Unhappiness and Insecurity in Your Teens and Twenties

Something that isn’t frequently discussed but has been on my mind a lot recently is the fact that seriously pursuing self-development from a young age has a significant chance of causing you to feel extremely insecure and unhappy at times for a period of several years. You could actually argue that self-development temporarily decreases the quality of your life at the beginning of your journey.


For example, if you opt to skip college and immediately enter the work force or go into business you’re likely to feel insecure about your circumstances for some period of time simply because the trajectory of your life is completely uncertain for several years until you’ve finally gotten yourself somewhat established.

Conversely, it’s extremely easy to feel comfortable in university simply because you’re doing almost the exact same thing as the previous twelve years of your life.

That’s not to say that going to university is an unintelligent or irresponsible decision. It may be for some people, but attending university can be a good choice for many people as well.

However, it’s undeniable that one of the reasons university is so appealing is that having the responsibility of figuring our your role as a contributing member to society temporarily deferred helps significantly in maintaining peace of mind, at least for the time being.

Of course, going to university with the self-development mindset and building for the future can cause significant stress as well. While others are majoring in fun but unmarketable degrees like sociology because it’s their “passion,” you’re grinding it out in a difficult major that’ll actually land you a solid career after school.

You’re hitting the books hard in your business classes while trying to get internships so that you can get a decent gig on Wall Street after school.

Otherwise maybe you’re building crazy things in your computer science classes while also getting paid absolute shite (or even nothing) to code for a start-up on the side that’s providing you with an awesome educational opportunity and connections.

Regardless of whether you find Wall Street or computer science rewarding it’s undeniable that there’s aspects of every career that suck.

You may enjoy 80% of your work if you picked an appropriate major for yourself, but that still leaves 20% of your work as shit you’re going to have to sling your way through even if you want to rip your eyes out in the process.

Part of being a young man that wants to establish himself quickly also means that you’re going to be working LONG hours, and this phase of your life with a poor work-life balance will likely last many years. This is a prime example of deferred gratification and at least in part sacrificing the present for a better future.


Whether you’ve chosen to go to university or not you’re again playing for deferred gains. I’m sure you’ve heard the Napoleon Hill quote, “The man who does more than he is paid for will soon be paid for more than he does.”

This is great; when you’re the guy being paid for more than he does. For now, however, you’re going to be the little guy in the dirt that society does not yet value. In addition to lacking professional status you’re also working harder than your superiors (who you may even be more intelligent than), but your income is only a fraction of theirs.

Quick advancements up the corporate ladder, or the success of your independent endeavors usually require that at least initially you work a TON of hours and take on lots of shitty projects nobody else wants to touch.

Long hours, demanding work conditions, and poor compensation that results in shitty living conditions. Sounds like fun!


Japanese Women Magazine

Your value as a man on the dating market isn’t going to hit its prime until your mid-30’s. Although it’s obviously possible to date attractive women while you’re young it’s significantly more difficult to do so.

You’ve likely only had a couple experiences with women (if you’re really young or had social anxiety growing up perhaps none) in your young life thus far. Therefore, you likely lack the charisma and social skills necessary to get with the most desirable women. In addition women simply don’t like to date younger men.

Let’s not forget that you’re working extremely hard which is likely to result in you being more stressed than the guys who just chill, plus the fact that you don’t have access to significantly more resources than the guys who have taken the path of least-resistance and refused to put themselves in environments that stress and challenge them.

You’ll certainly have more value than these men in the dating market in a decade, but very few women have a wide enough perspective to see that (nor should they as it’s not their duty to take themselves off the market when they’re most valuable to date a guy that is years away from having comparable value).

As a result the guys who have less cortisol running through their body (from not putting themselves through the fire at work), and that have a greater ability to be chill with women because they’ve spent their whole lives doing so get the best girls over you. Shucky darn darn!


By seriously pursuing self-development and being the type of person who would read this blog you’re likely weeeeeird. I’m not saying that you lack basic social skills and are afraid to talk to the cashier when you go to the grocery store (though that could certainly be possible as difficulty socializing and the pain of social rejection drives a lot of men looking for a solution into self-development).

