These are some of the most important lessons I have learned in the 33 years of my life, which started as a pretty informal checklist and expanded to become the full notes below after a 3-hour sit-down with several of my younger relatives. I sent them the following afterwards:

I know that it’s easy to read things like this, nod studiously to yourself, and then promptly walk away and ignore it all.  I hope you’ll treat this a bit differently… really *think* about each item here, how I might have learned it and how you might actually apply it to your hypothetical life.  Because this is exactly what I would have taught myself when I was 12, 15, 18, or even 25 years old to save myself *years* of difficult learning along the way.  

I’ve learned many of these myself but had lots of help too.  This includes reading hundreds of books and blog posts along the way and, most significantly, I’ve talked to other people.  Some lessons come from people who have made tens of millions or hundreds of millions of dollars in business and others from people who have managed to achieve the difficult task of having healthy, stable relationships with other people.  They are all valuable to me and I think a complete person is built from such lessons regardless of where they come from.

Many of these are addressed to people who are early in their lives or careers but I think some may resonate in unexpected ways regardless of age or experience because everyone has walked a different path to get here.

BUSINESS LESSONS

The following lessons generally apply to business, though it’s always difficult to put them into a single bucket.  We generally equate “success” with “made money”, but I’d also encourage you to challenge this assumption because really success should be defined by happiness and fulfillment… money is just a tool which provides more options along the way.

Life Scripts

Everyone subconsciously goes through life with a series of “life scripts” in their head. These scripts, like Hollywood movies, represent all the life paths that they or other people around them can “legitimately” take.  This includes good things like “went to a good school and became a doctor/lawyer” or “married their college sweetheart and had 2 kids by 25 years old” and even bad things like “came home from the army and started drinking and now…”.

A script allows you to explain your life in 2 sentences to other people — now that they know which script you are living, they feel comfortable with what your life looks like.  You are “normal.”

You usually don’t think about these scripts because they have been implanted into your head by a combination of the people you grew up with (eg your parents) and the media you have consumed (eg how the people on Friends lived).  They are often heavily influenced by the cultural norms you surround yourself with.

When you are on a script that everyone agrees is okay, life isn’t too bad.  Unfortunately, many times the generally accepted life scripts are not sufficient to make you happy or successful in your own life.  Most people choose to cling to the script they think they want to be living and ignore the impulse which tells them that it doesn’t fit.  You don’t have to do this.

There is a lot of friction when you step off of a life script and try something new.  The first part is what you expect — when you try something new, it is always hard to figure out what the “correct” path is because no one has shown you what that script looks like.  I met many people on my travels who have written their own life scripts, for instance running online businesses while living in Bali or practicing music in a commune in central California. Many of them had no idea they could do this before they fell into it.

The second difficult part of stepping off the script is something you may not have thought about… when you walk a different path, you have to *constantly* explain to *everyone* what you are doing and why.  This is because no one else understands the choice you have made.  It is not on their list of possible scripts.

For instance, when you have a very successful job on Wall Street and decide to quit so you can start writing a self-help newsletter, no one knows how to respond when you tell them this at parties.  Quitting a successful job doesn’t make sense to them.

In order to be happy you often have to step off the available scripts.  In order to be highly successful in business, you almost always must.  This is because the only way to be wildly successful is to do something that no one else is doing because otherwise it would already have been done.  The kinds of people who do this often walk a journey which forces them to make choices that seem strange to those around them.

The “real world” is NOW

It’s never too early to start thinking about your “real” life because the capability for you to affect it begins far easier than you might think or than you’ve probably been told.

Specifically, most kids don’t really put much thought into their career or what their life will look like until sometime in university when the horizon to begin that life is just a year or two away.  Even then, they often operate in a short term way, looking for their first job with an attitude that it should just pay the bills and then someday later they can figure out what they actually want to do.

The amount of useful knowledge that you learn during the course of your education decreases each year until you graduate.  If you were to leave school halfway through high school, it would probably take you only a few months of hard work to get to the level of useful skills of someone who has already graduated from university.

What this really means is that you can do a lot more than you think a lot earlier than you think.  If you are 14 years old, you can pick any career out there which looks interesting and begin learning how to do it on your own.  You can start researching the necessary background knowledge, getting to know the relevant people, responding to comments or blog posts and even start writing on your own.  If you do this opportunistically on a few nights and maybe weekends each month (and especially during the summer), it takes very little time before you can start adding real value.

You don’t even have to pick a *career* that seems interesting, especially since it can be hard when you are young to even know what career types there actually are.  I can say that the “career” path I have now didn’t even exist when I was young!   So, if you can’t find an adult with an interesting-sounding job, just figure out some Big Problems in the world that seem interesting enough to solve and start working on solving them.  Seriously, that’s all it takes!  Passion, creativity and a hunger to fix stuff has created the most successful careers and companies in history.  And a company is really just a formalized way of getting a group of people together to solve a particular problem anyway.  You can do that at any age.

The best way to learn more about Real Problems is to ask people who know.  If you reach out to people who seem famous or hard to access and tell them you’re a curious 14 year old, they’re much more likely to respond to you than some random 20-ish-year-old because they are curious about your potential.  Try to get used to asking accomplished or famous adults hard questions like “how much money did you make early in your career” and see if you can get them to answer… it’s good practice for you and good for the relationship because smart adults like bold youngsters.

For careers with a more hands-on component, like computer programming and technology startup, you can actually start building stuff very quickly.  You can launch actual websites, build actual products and start actual businesses at *any* age!  Even better, the people you’re selling stuff to have no idea what age you are.  On the Internet, nobody knows you’re a dog.

