October 13

A Skeptics Guide to a Good Life

Religious scholars, philosophers, psychologists, and humans have been searching for answers to their questions for thousands of years. They’ve searched churches and bars, books, and seminars. They’ve asked Google, Siri, Alexa, and God.

There’s one universal question in every human’s search for answers: how do you live a good life?

This Article Won’t Change Your Life

If you’re someone like me who has read enough self-help books to start a side hustle as a therapist, you might be asking yourself, “Then why the hell am I reading this?

Notice that you never ask that question about the book that promises you more sex, more money, and more of whatever it is that you think is missing from your life. But how often do such books fulfill the promises they make to their readers?

If the thousands of books on my shelf were an accurate reflection of the outcomes in my life, I would:

  • Be a billionaire
  • Write a best-selling book every year
  • Be the most self-actualized, charming, and enlightened human being on the planet
  • Wake up every day of my life like a Zen Buddhist on ecstasy

And yet none of these things are true about my life.

I’m not suggesting you stop reading these books. After all, I’ve made a career out of writing such books and promoting those who do. I’m effectively a merchant of life advice, much of which hasn’t worked in my life. What I am suggesting is that you approach it all with a dose of skepticism to become more self-aware.

I’ve spent more than a decade talking to insanely interesting people from all walks of life. They’ve included bank robbers and billionairesporn stars and presidential candidates, best-selling authors, and iconic artists. They’ve given me an education that kicked the crap out of the one I got in school.

But the most valuable things they’ve taught me are to:

  1. Question the validity of what I learn from them
  2. Never follow their advice to the letter
  3. Treat them not as gurus spouting gospel, but as teachers who offer guidance and increase your awareness

Hence the reason my friend and mentor Joseph Logan calls The Unmistakable Creative “A skeptic’s guide to a good life.”

I’ve even gone so far as to joke that my book Unmistakable: Why Only is Better Than Best could just easily have been titled Everybody is Full of Shit. But it’s unlikely that my publishers would have wanted that on a book cover since they themselves are merchants of life advice from people who are “experts” in their fields.

The self-help industry and cult of optimism lure us in with seductive promises of making more money, having more sex, and fixing everything we think are broken or anything we don’t think we have enough of.

  • Life coaches who couldn’t figure out what to do with their lives start businesses telling other people how to live theirs.
  • In the heat of passion and under delusional dreams of grandeur coupled with intense desire, ire people spend money they don’t have. They make decisions in the name of self-improvement that paradoxically ends up being detrimental to their lives.

But what Edward Bernays wrote in his book Propaganda is as true for the self-help industry as it is for any other area of life:

We are governed, our minds are molded, our tastes are formed, our ideas suggested, largely by men we’ve never heard of.”

The only difference is that we know their names, read their books, and follow their lives on social media (which we mistake for reality).

No book, person, coach, or mentor changes your life. They make you aware of how YOU might be able to change it. Without the courage to question everything we read, learn, and hear, we lose our capacity for self-awareness.

What I’m offering here comes from my life experience and perspective. And this is true for all of the books or articles you read, the podcasts you listen to know, and the knowledge you acquire.

As any good skeptic would, I suggest you read it with skepticism, doubt, discernment, and consider the possibility that everything I’ve written here is total bullshit.

By now you’ve either concluded that I’m out of my mind, or you’re curious about what I’ve written in the paragraphs ahead. Don’t let me or anyone convince you that you should keep reading. That’s a decision for you to make.

Awareness is not some mystical power you need to purchase at a new age gift shop. Right now, you’re aware of the words on your screen or page, the light in the room, and anything else in your environment that has a part of your attention.

“You need to have awareness of who you are and how you move through the world. What makes you tick? What makes you happy? If you don’t have that awareness, then you can’t extrapolate your life to greater things. You can’t then harness those things and create a masterpiece for yourself, because if you don’t have it, you’ll just bumble through life and go wherever life shows you to go. – Rhiannon Reese

Self-awareness comes from observing how you respond to the events, circumstances, and experiences of your life.

  • Working a job you hate makes you aware of the kind of work you should avoid
  • Dating someone you’re incompatible with makes you aware of what type of person you will be more compatible with

The challenging events: bad dates, lousy bosses, difficult co-workers, setbacks and bullshit increase your awareness more than the positive ones. Challenging events force you to ask questions.

