18 Rules for Ambitious Young Men in 2018

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Young men crave direction and opportunity for themselves.

After the age of ~18, young men have little to no guidance in their personal lives. What was once filled by church, a strong father figure, or a prominent community member is now either left empty or filled by celebrities, anonymous advice on reddit, or even women. Add in the extra dynamic of andogynizing advice and things get extra confusing. Yes, some pieces of advice (including a few on this list) work for both men and women. No, not all pieces of advice should be followed by both genders.

Here are 18 of my rules that I’ve learned from the mentors in my life and that I pass on to the young men with whom I work. Working with more young men younger than myself convinced me of a need to go beyond simple one-on-one rules and put this list together.

Health

Stronger people are harder to kill and more useful in general .
— Mark Rippetoe

1. Stop Eating Trash & Start Eating Real Food

Most food available to you today is complete trash.

Stop eating it.

In the mid-20th Century, a concerted effort by sugar farmers and companies to convince the American public that fat was bad for you and that low-fat foods would be better succeeded, leading to decades of misinformation about what you should be eating. The food pyramid and later versions of it are a good example of this, with fat and meat listed in smaller proportions than “grains,” dairy, and other sugar-based foods.

Wrong.

Most people today get that sugar is not good for you — yet the low-fat myth persists. Here’s the thing that makes that a weird trade-off: most low-fat foods have to have some kind of additive to maintain the flavor and consistency that the fat would otherwise bring it. For a lot of these foods, sugar is that new additive. Although it comes in different forms and names — not always the dextrose of sugar jars that you’d expect — the sugar in your food is burnt by your body like lighter fluid on a cookout. You get a quick surge of energy and then a crash (i.e., a sugar crash) instead of getting a long, constant burn of energy.

Understand that food is fuel for your body. If you put garbage fuel into your body, expect garbage results. The body is the hardware for the software of your mind and for everything you want to do, achieve, and become. Damage the hardware and you make it harder for the software to meet its goals.

There are a few things you can do right now to improve your nutrition over 90% of your peers.

First, stop drinking soda. There’s nothing redeeming about soda. The sugar and caffeine build a dependency for your body and your body stores the sugar in fat cells to be converted to energy later. If you like the carbonation of soda, drink mineral water instead. If you like the caffeine in soda, drink coffee (without sweetener) instead. Soda is probably the number one sugar delivery mechanism for most young men. Cutting it out will take some work and a few days of cravings. After a week or two, you will notice your craving for soda is almost entirely gone. Keep your eyes on the end-goal of having more energy and vitality to do what you want to do when you feel tempted to pick up a Coke instead of a bottle of water.

Second, stop eating anything with vegetable oil in it. Despite the belief that vegetables are healthy, vegetable oil causes many of the ills from which modern people suffer, like weight gain an inflammation. This rules out most junk food.

Third, don’t eat out as much. Cooking simple meals at home is easier and cheaper than eating out. A trip to Costco or your local grocery store can get you a week’s worth of food for around $50 if you buy frozen meat, frozen veggies, and some olive oil or butter with which to cook. Buy a few Tupperware containers and cook all the food at once and save it for the week. In 1–2 hours, you have most of your meals for the week.

Fourth, minimize snacking and focus on meals. If you eat good, whole foods that are primarily made up of proteins, fats, and, in some cases, select complex carbohydrates, I can guarantee you will find yourself snacking less.

What specific food pyramid do you recommend? Honestly, I recommend whatever is best for what you are trying to achieve. Unless you’re trying to achieve mediocrity, then the traditional food pyramid that places such an emphasis on grains and carbohydrates will not be a good choice. I switch between a modified paleo diet (I have no issues with dairy) and a ketogenic diet every couple of months based on multiple factors like whether or not I am traveling, whether or not I am trying to gain strength, whether I can get to the gym regularly, and other factors.

Experiment with different approaches.

2. Don’t Blow Your Money on (Most) Workout Supplements

Most workout supplements are a total waste of money.

Your body absorbs different minerals and vitamins in different ways and a lot of the supplements on the market are formulated in such a way for your body to filter out the active ingredients. To the extent that they do have effects, you have to wonder about the trade-offs and what else you could be doing with your money.

Even the ones that everybody relies on and are better absorbed than others, like whey protein, can be replaced or offset by whole foods like eggs, milk, red meat, and slow-burning carbohydrates like grapes.

Plus, you want functional strength. If you need to take a cocktail of minerals before you can lift something, how functional is that?

The few that have a strong record of working and have measurable effects on the body include:

Creatine — Creatine helps cellular ATP production, giving your muscle cells more energy to do high-intensity and high-stress workouts. (Be sure to drink plenty of water with creatine.)

High quality whey protein — Whey protein provides the body with a quick delivery mechanism for whole chain amino acids and other vital nutrients. This is particularly useful if you don’t have time to eat around going to the gym. More here.

Vitamin D — Most people do not get enough vitamin D. Young men particularly need it because it is one of the building blocks of testosterone and helps protect against Seasonal Affective Disorder (i.e., feeling crappy when you haven’t seen the sun for weeks in the winter). Taking a vitamin D supplement is particularly important if you live in a cloudy and gloomy climate.

(h/t to Rogue Health and Fitness for part of this list.)

Otherwise, eat more eggs, milk, and red meat. Red meat naturally contains creatine, eggs contain follistatin, which helps with muscle growth by inhibiting a negative regulator called myostatin. Milk has a lot of fat, protein, and some sugar, making it a strong source of calories.

Don’t buy anything for boosting testosterone at your age. Working out regularly and taking vitamin D/getting sunlight will do everything you need it to do. In fact, supplements and steroids that drastically and unnaturally increase testosterone can cause your body to freak out and produce more estrogen in response. This is why men on steroids sometimes develop man-boobs.