You probably still want to finish school, but if you start doing this early, you will be *much* better informed than your classmates about how the world actually works and *much* better prepared than they are by the time you have to start making real decisions about what to do after school.  If you want to join a company at that point, you will be a much more obvious person to hire (because you actually have experience) and you will probably already know people you want to work for anyway.  If you have already spent several years trying to start companies or create products of your own, you will be much more likely to succeed now because you already made the early mistakes while it was cheap and easy to do so.

Remember — you can learn *anything* on the Internet so the only question is whether your curiosity will uncover something really interesting to you and if you have the motivation to learn it.  

If you’re not exactly sure what’s out there, I recommend asking unusually specific questions of adults about their jobs and the problems they are solving.  Use the 5-why’s technique to uncover what exactly they do.  The younger you are, the more challenging it will be to get them to take your questions seriously but keep pushing — once they realize you really do want to understand the details of what you do, they’ll be really engaged.  

Just note that this technique is effective on *most* adults but works *best* on those adults who actually like (and chose) their jobs rather than those who only do it for the money or because they didn’t have other options.

“Time for Money” is not how to get rich

The most expensive person I have ever interacted with professionally is a lawyer whose firm charged $1200 per hour for his time.  Actually, most of the most expensive people have been lawyers…

But if you somehow managed to survive law school and another grueling 10+ years doing difficult and often boring legal work for clients, sacrificing all hope of having a normal personal life, you still have your earnings fundamentally limited by the number of hours that you can book.  Sure, working overtime to make a million dollars a year allows you to afford a strong lifestyle but you’re still fundamentally limited by the hours you work and you get yelled at by the clients (like me) who are your bosses.  If you take a vacation and do not bill any hours, you make no money.  You are constantly on the treadmill running as hard as you can to keep earning.

The same principle applies to employees at companies too.  Regardless of whether you work hourly for clients or get paid by your boss, you are always limited by either how many hours you work or whether your employer decides to keep paying you.  

You have neither freedom nor great wealth as an employee or an hourly contractor.

The only way to become truly wealthy or truly free is to separate your earning power from your number of hours worked. And the clearest way to do this is by becoming an *owner* rather than an employee.

If you own a business, you will certainly start by working your butt off.  You may fail.  You may be overwhelmed.  But if you do it right, you will build yourself an asset.  You will create *equity* which has real value.  And once you build a machine that runs on its own (or with little input), you can decide whether you want to take your time back and work less hours (freedom!) or cash out by selling the business to someone else (wealth!).

Your employees, however, will need to keep working.

Every single person on the “top richest people in the world” lists who didn’t inherit the money did so by owning a business.  Bill Gates (Microsoft). Jeff Bezos (Amazon). Mark Zuckerberg (Facebook). Larry Page and Sergei Brin (Google)… and so on.

You probably don’t need to become *that* wealthy to achieve your goals in life.  It comes with too many problems and forces you to sacrifice too much anyway.  But the principle of ownership is the thing which will allow you to achieve whatever combination of freedom or wealth that you use to define your success.

Success is driven by Hard Work, Learning and People

I’ve met a lot of very successful people during a couple of career arcs working on Wall Street and in Silicon Valley tech startups.  I’ve developed some pretty clear heuristics for what creates uncommonly large success.  If we assume that your intelligence is fixed from the start, it comes down to the following three factors, but not entirely in the ways you might expect:

1. Hard work
2. Learning
3. People

Hard Work is probably the easiest to understand and that’s what it takes. Smart people often compete with other smart people to make what they are doing look as easy as possible but that’s usually a lie — the most successful people work very hard and do whatever they have to in order to stay focused.  They modify their sleep, their diet and even their mindset to figure out how to make themselves more effective.  

You must work hard to succeed in a competitive field because your competitors are also working hard.  

This shouldn’t convince you that it’s better to work *hard* than to work *smart* because that’s obviously not true — you shouldn’t put your head down and just work hard only to make yourself feel good. It only matters if you’re working hard doing the *right* things!  But you will still have to work hard, even if it is just to keep learning about new things.

Learning may sound obvious but it’s something that most people take completely for granted.  You assume that when you’re sitting in front of a textbook, you are learning the material and that’s just how it works.

Those who are successful learn *endlessly*.  They are constantly curious about their environment, about technology, about people, about politics… regardless of what they do or how old they are, they’re always learning.  

You will need to learn about things as broad as industries and markets, as functional as specific roles or jobs and as fuzzy as how to manage other people.  No successful path is straight and the single most important factor in your success is how quickly you can learn in order to keep up.  The path to success almost always involves getting constantly (metaphorically) punched in the face by unexpected problems.  To get past these problems, you must react quickly enough to decide what to do next and then probably learn a completely new set of skills in order to do it.

One of the best expressions I’ve ever heard is that “a little bit of slope makes up for a lot of y-intercept” — which borrows from graphs where the line with the higher slope (learning) always overtakes one which originally started in a higher place (experience/knowledge).  You see this all the time — someone late in their career often has a couple decades of experience doing something so they are objectively better at it but someone hungrier (and often younger) than them fights every day to learn the skills and quickly overtakes the more experienced person.

So treat learning itself as a skill.  Don’t just learn the stuff in the textbook for your quiz — figure out what is the *best* way for you to learn it?  What combination of sleeping patterns, note taking, flashcards, test and supplementary Internet resources allows your brain to absorb the material most effectively?  If you treat learning as a skill and become good at it, it will pay off every single day for the rest of your life.