Observe changes in your awareness and the broadening of your perspective. Contemplate the questions that arise and choose your own adventure. Then pay it forward by sharing it with someone and giving them a question to contemplate.

But if you want to get the most from this article, I’m going to make what might seem like an odd suggestion for an author or blogger. Don’t ever read it again.

1. Don’t Follow Conventional Wisdom (All Wisdom Eventually Becomes Conventional)

woman in white dress sitting on ground under tree during night time

Reality is nothing more than a series of collective agreements between a group of people. Once that group becomes large enough, collective agreements become conventional wisdom.

Society’s life plan is a form of conventional wisdom which teaches us to cross off a series of checkboxes that are pre-determined by other people:

  • Go to school
  • Get a job
  • Go back to school and get a better job
  • Climb the ladder, but don’t ever ask whether it’s even leaning against the right wall

Once people stop questioning conventional wisdom it becomes like water to a fish.

Non-conformity starts as a form of unconventional wisdom which teaches us to:

  • Quit our jobs and move to some foreign country
  • Start a side hustle
  • Work our own hours
  • Live the life we envy on Instagram

But as any form of unconventional wisdom spreads through the zeitgeist, it becomes conventional wisdom. Instead of peers, parents, and society, the messengers of that wisdom are best-selling authors, lifestyle design bloggers, life coaches, and personal development gurus.

If you’re content, fulfilled, and happy with society’s life plan, there’s no reason to let someone else plant seeds of dissatisfaction. And if you’re not, by all means, challenge the status quo. But do it because YOU want to, not because a book or some author like me says you should.

Conventional wisdom comes from external sources, while unconventional wisdom comes from within. It’s about having the discernment to figure out what makes you happy, not what other people tell you will make you happy.

2. Context Matters

“The world around us is constantly pulling our strings, coloring how we think, and guiding how we behave. And yet we barely notice.” – Samuel Sommers, Situations Matter

Context plays an important role in everyone’s worldview, achievements, and life outcomes. When you ignore context, you overlook multiple variables that throw off every formula for success.

Upbringing and Environment

My parents prioritized security in the process of building their careers. When they were growing up in India, life outcomes were binary. It was poverty or security, with nothing in between. So the advice they gave me and my sister about careers made sense in the context they had lived in.

Outlier Advantages and Circumstances

Some people have outlier advantages that are impossible to replicate. With the Unmistakable Creative podcast, I was the beneficiary of a decade-long head start on what’s become a massive cultural trend and a generous mentor who took me under his wing. Even if I taught a podcasting course and shared everything I knew, parts of my path are impossible for another person to replicate.

Someone might have grown up in privileged circumstances or extreme poverty, with loving parents or abusive ones. As a result, they’ll have different strengths and weaknesses. The person with a difficult past might be more emotionally resilient while another is more educated.

Whether it’s in business or life, advice of any kind becomes more effective when you modify it to fit the context.

3. Challenge Authority When It Makes Sense

We’re taught at an early age not to challenge authority. As we get older, it becomes our default way of thinking. If nobody challenged authority, nothing would ever change. The world would be run by dictators, middle managers, and yes men.

If people didn’t question existing scientific evidence, there would be no breakthroughs in any field. Incumbents would dominate every market and nobody would create a startup if they weren’t willing to challenge the 800-pound gorilla.

Authority Bias

We all have an unconscious authority bias. When someone is an authority on some subject, we assume everything they say is true.

Authority bias is so powerful that we can become victims of it even when we’ve managed to transcend it. In 2013, I stopped waiting for permission to write a book and self-published The Art of Being Unmistakable. And shortly after, I got permission to write two books with a publisher.

The irony is that I’ve spent the last two years waiting for their permission to write another book (based on the ideas in this article) because I fell victim to the authority bias I thought I had managed to transcend.

There are times, however, when it doesn’t make sense to challenge conventional wisdom. It’s not like you can challenge cancer research by smoking two packs a day. That’s not rebellious. It’s stupid.

Half the battle of challenging authority is letting go of the belief that you need authority. The founders of Airbnb weren’t authorities in the hospitality industry. They were just two guys who needed a way to pay the next month’s rent.

Challenging authority isn’t about outright defiance. It’s about having conviction in what you believe for meaningful progress and a better future.

