is well-read far beyond his immediate world of engineering. Jack Dorsey didn’t just start Twitter, but also founded Square, which is doing more for the world of modern finance than most realize.

I’ve been reading a lot about cryptocurrency lately. Many of the thought leaders in this space keep talking about the “game theory” involved in crypto’s widespread adoption. I know more about the mating habits of wombats than I do game theory. So I downloaded a $4 book to my Kindle and started reading about game theory.

You never know when new information, connections, or skills will come in handy. The worst case is you’ll be a more well-rounded, interesting person. Assume everything you see and every person you meet is an opportunity to turn on your curiosity radar and grow as a person. The best of the best are rarely one-dimensional.

Choose your responsibilities wisely

A year after my wife and I got married, we bought a dog. Remi is an awesome dog; he is a 130 pound purebred Bernese Mountain dog. He’s beautiful, well-behaved, and sweet as can be. He was also a very expensive mistake.

You see, when you enter “the real world,” there are responsibilities you will (or ought to) take on whether you like it or not. These responsibilities include managing finances, building a career, (likely) investing time in a meaningful romantic relationship, and maintaining a home of some kind.

All of these responsibilities are great, but they take time and money. Every subsequent and optional responsibility you take on – keeping up with a motorcycle or a boat or a dog – will be more substantial than you realized. With Remi, we spend $60+ a month for food and several hundred dollars each year on baseline medication for ticks and heartworm prevention. I spend every morning vacuuming to keep up with the ridiculous amount of shedding. The vet, while close by, is a hassle and expensive. We travel a lot so we pay a kennel a few thousand dollars a year to transfer all of this responsibility to them while we are out of town. On top of that, we have a lot less time for him now that we have two kids. We love him, but he is not one of our children and takes a very distant priority behind them. Good dog, bad decision.

Don’t get suckered into new, big responsibilities because the puppy is cute or the motorcycle is cool. The total cost of ownership, both in terms of dollars and occupying your mind, is way higher than you realize. I’ll reiterate: choose your responsibilities wisely.

Don’t waste your evenings

If you have any ambition to make your life more grand than a normal 9-5 job with two weeks of vacation per year, focus time each evening on finding ways to get to that grander life. If you watch TV or play video games for just one hour each night, you will spend over 14,000 hours doing so between the ages of 20 and 60.

That is 1.6 years of this precious gift called “life” that you will spend looking at a screen just to numb yourself at the end of the day. And most 20-somethings are probably spending a lot more than an hour a day. Two hours a day doubles that number, three hours triples it… you can do math.

Someday you will die. Don’t regret that you didn’t live better.

Find your “five people”

It’s been said that you are the average of the five people you spend the most time with. That may not be precisely accurate, but it falls within a rounding error of the truth.

Start to get ruthless early about who you spend time with. If you want to own a business and get fit and do awesome things, go find other people that are starting businesses, working out, and doing awesome things.

If you hang out primarily with pot-smoking, aimless gamers, you will probably become something resembling or identical to a pot-smoking, aimless gamer. If you wouldn’t take advice from them, give them the boot. Your life is worth so much more.

Find five people (at least) that you can be in near-daily contact with on your goals and ambitions. Support and encourage them and make sure they return the favor. You both need it.

Learn to set rules for yourself

Most overweight people are overweight because they don’t set rules for themselves.

I have a rule that I don’t eat (except for social occasions) after 8pm. I also don’t eat again until noon on any normal (non-travel or “cheat”) day. Trying to live by “I’m going to try cutting my sweets” is a hell of a lot harder than telling everyone you know, “I don’t eat sweets Sundays through Friday – only on Saturdays.” Now you’ve got a rule and some accountability.

I read at least one (and usually two) chapters of the Bible everyday. I don’t eat sugar six days a week. I write in my journal every night before bed.

These are all “rules” I’ve set for myself, one of the few things in this list of advice that I did fairly well in my 20s. But I’m doing better in my 30s.

If I’m hungry after 8pm, tough luck. If I’m craving sugar on Tuesday night, it doesn’t matter because it’s not allowed. If I don’t write in my journal at night… well, that doesn’t happen because I always do.

This is not the easiest skill to acquire. But here is what I always ask myself if I’m tempted to break a rule: “Am I really so weak that I’m going to cave on this for the sake of immediate gratification? Am I just an impulsive child?”

Usually that kicks me back into gear. Setting rules is hard, but living with the consequences of a lawless life is harder.

Marry well

Most of you will get married. If you do, keep this in mind:

Who you marry is, practically speaking, the only major decision you will ever make that matters.