The fun thing about being able to learn quickly is that it applies to any skill as well.  If you get really good at learning, you can look at a foreign language, a musical instrument, or advanced calculus and they’re all essentially the same — you have to figure out what the scope of knowledge is, map out a path through it and find the best way to absorb and test it.  Suddenly, no challenge is actually overwhelmingly difficult. 

People is one you may not be ready to hear if you’re a smart, hard-working type.  And you’ve probably heard it before — “people are everything!” — and mostly ignored it because you thought you could just work harder or smarter than the rest and do just fine.  And you *can* do just fine… but you won’t be wildly successful.

In the business world, we generally distinguish between “individual contributors” (ICs) who do a specific job, managers who build teams and executives/owners/leaders who run businesses.  ICs can be very successful — the best ones at tech companies (gifted software engineers and computer scientists) make very good money (the very best can make over a million dollars a year) and have a lot of freedom (they usually get to wear anything they want and work whatever hours they want).  But they will almost never be truly wealthy because they either end up trying to work on their own ideas but doing so alone (which limits their ability to achieve massive success) or they have to work for someone else.

Managers usually have a harder job than Independent Contributors because they actually have to get the team functioning. And running a team is hard!  When you’re a manager, you never have a perfect team.  There are always personalities who don’t get along well and the first person they tell is you.  You are the psychologist and babysitter as much as you are a professional task manager.  Managers generally need to understand how to contribute on an individual level (usually because they were formerly an IC) and how to work well with people.  But, on the plus side, at least managers generally have a pretty well defined team and set of problems so it’s not too bad and you can hack your way through management to some degree even if you aren’t really a “people person”.

Owners or executives don’t get that kind of clarity in their responsibilities.  The job of a *leader* is to rally people around you, set a vision for them and inspire them to follow you.  As an executive, I’ve usually spent up to HALF of my hours every week on the phone with people trying to convince them to join my team because the only way to be wildly successful is to have a strong team and the kinds of people who I want on my team have tons of other good options to choose from.  Think about that… you start a company because you want to solve a particular problem and end up spending half your time actually working to recruit other people to solve that problem!  I also spend a lot of time trying to wrestle with uncertainty and convert fuzzy problems into clear to-dos for my team. 

This combination of dealing with people and handling uncertainty is not a skill that comes naturally to most smart, hard-working types.  This is particularly true because most of the challenges you are used to solving as one of these types have been explicitly structured for you by your teachers in school so you are subconsciously trained to operate with clear guidelines. When you’re a leader, you suddenly don’t have any guidelines!  Your actual job is “do whatever is necessary to solve the problem we built this company to solve.”  You have to face the constant ambiguity of solving unknown problems while telling your team exactly what to do.

So, if you thought you could just put your head down and hard-work your way to great success?  You’re completely wrong.

Do you remember that person who always seemed to be hanging out with friends when you were studying?  Who doesn’t get the best grades but does well enough to stick around and keep advancing?  Who maybe led the sports teams or participated in student government?  In university, sometimes these people are the biggest screw-ups who drink too much, stay out too late and party too hard.

But somehow, a few of these people end up doing quite well.  In fact, some of them end up running the teams where the smart hard-working people work.  That’s because while you were studying for the exam your teacher carefully created for you, they were out learning how to get better at understanding and interacting with other people.  They are building a network of friends who they will call over the next 30 years for advice, for introductions to potential employees and for potential investors.  Each of you was studying, in your own way.  The mistake you made was thinking that the only skill to study was what’s on the test.

Because the smart hard-working person is used to being told what to do, they often end up actually working for someone else… often someone with stronger people skills.  They never trained how to come up with their own vision, to fight uncertainty and to lead other people.  So they’ve really been trained to be very effective employees rather than leaders.  They’ve fallen into what I call the “trap of employee mentality”.

All of this isn’t intended to make you stop studying and start drinking beer.  It’s intended to make you understand the trade-off you are actually making when you decide to over-optimize your time for achieving academic success.  Despite what the entire education system and most jobs try to convince you, true success requires you to build and leverage large networks of friends and professional contacts.

Luck is a bonus factor that’s well worth mentioning because it’s entirely underappreciated.  

You are in the driver’s seat of your career and your life but just like you can die of cancer at an early age or be blessed with an athlete’s body from birth, you could execute on a business idea and get your company killed by a stock market crash at the wrong moment of your fundraising or have your company get acquired by another and your whole division laid off because it didn’t fit with what they wanted.

Some people will get pretty wealthy just by taking an early job at a startup that grew to a billion-dollar giant while others who are smarter (and better looking) may spend decades trying and failing to achieve meaningful wealth.  It sucks but it’s true — so don’t over-index on someone’s success or write them off because of their inability to catch a wave.  And don’t over-index your own happiness on your level of financial success because there are no guarantees and you shouldn’t spend your whole life chasing something that may never happen.

A career is made at the intersection of Passion, Value and Skill

Since I’ve written on this topic before, I’ll refer you to my blog post on it.  Basically, if you want to choose the right career, figure out the intersection of what you’re really passionate about, what actually creates real economic value (makes $), and what you’re good at.  A lot of people mess this up — they choose careers that only hit 2 out of 3 of them.  And it’s hard to figure out because it often takes lots of time and lots of attempts to figure out what each of these things are.  But you’ll know it when it happens because working won’t even feel that much like work and success will be a side-effect rather than the main goal.

An opportunity is found at the intersection of growing megatrends

In the game of Poker, the most important factor in your success is not how good you are but which table you sit at.

