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20 Rules for Your Twenties

Many of our emails tend to come from MBAs and college students so we decided to compile a post of twenty rules that you should abide by in your twenties. Notably, we have each messed up on at least one of these rules in some form or another but if we could go back and become twenty again this is the blueprint.

1) Minimize Debt: This is one of the biggest items on your to do list. Debt is a vice around your wrists that is slowly cutting off your blood circulation, if you don’t release the pressure you’ll be dead before thirty… the Prime of your life. If you are able to spend money on assets that depreciate in value (cars, clothes etc.) you better be debt free and saving large amounts of cash.

2) Change Your Friends: We have given a quick blue print to choosing friends, however the biggest mistake is not upgrading your social circle as you move on. We know, you read the word upgrade and immediately thought the word is heartless. It is not. You need to surround yourself with like minded individuals, even if you have known a childhood friend for 15 years, if they begin using drugs for entertainment purposes and falling off of the grid you have to say goodbye. Your life is too short to spend catching falling knives.

3) Learn to Help Others: This sounds contradictory to point number two, however it is paramount that you learn to help those that wish to improve. The key is their interest in improving, if you attempt to convince a man of self improvement when he does not care, you’ll burn a bridge. Hyper competitive and intelligent young men tend to develop a “put down” mentality where you compete at each others throats 24/7. Not only is this not sustainable, it is not healthy and does not help you in your career. Instead, pass along helpful information and you will find your friend count increasing.

4) College Should Be Tough: Everyone else goes to college to drink and try to sleep with hundreds of women. These guys usually end up unemployed or making $40K a year at a soul crushing job with no skill set to jump into another industry. Their entire life is now 100x more difficult to fix and you’ll be shocked at how difficult it is to come back when you’ve built no foundation. Build a foundation. You can have fun in your spare time.

5) Get Internships: Even if you have a 4.0 GPA from a top university, no one will care if you have zero work experience. In addition to obtaining line items on your resume you will realize that your network expands drastically. You’ll be in contact with people in their 30′s who are well outside of your current social circle of 20 somethings.

*Note internships was intentionally plural.

6) Find Mentors in Their 30′s: By the time you are in your low twenties you should have a handful of men to speak to regarding life decisions. Each man does not need to know every aspect of life, however the more the merrier. You’ll quickly realize that your peer group is older than you as soon as you receive your Diploma (MBA or Bachelors). This is a good thing. Generally speaking, older men make hiring decisions.

7) Your Co-Workers Will Screw You: This is the most common miss. If you are in the same peer group, none of your co-workers are out for your best interests. If you party with your direct co-workers, as soon as layoff rumors begin making the rounds, be certain you’ll be thrown under the bus . See point number one for why they would be more than happy to see you fail.

8) Read Books Daily: If you are not reading books outside of the classroom you are allowing the collegiate system to have more influence on your upbringing than it should. The topic of interest is less important than the act of reading. You can read about health, fashion, coal mining, animals, chemistry, art and the list goes on. Reading is similar to investing as the payoff is far in the future, one day you’ll have a chance to make a connection with a higher up on an obscure topic and ideally you’ll have the ability to add to the conversation. Don’t forget that wealthy men and women are typically eccentric.

9) Learn About Basic Fashion: Before we get comments about books beyond finance, you can simply start with learning about basic fashion. Learn what colors work for your skin tone, eye color and hair color. Once this is mastered find the right brands to accentuate all of your positive features and build a sustainable wardrobe. Better to learn and earn before you have some cash and see it burned.

10) Exercise Five Days a Week: Unless you are forced to burn through 100+ hours a week for several weeks straight, you should find time to lift weights five days a week. No excuses. Your health is the only thing that will outweigh your aspirations for wealth. A man who has a healthy mind and body with a heavy wallet is free. There is nothing more valuable than complete freedom to do as you wish.

11) Procrastination is Valueless: If you find yourself  procrastinating on tasks it means that you have nothing to do with your free time. In an ideal situation you are constantly moving and improving your life. You don’t have time to procrastinate because you’re too busy taking action. The day you find yourself sitting and staring at a computer screen for 2-3 hours in a row is the day you either walk outside to exercise or immediately buy a book online. This is the minimum.

12) Ignore the Lazy: You will meet many people who suggest you simply relax and live in the moment. Avoid these men like the plague. You should live in the moment for a calculated risk not to simply feel good for a short period of time at the detriment of your future. Much like investing, 20 years from now they will have a hard time getting by while your life is already on cruise control because you’ve built an unbreakable foundation.

13) Don’t Get Married: No matter what you do, do not tie the knot in your 20′s. The truth is that many women in their twenties are most attracted to men in their low thirties. Run the math. Your future ex-wife is still in high school right now, so don’t fret over anyone within ear shot for a long-term relationship. We recommend not getting married but if you decide to keep one, wait until your 30′s.

