Over the course of the last ten years, I’ve read 100’s of books and interviewed more than 700 people. One of the primary motivations for my work is that I was seeking answers. We have an ongoing joke at the Unmistakable Creative that my guest choices are usually a reflection of some problem that I’ve been trying to solve in my life. Fortunately for me, it seems like most of our listeners are interested in those same issues.

But if there’s one thing that’s become apparent to me, it’s that there are many life skills that we should have learned in school but never did. I can’t help but think about how differently I would have approached college, my career, and my relationships knowing what I do at age 39.

Our current model of education is not only outdated; it’s not particularly effective. In a world where access to knowledge and information is ubiquitous, the value of memorizing information to regurgitate it, pass tests and get good grades quickly becomes far less valuable. According to Chase Jarvis, we’re moving towards a portfolio model of careers, a world in which kids growing up today will probably have five jobs at the same time. But the current model of education is preparing them for a future that doesn’t exist. If the purpose of education is to turn us into fully functional, happy and healthy adults, it is failing on numerous levels.

When I started writing this article I asked my community on Facebook what they thought you should have learned in school but never did, not only did I get more responses to a question than I’ve ever received, three themes kept emerging.

Before we get started- this is one of my longer pieces at 5500 words. If you’d prefer to read it later, download it as a pdf here. You’ll also be signed up for my newsletter, where you’ll receive a weekly article like this as well as immediate access to a swipe file with my best tips on honing your daily habits, productivity, and creativity. Get it here.

1. Managing Your Psychology

At the beginning of 2007, in 2 months, the girl I was dating had an abortion, during an already a tumultuous relationship, I almost got fired from yet another job, and I got rejected by every business school that I applied to. It was one of the major low points in my life.

And it didn’t get much better when I graduated from the MBA program at Pepperdine and found myself broke, jobless and living with my parents at the age of 31, while my sister got accepted to medical school after having one of the highest GPA’s in her graduate school program. I felt like she was the source of their pride and joy and I was the source of all their disappointment. This was a major test of my own ability to manage my psychology and was the catalyst for my 10-year journey of building Unmistakable Creative into what it is today. 

Managing our psychology is essential to navigating what one of my mentors referred to as a world of diminishing permanence. We have to deal with highs and lows, not tie our self-worth to external events and circumstances, and in the midst of that somehow show up in the world as a fully functional, not completely screwed up human being.

But none of this is ever taught in our schools. Instead, we objectify students with letter grades, test scores, and the pressure of acceptance to prestigious colleges. This chase for accolades and validation continues into adult life. We chase our self-worth through prestigious jobs, more money, and potential partners. We spend almost no time teaching people how to manage the relationship they have with themselves, even though it’s the most important relationship they’ll ever have.

No matter what it is that you’re trying to accomplish, whether it’s building a startup, having a romantic relationship or finish some creative project, you absolutely must learn to manage your psychology. For this article, I’ve broken up managing your psychology into the following categories:

Self-esteem and Self Worth

Validation: So often our self-worth and self-esteem are determined by some form of external validation. For some people it’s a promotion at a job, having their book become a bestseller, or selling their startup. For others, it’s their romantic partner. But as long as you’re trying to fill a void with something external, you’ll be attempting to fill a bottomless pit. When one problem gets solved, another one shows up.

In the years that I was building Unmistakable Creative, being able to move out of my parent’s house was the elephant in the room. It was my primary focus. Then it happened. Not only did it happen, but I also ended up 2 minutes away from the beach where I’d wanted to live ever since I caught a wave there nine years ago. I was getting paid to speak, traveling all over the country, and writing my second book with a publisher. For about two months I was on cloud 9. It became my new normal and another problem took over, dating.

With my 40th birthday around the corner, I felt this immense pressure to meet someone. But in the process, I had handed over my self-esteem to something else external, approval of the opposite sex. This pattern will keep repeating in our lives until we come to terms with the fact that our self-worth can’t be gained through external means. As long as we continue to seek our self-worth through something external, it will always fluctuate.