3. Either Lose Ten Pounds…

Do you have a paunch?

Man-boobs?

Do your chin and neck blend into each other as smoothly as a dusk horizon?

Are you simultaneously pretty weak for your size?

You’re too young to have yourself in this shape. If you are carrying extra weight that is not serving you (i.e., is not the product of gaining weight through strength training), then your number one focus should be to set up a system that helps you drop that weight and keep it off without sacrificing the muscle that you need to give you the vitality a young man should feel.

Young people today are fat for two reasons:

  1. They eat garbage. They eat food that their bodies do not burn and instead convert to fat to be stored as an energy source accessed later on. Sugars are particularly dangerous for this reason. The body converts and stores these sugars in fat cells as glycogen.
  2. They don’t move enough. You’ve probably heard people rail against sitting down so much (see Rule #6). The issue with sitting is less that sitting is inherently bad for you and more that people were designed to move. Your body is not designed to have access to a lot of calories for little-to-no cost and simultaneously be in one place for several hours at a time.

If you follow Rule #1, you should see yourself drop a lot of excess weight pretty quickly. Chances are you are eating more than you need to eat and what you are eating is garbage. Cutting out soda, sugary sweets, and anything with vegetable oil in it makes a huge difference.

While cutting out the garbage and replacing some of it with healthier, fuel-oriented foods, start moving more. Get to the gym and lift weights. Forget the treadmill and jogging. Practice some high intensity interval training.

More than anything else, focus on eating less garbage and less that can be stored in fat cells later. Reduce your carbohydrate intake to less than 30% of your daily caloric intake. Start eating more protein and healthy fats (i.e., avocados, salmon, olive oil).

You’ll feel better, look better, and will command more respect when you’ve lost the weight that is holding you down.

4. …Or Gain Ten Pounds

You know who you are.

You weigh less than many women your age.

You can’t lift up a heavy box of books, let alone a barbell at the gym.

You need to gain some weight.

Before you get too far ahead of yourself, no, you really cannot gain weight without gaining some fat. A lot of the young men I know who could use an extra ten pounds on their frames are nervous about the idea of getting “chubby” and refuse to be proactive about getting to a healthy weight out of a false notion that they would look better as a dweeby twig than as the solid strength they should have on their frames.

Here’s the thing, though: losing weight is actually a lot easier than gaining weight. If you are so absorbed in the idea that you cannot have a little bit of fat on your body (a notion against which I would argue, anyway) and won’t allow yourself to gain some muscle weight out of fear of adding that fat, know that you can lose that fat more easily than gaining the healthy weight in the first place.

This is all even more true if you are a young man of below-average height. Despite jokes about Napoleon Syndrome, gaining more solid weight on a smaller frame will not only make you appear bigger but will also allow you to command more of the respect that taller men are usually unconsciously given as a function of their height.

To gain healthy weight, you have to do two things:

  1. Put good fuel in your body. Not all calories are created equal. 1000 calories of sugar and vegetable oil are not at all like 1000 calories of protein and fat. Replace your diet of sugar, takeout, and snack foods with whole foods. Mark Rippetoe (in)famously recommends drinking a gallon of whole milk every day while strength training and eating 5 meals. There’s a reason for that — the macro breakdown of whole milk is mostly protein and fat with some sugars from lactose, making it a great source of fuel for muscle synthesis. You don’t have to drink a gallon of whole milk every day, though. Just make sure you are eating more than usual and better food. It will feel like you are eating too much at first. Peanut butter makes a good snack food in this period with its high protein and fat contents.
  2. Put that fuel to good use through strength training. If you just ate a lot more, then sure, you would gain unhealthy weight. You have to put that fuel to good use by engaging in strength training. If you are fortunate enough to know somebody who is skilled with a barbell or can hire a trainer who is, that is one of the best and fastest ways to gain functional strength. While machines are simple and easy, isolated workouts done on machines do little to add to overall functional strength (but is still better than nothing). Figure out your baseline and put your body under increasingly heavier stressful loads of weight. If you are eating enough decent food, you will notice weight gain. And you’ll feel better at this heavier weight than you did when you were thin.

Squats can be some of the best exercises for adding strength and weight. Just be sure you know what you are doing before adding too much weight. Poor form can lead to injuries and/or unrealized gains.

5. Get a Gym Membership and Actually Go

Get a gym membership and develop a habit of actually going.

If you need to figure out which gym you should join, keep in mind that the number one factor that determines whether or not somebody makes it to the gym is location. Choose the gym closest to you. I go to an older and not-very-well-equipped YMCA because it is a block from my house. Could I afford to go to a Gold’s Gym downtown? Sure, but I would not go every other day like I do to my Y.

My dad once told me a story about a gentleman with whom he trained when he was growing up. This man was one of the best-trained men he knew and had been training for years, even through moving across the country multiple times. How did he keep his schedule and momentum up? He chose where he lived based on where the gym he wanted to attend was. Sometimes, like in LA, this meant living in the ghetto. Sometimes it meant finding an apartment in an area that had very few.

He knew that the number one factor that determines whether you pull yourself together when you don’t want to and get your ass to the gym is location.

You don’t have to be this radical, but don’t delude yourself into believing that you’ll go to that gym across town. Choose one close to you.

Then actually make a habit of going.

The benefits of going to the gym regularly are two-fold:

  1. Health — You will feel stronger, more energetic, and generally healthful if you make a habit of going to the gym and working out.
  2. Psychological — Regularly going to the gym helps build your sense of self-efficacy. That is, it helps you see yourself as capable of taking on increasingly large challenges.

When you first start going to the gym, you’ll notice huge leaps and bounds in your strength. One week you’ll barely be able to lift the bar and the next you have no problem whatsoever. After a single workout, you feel considerably stronger than before. You experience near-linear growth for the first few weeks you go.

