Three Things Matter in Your Twenties

[Instead of telling kids they can be anything they want to be]
Tell the kids the truth. You can be anything you’re good at…as long as they’re hiring.

And even then it helps to know somebody.

— Chris Rock, Tamborine (2018)

How irritating would it be if you clicked something suggesting only three things matter in the formative time of your adult life and you had to scroll far to find them? So, here they are:

  • getting good at something that people will want (expertise)
  • relationships
  • organization (two types)

By focusing on these (and saying no a lot) for a decade, you will likely have more options available to you on how you live the rest of your life than you would otherwise.

Characteristically, this post sat in the virtual garage for a while because I wanted the list to be concise. Travel, for instance, is highly valuable to personal development, but it feels awkward saying that it is one of the only things that matters. Your author has meal-prepped spinach smoothies (much to the aesthetic dismay of his coworkers) almost every week for 6 years, so I wanted to include health and fitness, but I also wanted to remain unbiased. Some people sacrifice health and fitness in their twenties to work, and those people may soon have the choice to eat wild salmon and ride bicycles from their 30th birthday on.

As the post gathered electronic dust, it occurred to me that if someone forced me to present this to a group of people beyond their twenties, these suggestions would only shift slightly (and I would have to add health). The two diagrams below show the suggestions for the two age groups (capital means wealth). The distinction is made between them because thinking about money is energy-consuming. Once you start thinking about it, and especially if you have to think about it, it is difficult to think about other things (like becoming a doctor). Further, organic (i.e. earned, non-inherited) wealth creation takes time, usually decades. If you want apples, planting apple trees is more fruitful (had to do it) than thinking about apples.

If you are in your twenties and you are not building relationships or getting good at something, you are likely wasting valuable time. Organization is a broad term. My original intent was to specifically suggest that we organize our thoughts — clearly labeling ideas and feelings in a structured way, equipping us to see gaps in our understanding and our motivations — but I realized that being organized generally (i.e. having your shit together) is beneficial in obvious and non-obvious ways. In fact, it is hard to focus on important things like relationships and developing expertise if you are disorganized.

Let’s look at each of these individually.

Expertise
An eternal tension exists between being a generalist and a specialist. I think about it directly or indirectly every day.

You do not want your dentist and your proctologist to be the same person. This is easy to say from the outside view, yet when it comes to ourselves, we generally like trying out different jobs and having other interests. Otherwise, life would be painfully dull. Plus, there are penalties for staying in our own narrow focus. Without a basic understanding of psychology, we are likely to get taken advantage of by advertisements and the major news outlets. Without a basic understanding of finance, we will have a hard time holding onto money. Without a basic understanding of math, we might play the lottery.

There are some notable examples of well-paid generalists (e.g. the best CEOs are by definition generalists). Having said that, nobody wants to pay extra for average. We pay premiums for expertise.

What do we do then?

My favorite solution to this intractable problem comes from British biologist Thomas Huxley who suggested we try to learn something about everything and everything about something.

If you want to test whether you have gotten good at something, see if you can write a primer for beginners.

Above, I said getting good at something that people will want because eventually you will need to be financially independent. How would you like to work your for ten years to become the best floppy disk repairman and find out no one values the set of skills you worked so hard for?

As long as there are people, there will always be wants. And as long as there are wants, there will always be problems. Fortunately for you, if you can give people what they want and solve their problems, they will often give you money. Remember in high school when they taught you how to do that? Me neither. That’s why I respect trade schools.

In high school, it seemed like an unspoken challenge to be able to barely study for tests and get good grades. It made sense as a strategy if you thought there was no point in learning the material because most tests in school involve rote memorization. Memorization is a low-value skill. Why? First, we have a million ways to document things that are better than human memory (e.g. pen and paper). But more importantly, you don’t solve new problems by memorizing facts and spitting them back up. You solve problems by understanding cause-and-effect relationships. When I was 23, my roommate doubted that I could memorize all of the presidents in one night, so naturally that was all the motivation I needed to memorize the presidents that night. That might have been cool for 10 minutes, but that told me nothing useful about presidents or politics.

If you do not have knowledge in a readily accessible or usable format, what do you have? You might have resourcefulness, but the further you get in any field, it might not be enough. Consider the difference between a quarterback who has memorized all the plays compared to one who goes a step further and knows when to call an audible. The quarterback most famous for this ability to anticipate what a defense is going to do then change the play accordingly is of course Peyton Manning. At that level, most quarterbacks are experts at throwing the ball and as far as speed goes, it isn’t guaranteed that Manning could beat Jonah Hill in a 40-yard dash, so his physique is unlikely responsible for him being one of the best of all time. It is his judgment, derived from a deep understanding of the game. There are no shortcuts to cultivating understanding, expertise, or good judgment. These are worthy pursuits in anything we choose to get good at.

Speaking of quarterbacks, regardless of their level of expertise, they literally cannot do their jobs without other people. Which leads us into…

Relationships
Certain words trigger contempt when you hear them in an advice context. Relationships is one of those for me, up there with positive thinking. The reason these get used too much is because they are true and they are open for interpretation. The reason for the contempt is because words alone are useless and people cannot do much with abstract concepts. Be a good friend and have a good attitude are meaningless, whereas, always return texts and calls and talk to your coworkers as respectfully as you would talk to your grandmother are actionable.