True confidence is being more invested in your perception of yourself than someone else’s perception of you. – Mark Manson

How someone else perceives us should never be the determining factor in our self-worth. As my coach, Nick Notas told me when I asked him if meeting another girl would make forget about the ones things didn’t work out with he said: “yes but you’re still chasing your self-worth through something external so it’s a bit like being a heroin addict. If that doesn’t work out, you’re back where you started”

There are few things more liberating in life than giving up the need to be liked by everyone. Not only is this impossible and out of your control. It’s exhausting.

Once you give this up, two things happen:

  1. You stop wasting a tremendous amount of time and energy

  2. The depth and quality of the relationships you do have with people in your life increases dramatically.

You get to show up in the world as a non-apologetic, no bullshit version of who you are. This, in turn, increases your sense of self-worth because your value is no longer dependent on whether or not someone else approves of you. Your attitude becomes “this is who I am, take it or leave it. And if you choose to leave it, then it’s not the right fit for the job, for the relationship, for the partner, etc.

Self Acceptance and Being Uncool

“When we value being cool and in control over granting ourselves the freedom to unleash the passionate, goofy, heartfelt and soulful expressions of who we are, we betray ourselves.” – Brene Brown

Self-acceptance means having the courage to show up as a vulnerable, authentic, no bullshit version of who you are It means not hiding your quirks and rough edges behind masks. In fact what you’ll likely find when you show up as the no-bullshit version of who you are is that the world seems lighter. People who don’t accept you don’t matter because their validation is not the determining factor in what you think of yourself. You’re selective about whose opinion matters.

We don’t learn this in school. And the result is kids who feel unpopular, unseen uncool and in the darkest of scenarios feel compelled to shoot up a damn school. Perhaps the path out of school shootings is teaching students how to manage their psychology.

It’s amazing how much energy and effort we all put into trying to be perceived as “cool.” We deliberately curate our Instagram pictures and Facebook status updates. We’re cautious about what we choose to reveal out of fear of being labeled uncool. But the effort we put into being cool, to sanding off our rough edges can be truly exhausting. Sadly, school doesn’t teach us how to own our stories and come to terms with how uncool we might be. Instead, it teaches us to desperately seek validation from people whose opinions have no relevance in our lives.

I think I’ve come to terms with the fact that are things about me that are uncool.

  • It’s uncool to be 39 and have the pop culture tastes of a teenage girl. But I’ve binged watched The OC more than once.

  • It’s uncool to lose your shit and yell four letter expletives at people in traffic who can’t hear you. But I’ve been known to do this from time to time.

  • It’s uncool to have no filters to what you say on occasion. But I’m not running for office. That shipped sailed a long time ago.

  • It’s uncool to love sports video games and not know a thing about sports.

The list goes on and on.

And what I’m starting to realize is just how uncool we all are. Whether you were the hottest girl in school, the best player on the team, or the most likely to be promoted at your job, underneath all that we’re all on some level uncool.

It takes far more courage to be uncool than it does to be cool. When own our quirks, rough edges, and idiosyncrasies, the masks we wear, the stories we tell ourselves and the labels we hide behind all fall. Being cool comes with the heaviness of living up to the expectations of others. Being uncool comes with a lightness that liberates us from those expectations.

And the strange paradox of being ok with how uncool you are is that you’ll suddenly be perceived as cool. As my friend Terri Cole said in an episode of Unmistakable Creative “when you approve of yourself


Out of fear of rocking the boat or upsetting another person, people often have loose boundaries. They tolerate behaviors that they’re not ok with, let people walk all over them and end up resenting them. But having loose boundaries more than anything indicates a lack of self-respect. Lose boundaries reduce our self-worth. With strong boundaries, we might piss some people off, but we’re also less likely to find ourselves in situations that are ultimately toxic to our well being. Strong boundaries reinforce our self-worth.