Taken from Mark Rippetoe’s article, “Who Wants to Be a Novice? You Do.”

And that’s a great feeling. People, especially men, thrive on a feeling of growth and progress in themselves. The gym is one of the few places where you can set a (reasonable) goal, do your research, put in the work, and hit that goal 100% of the time.

As you keep this up, you eventually hit a plateau. You experience diminishing marginal returns as you have to put in more work to get that extra 5 lbs than you had to get the first 150 lb increments all the way to that point. It’s here that a lot of people stop going regularly.

Don’t let this happen to you.

Even when you have to put in more work to get fewer returns, you still want to keep going for two reasons. First, most things in life do not come easily and require multiple repetitions at the same activities until you see progress. Second, and this has been huge for my own mental effectiveness, starting your day with a successful trip to the gym allows you to see yourself as effective in the day and makes it easier for you to take on bigger challenges. You want to begin your days with momentum — starting with a trip to the gym is a great way of doing that.

6. Your Posture Matters. Stop Sitting Down So Much and Stop Looking at Screens All Day

image credit: artofmanliness.com

Human beings were not designed to sit down for hours every day and slouch over paper or a computer screen. Years of sitting down during school hours destroys the alignment of your back and neck posture, makes it difficult for you to run properly, and causes general tension throughout your back. Try not to sit down so much.

Some years ago, I went to see a physical therapist for some muscular pain in my neck. Before feeling around my neck, they had me take an X-ray to see how the muscles and vertebrae were aligned. The result was worrisome. My head was a good 1–2 inches in front of my shoulders and the muscles had grown in such a way that supported that structure. This was putting undue stress on the shoulders and mid-back, I was told, and created a lot of the pain I felt.

An illustration of the extra weight placed on your neck and shoulder muscles according to where your head is placed.

This was caused by years of sitting at a desk, reading books, reading a computer screen, and looking at phone screens and took years of training and therapy to correct.

I am far from alone. This is one of the most common physiological adaptations among young people today. I see it in the young men I work with and will walk behind them and physically push their shoulders forward and their heads back.

When sitting over a computer or a phone, try to keep yourself from slouching forward towards the screen. Keep your neck straight and your head back. Sitting down less will make this easier for you.

Evolutionarily and biologically, you will feel better with your head back, your shoulders lowered and back, and your eyes looking forward. Your spine will elongate and you will look taller and bigger. Your breathing becomes less shallow, letting you oxygenate your body more easily, and you will look and feel more confident.

This is the time of your life where feeling confident pays the most dividends and where feeling pathetic brings the most pain. An easy way to help with that confidence is by fixing your posture and sitting down less.

Recommended books:

The Case Against Sugar by Gary Taubes— Taubes is an investigative reporter who breaks down the history of the “low-fat” movement and the proliferation of sugar in the SAD (standard American diet) in this book.

Starting Strength by Mark Rippetoe — This is really more a textbook than anything else, but Starting Strength provides a good foundation for understanding how to do barbell exercises like squats, deadlifts, overhead presses, bench presses, and power cleans. If you are going to try barbell exercises and have not worked with a trainer, I recommend at least skimming this book.

Primal Endurance by Mark Sisson — If you absolutely must do endurance training (9 times out of 10, you’re better off focusing on strength first…but some people like running), pick up this book by Mark Sisson to see how what you put in your body can drastically affect your endurance training. Mark also goes into good detail on High Intensity Interval Training throughout this book.

Deskbound: Standing Up to a Sitting World by Dr. Kelly Star — This is the book that convinced me that all the talk about sitting being the new smoking was right. Deskbound will help you find out how badly sitting has affected your posture and health and walk you through exercises to reclaim something so vital to your success and longevity.

Recommended blogs:

Rogue Health & Fitness — PD Mangan’s blog on health and fitness is one of my favorites. His focus is primarily on anti-aging for middle aged men and older but the research he captures and simplifies on the blog is often applicable across the age spectrum.

FoundMyFitness— Dr. Rhonda Patrick is known for her appearances with Joe Rogan and Tim Ferriss. Her blog includes a podcast in which she interviews experts in fitness — often other doctors and researchers — and simplifies their insights. I particularly enjoy her guide to heat resistance training (i.e., using a sauna).

Wealth

He who lives by the crystal ball will eat shattered glass.
— Ray Dalio

Full disclosure: I do not believe you should listen to anybody’s financial advice without seeing their asset spread. I primarily invest in index funds and own a handful of bonds and speculative assets. I do this because investing is not my job and I want to save the mental energy from active investing to focus on growing my skills to earn more money.

A breakdown of my primary investment account through Wealthfront with a Risk Score of 5.0. This is an automated breakdown based on my investing risk tolerance and not to be interpreted as a recommended spread.

For me and my skillset, it’s better to spend my time creating and becoming better at what I do than actively managing investments.

Wealth is about more than investing and getting your finances under control. It’s about investing in yourself and using this time of opportunity to earn more time and money down the line. You have low opportunity cost when you are young and relatively unskilled. Use that to your advantage by taking on the work at which others balk and enjoying the grind.

This is how I got ahead.

7. Get a Credit Card

The number of young people I meet without a credit card baffles me. I don’t know if it extends from their parents having bad experience with debt or never teaching them the importance of building credit but you should get a credit card as early as you possibly can so that you can start building your credit score up. A good credit score can save you thousands of dollars in interest rates and allows you to get better credit cards with stronger perks (like my personal favorite, the Chase Sapphire Reserve card) earlier.

If you have a thin credit file — or no credit — you can start with something like the Capital One Secured Mastercard. Put a few small purchases on it every month and pay it on time.