Back when I used to play online (we’re talking about 2004 here), I had a software program which would record the hand histories for every other player I could find on the website and assign them with a rating based on how likely I would be to win against them.  Then, when it was time for me to start playing, I would look through all of the available tables and sit down at the 2 tables which had the best blend of opposing players.

Doing so, I quickly learned, was the difference between making $100+ per hour and losing $100+ per hour playing.

It turns out that life operates very similarly… putting yourself in the right environment is the single biggest factor in your success. Think about the different likelihoods of major financial success between being born in sub-Saharan Africa and being born in the suburbs in Europe or the US if you want to appreciate how much it matters which “table” you sit (or start) at.

But, unlike where you are born, many “tables” you *can* control and you should control them.  This is partially why you should still try to go to the best schools you can — you want to surround yourself with the best classmates you can because your success will be determined heavily by this.  And, in business, success means setting yourself up in the best possible table before you even begin “playing”.

The path of world through time is primarily governed by hundreds of “megatrends”.  These are things from “the aging of the Baby Boomer population” to “mobile phones putting internet in everyone’s pocket” to “the pace of drug discovery by pharmaceutical companies keeps dropping”.  As a whole, each of these things takes many years or even decades to fully play out and, especially when you’re young, you don’t actually see them as moving at all.  But these megatrends are all around us and, if you hook into them properly, they provide the foundation for massive success over many many years.

Similarly, a business is solving a problem in a particular market.  A business is made up of one or many products.  These products are created by individual teams.

What’s the best way to “easily” become successful? Position yourself at the intersection of as many growing megatrends as possible and make sure you are doing so in a growing market with the best team of people possible.  Then just do your damnedest to learn as quickly as possible.  It’s hard to go wrong betting on technology here but it’s not the only megatrend that matters.

The interesting thing is that when you first start working, you realize that many people in existing organizations don’t really want to learn and they don’t really want to change. So if an opportunity comes up which requires tons of learning because it deals with these new (and sometimes fast-moving) markets, trends or technologies, you as a fast-learning person can easily raise your hand and say “I’ll do it” and get more responsibility than you otherwise would.  Then all you have to do is keep getting better while the trend keeps getting bigger and soon you’ll find yourself an “expert” in something new that baffles everyone else and in a great position to be successful.

You will have many friends who do this purely by accident — they get lucky enough to find themselves at the middle of several trends that take off and were just smart enough to lean into it.  But you can also do the same thing intentionally yourself and it will provide you with the highest likelihood of success.

Understand the system to beat the system

The people I know who have achieved at least moderate success all have the same quality — they are very curious about understanding systems in the world at large or at least in their area of expertise.  They may not do this consciously but they definitely do it.

Every piece of the world is made up of systems.  The most obvious sort are the technical systems. For example, the way that your web browser communicates with the server across the infrastructure of the Internet to deliver you a customized webpage.  Or how your phone actually works — all the hardware components that went into it and how they’re placed in the case to work properly.  Or how all of the independent mechanical systems inside your car make up the engine (drive system), air conditioning (AC/vent system), radio (electrical system) and so on.

More interestingly, there are the systems behind the systems.  These are based not on the technical properties of circuit boards but on the incentives of people.  Think about all the systems that tie back to financial gain.

You are a valuable resource.  Every day, you do things that require you to spend money — you eat, you drive, you use electricity, you buy clothes, you go to school, you pay taxes, you use public roads, etc.  And the sole job of literally millions of people out there is to figure out how to get you to spend money on their thing as opposed to their competitor’s thing.  Because this is so valuable, almost everything ties back to figuring out how to get a bigger share of your money.

All of these people have worked out vast systems to compete for your money and it affects literally every aspect of your life.  The obvious ones are the marketing and advertising systems which try to influence you to choose a particular brand. The less obvious ones require you to think about the individuals who make up the systems… 

Think about how a business who sells a product will hire a PR agency who has a relationship with a journalist to pitch stories to the national newspaper which mentions the brand just once because it will give them credibility and make you buy.  

And think about the journalist who wants to maintain integrity and credibility but who is busy because they are required by their editors to file 4 stories per day because the newspaper is losing readers to free online sites so they need stories which can be easily shared so they can try and make some advertising income so the journalist doesn’t have time to properly research the story and runs the press release from the PR agency almost word-for-word.  

These are the kinds of systems which dominate everything from business to politics and these are the kinds of systems that, when you understand them, you can hack them to your advantage.

If you operate *within* the system, you are limited to either consuming what the system has given you (eg reading the newspaper article thinking it is completely impartial) or, in business, to being only as successful as that particular system (eg trying to sell on Amazon’s marketplace) will allow.  To achieve great success, you have to *beat* the system rather than operating within it. The fundamental thing you need to know, however, is that if you want to beat a system you must first *understand* the system.

This is where the “hacker mentality” comes in.  Hackers are generally given a bad reputation in public news because the bad ones steal things, break important systems and generally make life harder for the rest of us.  But the mentality they use is incredibly important and it’s at the heart of all success.  That’s because “hacking” is really just figuring out a way to get around a system.  In bad cases, that is the security system guarding some information but in good cases it might be the hard system of some outdated industry or the soft systems that make up “the way it’s always been done”.  

If you think of yourself as a hacker in general, your job is to identify a system and figure out if there are any useful ways to go around that system.  This is a very useful mindset!