4. Don’t Always Think Positive

“Ceaseless optimism about the future only makes for a greater shock when things go wrong; by fighting to maintain only positive beliefs about the future, the positive thinker ends up being less prepared, and more acutely distressed, when things eventually happen that he can’t persuade himself to believe are good.” – Oliver Burkeman, The Antidote

The Power of Positive Thinking by Norman Vince Peale sold more than 5 million copies. And because he was a pastor, he literally turned guidance into gospel.

There’s only one problem. It turns out he was full of shit. Or as a respectable media outlet like the New York Times might say, he was a fraud. Fun fact: he was also Donald Trump’s pastor.

There are times when positive thinking is actually delusional thinking.

If you’re crossing the street in a country like India where this amounts to playing a real-life version of Frogger, positive thinking doesn’t get you to the other side of the road safely. Common sense does. The only thing you should be positive about is that running into oncoming traffic will ensure you get hit by a car.

If you bet your monthly paycheck on one hand at a blackjack table, positive thinking isn’t going to make you rich. It makes the casino more profitable. Vegas was built on the delusional dreams of positive thinkers.

Sometimes it’s smart to anticipate something negative to prevent it. This isn’t about looking for the worst and expecting it to happen. You already do this in many areas of your life without realizing it.

  • You drive somewhere at specific times to avoid getting stuck in traffic (this is anticipation of the negative). Nobody who lives in LA believes positive thinking will prevent them from getting stuck in traffic if they get on a freeway during rush hour.
  • People who surf big waves, base jump, or ski difficult terrain anticipate the negative so they can take action to prevent it. Positive thinking doesn’t prevent anyone from plummeting to their death if they jump off a building without a parachute.
  • When you pick a life partner, you look for the best in them. But you’re also anticipating things that might make you incompatible to prevent a bad decision. One of my roommates and his fiance went to counseling before they got married. They’re still married almost 20 years later.

If you believe in the law of attraction, this might have made you cringe. Don’t fret. I’m all for vibrating at a high frequency which makes all of us sexy.

A literal interpretation of the law of attraction is the problem. Did all of humanity sit around thinking about a deadly virus that would lead to a global pandemic and manifest it?

Single guys were probably thinking a lot more about sex than a global pandemic. But instead, they manifested a deadly virus that killed hundreds of thousands of people and cockblocked them? I sure as hell didn’t.

First, it’s impossible to always think positive. If you’ve ever tried to control every thought you have during the day to make sure it’s positive, you know how exhausting it is. You’re basically in a fight with yourself.

You might have had a negative thought like “Srini is high” or “I hate this guy” while reading this. You didn’t plan that. It just happened.

Second, there are times when it doesn’t make sense. If you anticipate the negative in the short run, you’ll avoid it in the long run.

Think positive, but don’t always think positive.

5. Life Plans are like Fortune Cookies

“Formulating a vision for the future requires by definition that you isolate some aspect or aspects of your life, or your organization that, or your society, and focus on those at the expense of others. But problems arise thanks to the law of unintended consequences, sometimes, expressed using the phrase ‘you can never change only one thing’. In any even slightly complex system, it’s extremely hard to predict how altering one variable will affect the others. – Oliver Burkeman, The Antidote

You can speculate all you want about the fortune inside of the cookie. But until you crack it open, you won’t know what’s actually inside. Life plans are the same. Until you’ve lived some of your life, you won’t have a clue how it will turn out.

When you let a life plan you made at 20 determine the person you are at 40, you become rigid. You don’t install a 20-year-old operating system on a new computer and expect it to work.

If you focus on how you thought it would be or should be, you overlook how it could be. “Shoulds” and “woulds” limit the possibilities in your life. “Coulds” expand them and makes them infinite.

Life isn’t static. It’s dynamic. People who thought they would be married forever get divorced. People who thought they’d be working somewhere for the rest of their lives find jobs that didn’t even exist 20 years ago.

Having a rigid life plan is a bit like traveling with an itinerary that doesn’t leave any room for serendipity. Instead of experiencing the places you visit, it’s just another item to cross off a never-ending to-do list.

It’s not hard to find a self-help book that teaches you to set goals, But it’s rare to read a book that encourages you to abandon your goals. My friend Matthew Monroe is one of the happiest people I know and he doesn’t have goals. He has a world view which can be summed up in three phrases:

  1. Go to interesting places
  2. Meet interesting people
  3. Do interesting things

When you look at life through that lens, you start to see that goals limit what’s possible in your life, a worldview expands what’s possible. And anybody who has met Matt Monroe will attest that he’s one of the most interesting people they’ve ever met.