Remember, debt is a tool. It is neither evil nor good. Debt can be good if you use it properly. What you want to avoid is getting trapped in debt because of poor decision-making and getting slapped with high interest rates because you procrastinated on getting a credit card.

Once you’ve built up your credit, go for a credit card with great perks associated with what you want to do. I travel a lot, so I like the Chase Sapphire Reserve card, for example. This gets me a lot of travel perks like free TSA PreCheck, discounted rental cars, and discounted stays at luxury hotels. Use CreditKarma to check out what cards you are most likely to be approved for and what their perks are.

8. Invest in Yourself First

There are a few categories of purchases for which I have very lax budgetary requirements. The biggest is real education.

I have no budget on books, courses, seminars, if I believe that they will substantively help me increase my earning power.

This rule has yet to fail me.

While some people bitch and moan about the cost of a book or a weekend seminar with an expert and then go out and spend hundreds of dollars at bars through the weekend, the most successful young men I know have no limit on purchasing things that will help them earn more money and become better men.

Some $20 books have saved me thousands of dollars. Some $1000 courses have earned me 10x the cost of the course.

Remember, no matter how trustworthy an investment looks, the only reliable investment is yourself.

To get what you want in life, you can either cut back on frivolous items (e.g., the classic example being a $3 coffee at Starbucks) or you can earn more money. For a short period of time, before you get your professional grounding under yourself, you’ll probably have to go without those fancy coffees and the fun car. Once you’ve built that foundation, though, it is easier to earn an extra $10,000 (or even $100,000!) than to find an extra $10,000 to cut.

Poor people think only in terms of saving money.

Rich people think in terms of earning more money.

When evaluating whether or not to make a purchase on an item that could help you earn more, avoid turmoil, or save time, ask yourself these two questions:

  1. What else could I buy with this money? This is called thinking on the margin and has been a powerful tool for me in overcoming a cheap mindset and moving into an investor mindset. If you want to spend $20 on a book, could you instead spend that $20 on a seat at a seminar? Or would you spend it at the bar? On pizza? If buying the item is the most empowering thing you could do with the money, you should buy it.
  2. How much money would I give up to solve this problem once and for all? What is the problem or pain-point the material purports to solve? Is it earning more money? Helping you feel fulfilled in your work? Learning more skills (that will translate to more money)? How much do you value these things? If you value any of these things more than the price of the item, you should buy the item.

You have the added advantage of being a young person. When you’re young, your opportunity cost is low and you can get ahead because of this. Use this time to learn skills and strategies when your older competitors are busy providing for their families, paying their bills, and fulfilling obligations.

Spend this time to invest in yourself.

9. Work Before You Dive Headfirst Into Debt and a Career Track

The idea that you should immediately jump into years of training and tens of thousands of dollars of spending and debt without having any real experience of working in the world is insane.

Unless you’ve been working professionally since a young age, you probably have no idea what you want to do. That’s okay so long as you approach your education as the opportunity to learn more skills that help you increase the value you can add to others.

What’s not okay is diving headfirst into an education and career track that you have no idea whether or not you’ll enjoy and that is incredibly difficult to escape once you get into it.

When I was in college, I met a number of people, both current students and alumni, who went to work in investment banking and consulting. I met a weird number of these people. These are prestigious but not-very-enjoyable jobs that are best for people with very specific personality types and very specific goals. Very few of the people I met also met those requirements. But they wanted to be i-bankers and consultants because that’s just what you did with a prestigious Ivy League degree. “Plus,” they’d say, “I’ll just do this for a few years, earn a good bit of money and get the experience of working for EY/Deloitte/Goldman/etc. and then quit and go do something I enjoy more.”

I’d run into several of them years later and very few of them had quit or were able to quit. I even ran into a much-older alum who told me about this trap. People would get attracted to certain career tracks because they sounded good, sounded prestigious, and sounded like they made a lot of money and would find themselves unhappy working in them. On top of that, they could not easily quit because their lifestyle inflated with their job. They got used to going to the expensive bars, doing the expensive vacations, and renting the apartment in Manhattan.

You don’t have to be a miserable prestigious i-banker to fall into this trap, either.

I was giving a talk to a high school once about careers and told the story about my peers in college. The economics teacher at the back of the auditorium spoke up, saying that even in his job as a modestly paid economics teacher at a public high school in suburban America, he felt that pressure. He had a mortgage, a car payment, and loans he had to pay back, after all. Maybe he wanted to go do something else. Maybe he wanted to work multiple jobs across his life in different and varied industries. Maybe he discovered that teaching wasn’t his forte and he’d rather spend his time working on marketing problems. Regardless, he could not leave the security of his job with the obligations on his plate right now.

You have an opportunity now, as a young person with relatively few obligations, that is difficult to come across later in life. You can try new things, work in different environments, shadow different professionals, learn new skills with ease, and explore different professional realms without the baggage of an older professional.

Use this time to get as good an idea as possible of what you don’t want to do and what you do want to do (what you don’t want to do is more concrete and stays more static through your career).

The conventional knowledge that you have all the time in the world and should put this off until later is wrong.

Spend this time investing in yourself by figuring out how you should spend the rest of your career.

10. Automate Your Investments Starting ASAP

Day-trading and buying specific stocks can be fun and sexy (until you get destroyed by somebody else). Taking the time to “manage your investments” or “hire a financial adviser” can also make you feel significant and important.

But these are neither important nor necessary.

The best way to get started on using your money for yourself and becoming an accumulator of capital and not just a consumer is to set up an automated investing system. It’s not fun. It’s not sexy. It’s not time-consuming.

That’s the point.

Here’s the thing about the psychology of investing. When you read about investing in the past and you see people who got out at the bottom of a market or people who bought in right before a bubble burst and think, “well, that was dumb!” you are operating from a position of hindsight, which is 20/20.