14) Go International: By the time you’re in your mid 20′s you should have some international exposure that will wreck a lot of your current beliefs. By experiencing a new culture you’ll quickly see how many of your ideals are based on a US cultural phenomenon. You can do this with a single briefcase and you can do it alone. You’ll force your body into survival mode in an unknown city, your confidence level will grow by leaps and bounds.

15) Face a Major Fear: Heights, snakes, fights, the major fear you have does not matter compared to your ability to tackle it. If you’re afraid of being beaten down in a street fight, you should get into a ring and take a few kicks and punches. You should jump out of a plane if you fear heights and you should even consider purchasing a snake. There is no substitute for repeated exposure to eliminate a major fear in your life.

16) Turn Family Into Friends: For many, your family members are dragging you down and for others they are a positive in your life. The key is to separate your life decisions from their opinions – their opinions should have no weight on your emotions. At this point you should not use your family as a safe haven in life. If you lose your job, if you want to move cities, if you want to take a risk, it is on your shoulders. Remove the safety net.

17) Stop Complaining: Maybe you didn’t land that Bulge Bracket job, maybe you didn’t get ranked number one in your class, maybe you hurt your wrist and can’t lift for a month, no one cares. By the time you’re well into your 20′s your interest in complaining should be zero. Complaining gets you no where. All it does is increase your stress levels. When you are stressed out, no one wants to be your friend. If no one wants to be your friend, your contact list is not improving and if your contact list is not improving…. you’re dead.

18) Wake Up Early: Unless you’ve obtained a job in investment banking where you’ll eat garbage for multiple years straight to earn your stripes, you should wake up early to get ahead of the rest. Read, go to the weight room, build a website, it does not matter. Your brain functions well in the morning, use your most productive time to invest in the most important person in the world. Yourself and your future.

19) Earn a Voice: Many men will destroy their careers in a few short years by never earning a voice. When you are in your twenties there is not a single person who will care about your world view so it is best to remain quiet and diligently improve while waiting for an opportunity. Instead of dishing out advice, take advice and remain quiet. As soon as people begin asking you for your contributions you’re officially of value. You have earned your keep in a specific niche.

20) Fail: The last piece of the puzzle is the most obvious and the most undervalued. Fail as many times as possible in  your twenties while you have the time to recover. We do not recommend dropping out of college as a failure or taking up a humanities major as a failure (this is simply financial suicide for most), instead we recommend you fail at trying to create value. Try to create a mobile app. Try to learn how to code. Try to learn a foreign language in a year. Try everything.

Assuming you follow these rules, you’ll look back on your life when you hit thirty and know, not believe, you have done everything to make your life better. If anyone attempts to say you’ve worked too hard, write them off as whiny complainers who have to live with the knowledge that they could have been better. They could have improved, they sold themselves short.

28 COMMENTS

  1. excellent drop

    only take issue w/ the waking up early (before 8). mornings are not peak for my body…of course, i’m not in ib though

  2. Another great post, I feel this is the right length for your audience.

    Are you guys going to do a post on how to manage your thirties?

    1. We will come up with a life timeline first to explain how we think about your life as a man and how to mitigate ups and downs when they inevitably occur.

  3. Plurs,

    How do you get past bureaucracy at work?

    I moved from San Diego to Rio de Janeiro a year ago for a job in project management (I’m 26- 3 years out of non-target university).

    The only way I get my ideas through is by making my boss (The owner’s brother – 25 years in this position) believe that he was part of creating it. Once that happens, he uses my spreadsheets/macros/ideas and presents it as his.

    I’ve decided that I’ve lived my dream here, learned the language, and I’m ready to leave- I’ll be back to pick up a wife when I’m 35…

    I keep running into bureaucracy problems at all my jobs… any advice?

    Obrigado!

    1. You have the answer in front of you. If the Owner’s brother likes you. Continue to create projects that eventually the Owner approves of. Develop a strong relationship with the brother, then simply have him bring up your contributions during a review.

      Remember to do this intelligently, make it seem as if the owner’s brother has “spotted” an intelligent hire (he gets credit) and then have him give you a rave review = the owner will now respect you more.

      This is normal, if you’re adding value, simply find a way to have it slowly raised up appropriately.

      1. Yeah,

        The owner’s brother does not like or dislike me, he just wants to justify his own salary (my opinion).

        How do you get past a boss that is scared of your potential?
        I’m a big fan of Dale Carnegie’s “How to make friends and influence people” but I have a hard time applying the principles to people in higher position that are insecure. Are the 20s like this until we finally get our break?

        Thanks

    2. Read the art of war, “all warfare is deception”. Get that guy to think he’s done the work, sooner or later you’ll be called to explain what he didn’t know. This is your moment. Invest everything, the top guys will work out who’s really making hay.

  4. Out of all of these “don’t dos” which one is the absolute must to avoid? We all have fallen victim to at least one of these?

    My vote is the marriage one.