One side effect of seeing systems is that it becomes more difficult to take things at face value. When you see a picture of some celebrity on Instagram, you don’t see the person but instead you see all the gears turning behind the scenes which put that picture there. You see the makeup, the research about exactly which posts at which times to which audiences create the most engagement, the way they emailed the hotel they’re taking the picture at the hotel manager who is desperate for guests who will spend money at the poolside bar, etc etc etc.

Despite this strange effect, it is a very good thing to see systems around you because you become properly skeptical. You see all the reasons *why* people are saying things rather than listening to exactly *what* they are saying.  And you have created the right mindset to think about how you can *actually change* the world rather than just accepting it and “doing your best”.

Be contrarian and right

A simple tenet of success was provided by the famous investor and creator of Paypal named Peter Thiel.  He says that in order to be extremely successful, you must be “contrarian and right”.  That’s because if you are not contrarian, by definition you are thinking the same way as many other people and any opportunity that you find will have already been seen by those people.  So to find outsize opportunities, you must not just find something that is contrary to popular understanding but, of course, be correct in that assessment.

It’s a simple truth that reminds you how powerful it is to be a contrarian thinker, particularly in a world where the power of social media has helped to strictly enforce cultural norms in a broad fashion.

Peter’s book Zero to One is one of the best business books of all time.  It is a bit difficult to find valuable before you have some experience in the business world and requires a lot of thinking but it is the only book I try to read every single year.

So, if you have an idea for a product or a business or a career, how many people already think it’s a good idea?  Usually, the more people who think this as well, the less likely you are to achieve outsized success from it.  You can probably have a reasonably high likelihood of a reasonably ok outcome this way but you will not have extraordinary returns.  You are better off finding the things which many people think are bad ideas or don’t even notice at all.

Take tons of risk, especially when you’re young

Very few people take real risks in their lives. Risk is related to what you could lose if something goes wrong.  And most people vastly overestimate what they can lose if something goes wrong.

The worst case scenario for you is probably that, if you try something and fail terribly, you’ll have to swallow your pride and hide at your parent’s house for a few months while you get your life back in line.  For most risks, the downside is much much less and just means you have to choose something slightly less interesting or rewarding to do.

But people are terrified of taking risks!  And yet, when you ask them later, people don’t regret the things they have done, they regret the risks they didn’t take.

As we learn in finance, there is almost never an ability to earn a return without taking a risk.  Put another way, if you’re afraid to fail then you can’t ever do anything and that totally limits the amount of success you will ever have in life or in business.

When you are young, you have the least downside for taking risks than you will at any point in your life.  You have low expenses and a support network of people willing to help you out if you fail. So when you are young is when you should take as much risk as you can!  Try the things that seem incredibly hard.  Fail. Fail again.  You’ll realize quickly that what you consider “failure” doesn’t really matter to anyone else.  It starts getting easier and then you realize you can start taking bigger and bigger risks to try and achieve bigger and bigger successes.

That just takes practice, a willingness to fail and an acknowledgement that if you do fail, it’s really not that bad.

LIFE

Comparison is the enemy of happiness but… compare with the best

This will be a bit of a difficult lesson for me to explain because it goes in the face of what I know about happiness.  That’s because the enemy of happiness is comparison.  History is littered with stories of cultures and psychology is littered with cases of people who have started out happy and relatively isolated and then become deeply unhappy after being exposed to other people.  If I have a house, I am happy.  If my neighbor has a bigger house, I become unhappy despite nothing changing about my situation.  Humans are social animals!  We define ourselves so strongly by what we perceive as our social status that comparing ourselves to other people, which we do more and more every day in the Internet and social media age, is almost always a way to make ourselves less happy.

In that sense, the most important measuring stick for your success or happiness should be *yourself* and not where you are relative to those around you.  In most cases, this means becoming happy with what you already have rather than trying to achieve something new.  There’s really no arguing this… third-party research and my own experience have taught me again and again that happiness is a mindset that’s completely relative.  Two people can be put in exactly the same situation and their respective attitudes about life will be the most important factor which determines whether that situation will make them happy.

But unfortunately, some people (including me) have the bug known as Ambition… which is essentially the gap between what you already have (or who you are) and what you want to have (or be).

In many ways, the path to happiness lies in “curing” ambition by becoming happy with what you have.  BUT, if you must proceed…

If you want to be a great football player, don’t strive to be the best in your school. Be the best in the world!  The size of your goal matters because, if you want to be the best in the world at something, you will have to take far more risks along the way (which is good).  You can’t become that good at something without forcing yourself to learn more and train smarter.  

Best of all, if you fail to be the best in the world, you will almost certainly be the best in your school.

Self improvement is a journey not an end

I noticed something interesting when I got into my late 20s and early 30s — people around me started talking about getting therapy a lot more.  There’s a point that many people hit after 5-6 hears in their professional careers when they feel sufficiently secure and are finally making enough money that they begin to concentrate on other areas like self improvement.  Often, this means they finally begin to get therapy.  I have had a passenger seat with many friends who have gone through journeys in therapy, whether official or unofficial, and it revealed an interesting truth.

When you first discover self-improvement and start reading everything on the internet about how you can become better/faster/stronger or just more emotionally stable and secure, it feels like the whole world is at your fingertips.  There are *solutions* to the problems you’ve been having!  Maybe you can finally achieve that perfect version of yourself!

So you try one approach for a few months before realizing that, while it helped, it didn’t quite fix things.  Or maybe it brought up some new problems that ran a bit deeper.  So you try another approach and, several months later, it is the same story.  Some people continue on this treadmill infinitely, always expecting that there is actually a path to become the perfect version of themselves out there somewhere.