When you are actively managing investments, you always think during good times, “is this the top of the market? If so, I should get out, right?” During bad times, you always think, “how much lower can the market go? I should get my money out before it goes any lower!”

This is how people make poor investment decisions.

Your investments should improve the quality of your life, not diminish it.

Being a young person, you have the advantage of being able to keep investing through poor and strong markets.

Starting young gives you a huge advantage over starting when you’re older and have more money to invest, too. Starting at (or before!) 25 and investing just until you’re 35 puts you in a stronger position than somebody investing between 35 and 65.

Set up an automated system and sit back and let it do the work for you.

image credit: business insider

I recommend setting up on Wealthfront and automatically deducting 5–10% of your monthly earnings to a Roth IRA. Wealthfront lets you do all of this. If you use my link here, you’ll get your first $15,000 managed for free.

11. Ignore Anybody Who Tells You to Invest a Sizable Chunk of Your Net Worth Into One Asset Class (Unless You Are an Expert)

Your goal of investing early in your life is not to get rich quick (if you do, that’s icing on the cake). Instead, it’s to build up financial security and independence in your future. Anybody who encourages you to invest in anything should have to pass a high burden of proof for you to part with your money. You can afford to lose money on some risky investments at this stage of your life, but keep in mind that investing is to trade something now for more in the future.

The biggest red flag should pop up when somebody tells you to dump a big chunk of your current net worth into any specific area. A well-diversified portfolio includes some real estate, precious metals, and cryptocurrencies (most of which you can get through investing in ETFs, though). A poorly-diversified portfolio has one area far outweighing the rest. Unless you are an expert at real estate, or precious metals, or natural resources, or cryptocurrencies, you do not want to tie a good chunk of your future to one of those areas. Somebody will eat your lunch.

I have a few friends who have all tried their hands at day-trading stocks and options. I don’t blame them for trying. It sounds fun and you occasionally hear of somebody getting rich off of doing it well.

They all had their lunches eaten.

The experts know a lot more than you do and this is often their job. In the case of day trading, most experts use machines that trade so quickly that increasing the speed of an order by a millionth of a second earns them more money. That is a game you cannot win.

Ignore the talking heads on TV, too. Since you’re young, pending the complete downfall of the US government, any implosion in the stock market about which they love to talk won’t really affect you negatively. In fact, if you buy during a downturn, you will be better off.

Don’t worry about investing. Set yourself up with an automated system that protects your downside and use the extra mental energy and time to build out your skills and earn more money that you can use now.

12. Build Social Capital to Accelerate Your Career

There’s a type of capital more valuable than cash or gold and it is social capital.

Social capital is the pull you have on other people for them to put their skin in the game for you.

Be not forgetful to entertain strangers: for thereby some have entertained angels unawares. — Hebrews 13:2

Having a lot of social capital with somebody can be the difference between successful and unsuccessful deals, between new businesses and being an employee, and between a mentor for life and just a business dealing with an individual.

Use this time as an opportunity to build social capital with people who have more sway than you.

This does not mean that you should be a sleazy networker who just tries to meet with as many people more successful than yourself as you can. People can sense those intentions and you will end up hurting your long-term prospects. Rather, it means taking a perspective of “how can I help this person and add value to their life?” in every professional interaction you have.

The cool thing about being a young person with relatively few skills and little experience is that your time is not incredibly valuable. If you find people whose time is more valuable than your own (i.e., most people at this stage of life) and you prove yourself capable of taking up tasks for them that they would otherwise perceive as being too low-value for themselves to do, you can open amazing doors for yourself.

This was largely how I opened up opportunities for myself at Praxis, where I eventually got to lead the company’s first major business development expansion. As a relatively unskilled college student, I asked the founder for every opportunity to pick up some slack and do work that needed to be done but that was lower on his priority list than more skilled work.

A lot of the work was menial. I spent hours after studying or class sitting around checking for dead links and typos, down to a comma in the wrong place, in the original education portal the company was going to use upon launch. I didn’t care. It let me be productive with my time and, later, opened up doors for opportunities I would have spent many more years building if I had gone the traditional, “study and work your way up the ladder” route. And that job led to the experience that let me write The End of School and meet with billionaire investors and prolific entrepreneurs.

What I did was take the fact that I knew that a startup founder (or really anybody trying to start anything important) was going to be a very busy man and make use of my downtime by taking things off his plate. Sure, the work was far from glorious — but it allowed me to accelerate my opportunities in ways I could not have possibly imagined. (Much of Praxis’ model with their participants is based on this philosophy, too, and it has worked for many of them.)

You can apply this strategy passively and actively.

To apply it passively, ingrain in yourself a value-added mindset. Always ask yourself, “how can I help this person?” with everybody you meet. Sometimes, often, you can’t help them. When you can, offer to help and ask for nothing.

To apply it actively, find an individual who is trying to do something hard and who is a lot more skilled and experienced than you. This could be an author (Ryan Holiday apprenticed under Robert Greene), an entrepreneur, an artist, or any person trying to build anything. Bring with you your track record of basic competence. You don’t have to be skilled at any one thing. You just have to be able to execute on small tasks on time and in an organized manner. Offer to take 10 hours/week of work off their plate through research, data entry, administrative work, or any other thing that does not require a high level of skill but still has to get done for them to accomplish their tasks.

If you do this well for a long-enough period of time, you will make yourself indisposable. As your opportunity cost slowly creeps upward, they are forced to either compensate you directly or try to find somebody as competent as yourself to replace you (which has other costs like searching, training, and retaining that person). The vast majority of the time, they’ll keep you around. Your ability to do more substantive work grows as your skills grow, which opens up new opportunities for you to work with other people.