Rather what I’m saying is that by taking the “red-pill” so to speak you likely lack compatibility with most people. If you don’t watch sports, you don’t play beer-pong, and you don’t gossip at work, well god man what do you do? That’s the perspective of the masses.

However, let’s say you’re not shouting your non-conformity to the world. Let’s say that most people just see you as a hard-worker and aren’t aware of your bizarre “red-pill” world-view and the extent of your aspirations. Let’s even say that most people like you because you’re a generally positive person who is actively trying to give more to them than you take.

The reality is that it’s still lonely at times. Sure, you’ve got your dreams and goals and they’re coming more into focus with every passing month, every passing year. You love that.

The discouraging reality, however, is that there’s still a huge gap that needs to be closed before you achieve them and in the meantime you’re stuck trying to interact with people you have difficult relating with on anything but the most superficial of levels.

It’s not nice to say, but the truth is it’s difficult to have meaningful conversations with most people because you’re forced to parrot their own beliefs back to them.

If you say anything that threatens their current beliefs they become defensive and if you expose the various inaccurate assumptions in their belief-system you’re more likely to lose a friend because you were “being mean,” than to help them form an improved set of beliefs that better serve them.

It’s also difficult for you to find other driven people you can connect with. Why? First because driven people capable of having intellectually stimulating conversations and willing to go on crazy adventures with you are extremely rare.

I left my comfortable home in the small town of Racine, Wisconsin and skipped the well-trodden path of a four-year degree to move to Vietnam and join the digital nomad scene here at age 18. Do you know how impossible of a task it would’ve been to find someone from my high school to come with me?

So Steve I know you’re going to college to become an electrician, but I got an idea. Why don’t you save every penny you earn working at the bowling alley for the next year, tell your girlfriend you’re skipping junior prom to save money, and graduate high school a semester early with me to go and have an uncertain chance of building a location-independent business in Vietnam together? 

Even just writing this caused me to literally laugh out loud. You could actually try saying that, and it’d be an awesome joke for your self-amusement because it would be so far out of the average teenager’s reality that they wouldn’t even know how to respond.

The chance of stumbling upon people you can form legitimate connections with and not have to dumb yourself down is essentially nonexistent. Especially in your teenage years; you’re basically crossing your fingers and praying you’ll meet someone that has a brain… and you’re unlikely to if you’re not proactive in your search.

The only realistic paths to meeting other driven people are to:

Go to prestigious universities or join high level athletic teams (The discipline it takes to attend Yale or become a college athlete means the average person you’re surrounded by is far above average.

There’s likely many book-smart people that are useless outside the classroom or meatheads useless off the court, but at least being in these environments gives you a better ratio of future-successful peers and attracts some of the other truly intelligent people our age.

Become highly successful in business (which is unlikely to occur for a number of years until you develop the skill-sets and knowledge for success).

Pay for mentorship, do grunt work for a mentor, or otherwise provide value or luck into a relationship with a driven person that’s achieved success.

Move to Chiang Mai, Saigon, or some other city where other nonconventional thinkers and freelancers/business owners congregate.

Perhaps I’ve overlooked something but the point is this; until you get into a position where you’re bringing lots of value to society and your peer group organically improves you’re going to have difficultly and have to be extremely proactive if you want to find people you can relate with.

The reality is that most young people on our path simply don’t make enough of an effort to find others to relate with and are as a result are at least somewhat lonely. Perhaps something that could help you if you’re in this camp is getting a girlfriend (which is ironic because we just discussed why doing so can be somewhat difficult).

She almost certainly won’t be able to relate with you on an intellectual level (of course like we just said most guys can’t either). However, At least you’ll be  relate and share pleasurable energy by being romantic and sweet with each other as well as connecting on a sexual level.

Final Thoughts

Tokyo Dome

I’ve done a lot of diagnosing of problems in this post, but have done little in the form of offering solutions. The reason is that I’m just another guy like you trying to figure things out. Maybe in a decade I’ll be able to authoritatively say do this, this, and this.