The most interesting and rewarding experiences of my life have been the ones that I didn’t plan. I never planned to:

Be at my sister’s wedding without a date

When I realized I’d be given a captive audience who had to listen to me, I used my public speaking skills to put the aunties to work on my behalf. I opened my speech with a slide of my phone number and encouraged all of them to text profiles, pictures, and other relevant information about potential suitors to me.

The speech was a hit and the aunties, unfortunately, turned out to be the worst unpaid employees in the world. They’ve all been fired.

Learn to Surf

When I was a kid, the swim instructor asked my mother not to bring me back to the class because my fear of water was so disruptive to the class. Since I’m Indian, I’m not genetically predisposed for something as athletic as surfing. Becoming a surfer at the age of 30 was definitely not in the cards.

Start a podcast

Fun fact: the ability to listen is my greatest strength as a podcast host and greatest weakness as a human. When listeners of Unmistakable Creative have set me up on dates with their friends, I get phone calls and messages saying, “My friend said you talk too much, which is shocking considering what you do for work.” All I can say is that I’m working on it.

Write a book

There was a time in fourth grade when I was failing reading. The teacher suggested to my parents that I might have a learning disability. They concluded she was just a shitty teacher. A learning disability is not exactly indicative of someone who is going to have much of a future as a writer.

Be on a reality TV show

The truth is that I hate reality TV. But I figured that if nothing else, the experience would make my life a little more interesting and it certainly has.

Move to Colorado

Every week my friend Matt Cooke would come to my apartment to play NBA 2k19. Sometime last summer, he came over on a Wednesday and told me he was getting divorced. I’m more of an asshole than I appear to be and I immediately thought, “Well, he’s going to need a roommate, and then we could play NBA2k every day.” Fortunately, I was sensitive enough to wait a few weeks before I suggested this.

How interesting something is has been the primary filter for everything from how I choose podcast guests, make travel plans, and pursue creative projects. The life plan I had at 20 looks nothing like the life I’m living at a 40. So, I’m inherently skeptical about plans that appear to be set in stone and people who claim that they have it all figured out.

After all, what’s fun about a life in which you know exactly how everything is going to turn out?

You can sit around wishing your life has gone according to plan, or come to terms with the fact that it rarely goes according to plan. As CC Chapman says, amazing things will happen, and more often than not, the most amazing things happen when life doesn’t go according to plan.

You could create the Magna Carta of life plans. But the moment you put stop reading this, something could happen that wasn’t part of your plan. The only thing that’s certain about a life plan is that it will change and so will you.

A life plan is nothing more than a prediction of how the future will look. But the future is always unwritten regardless of how detailed your life plan is.

6. The Purpose of Self Improvement is Self Awareness

The purpose of self-improvement isn’t to fix what you think is wrong with your life. It’s not to get six-pack abs or earn a six-figure salary. Those things might happen as a result.

The knowledge you acquire from reading books, hiring coaches, or working with a mentor doesn’t eliminate your problems or get rid of your imperfections. It expands your awareness, illuminates your blind spots, and allows you to learn from someone else’s experience. Sometimes others can see in you what you can’t see yourself.

Don’t focus on a person’s accomplishments when it comes to your teachers, role models, and mentors. Focus on the process that enabled those accomplishments. This will give you access to skill, insight, universal principles, and timeless wisdom.

Transform those principles into individual principles. Use the knowledge you acquire from others to inform your life rather than define it. You want to fulfill your destiny, not replicate someone else’s.

No book or person changes your life. They make you aware of how YOU can change it.

Awareness expands your sense of possibility and gives you more perspectives. The purpose of self-improvement is self-awareness.

7. Other People Give You Keys that Open Doors to Higher Self Awareness

Everything and everyone who comes into your life give you a key that opens to the door to higher awareness.

  • The person who pushes your buttons gives you the key to patience
  • The one who breaks your heart gives you the key to love
  • The person who causes you pain gives you keys to persistence and resilience

But there will also be times when you don’t realize you were given a key until you open another door to higher awareness. There’s no way to know which door that will be.

Higher awareness illuminates aspects of reality that are invisible at lower states of awareness. You know more about yourself today than you did last year. And you’ll know far more about yourself twenty years from today.