You get to trade-up career steps in this way. Always be on the lookout for new opportunities to take work off somebody else’s plate and make their life easier. This might just let you get ahead while others are busy pushing pencils.

Recommended books:

Rich Dad, Poor Dad by Robert Kiyosaki — Kiyosaki is best known for his support of investing in real estate to build wealth. I don’t agree with that part. The important lesson of this book is using money to build wealth. Kiyosaki introduces an idea called “cashflow” that is a paradigm shift for most young people who read it.

image credit: isaboutfreedom.com

Unshakeable by Tony Robbins — This short book by Tony Robbins is a great introduction to investing in simple, diversified index funds and why the stock market is going to be the most reliable place to build that base. If you want to go deeper, you can pick up his book Money: Master the Game.

I Will Teach You to Be Rich by Ramit Sethi — Sethi’s book is a great guide to automating your finances. Instead of telling you to cut back on lattes like the financial gurus of your parents’ generation, he encourages his readers to set up automated investing for their retirements early, learning the skills to earn more, and to set aside a fixed amount of money for guilt-free spending on things you enjoy. What’s the purpose of becoming rich if you can’t spend it on things you enjoy, after all?

The Four Hour Workweek by Tim Ferriss — While I generally don’t like the idea of telling young people that they can have a four-hour workweek (Ferriss himself had to work a crappy job and build a business while nearly burning out before he could write this book), a lot of the concepts in it are really helpful, like building multiple streams of income through systems that don’t require you to be at a desk between 9 and 5, useful tools for outsourcing some work so that you can increase your productivity, and generally helpful ways of reframing work.

Recommended blogs:

I do not really recommend a ton of blogs in this space because there are so many people not following their own advice. I’ve heard great things about MrMoneyMustache and have enjoyed what I’ve read on there. I reference IWillTeachYouToBeRich from time to time, as well.

Wisdom (and Women)

You either learn your way towards writing your own script in life or you unwittingly become an actor in somebody else’s script.
— John Taylor Gatto

Purpose, drive, and meaning are the cornerstones of human existence. A man with a strong sense of meaning can cure a disease, raise an army, move a nation, and build an empire.

The same man with little sense of meaning wastes away on the couch fiddling with idle amusements like drugs or significance-oriented prizes like low-quality relationships.

Much like everything else here — learning how to create a sense of meaning is not something that people are taught to do today. And unlike the past, they are not given the flexibility in young adulthood to engage in the real world in such a way to discover that sense of meaning themselves.

Developing that wisdom of having a feel for the direction in which your life is heading can help you not just accelerate your own success but avoid a lot of the pain that many young men face in groping in the dark for this.

13. Figure Out What You Don’t Want In Life

Purpose is everything.

But when most people start asking themselves what their purpose is or should be, they’re overwhelmed and have no idea where to start.

I run into this all the time when I am working with people anywhere from 16 to 25 years old. They’re constantly encouraged to set goals and to put together visions for the future for themselves but, even with some of the most successful ones I know, they constantly come back to, “but I don’t know what I want!”

I was recently at a convention running a workshop where I introduced my AmbitionMapping exercises to some high school teachers and I polled the audience of several hundred teachers with this question:

“How many of you, when you ask students what they want to achieve in life, the vast majority say, ‘I don’t know’?”

Almost every teacher raised his or her hand and this was at a convention of teachers at prestigious private schools.

This makes sense when you really think of it. See Rule #9. Young people today, through a twelve-year sentence to sit at desks and learn state-mandated systems of math and English, are deprived of every opportunity their ancestors had to discover what they were talented at and what they would enjoy. Fewer young people today even have summer jobs in high school because of increased pressure to spend that time padding a resume for yet another set of years removed from any application of skills and gaining of experience (i.e., college).

Pending the collapse of this classroom-to-cubicle pipeline, one thing you can do is work relentlessly to discover what it is you hate.

Boutique gift stores and motivational quotations will tell you to discover what you love and pursue that.

Bull.

This is bad advice (unless you grew up from a young age knowing you loved a certain craft) for a few reasons:

  1. Figuring out what you love takes a ton of time. If you’re like most young people who have spent the last decade of their lives sitting in a desk, you probably have no idea where to start when it comes to things you love. Where would you start? Any “subject” you think you might enjoy breaks down into thousands of constituent parts, many of which have nothing to do with one another. Mechanical engineering and chemical engineering and software engineering are all very different and require different skillsets beyond a basic analytic mind.
  2. You’ll always second-guess yourself. “But am I really doing what I love? How do I know that this is what I love?” You’ll second-guess yourself if you’re constantly searching for a superlative state. Consider what state of mind you’ll be in on bad days, when the going gets tough, and when you feel totally incompetent at something that you once thought you loved. If that thought creeped into your mind, would you be comfortable having to answer it with there being a possibility that, no, you are not doing what you love?
  3. What you love changes. People’s values change, their priorities change, and their interests change through life. What you enjoy at 18 when you matriculate into college is different than what you enjoy at 23 when you graduate. What you enjoy at 23 is different than what you enjoy at 35 when you marry. What you enjoy at 35 is different than 50.

Instead, ask yourself what you hate.

(Important to note that hate means something that you dread doing because it chips away at your purpose and your soul, not because it is hard. A man should be willing to step up to a worthy opponent in a challenge and not shrink away. If you hate something because it’s hard, you need to work on your sense of self-efficacy.)

This lets you move through a process of elimination, getting the field of things you can do smaller and more enjoyable all the time. What you hate when it comes to work rarely changes throughout life — if you hate dealing with numbers and details at 22, you’re not going to decide at 30 to become an accountant.

As you become more skilled and are presented with more opportunities and experiences, you get a better model for what you enjoy and what you hate. Once you discover the things you hate, be relentless about removing them from your life or setting yourself up so that they may be removed from your life.