What I’ve realized is that there is no perfect version of you.

Comparing yourself to an idealized version of yourself is a fast path to unhappiness and it’s completely unattainable.  In reality, you can’t “fix” yourself completely.  The things about you which are problems are a core part of your good parts too.  So, while you will certainly improve by addressing problems, going to therapy or talking to other people, it is important to realize that this is more about the journey than the end.  The way you “win” isn’t by figuring out how to fix yourself and make yourself “whole” once again, but to accept who you are and get a little better every day.  Don’t plan to make this a 4-month journey with a goal because you won’t ever get there… plan to make it a lifetime of being good to yourself, improving yourself, and figuring out how to leverage all the little things that make you kind of crazy into positive manifestations instead.

Accept who you are now and try to get a little better every day.  That’s all you can do and it is enough.

Relationships are completely about Trust and Communication

Relationships of all sort, whether romantic, familial or business-oriented, all boil down to the same two key factors: Trust and Communication.  For a relationship to be fully stable, both of these are non-negotiable must-haves.

Trust means you have faith that the other person will do things which are consistent with how they have acted in the past and which have your best interests at heart.  Trust must be equally shared on both sides and takes a long time to earn.

Communication means that you have created a safe way between you to discuss everything from the easy stuff to the difficult topics without blame, emotional blowups or resentment.  

Both of these things require you to work hard at them!  Often, you will have to refresh them if they fade over time.  I want to dive a little deeper into each one:

Trust is often described as “consistency over time”.  To teach trust to children, my brother used the analogy of a jar of marbles.  Every day that they operated in a trustworthy manner, it was like adding a single marble to the jar.  The more marbles in the jar, the more adults trusted them to behave and the more responsibility they would get.  When they did something bad which violated the trust of their parent or a teacher, it was like emptying out the whole jar and starting over again.

In the most stable relationships I’ve observed, both participants trust each other completely.  That means it doesn’t matter whether one of them goes out drinking with an ex-partner or if their personal notes are left on the desk — the expectation is that the other person will act in good faith and worthy of trust.

To create trust in a relationship, you must both be able to *receive* trust (be trustworthy) and *give* trust to your partner.  

Being trustworthy means living your life in a way where your actions are entirely worthy of the other person’s trust.  The best test for this is to ask yourself whether the other person would be sad or angry if they saw you doing what you’re doing.  This test removes all doubt!  Sometimes people use language to try to hide their actions (“well, I said I was visiting a *friend* and my ex-boyfriend *is* a friend, why are you mad?”) but you know deep down that what matters isn’t what you actually did but how it fits into the other person’s *expectation* of what you were going to do.

Being trustworthy also means allowing the other person to trust you with their vulnerability. It means giving them the psychological safety they need to share themselves with you.  It means letting them know that they can be their weird self without you judging them.  It means letting them know that they can tell you a difficult story without you using it as ammunition in an argument against them later.  

To *give* trust, you have to allow the other person the space to be themselves without constantly watching over them or worrying about what they are doing.  This means you have to allow them to potentially hurt you, which is hard!  And, yes, they may violate your trust and actually hurt you. 

But think of it this way… If they violate your trust, you have identified a bad relationship and can fix it or move on.  If you don’t ever give trust, you will never have a good relationship.  Which is worse?  It is better to lose or fix something bad now then to never have something great at all!

You may have difficulty trusting *anyone*, which means it will be impossible to have a fully secure relationship.  The best fix for this is to figure out why this is the case (often it has to do with a lower sense of self-worth) and fix yourself first.  Yes, it turns out that having good relationships with other people does require you to work on yourself too 🙂

Trust violations (like lying) happen sometimes because people are human and they make mistakes. If there is a path to fixing a trust violation (easiest if it is relatively minor), the way to do so is through effective and very pro-active communication.

Communication 

People generally underestimate how important communication is both for the relationship and for trust itself.  If trust is the core factor that makes a relationship, communication is how you build that trust in the first place and fix it when it’s broken.

Good communication means actively opening conversations about any issues that come up and then, when you are talking, creating a safe space where you can talk without being afraid of getting each other so angry you stop communicating.  This can be difficult — you can’t run away mid-conversation, you can’t bring up things from the past to try and “score points” to win the argument and you can’t save up ammunition for future arguments.  You have to get good at admitting you were wrong, saying “I’m sorry” and forgiving each other.  You have to be okay with not becoming defensive if what they say hurts or isn’t quite fair.  Basically, you need to get good at using clear and direct words to say what you’re actually feeling and what you actually mean rather than trying to hide your thoughts or emotions. 

The real super power of communication is empathy.  If you get good at seeing things from the other person’s perspective and assuming that whatever they are saying is coming from a place of love and care, you will find it very difficult to get angry at them or run away before they can say their piece.

What does good communication look like in practice?  I know many people who are in consenting relationships with multiple romantic partners, which is a situation that many other people would assume involves lots of cheating and lying.  But my friends do this by communicating exceptionally well with each of the partners and being very clear where they stand with each other.  Some of them schedule monthly “relationship check-ins” where they spend several hours talking about the state of their relationship.  Whenever issues like jealousy or mistrust or hurt arise (as they usually do in some form with any relationship) these people are very proactive about discussing the issues with their partners. 

The ones who resolve problems successfully see that there is an issue, tell there partner “hey, I think there’s a problem, let’s talk about it”, and then create a safe space for discussion where they can communicate without fear of having things held against them later.  That doesn’t mean communication is easy — you often have to have painful or difficult discussions — but it’s much better to have those discussions and repair your relationship than to avoid them and make the trust problem worse.