The more you experience, the more self-aware you’ll become. The only life hack for higher self-awareness is to live your life. Use the keys that other people give you to inform your life, not define it.

8. There are Very Few Universal Truths in Life

If the words “everyone should” appear in a book title, blog post, tweet, or status update, question their validity. There are only a handful of universal truths:

  • Don’t kill (unless it’s inevitable)
  • Don’t do something will get you killed
  • Pay your taxes
  • The sun will rise and set
  • One day you will die

When an authority figure or person with status says everyone should do something, it’s very tempting to believe it’s true and that they are right. But what’s true for one person may not be true for you.

When you treat guidance as gospel and opinion as a universal truth, you let people who will never live with the consequences of your choices determine how to live your life. You let other people become dictators who rule your life.

9. Stop Playing A Game You Didn’t Choose With Rules You Didn’t Write

Life is a series of games we are taught play with rules we’ve been instructed to follow. But we’re often playing a game we didn’t choose with rules we didn’t write. All of these games are illusions that create a filter for how we experience our lives.

If we don’t question the rules or the games, we mistake these illusions for reality.

The rules of one game might be that you have to choose from the options in front of you. A different game with different rules could reveal the other possibilities that surround you.

Spiritual teachers, gurus, experts, and people like me who write books might expand your awareness, but they also cause you to play a game you didn’t choose with rules you didn’t write.

Inflating vanity metrics on social media is what Naval Ravikant calls a stupid game with stupid prizes. Yet another game you didn’t choose with rules you didn’t write.

Skeptics question the games they’re taught to play and the instructions they’re taught to follow in their quest for a good life.

When you question the rules and the games, you become aware that they are all illusions. The more you increase your awareness, the more power you’ll have to choose your own game and write on your own rules.

It’s hard to live a good life if you’re playing a game you didn’t choose with rules you didn’t write.’

10. Accomplish Your Goals Doesn’t Solve Your Problems. It Creates New Ones.

When I was living in San Diego, struggling to meet a romantic partner, my friend Mike Harrington said, “You see dating as a problem to solve rather than a process to enjoy.” If you’re married or in a relationship, I’m guessing you don’t live a life without any problems.

In the early stages of a business, it’s tempting to think that you won’t have problems when the business becomes more successful. Mark Zuckerberg’s life is full of problems that he didn’t have before Facebook became the behemoth it is today. Between privacy issues, election meddling, and former employees who have been critical of the company, all that’s changed is the magnitude of the problems he’s dealing with.

As my mentor Greg Hartle said to me over and over, the problems don’t go away. They magnify. And that has been true throughout the process of building Unmistakable Creative. Between friendships ending and hiring lawyers to deal with intellectual property issues, there was a time when I even thought that building the Unmistakable Creative had done more harm than good in the world.

When you solve any problem in life, it creates others. Greg shared the following example in his interview on the Unmistakable Creative:

When you set an intention, also write down the anti-intention.

You want to you want a million dollars? Great. That’s the goal. Now write down all the things that are going to suck about having a million dollars because there will be plenty of things that are going to suck about having a million dollars.

You want to be on TV or have your own television show? Fantastic. Now write down all the things that suck about you having your own television show. Like you can’t go to a restaurant anymore.

If anyone promises you that they have the solution to all your problems, it’s safe to say they are selling you snake oil.

But that doesn’t mean we live our lives as a series of problems we have to solve. Jim Kwik once asked Quincy Jones if he has any problems. Jones said, “I don’t have problems just puzzles.” When we reframe problems as puzzles, then life becomes a process to enjoy than a series of problems to solve.

11.What You Think Of As Your Own Definition of Success Might Not Be

Our definition of what it means to be successful is largely determined by the world around us. We inherit it from parents, peers, media, and society. Money, prestige, status, fame, and power are what many people consider success.

It doesn’t matter if you get into Harvard, win a gold medal, hit the NY Times Best-seller list, sell your startup for a fortune, or date the hottest girl in school. You’re still measuring your life with someone else’s yardstick.

  • Getting into Harvard is a collective agreement about prestige and intelligence
  • The person everyone says is the hottest girl in school is a collective agreement about beauty
  • Hitting the NYTimes best-seller list is a collective agreement among a bunch of old white guys sitting in a room about what makes a book great
  • Selling a startup for a fortune is a collective agreement about what it means to succeed in business

All of these things are just conventional wisdom about what it means to be successful.