As a culture, we are obsessed with the idea that something is missing in our lives, and that to be ok we have to bridge the gap between expectations and reality. This ultimately stems from the beliefs that we are not enough, we don’t have enough and there isn’t enough to go around. As a result, we attempt to fill voids in our lives and the holes in our hearts with something external. When our default worldview is that something has to change for us to be ok, we’ll always be operating from a place of deficiency rather than sufficiency, scarcity rather than abundance, only to discover that nothing or nobody can ultimately fill the void. We’ll always feel deficient in some way.

But when our perspective, worldview, and beliefs shift to the idea that we are enough, have enough, and there’s more than enough to go around, we start to see that almost nothing is a finite resource. That’s the strange paradox of busting our asses to make a change. The more desperately we resist what is, the more it persists.


Prioritize Your Happiness

When we prioritize other people’s happiness over our own, we do ourselves and them a great disservice. We’re not authentic and the exhaustion of the facade will lead to an inevitable debacle. Whether it’s the job we take, the person we date, the friendships in our lives or the projects we say yes or no to, when we settle and compromise our own values and standards, we lose our power and diminish our joy. Sometimes it’s only in letting go of that which doesn’t serve us that we can find real joy and show up as the best versions of ourselves. The willingness to walk away is not stubbornness as much as it is a commitment one’s own values and standards. If we’re not mindful, our compromises can eventually turn into resentment

Process Orientation

Unfortunately, we’re taught by school to have an outcome orientation. Grades determine how good you are at something. And something temporary often becomes permanent. This creates unhealthy attachments, expectations, and disappointments. In the worst case scenarios, it causes people not to take any action at all. But nearly all successful people focus on the process instead of the prize.

When you’re process-oriented, outcomes can exceed your expectations. And process orientation allows you to experience progress, which in turn increases your motivation, creating a self-perpetuating cycle that ultimately causes momentum

Self Love and Self Care

Self-worth and self-love usually begin with acceptance and surrender to our circumstances. But there’s a difference between surrender and resignation. Surrender comes from a place of acceptance and abundance. Resignation comes from a place of resistance and scarcity. When our self-criticism is harsh and frequent, this causes us to live an unfulfilling life. We must consider a question that Anna Yusim poses in her book Fulfilled: How the Science of Spirituality Can Help You Live a Happier, More Meaningful Life.

Has this self-criticism produced any positive sustainable changes in your life?

Our self-worth and self-esteem are reinforced by doing everything you can to make the relationship we have with ourselves amazing. That means that we have to make self-care a priority and invest in ourselves.

Self-care is about far more than eating healthy and exercising regularly. It’s about doing things for yourself that add to joy to your life. I’ve even heard some spiritual teachers say that smoking a cigarette when you feel like it and washing it down with whiskey could be self-care. Of course, I’m not encouraging that. But sometimes self-care means splurging on a 200 dollar pair of jeans or going into a barber shop for a shave, haircut, and Godfather-like moments. Self-care is a form of benevolent selfishness.

I know for a fact that I’m a much happier person when I’m surfing and snowboarding on a regular basis. They are non-negotiable parts of my self-care. Because of that, I’ve made adventure one of the biggest priorities in my life this year. I’ve booked multiple snowboarding trips and a surf trip to Sri Lanka.

The relationship you have with yourself is the foundation of your ability to manage your psychology. Make it a priority and love yourself like your life depends on it.


There will be times in your life when you fail a test; somebody unexpectedly leaves your life, you get fired from a job, or lose someone you love. Adversity and obstacles are par for the course if you’re going to live fully and die empty.

There are few times that it is more important to love yourself than when you’re in the face of adversity, disappointment, and setbacks. And this is when it is the hardest. This is when our self-criticism tends to be the harshest and we ruminate on how we might have changed the past. By all means, learn from your mistakes. But realize that your failures do not define you. As longs as you see failures as defining, you will suffer

When we think that we will forever be defined by failure, we take something temporary and make it permanent We take one person’s opinion and make it a universal truth.

  • If one person doesn’t love us, we assume nobody will.

  • If one employer doesn’t hire us, we think none of them will.

  • If we get a bad grade, we believe that we are stupid.

We have to remember the lesson that one of my mentors drilled into my head over and over. Your temporary circumstances are not your permanent identity.