If everyone already talks about relationships, why am I? Because they are that important. When I left my first job, I realized what I cared about was who I could call if I needed them in the future, not what I learned. Wait, didn’t I just say that expertise is one of the only three things that matters? Yes. That’s how important relationships are.

We can put relationships into four categories:

  • Romantic
  • Family
  • Friendships
  • Professional network

On a snowboarding trip to Snowshoe in college, an embroidered list of life tips was hanging in the kitchen of our rental house. At the top it said 95% of your life’s happiness will depend on who you marry. I have been around a lot of married couples since then and I doubt any of them would argue with the embroidery. We went in-depth on that topic in The Millennial Marriage Manifesto.

Other than the relationship with your grandparents, the rest of your familial relationships will transition from necessary to optional. For instance, once they no longer have a say in what you do, your parents in a way stop being your parents and become more like an equal or friend. In some circumstances, at least one of them might become your best friend.

Romantic relationships are unique because you don’t get to pick who you fall in love with and attraction is complex. However, with friends, family, and your professional network, one question can take you a long way for the rest of your life: Are you reliable?

Are you there to pick your friend up from the airport? Can your customers rely on you to solve their problems?

The line between friends and “network” should be gray at worst. Borrowing a thought from Naval Ravikant, if you would not do business with someone for the rest of your life, do not ever do business with them. For many of us, that decision is outside of our control in the short term, but it can be a Northern Star, something to head towards in our career.

According to The Atlantic, it takes about 50 hours of socializing to go from acquaintance to casual friend, an additional 40 hours to become a ‘real’ friend, and a total of 200 hours to become a close friend. It takes about one week in the real world to realize how hard it is to find that much time for anything. That is one reason friends made after school will reflect more of your own traits & characteristics because you would never let yourself waste that much scarce time. This can serve as a perpetual personality mirror.

My high school football coach may or may not have known who Ralph Waldo Emerson was, but both men said, “What you do speaks so loudly I cannot hear what you are saying.” In all of your relationships, pay the most attention to actions.

Organization (Two Types)
More things are competing for our time and attention than ever. Focusing is harder than ever, too. This is why you must be organized and it is one reason why I choose to look at life as a design problem¹.

Type I (Getting Squared Away)
If you want to get technical, what we are talking about here is fighting entropy.

What is entropy? Your kitchen gets messy and disorganized which requires energy to clean it – that’s entropy. Everything in the world (and apparently universe!) is fighting this same battle, right now.

One of the wealthiest men in the United States (Munger) says, “It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”

I would add simply being organized. I have watched business owners, who have expertise and good relationships, lose millions of dollars by being disorganized.

How is that possible?

Many businesses rely on banks for loans. In turn, the banks need reliable information about those businesses to make the loans. If the business owner makes plungers, she thinks everyone in the world already knows about plungers because without them, the world would be a crappy place to live. But everyone doesn’t know about plungers; she knows. She needs to be able to explain in a few sentences how the business makes money. She needs to be able to provide three years of accurate financial statements, tax returns, and her personal financial information in an electronic format. She needs to be able to explain why sales are plunging (okay I’ll stop).

The point is businesses have an enormous incentive to get these things right and have this type of information, which is seemingly obvious, yet they often do not. If businesses fail at doing this, individuals are at least as likely to make the same mistake.

You are going to want a lot of things, like an apartment or home. You are going to need to have check stubs, rental history, references, et cetera. Further, these things are going to depend on someone you don’t know saying yes to your request. If you want someone to say yes to anything, then you should make it as easy as possible for them to do so. They are not going to be able to say yes if you do not have the information they need to make the decision.

I am always looking for practical takeaways, so here are a few:

  • Pick a file-sharing site (e.g. Dropbox), create folders for the categories of your life (Auto, Medical, Housing, etc.), and keep everything important so you can easily access it. Bonus points if you have a system for naming files.
  • Create and maintain a personal budget with monthly cash flows in Excel.
  • Never pay a late fee for anything.
  • Get a whiteboard (it will help with Type I and Type II).

Type II (Waking Up)
You might have heard people say, “You don’t know anything when you come out of school.” How can they say that when you have spent your entire life presumably learning? One interpretation is that we are relatively unconscious of the workings of the world at that age because many of us have been insulated from parts of reality (e.g. growing up in the suburbs, the massive amount of raw information to be processed, etc.). A metaphor for gaining consciousness is waking up. I think of it as a combination of intellectual and emotional maturity and an existential ah-ha moment. From what I can tell, this is not inevitable, so it must be deliberately sought out, by paying attention and thinking.

If you do not organize your thoughts, you do not know what you really think or why you feel a certain way. There are many ways to do this. One of my favorites is writing because we don’t think in paragraphs and essays, we think in words and sentences. Without writing those thoughts down, they can disappear or trail off without cohesion. Putting them together in a way that makes sense takes work. That is why good writers are good thinkers.

Take superstition. If people say their superstitions aloud, they often get embarrassed because they sound ridiculous under scrutiny (e.g. Your team wins because of your lucky underwear? How?). You can do this with anything. If you are willing to go through this process, you will not only get to know yourself better and form more accurate perspectives, you will become more persuasive and be able to get more things done.

These two types of organization will help you think clearly and clear thinking is priceless.

As you can see, expertise, relationships and organization take time. You will find that habits are more important than motivation.

There are 521 weekends in any decade of your life, which may sound like a lot, but if you trust me on anything, trust me that this particular one goes by fast.

Don’t forget to have fun.


  1. Designing Your Life

Disclosure: Long DBX