This later means learning the skills, putting in the work, and gaining the experience to allow you to transcend those things you hate that are barriers to your success.

Here are some sentence stems you can use to ask yourself what it is you hate and start working towards a life you will truly enjoy. You can write the stems down on a piece of paper and then finish them with the first thought that comes to your mind:

I feel most unhappy when I…

I dread …

I am good at but do not particularly enjoy…

I cannot imagine doing … every day for the rest of my life.

I don’t understand why anybody would…

… does not appeal to me.

14. Read Old Books and Don’t Be Flippant About Centuries-Old Knowledge

Turn off the news and go read classics.

Nassim Nicholas Taleb has popularized an idea called the Lindy effect.

It essentially goes like this:

The future life expectancy of a given idea or technology is proportional to its current age. So, if something is really old, you should expect it to last a lot longer.

Taleb says:

If a book has been in print for forty years, I can expect it to be in print for another forty years. But, and that is the main difference, if it survives another decade, then it will be expected to be in print another fifty years. This, simply, as a rule, tells you why things that have been around for a long time are not “aging” like persons, but “aging” in reverse. Every year that passes without extinction doubles the additional life expectancy. This is an indicator of some robustness. The robustness of an item is proportional to its life!

In other words, things that have been around for a long time are likely to continue to stand the test of time.

The importance of this concept for your own wisdom hits me in the face any time I hear a young person talk about how irrational an institution like marriage is, how outdated uncivilized religion is, or how crazy it is that students in classics programs read books by “a bunch of dead guys.”

Instead of getting emotionally riled up at something we think is unjust or outdated, in the case of things that have lasted the test of time, it’s useful to at least ask, “what other purposes or ends might this thing be serving? Why has it lasted so long? Is it possible that I am wrong and it provides a lot more utility than I thought?”

So, humble yourself to the limits of your knowledge and the imposing value of robust and aged knowledge.

When trying to choose between a new book and a classic, choose the classic for this reason. The classic has often stood the test of time because it conveys a truth captured in archetypal human stories about the importance of certain virtues or ways of living your life that themselves have stood the test of time.

The stories of Greek heroes are still (ostensibly) read today because the hero’s journey and the virtues of courage and valor strike a chord that has held human society together over generations.

15. Build a Powerful Peer Group of Men Pushing You to Do More

You’ve probably heard that you’re the average of the five people with whom you spend the most time.

This is more than just a fun saying.

What you perceive as possible and impossible, as worth pursuing and as a waste of time, as a worthy opponent in a challenge and as an intimidating mountain, is determined by the norms and expectations set by your peer group.

Your income is a reflection of your peer group (take the time to think of the average income of your peer group and compare it to your income).

Your relationship status is a reflection of your peer group (are divorced and unhappy men more likely to hang around with fellow divorced and unhappy men or with men in loving relationships?).

Your health is a reflection of your peer group (if you hang out with people who admire vitality and strength, are you more or less likely to make sure you get to the gym and stop being a dweeb?).

Your professional status is a reflection of your peer group.

The biggest determining factor regarding whether somebody becomes an entrepreneur or not is that they know somebody who is an entrepreneur.

The people with whom you spend your time matters. A lot.

There’s a reason that this rule is to find men pushing you to become more.

You need mentors and they need to be people who can pass on applicable, tacit knowledge for navigating life.

For the vast majority of human civilization, knowledge was passed on between generations from old to young. The invention of writing and later other forms of recording allowed us to take knowledge and make it age-less. Something learned by a young man did not necessarily have to be taught by an older person because it was recorded (by somebody who was taught it by an older person) at some point and duplicated so many people could access it.

This works really well for a lot of knowledge, especially technical knowledge. Grammar, mathematics, science, physics, chemistry, history, and all other cut-and-dry facts-based knowledge can be captured here. Values-based knowledge was captured through storytelling and archetypes (e.g., hero-myths).

This does not work as well for knowledge that changes quickly, is highly context-dependent, or goes against the grain of politically correct opinion at the time.

Spending time with people wiser and more experienced than yourself who can play the role of moralizer — who can tell you to knock it off when you are hurting yourself or others and who can tell you which traps to avoid — revives this form of tacit knowledge lost through a dependence on recorded thought.

This is training and knowledge young men and women had for generations from their ancestors that modern society greatly undervalues. Go out and find it for yourself.

You’ll be the wiser for it.

16. Stop Dressing Like a Child

You will feel better and people will treat you better if you put a little effort into dressing well.

This does not mean that you need to go out and immediately buy a pair of $300 dress shoes.

It does mean that you should actually own a pair of decent dress shoes.

This also does not mean that you need to get self-absorbed in fashion and how you look constantly.

It does mean that you should take some pride in how you present yourself.

If you don’t take pride in yourself, who will?

If you’re a scrawny guy, the best thing you can do to start is to put on a little bit of muscle. Clothes that you can fill out (instead of somehow making an XS look baggy) will look and feel better on you.

Beyond that, specific steps depend on the norms of your community and subculture, your complexion, and your own personal style. It is possible to dress decently even if you are in uber-casual San Francisco, though.

General rules to follow:

  1. Wear clothes that fit.
  2. Own a pair of brown business casual shoes.
  3. Opt for simple over complex or gaudy (e.g., if you have a plain t-shirt, that often looks better than a graphic tee. A t-shirt with a simple company logo on it is better than one with a crazy piece of artwork.)
  4. Get your suit tailored. It costs ~$25 and makes you look like much less of a child. When you need to wear a suit, a young person in a suit can either look impressive or like a tiny monkey in a suit. Don’t be the latter.
  5. If you do work that requires you to wear dress shirts, get your measurements and order custom shirts. I recommend Charles Tyrwhitt shirts.
  6. Burn cargo shorts.