Adversity is often one of the most significant tests of our self-worth.

Fortunately, we do have ways out of adversity. A few days ago I came across this equation Dan Harris new book, Meditation for Fidgety Skeptics.


And I realized that I’ve always done everything I could to resist the pain I was feeling. I always tried to numb it with alcohol or drugs. But with pain and adversity, sometimes that fastest path out is through. Love, whatever happens, see the opportunity in the loss, endings as new beginnings, and that The Obstacle is The Way. Adversity forces you to confront some of your most painful truths. But you also will usually emerge stronger and more whole for having gone through the pain.

2. Interacting with the Opposite Sex

This might have been the second most frequent response to my question. And for a good reason.

Sometime in 5th-grade kids are brought into a classroom and shown a video of sperm swimming under a microscope. That’s the extent to which your taught to interact with the opposite sex. If you’re lucky enough, you have parents who have a healthy attitude towards interacting with the opposite sex and they talk to you about it.

But if not, you’re left to fend for yourself wondering why you get an erection when the teacher is hot or Cindy Crawford is buying a Pepsi. If you grew up in the 90’s, you’d get the pop culture reference. Of course, you were still completely clueless. But I digress.

I was particularly clueless because I had no model for how romantic relationships occurred. My parents had an arranged marriage. My dad couldn’t pass on any knowledge about courtship to me. So I bought into this delusional, idealistic and Disney Movie version of romance. It didn’t exactly lead to a fruitful dating life.

Considering that interacting with the opposite sex is essential to our survival and well being, It’s absurd that we aren’t taught this in school or earlier in life. Instead, we’re forced to figure it out through trial and error or turn to other means to solve our problems.

In one of my most revealing interviews I’ve ever given, my friend Khe Hy asked me about my teenage, college and early 20’s dating life. I told him there was nothing for me to tell him. I never had a girlfriend in high school, college or in my early 20’s. When he asked how I self-diagnosed, I told him something was wrong with me. Then I told him something I thought I’d never want anybody to know about: I spent four years in a cult that eventually became known as the seduction community. It was something I had a great deal of shame about for a really long time.

But, the more I talk to other men, the more I keep discovering the seduction community was their entry point into personal development. Perhaps the most misunderstood thing about this community is that most of the men who were there came with good intentions. Many of them were honestly looking to become more confident, and have more fulfilling romantic relationships, not just sleep with as many women as possible. But under the guidance of any charismatic and manipulative leader, good intentions can quickly be turned into a series of screwed up emotions. When guidance becomes gospel, advice turns into dogma and that’s where personal development can cause more harm than good.

Nobody faults an athlete for hiring a trainer to help him improve his game. Nobody faults a business owner for hiring a mentor to help him increase his revenue. But when it comes to working with someone to develop our social skills or ability to interact with the opposite sex, there’s a great deal of stigma and shame that’s associated with it. Admitting that you need help in this area of your life can make you feel inadequate. We tend to overlook the lifelong ROI of coaches and mentors out of ego and shame. And instead, we blame fate, bad luck, etc.

The definition of insanity is doing the same thing and expecting different results. So after nearly a year of dating people that I didn’t’ seem to be connecting with, I hired Nick Notas to help me. A good amount of our work has been around managing my own psychology and recognizing my own worth in situations.

Given that our social relationships are one of the greatest predictors of our happiness and well being, why wouldn’t we ask for help in this area of our lives? And why aren’t we taught about it in school?

If you haven’t seen it, I recommend watching Michael Moore’s documentary Where to Invade Next and pay close to attention to how French school children learn about sex. Instead of sperm swimming on a screen, they’re taught that their first sexual experience is something unique to be enjoyed. In a conversation, I had with Layla Martin, about the biology and psychology of sexuality she said the following

To me, we have a sexual health epidemic that people aren’t talking about. We have porn addiction, we’ve got sexual dysfunction, people just not having sex in their long term marriages, sexual traumas, sexual abuse, etc. Harassment is just the tip of the iceberg and we’re finally having that conversation in society right here, right now…. We don’t have healthy models of sexuality. We don’t have people having the conversation and modeling what it looks like to be a healthy, sexually integrated being. Not only that, but we actively suppress that conversation in society. You can’t talk about it and run an ad on Facebook. You can’t talk about it and have a career on CNN. It’s crazy how much this conversation is still being suppressed and how much it’s needed.