For the time being, however, I’m working more on solving these problems in my life before I become the guru for others. With that being said there are a few insights I have had that you may find useful.

The first is that it’s normal to feel insecure and unhappy for much of your teenage years and early twenties. This is in part because you’re working hard, and deferring your gratification to the future.

Unfortunately you haven’t yet spent enough time working hard that you have high-quality life circumstances and past deferred gratification to rely on. Because of that you’re forced to go through a painful period of time when you’re working harder than your peers but experiencing the same or even fewer rewards than them.

Another cause for insecurity and unhappiness is that there’s a large gap between the person you want to be and who you are today. Feeling hungry and motivated by this fact is good.

Beating yourself up over it is unintelligent because you can’t change your past actions nor is being too harsh with yourself going to be productive for your ability to create a better future.

For that reason, you should acknowledge where you’ve come short in the past and where you can do better in the future, but then let go and not feel the need to kill your self-esteem in the process.

Of course this is easier said than done. It’s difficult to change the way you feel about this contrast. Do your best though.

In our discussion about women we said that you’re probably at least a decade away from reaching your prime as a man on the dating market. What’s important to realize, however, is that this doesn’t mean you shouldn’t date.

I don’t advocate chasing endless tail and throwing every night of your life at women like most partying guys our age are doing, but I do believe there’s a lot of self-growth that can occur from interacting with women.

Dating women is also nice because it’s the exact opposite of working. After being in your head in a logical mood all day you can joke around with girls, stimulate and connect with your emotional side, let go and refresh from work, and manage your natural need as a man to release without porn fucking up your brain.

The women also benefits from your relationship as well because you’re likely a far better influence on her life than most guys your age would’ve been.

Let’s not forget that women can also provide significant motivation for you to excel in life as well. When a girl you really like doesn’t want to be in a relationship or sleep with you it’s possible to use that as leverage to hit the gym, or work on your social skills.

Of course, women can also be destructive if you date the wrong ones or don’t properly channel motivation from them. This is something you’ll improve at with time.

Ultimately, even though you’re likely going through some insecurity and unhappiness at this stage of your life that doesn’t mean you’re on the wrong path.

This doesn’t mean everyday should be a painful struggle and hellish nightmare you debate whether it’s worth crawling through. There’s a balance, but you’re smart enough to know that.

It’s also important to acknowledge that there is a long-term payoff for going through this period and that even though you’re on the grind there’s still a lot of great things going on in your life.

There’s many reasons for you to still be happy most of the time, and if you’re managing your life real intelligently you can even be happier than the masses despite being in the midst of the most painful and emotionally challenging period of your life.

Take pleasure in the little things each day; the high off of endorphins you get after hitting the gym, the abundant energy you have as a result of being in your youth and eating a healthy diet, intellectual growth you experience through reading self-development and other educational material, seeing your dreams come closer and the circumstances of your life improving everyday.

When you’re feeling insecure about your future don’t hope for a better tomorrow. Take massive action to create it and realize there’s so much to be grateful for and your position is so much more enviable than someone who’s just coasting and is going to spend the rest of their life paying for their refusal to build a solid foundation in their early years.

Going on this path of serious self-development and deferring much of your gratification to the future can be extremely difficult at times, but both the person you’ll become as a result of this challenge and the circumstances you’ll eventually find yourself in will ultimately have made your efforts worth it ten times over.

One day you’ll look back fondly on this period of your life, the struggles you overcame, the adventures you went on, and you’ll be forever grateful you made the decision to keep pushing forward.


My just released book How to Get Your First Girlfriend is currently free. If you’re looking to improve your dating life or learn how to create a romantic relationship for yourself check it out!

(First picture is a magazine stand in Tokyo. Second picture is the Tokyo Dome. Both pictures taken in Japan last month.)

[grwebform url=”http://app.getresponse.com/view_webform.js?wid=12610802&u=BS1kr” css=”on” center=”off” center_margin=”200″/]