When Yanik Silver was a guest on our podcast, he told me a story about a client who wanted to become a billionaire. It was an arbitrary goal. Yanik asked the client what he thought a billion dollars would give him and the client realized that he didn’t need a billion dollars for anything he wanted.

I told my mentor Joseph the only reason I need a billion dollars is to buy a professional sports team (a weird goal for a person who only plays sport-related video games, but doesn’t watch sports). He asked me what that would do for me. All I could come up with was courtside seats and making Laura Belgray’s premonition that I would one day own a hockey team come true.

Ask yourself why these things are important to you. After reading Ryder Caroll’s book The Bullet Journal, I came up with a financial goal that would let me:

  • Pay off my student loans
  • Travel, surf, snowboard
  • Buy an engagement ring and start a family
  • Indulge in the occasional luxury like a fancy restaurant or night in a really nice hotel room

The goal of becoming rich enough to buy a sports franchise became an arbitrary one.

If you don’t ask why you want things, getting what you thought you wanted might leave you disillusioned and dissatisfied. You’ll end up living your life according to other people’s expectations and their definitions of success.

12. Blend Skepticism with Rational Optimism and Practical Realism

Spend enough time in the self-help section of your local bookstore, and it’s hard not to conclude something is either wrong with your missing from your life. According to the self-help section at my bookstore, I’m neurotic, need to earn more money, and, the greatest irony of all, need to Do Less (the title of a recent productivity book I saw on the shelf).

I’m what you might call a blend of rational optimism, spiritual skepticism, and practical realism. Or as some people think, out of my mind.

The first time I met an energy healer, I asked her if the work was just a bunch of “new age bullshit.” A week later I made an appointment with her. Because of my insatiable curiosity, I had to find out for myself if there was any validity to what she did.

A couple of days after my “healing session”, I’d stopped thinking about the break-up that had been on my mind for almost two years. So I finally understood that there are mysteries of the universe we’ll never be able to explain with logic or reason.

That being said, I’m skeptical about magical thinking. If we’re not careful, it’s easy to let spiritual practices become a crutch in our quest to live a good life without actually living one.

Some people present the appearance of “being conscious” through poetic status updates, pictures on Instagram of themselves doing yoga, burning incense, and worshipping idols from religions they read about in some book. But they’re often disconnected from reality and getting high on personal development.

Personal development literature is notorious for perpetuating platitudes like “follow your passion” and other inspirational memes. But the most important thing you can bring to your personal development efforts is a bit of skepticism and doubt.

Just to be clear, skepticism is not pessimism. It’s about discernment and having the courage to question what you read, hear, and learn and decide for yourself what it means to live a good life.

13. Try Not to Join a Cult – You Might Already be In One

When I was in my 20’s I joined a cult that people know today as the “Seduction community.” Charismatic geeks who transformed themselves into modern-day casanovas sold men around the world their plans for how to become more successful with women.

It wasn’t long before, groups of women became “sets”, dates turned into “field reports” and the only purpose of going out was to “improve my game.” At a certain point, the cult you’re in becomes the lens through which you view the world. It for me and I was more fucked up than I had been before.

When I hired Nick Notas as a dating coach, he told me that guys who have been through the seduction community are some of the most challenging for him to work with because there’s so much bad programming that has to be rewritten.

The seduction community is just one of many cults that fuel the multibillion-dollar self-help industry.

  • If you’re spending every second of your life and dollar in your bank account on self-improvement, you’re probably in a cult.
  • If any organization that isn’t paying you is dominating so much of your life, you’re probably in a cult.

As Werner Erhard, founder of the Landmark Forum once told Dan Kennedy, we sell independence but breed dependence. Life advice merchants are masters at creating the kind of cults that most of us don’t even realize we’ve joined.

14.Outliers are Lousy Role Models for the Rest of Us

yellow and white trophy

Outliers become our role models for success because of their visibility. Billionaires and celebrities end up on magazine covers and talk shows. People with the largest audiences on the internet reach the most people with their blogs, podcasts, and YouTube channels.

But what you never hear are the stories of the aspiring individuals who spend years lingering in obscurity and die penniless.

Nobody writes a book about the person who spends 10,000 hours on something that doesn’t amount to shit.