To do all of this, you usually have to start by getting good at managing your emotions and having intellectual discussions about tough topics.  But once you have practiced it a lot, especially with one partner, it becomes much easier and it allows you to approach difficult topics without even engaging emotions at all because you trust the other person is acting in good faith.  

The best part of being good at communication is that it really helps everything else too.  Good communication means that you will find it easier to give trust because you feel comfortable telling the other person when something they do or did hurts you.  It means it’s easier to be trustworthy yourself because you can have frank discussions about the things which each of you assume about the other’s actions.  It means you don’t have to tell lies because you can always address issues head-on and know that you will be heard.  And, best of all, it means that you know you can fix any problems that come up in your relationship so it gives you much more freedom to be yourself, which will make both of you much happier.

***

Most relationships need work.  You may have difficulty trusting the other person or maybe you don’t think you can tell them hard truths because you think they will react emotionally or may feel hurt.  You may find that you can’t have a discussion without one of you bringing up something unrelated.  You may find yourself becoming defensive or hurt easily so you try to hurt the other person instead first.  You may lie or tell half-truths because you don’t want to admit what actually is going on inside your head. Sometimes this is because you don’t feel safe trusting the other person with the real knowledge.  Relationships are hard!

Usually, the first step to fixing a relationship is fixing the lines of communication.  There’s a reason why one of the most important things that the US and USSR did during the cold was was to install a red phone that had a direct line between the White House and the Kremlin to avert nuclear war!  If you can’t communicate well, you will find it nearly impossible to build good trust.

So, if I can provide actionable advice, start by having a conversation about having conversations… talk about how each of you communicates, admit where there are differences in your communication styles, and establish the “rules” you promise to play by during future conversations (eg “I won’t get angry, I won’t hold anything against you later” etc).  If you can talk about talking, you’re on the way to better communication.

My final note is that it takes time to get good at this stuff.  I didn’t even realize I needed to get better at it until I was older than 25.  So cut people some slack and help them get better because not everyone is as woke as you are now 🙂

Clearings

In my house, a number of people have taken a training called the Conscious Leadership Group and programs related to it.  This is a course for business leaders to become more effective but it really applies directly to every facet of life.  In particular, the way they teach communication is very interesting.

Before going into that, the core concept for effective communication that I’ve learned is that, when you experience an event, there are two things which occur — first, there are the facts of the event (things which anyone looking at it would not argue with).  Second, there is the story you tell yourself about the facts (aka the “narrative”).  This story is what actually causes you to react emotionally.

For example, if you go into the kitchen and see that there are dirty dishes in the sink, the facts are pretty obvious. But you might get angry because you tell yourself a story that your roommate clearly doesn’t care about you because they know they are making more work for you by leaving things dirty and assuming that you will clean them.  The reality may be different — they may have forgotten their dishes in the rush to get to their exam — or maybe it’s exactly the same as your story.  But the point is that it’s the *story* which triggers you to become angry.

Thus separating the facts from the story is important.

A communication exercise which our housemates borrowed from the Conscious Leadership Group is called a “clearing” (https://conscious.is/video/how-to-use-the-clearing-model).  A “clearing” is when two people address an issue that lies between you using a particular format.  It’s called that because you are “clearing” the air between you.

Clearings work by giving you a specific template for communicating about the issue. Note that you don’t actually need to *resolve* the issue — sometimes issues don’t have clean resolutions.  This is about *communicating about* the issue, which is always the first and most important step towards resolution.

The template allows the person who has the issue to speak about the problem and then for the receiving person to acknowledge the issue.  It starts by the person who has the issue sitting across from the recipient and doing the following:

1. State the facts.  Describe exactly the actual facts that occurred.  Don’t put any emotion or judgement — this is literally what anyone who sees the event happen would have seen.
2. State how this made you feel.  You only have 4 options: Angry, Sad, Happy or (obviously only applicable in some situations) Aroused.  It is important to use only these 4 options because every other word you use to describe an emotion is actually just code for one of these.  “Frustrated” is actually just a softer way of saying how you really feel — Angry.  “Jealous” can usually be either “Sad” or “Angry”.  You see the point, I hope. It’s important to be honest and clear about the emotion that was created.
3. State the narrative you created from the facts.  This is your chance to be a bit vulnerable and describe the story that’s in your head.  Why did you actually feel this emotion based on those facts?
4. State a request you have for the recipient. This means — what action do you want them to take to help you resolve this? They don’t necessarily have to do it but this helps you show them what would make you feel better. For example, you might say “I want you to say thank you when I do the dishes because it lets me know you appreciate me and do not take me for granted.”

The recipient is not allowed to react to any of this while the first person is speaking. They can’t speak, they can’t defend themselves, they can’t roll their eyes.  After the first person is done, the roles switch and the recipient is allowed to speak while the first person must stay quiet.  The recipient:

1. Repeats what they just heard — the facts, the feeling, the narrative and the request.  The first person can correct specific things but this is *not* a discussion.  The first person can acknowledge when it is all there.  This helps make sure the first person is fully heard by the recipient.
2. Ask, “is there more?”.  This is important! Usually, the first person will hesitate to tell everything because communication is hard.  When you ask “is there more?” you allow the first person to really open up about what is going on.  
3. Say “thank you” and move on.

Again, this format is specifically *not* intended to create a long discussion.  It is intended to help one person show the other person how they feel, to feel like they are heard, and for the recipient to have a way to fix that feeling (if needed).