Years ago, I asked a family friend for some career advice because I was considering transitioning roles at my job. He told me: “Don’t worry about it. You can change your job like you can change your pants. Who you marry is the only thing you should be concerned about.”

Don’t fall for someone because of looks or money or convenience or because “you get butterflies” when you’re with them.

Marry someone that will tell you the truth when you don’t want to hear it. That will tell you that you are beyond capable when you are feeling down and out. That will strive and grow with you. That will give (and take) good advice. That appreciates how precious and fragile a marriage can be, so it is never taken for granted.

But also keep in mind that finding a spouse is only 30% of the battle. You (yes you) are the other 70%. You know why? Because you’re not as awesome as you think. You are wrong when you’re completely sure you’re right. You make comments you shouldn’t make. You bring baggage and chaos to the relationship. Same goes for me.

The point is, quit trying so hard to find that perfect someone and work your ass off to become that perfect someone for someone else. I was blessed to find the right someone for me, and now I owe it to her to try being the right someone for her. I’m a work in progress.

Marriage is not simply dating plus living together. You will have real life disagreements with real consequences. You will cross bridges you didn’t want to cross at times. What you feel on your wedding day is a fleeting sense of euphoria. The good news is that with time, depth, and presence, your marriage can get better and better. Find someone that is willing to commit to that.

Have kids, but understand…

After a wonderful spouse, kids are perhaps the greatest blessing in life. I have a three-year-old girl and a 10-month-old boy. My advice? Have kids.

My daughter is pure joy. She is funny and makes us smile and laugh constantly. She is also tough as nails, which can be difficult to manage as a parent but gives me great pride in the strong woman she will be.

My son is just chubby and smiley and fun to snuggle and love. I can’t wait to see who he turns out to be in two, five, and 10 years.

Kids are the best. But they are also a lot of work and are, by definition, a major detour from the conveniences of kid-less life.

We now travel with car seats and a double stroller. About one hour of our evening consists of simply bathing kids, reading to them and making sure they are down to sleep at the right time. A full week of potty training with our daughter included a large amount of bodily fluids (and solids) on our living room floor, which we protected with taped-down trash bags.

Date nights require more coordination. Sometimes I miss getting home from work on Friday and asking my wife, “What do you want to do?” Nowadays, what I wasn’t to do is of little importance compared to what I need to do – love on my kids, snuggle them, read to them, discipline them (when necessary), get them down for bed, etc.

This might feel hard to reconcile, that kids are the best but that you also lose a massive amount of time and freedom. But it is true. It goes both ways.

My point is this. Have kids and soak in every moment, because it is fun and rewarding and goes fast. But live every moment of not having kids with a sense of ambition and gratitude. Ambition, because it is easier to strive toward big goals related to your career, finances, and so forth without little munchkins to slow you down. Gratitude, because you can travel with just a backpack, do whatever you want on a Friday night, and, without kids, you’ll still be the kind of person that might regularly go to trendy restaurants with your friends.

Your fire doesn’t have to die when you have kids, that is simply the unfortunate choice that some people make. But what makes your fire burn most certainly will change, in ways subtle and not. My advice is to have kids, but understand that your life will change in ways you don’t fully realize.

Work hard on your fun

Sitting in your apartment playing video games online with your friends every Friday night is not the kind of fun I’m talking about here. Sure, do that every once in a while. I have some great memories of doing nothing productive on many a college night. But that is lazy fun, and the memories are fleeting.

To me, the right kind of fun for a 20-something takes a bit of effort. Gather a group of friends for a game night. Have bourbon and cigars with the guys once a month. Decide on a book that you’ll read with your friends and discuss together. Take weekend road trips to anyplace within a six hour drive. Then go travel the world as work and cash permit – and don’t put it off until “someday.”

It is easy to flip on the TV or your PlayStation, but that is a cheap way of engaging with life. Make an effort to have the kind of fun worth having and remembering. You will most certainly forget who was the last man standing in Call of Duty on a random Saturday night in 2022. But you will never forget or regret a night by the bonfire with your best friends.

Youth lends itself to a type of fun that middle age, multiple children, and a lawn to mow don’t readily allow. Don’t take it for granted.

Even as I’ve written this, I can sense my advice falling flat. I don’t have the chops as a writer to fully express all that I’d share with my 20-year-old self.

A couple of years ago, I finished a good decade. A great decade, in fact. But if I had read these words, and taken them to heart as this humble writer intended for them to be taken, I would have made some changes. I would be further along. And smarter. And wiser. And more at peace with past decisions.

If you have the courage to reflect on what you are doing with your life, and to change what you know to be off, or wrong, or unworthy of the life you have, then good for you. Go to battle with yourself each morning, and you will be capable of anything.