    1. Marriage, Debt, Complaining and Not helping others (eg. not networking with higher ups).

  5. Sweet post. I’ve definitely wasted the first two years on excessive partying, but now my system is entirely desensitized to it. Time to focus on areas of real importance.

  6. If the frequency of posts going down means that we get posts of this length and this (high) quality, then that’s great news.

  7. Don’t get married. Wait until you are at least 45. Relationships don’t add any value to your life. They are a ball and chain. Stay free to concentrate on important things.

  8. I’m a 35-year-old in commerical banking in NYC.

    This is a good list. Some of the ones that stand out:

    1) Exercise five days a week: while I think this may be extreme, at least two days a week of heavy weight lifting is a must to keep you in good shape, keep your T levels high, and make you look better in good clothes. I hit major depression when I was 26 after a bad breakup and losing my father, and what brought me back from oblivion was 30 minutes’ intense aerobic exercise and lifting weights.

    2) Go International: I moved to Europe and worked there for a few years when I became 27. It broadened my horizons and destroyed my US-centric view. Traveling was amazing, and I learned to work in a completely different work environment. After two years my firm relocated me back to NYC to help open up an office here. They tripled my salary, and I’ve been getting big bumps every year since. I say I’m about five years ahead of my peers who chose to stay behind in NYC.

    If I could do it over again, I would move to Hong Kong right after college. Much better city than New York, fun party scene, great hub to go traveling.

    3) Don’t Get Married: while I’m not married yet, I’m seriously dating a beautiful 25-year-old Eastern European who can’t get enough of me. She wouldn’t have given me the time of day if I were her same age. You need to learn game, work up the corporate ladder, fail, and figure out what’s important for you, before involving a woman in long-term plans. Otherwise you’re setting yourself up for a divorce or marriage hell.

  9. One of the best articles i ever found on the internet. Every single point is true, no exceptions. Currently I am 19, I have a full time job and i’m studying finance at university, in this moment of my life this kind of article just gives me more strenght.

    Good work guys, you have just found a new supporter of this blog.

  10. Great list and rules!

    I only discovered Wall Street Playboys recently, but your content is gold and I will add you to my RSS reader immediately.

  11. About number 4, I know that given this is a Wall Street oriented blog, GPA is huge for success in life but I keep hearing mixed things about college GPA. I hear a lot of people saying how it is indeed a very doable thing to come back from a bad undergraduate performance.

  12. This article is gold. I just turned 20, I live in Scandinavia where going to university is free and I have the next 5-7 years planned out while following your rules:

    Tomorrow I have an in-person job interview (after passing the phone interview and getting my resume through) for sales in a disruptive start-up with a product that basically sells itself (It has so much potential and will potentially save a lot of companies a lot of money). They know that I have no sales experience whatsoever so they are hiring me for my potential and not my experience, the CEO seemed a bit bothered by this (but he told me that I said all of the right things over the phone and the Chief of staff emailed me saying that she could understand that the CEO and I had a good conversation), so I told him that I would not mind being paid in only commissions until I consistently hit quotas.

    I have already constructed a curriculum of 8 books and 5 webinars on various aspects of selling (Of course Cashvertising and Zig Ziglars is in there as well)+I plan on reading Scott Adams persuasion reading list. So when I get this job, my spare time will be spent lifting weights, learning and blogging about everything that I learn.

    When I learn selling and am consistently hitting quota, I start learning my other constructed curriculum which consists of full-stack web development, web design, big data analysis, digital marketing and general business administration/finance, this will take time but when done I will know some skills that are very relevant and marketable and I also have learned to efficiently sell B2B.

    This means it is time to create my own business. I’ll start a fiverr account (quick and easy work), an upwork account (more serious free lance work) and offer consulting/freelance work on my blog which should have a lot of posts which is good for SEO at this point.

    I will also try to learn E-Commerce and learn how to sell e-books and then use all of my skills and freelance work experience to create a business (E-Commerce is probably the most profitable).

    When I am consistently earning a living through my own business and/or freelance work, now it is time to start university. I will start in a university that offers a very specific BA in Information Technology that mix coding/software knowledge, communication, business administration, marketing and design, I will already have a lead on everyone else and I will ace my bachelor easily while developing my business.

    After the BA I will take a masters in entrepreneurial engineering which is a course that have specifically been created to teach students how to create tech or engineering start-ups and then I will plan what is next from that point.

    This post is very valuable because it essentially teaches a young’n in the beginning of his twenties to cut out the bullshit and focus on what really matters so he can create a positive reinforcement loop and set himself up so that success becomes an inherent part of him and not something he needs hand-holding or outside sources of motivation to achieve.

    Thank you.

  13. I’m a woman but still find this advice to be excellent. Wish I had found this blog before I started college (I’m finishing my freshman year right now and understand that I should have done things differently. Hopefully, I will improve my next year).

      1. A lot of your posts/advice apply to both genders so I’m not that surprised. Obviously, stuff like workout advice is gender specific but things like career choice or what to do in college is the same if you want to make a lot of money, regardless of gender.