The unfortunate result of not teaching this in our schools or the way we currently teach it in school: guys who behave like idiots, women who treat them like shit, people ending up with other incompatible people, and men and women ruining the dating process for each other.

3. Money

What’s the Story You’re Telling Yourself About money?

Money is a story. It’s a story for peasants who make three dollars a day and investment bankers who make three dollars a second – Seth Godin

There are very few things in life that have the kind of emotional impact on people that money does. Money is necessary for our basic survival. We need it to buy food, and to pay for shelter.

However, we tend not to think of it as a story. But if you ask people about money, you’ll quickly discover that a story follows it.

My sister and I grew up with very different money stories because of where my parents were at with their careers when we were growing up. I was often told that we couldn’t afford certain things. My parents gave me everything they could within their means (except a skateboard). By the time my sister was a bit older their means had increased so they could give her a bit more than they were able to provide me with at the same age.

This story led to some very self-destructive spending patterns in my early 20’s. I consumed in excess. I tried to compensate for everything my parents weren’t able to give me when I was young. I bought a pair of Air Jordan’s because I didn’t get them as a kid. I suck at basketball and never played again the summer after I bought the shoes. My life was all about accumulation and I didn’t even prioritize quality over quantity. It’s taken some hard knocks and quite a bit of work to change this story. These days I’m somewhat of a minimalist, but when I do buy things I limit the quantity and don’t mind shelling out for quality.

There’s a strange paradox that occurs when you prioritize quality. The things you own are more expensive, but you end up spending less because you might buy something once and not again for a long time. Take something as ridiculous as a pair of 500 dollar Ferragamo dress shoes. You buy them once and then it’s ten years before you need another pair. That’s 50 dollars a year for ten years. And of course, prioritizing quality allows every part of your environment to become a sacred space.

One of my favorite parts of Seth Godin’s Leap First audio seminar was when he talks about how to unwind the story you tell yourself about money by becoming a philanthropist. Donate every single time you’re asked or make a monthly donation. Give money to people busking on the streets. As Seth says “you can’t be the type of person who tips 20 dollars on a 6 dollar cup of coffee and still have this narrative about money.”

  • Bushra Azhar donated 10% of her check when she made 10 dollars a month and maintained the habit when she started making 10,000 dollars a month.

  • Brian Koehn used to believe that making money involved blood, sweat, and tears until he didn’t. Then he walked into a new prospects office and walked out with a 500 dollar check within a week of coming up with a business idea.

The story you tell yourself about money will impact how much you make, what you’re willing to spend it on, and how generous you will be with what you have. It will also determine how well you treat yourself and what you think you deserve. The idea that the pursuit of wealth is a spiritual quest might seem absurd to people. But it is as much an inner journey as much as it is an outer one.

So what’s the story you’ve been telling yourself about money?

The Toxic Social Program of Scarcity

It is not even that we necessarily experience a lack of something, but that scarcity as chronic sense of inadequacy about life becomes the very place from which think and act and live in the world. It shapes our deepest sense of ourselves and becomes the lens through which we experience life. Through that lens, our expectations, our behavior, and their consequences become a self fulfilling prophecy of inadequacy, lack and dissatisfaction. — Lynne Twist, The Soul of Money

Of all our socially programmed responses to life, the most toxic is scarcity.Scarcity causes us to make poor choices in virtually every area of our life.

  • If we seem time as scarce, we become impatient. And our impatience has consequences that are often detrimental. This often tends to happen as people get older. They worry that time is running out. Good decisions about life are rarely the result of being concerned that time is running out.
  • If we see career opportunities as scarce, we take jobs we hate and choose employers that don’t value us.
  • If we see potential romantic partners as scarce, we make choices out of desperation. We compromise our values, stay in toxic relationships, and settle rather than settle down. We stay and chase people when we’d be better off just walking away.