When outliers become our role models for success, we set ourselves up for profound disappointment and great dissatisfaction. It’s not that we can’t learn from outliers. But when they become the standard by which we measure our lives, we’ll inevitably spend the rest of our lives on a hedonic treadmill. As Paul Graham said in his collection of Essays, Bill Gates is not a good role model for the rest of us.

We chase success but never feel successful. We overlook the fact that successful people are often the beneficiaries of circumstances and advantages that are impossible to replicate. Thinking somebody else’s path to success will allow us to replicate their accomplishments puts us on a road that usually leads nowhere.

While it might feel disempowering or disheartening to realize that you’re not going to be the next Steve Jobs, Beyonce, or Oprah, it can actually be the most empowering thing you could do to live a good life. It forces you to ask yourself if that’s what you really need to live a good life.

When people become successful, they get opportunities to write books, give talks, and capture the attention and admiration of society. As a result, they transform individual perspective and experience into universal principles. Unless we ask ourselves if those principles are true for us, we confuse correlation with causation.

  • Elizabeth Holmes believed wearing black turtle necks and approaching life with a Steve Jobs-like intensity would cause her to change the world. But instead, she ruined people’s lives, lost fortunes, and is facing the possibility of prison.
  • When someone like Elon Musk works insane hours, aspiring startup founders mimick him, deprive themselves of sleep, and instead of launching rockets into space, they run their companies and themselves into the ground.
  • My path to where I am has included a piss-poor GPA in college, a resume of failures that look like a rap sheet, and some lucky breaks like having an editor at Penguin discover one of my articles. Trying to reverse engineer my path to whatever success I’ve had would be the height of stupidity.

Luck often plays more of a role in what successful people achieve than we like to acknowledge because that’s not an inspiring story. When David Letterman was reflecting on his success during his interview with Barack Obama, he said, “Mr. President, I’ve been nothing but lucky.”

It’s human nature to compare ourselves to people who have more money, status, have achieved more, and use them as our benchmark for what it means to live a good life. Without some doubt and skepticism about such benchmarks, we just end up with a greater inferiority complex.

The good news is that we can increase the probability of success when we define it for ourselves, focus on our unique gifts, and forge our path instead of replicating someone else’s.

15. Build a Portfolio of Meaning for a Good Life

As a society, there’s almost nothing we connect to our happiness and well being than our achievements, both personal and professional. And as Oliver Burkeman points out, “For a civilization so fixated on achieving happiness, we seem remarkably incompetent at the task.

But, happiness like sadness is an emotion that comes and goes. We can lose fortunes, lovers, career opportunities and so much more. What you create internally is the only thing that can never be taken away from you.

Whether it’s selling your startup for a fortune, meeting the love of your life, or reaching the heights of your creative career, at some point what was once a distant mountain becomes your new normal. Nothing you accomplish will lead to everlasting happiness.

As the new normal sets in, your reference groups change, and the goal post for success and happiness moves. There’s always going to be the author who has sold more books, the founder who has more money, and the girl or guy who has a hotter significant other.

As long as you keep telling yourself, “I’ll be happy when”, you’ll be miserable in the moment and anxious about the future. As Nataly Kogan said to me during her interview on Unmistakable Creative, happiness is an input into a good life.

Think of your life as a stock portfolio. When you give anyone thing too much meaning or significance, it can make you miserable. As Jenny Taitz pointed in our interview about how to be single and happy:

Your person can’t be your everything. That’s not gonna realistically fulfill you. Given the prevalence of relationships ending, it seems like a really poor investment let’s just say metaphorically to, take all your diverse portfolio and put it into one risky stock.

That’s not just true for relationships. It’s true for every goal you have.

What does it Mean to Live a Good Life?

You’re not going to find the answer to that question by meditating at an ashram for 10 years, hiring a life coach, listening to a podcast, or reading a book. The answer to this question is an inner journey with external sources as tools for higher self-awareness. And I’m guessing you don’t suddenly have all the answers for how to live a good life after reading this.

As I said at the beginning of this article, don’t ever read it again if you want to make the most out of it. As any good skeptic does, you should question everything I’ve written and answer the questions that arise for yourself. What it means to live a good life is different for all of us.

The only place you’ll get to with someone else’s map is a destination that’s already been reached. What’s interesting about that? Fulfill your destiny. Don’t recreate someone else’s.


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