Yes, this seems kind of strange.  At first, it feels kind of strange. But it is a great way to address and begin to resolve conflicts. Sometimes, it is the *only* way to address and resovle conflicts which are particularly difficult.

I mention this not so you can make all your conversations follow this format but so you understand that separating the story from the facts is the important first step of communication and I have found it to be really helpful for having stronger relationships with people, especially those who you are kind of stuck with (like housemates or family).

If you are interested in diving deeper into the art of communication itself, there is a movement called “nonviolent communication” (https://en.wikipedia.org/wiki/Nonviolent_Communication) which also has some interesting ideas about how we speak to each other and what that means.

If it doesn’t fit, it isn’t you

When I was in college, I joined a fraternity because it sounded like all the fun I had in my high school dorm but with drinking and women liberally sprinkled in too.  After a handful of parties and events, I stopped feeling that much interest in doing these things but that’s what you’re supposed to do so I kept going for another year before fading away.

In my first few years after college, everyone I hung out with went out to bars all the time. We mostly just drank beer, stood around making jokes and talked about trying to “get girls”.  When we went out to clubs, we bought too much liquor, drank too much, and shouted to each other over the music.  It wasn’t until I was maybe 27 or 28 that I finally realized I don’t like getting drunk, I hate bars and the whole idea of trying to meet people by shouting over the music seems kind of stupid.

It turns out, if something doesn’t really feel right, maybe it isn’t.  Question everything.  Just because all your friends are doing it or people accept that it’s true or your romantic partner says it’s the right thing doesn’t mean anything… think for yourself.  And don’t be afraid to hang out with other people if your friends do a bunch of things you actually don’t like.  It’s ok to make other friends.  Life is too long to hang out with people who do things you actually don’t like to do.

You are the sum of the 5 people you spend the most time with

There’s an expression that “You are the sum of the 5 people you spend the most time with” and I’ve found it to be quite true.  Imagine who these 5 people are to you now (you can weight them a bit based on the intensity of that time, of course).  Maybe this doesn’t feel quite right now, but think of this — every day that passes, they are having a subtle influence on you.  You may not “be” the sum of those 5 now but they really influence your personal growth curve so, over time, you will slowly become more and more like them (and they will become more and more like you).

The actionable part of this is easy — spend your life finding the 5 people you most want to be like and who push you to be the best version of yourself!  This is incredibly simple to understand and difficult to do in practice.

When you’re young, it’s easy to have friends who happen to be in your class, your soccer team, your bus… whatever.  Luckily, as you get older you start to realize that you don’t have time to spend with people who aren’t excellent for you.  The sooner you realize that you should focus on a smaller number of amazing people rather than collecting a large number of ok ones, the sooner you can stop investing in friendships that don’t add lots of value to your life.  The best (and most stable) friendships are those where both your and they are constantly supporting each other and helping each other improve.  The worst are the ones where a person is constantly taking your energy and leaving you feeling drained.

Find the good ones and either fix or drop the bad ones and your life will be much richer.

Journal

The most valuable habit I’ve ever developed was to write in a journal.  Some people do it every day.  I do it whenever I feel like I need to (some weeks it’s every day, some weeks not at all) but it has been incredibly valuable not just to remove thoughts from my mind and onto the page but also because doing so allows me to build on those thoughts in a way that I never would if they were kept circling in my brain.  It creates a path of understanding where a single thought can be interrogated and used as the basis for deeper understanding.  I’ve learned more about myself from writing things down than I ever did just by thinking.

Skills you should learn as early as possible because they pay off every single year of your life

You don’t need to learn any of these like a professional. Use the 80/20 rule… learn the basics in a short amount of time and feel free to stop when your rate of learning begins to slow down.

• Dance — At the most basic level, you should know how to do spins and to start feeling comfortable moving with music.  It’s also best to learn the basics of at least one partner dance (it doesn’t even matter which one, whether it’s Swing, Salsa, Blues… do whatever has fun music and fun people) so you always have some moves to pull out at weddings.
• Photography — Learn about how to understand light, composition, color and basic editing principles and every single photo you ever take will be slightly better.
• Cooking — If you understand the basics and feel comfortable in the kitchen, not only will all your meals forever taste better but you will be a much more interesting host and always have a good date idea.
• Learning — As I’ve mentioned previously, treat learning itself as a skill and get as good at it as you can.  Really examine how you can get better and faster at learning and everything else on this list will be easier.
• Exercise — learn how to go to the gym, how to stretch, how to take care of your body when it’s injured and you’ll always be able to go for a workout or a run and feel better about yourself.

The most important books for understanding people and relationships

1. Daring Greatly by Brene Brown. Start by watching her TEDx talk on vulnerability and her TED talk on shame first so you understand her ideas before reading.  This book presents a theory of the world where almost everything that anyone does stems from their desire and need for *connection*.  Once you realize this, you have the key which allows you to understand other people — and yourself — forever.
2. The 5 Love Languages by Gary Chapman.  Honestly, I never read the book itself because it looks like an over-commercialized load of crap (the marketing around it is truly awful) but the core concept which it provides has been incredibly valuable for understanding other people.  So maybe it’s best to read about these “love languages” in blogs online to get the point and apply them to your own life accordingly.
3. Attachment Theory — you can read one of many summaries to get the basic idea or the actual book when you’re ready afterward to help the concepts really stick.  Basically, this provides a model for thinking about how typical relationship dynamics — and especially “neediness” — are caused and why they work.  It has become a useful default model for helping me understand myself when I am in a relationship.