And most the issues that we deal with around money are primarily the result of a scarcity mindset or what copywriter Dan Kennedy calls a poverty consciousness.

When we view the world through the lens of scarcity, the way we see the world becomes incredibly limited. It’s the energy that we walk through the world with.

It’s virtually impossible to live a happy life when scarcity is your default worldview.

Making the Shift from Scarcity to Abundance

Fortunately making the shift from scarcity to abundance is where we can get practical with how we deal with money.

Dan Kennedy’s 90-day experiment

In his book No BS Wealth Attraction, Dan Kennedy recommends the following 90-day experiment:

Immediately establish a new bank account and call it your Wealth Account. It can be checking, interesting-bearing checking, money market. At first, it doesn’t matter. Next determine a fixed percentage of every dollar that comes your way that will be diverted into that wealth account. Something between 1% and 10%. You may think you can’t do this- hey, I pay my bills with 100% of every buck, how will I pay them with 90%. Well maybe you won’t But you aren’t now either. So just do it. Pick a percentage, deposit the money, and then do NOT touch it, no matter what. And make these deposits every time a dollar arrives. Daily if need be. The more often the better. The act of putting money into your Wealth Account does things to and through your subconscious mind that cannot be fully explained. The amount matters less than then act…

Now here comes the illogical one: giving. This is important because all wealthy people give. Giving has an incredible effect on your psyche. So immediately open another separate bank account and call it your giving account. Also predetermine a fixed percentage of every dollar that you receive to divert to your Giving account.

I’ve been following this advice ever since I read his book. And what I’ve found quite consistently is that anytime I donate, the money seems to come back in multiples. I’m not sure why it works that way, but I’ve stopped questioning it.

Tipping $10

This is a simple piece of advice my friend Joseph Logan gave me a few months ago when we were discussing how a person makes a shift from scarcity to abundance.

While this exercise might seem wasteful, it’s one of the fastest ways to start unwinding the story that money is something that we have available to us in limited quantity. Set aside $100 and decide that you’re going to give it away in 10$ tips. First, you’ll notice that people who receive the 10 dollar tip will light up. When I tipped 10 dollars on a 6 dollar cup of coffee the woman at Starbucks was thrilled.

Second, you’ll feel good because they light up, which in turn will reinforce your sense of abundance. As your sense of abundance gets reinforced, you’ll start to see opportunities everywhere to recoup that money. If it sounds hokey, try it. You might be out $100 or up a $1000. Small risk for such a big pay off

Take Opportunity Cost into Consideration

In the piece, I wrote about the five things I gave up to be successful I said that there’s an opportunity to cost to everything. During the first several years of my work on Unmistakable Creative, the opportunity cost was present-day earnings so that I could increase my earning potential over time. But this doesn’t just apply to jobs. There’s an opportunity cost to nearly everything in our lives.

  • You wonder whether you should get the lease protection on a new car. The extra 100 bucks not only buys you peace of mind but saves you potentially thousands in the long run.
  • Driving all over town to save a dollar here or there might make you feel as if you’re budget conscious. But the opportunity cost is time and gas.
  • It might be cheaper to put your bookshelf from IKEA together yourself. But if a task rabbit can do it in one hour and it takes you all day, the opportunity cost is not only your time but your state of mind.

If you want to manage your time more effectively, place a really high dollar value on it.

If you’re like most people, you didn’t learn most of these things in school. But, thanks to the internet you can give yourself an education that kicks the crap out of the one you got in school:

  • You can listen to podcasts, and learn how to manage your psychology from some of the best social scientists in the world.
  • You can hire amazing coaches to help you improve your social life and ability to interact with the opposite sex.
  • You can study and get better at managing your money from some fantastic personal finance blogs on the internet.

These are essential life skills we should have learned in school but never did. But that doesn’t mean it’s too late to acquire these skills and start improving these areas of your life.

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This article was originally published on Unmistakable Creative.