@WellBuiltStyle is a fantastic twitter account that regularly reviews, compares, and recommends different things in men’s fashion. I recommend following them

17. Focus on Your Work Before Focusing on Women

If you don’t know your purpose, discover it, now. — David Deida

(I cannot recommend enough wrapping your mind around the concept of feminine and masculine polarity as part of attraction, which Deida talks about in his book The Way of the Superior Man. This is a concept I only discovered after my own fair share of mistakes and missteps in the area of romantic relationships and one that would have saved me a lot of time and energy.)

For most men, their work is their purpose. Even if you’re in school, you’re (ostensibly) there to be able to do the work that allows you to accomplish the things you want to accomplish.

And for a lot of men, one of the things they want to accomplish is having a fulfilling and enjoyable relationship.

Yet a lot of young men will put pursuing (often low-quality) women higher than their pursuing their work. They let hormones and a newfound sense of freedom get in the way of focusing on the most important thing in their life at this stage: building their purpose.

Rarely does this work out for them.

They may get a few women and putz around for some time, but almost inevitably, those relationships fizzle out. If they don’t fizzle out entirely, the sense of passion and interest that pulled the people together fizzles out.

What (feminine*) women want to see in a man, at any age, is a sense of purpose and direction. They want to see somebody who is willing to do what it takes in order to build the life that he wants to provide for himself and those he chooses to include in that life. They want to see somebody who is competent and confident in his ability to navigate life — not shallow confident in the sense that he’s willing to insult a random attractive girl when he meets her at the bar.

Trying to attract (quality feminine) women by reading books about attracting women and dressing ostentatiously (i.e., “peacocking”) will prove less effective over the long run compared to focusing on doing quality work, developing a sense of purpose and direction, and becoming good at what you do will prove more effective at attracting women for quality relationships.

Quality women will see a man alive with direction and purpose who, if he isn’t already, will make his mark on the world. Even more, they’ll see this when most of your peers are too busy putzing around having no idea what it is they want to do or trying desperately to attract women and failing to create quality.

Focus on chasing women women instead of work and you’re likely to get neither.

Focus on work instead of chasing women and you’re likely to get both.

18. Don’t Become a Pleaser to Make Women Happy

When things get stressful — at work, with your family, with money, or in your relationship — it is tempting to become a “pleaser” in your relationship.

Do not do this.

This does not mean to be a jerk and it does not mean to bottle up all of your feelings of stress.

It means do not subordinate your sense of direction and purpose to the relationship for the sake of the relationship. Do not subordinate your ability to commandeer a situation to the relationship for the sake of a relationship.

Feminine women do not want to be with a man who is a pleaser, just like a masculine man does not want to be with a woman who is a domineering control-freak.

This sounds simple enough but sliding into pleaser-mode happens subtly and naturally if you’re not careful.

Everything starts to get stressful at work and you’re no longer enjoying your job, a major health crisis pops up with a loved one, your money suddenly becomes tight due to an unanticipated expense, or you’re just worn-down an stressed out. Next thing you know, there’s a point of contention or disagreement in your relationship. Worn-down and not wanting to expend more energy on it, you just acquiesce to “whatever you want” or leave the decision-making for your decisions up to your girlfriend.

This happens once or twice and no problem. This happens repeatedly and your girlfriend will soon start to feel like she’s dating a woman. At the very least, she’s not dating the purpose-driven man to whom she was initially attracted. The spark starts to fizzle. If you sense this, it’s easy to get confused or resentful, thinking that all you tried to do was help an make things easy.

Now, everything starts to bother both of you about the other. Little things that you would have ignored now grate on your mind (or on her’s) and one person snaps at the other.

Things slowly crumble apart. And it all started with you attempting to make things easy for yourself and your girlfriend.

Take the extra time and energy to compose yourself. Reframe the situation in your mind not as yet another opportunity for things to wear you down but instead as an opportunity for you to enter your natural role as a decision-maker and a leader.

When all hell breaks loose on the Titanic, be the captain at the helm of the ship through the chaos, not one of the men shoving women and children to get off the boat.

Recommended books:

Antifragile by Nassim Nicholas Taleb — Taleb is the sage of our days. Antifragile is one of those books that remade how I saw the world. Taleb starts with a simple idea: some things break easily (fragile), some things are hard to break (robust), and some things get stronger from disorder (anti-fragile). It’s hard to boil this book down to a few topics. I recommend that anybody seriously interested in understanding the world picks it up.

The Way of the Superior Man by David Deida — I never thought I would pick up a book like this and only did so on the independent recommendations of two mentors. I am glad I did. Once you get past any personal aversion to mystic-sounding language, Deida’s framework for understanding inter-sexual dynamics makes a lot of sense. Essentially, every person is either more masculine or more feminine (although almost always with some femininity or masculinity, respectively). For two individuals to be attracted to each other, they need to be opposites and preferably proportionately so. So, a masculine man is attracted to a feminine woman. Deida breaks down what traits make up masculine and feminine and how individuals can collapse into the other pole under stress (Rule #18). If I had read and internalized this book even 9 months before I did, I would have saved a lot of time and energy.

Not Caring What Other People Think is a Superpower by Ed Latimore — This fun little book is a great set of wisdom and actionable items on work, discipline, and focus from a man who grew up in the crack-ridden ghetto of Pittsburgh and went on to serve in the National Guard, study physics, and become a heavyweight boxer.


*I use this qualifier here because it is possible, although rare, for a straight woman to be masculine. To really get this though, I do recommend reading Deida’s book.


This list of rules was developed out of common problems and questions I saw between the young men I know and work with and my own personal experience — often learning the hard way.

It’s my hope that it can help other young men improve themselves.

Please share it if you found it helpful. Leave feedback where appropriate.

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