January 1

20 Valuable Life Lessons I’ve Learned in 2020

Every year, I take time to reflect on what I have learned from the people I have interviewed, the books I have read, and the experiences I have had.

Podcasts guests give me an ongoing education that kicks the crap out of the one I got in school.

Books help me learn what we should have learned at school but never did.

Life experiences are a way of field testing the lessons from books and podcasts.

This year has been unlike any other that most of us have seen and hopefully will ever see again in our lives. But the most difficult chapters of our lives often contain the most valuable lessons.

1. Ask $30,000 questions instead of $3.00 questions

How much time have you spent comparing prices on Amazon, choosing between coffee drinks at Starbucks, or deciding between generic vs name brands at the grocery store? But more importantly, is the difference noticeable or negligible? In almost every case, it’s negligible.

In my interview with Ramit Sethi, he said the following:

Most of us have been raised to ask $3 questions. I was raised to think about those questions myself, but we really should be asking $30,000 questions. The big ones:

  • Do I have a good job and am I paid well?
  • Am I automatically saving and investing?
  • If I’m married or if I’m in a relationship, is it with the right person?

But most of us are asking three-dollar questions like should I buy a latte. In reality, if we get these five to ten big wins in life, we will never have to worry about lattes or any other $3 question.

Not only have we been brought up to ask such questions, but we also waste a hell of a lot of time doing it. If you earn $50.00 an hour but spend an hour on Amazon comparing prices to save $3.00, you’ve lost more than you’ve saved.

If you want to live a rich life, ignore negligible differences, and ask $30,000 questions. You also save a lot of time when you avoid thinking about decisions that ultimately will not have much of an impact on your life.

2. Stigmas are false perceptions

There’s probably no profession that our culture stigmatizes more than sex-work. If you’re a parent, it’s probably the last thing you want for your daughter. However, stigmas create false perceptions and false judgments.

One of my goals, when I interviewed porn star Sarah Vandella, was to destigmatize and demystify the adult film industry.

3. Ignore your press

The Internet gives everyone a microphone and the opportunity to be a critic. If you are in the public eye at all, you will have people giving your books 1-star reviews or calling you a loser on national television. And if there is one thing my 15 minutes of fame on Indian Matchmaking taught me, it was to ignore the press and attention.

It does not matter if this attention is negative or positive. People who know nothing about you will make assumptions about who you are and how you are. Media shapes perception, but this perception is not always accurate.

Some people see me in public as a person who creates inspirational content. Behind closed doors, I’m in a PR crisis every day.

It is ALWAYS better to be a creator than a critic. The paradox of dealing with critics is that reaction makes you weak and restraint gives you power. There’s no point wasting your precious life trying to win the cultural arms race for impressive biodata.

4. There is no formula for love

In February, I went on a date with a girl. We spent 6 hours asking each other the 36 questions that could make you fall in love with anyone. It was a wonderful date. But in the end, we didn’t fall in love and things didn’t work out.

I also made a podcast episode in which my roommate and the girl he was seeing asked each other the questions. Listening to the episode, you might think that they were star-crossed lovers destined to be together. They broke up a few months after we published the episode.

I remember a time when I thought that love was what you see in movie scenes and hear in music lyrics, but that is only in fiction and fantasy. Love in the real world is more complex.

  • People who thought they would be married forever get divorced
  • Someone who makes your heart sing today breaks it tomorrow

Until one of these things actually happens, you’re what Rachel Resnick calls a “love junkie.” You believe that weird feeling in your stomach, shit-eating grin on your face, and the bright lens through which you see the world at every moment is love.

You confuse infatuation with love.

Love is a puzzle that cannot be solved with any formula.

5. Shit hits the fan no matter how well you plan

Think back to the beginning of 2020. You probably set yourself goals, designed vision boards, and were determined to make this the best year of your life. It was impossible to predict how the rest of the year would unfold.

I doubt that any company agenda at its annual planning meetings included “contingency planning for a global pandemic.” But most of our plans went to hell when we realized that we were in a global pandemic.

6. Fear is a reaction and creativity is a response

In an interview about how to achieve an impossible goal in 90 days, I asked Michael O’Neill how anyone could think about such a goal with the world on fire.

He said, “Fear is a reaction. Creativity is a response.” No matter how you cut it, crisis sucks. It destroys the structures of our lives as we know them. But as my friend Joseph Logan said in his TEDx talk below, crisis creates change and change creates opportunity.

We can react with fear. Or we can respond with creativity. The latter will always lead to a much better future.

7. Sometimes the messenger counts more than the message

Have you ever noticed how one person can tell you something and you think it’s bullshit, but if a different person tells you the exact same thing you think it’s brilliant? When it comes to advice, bullshit and brilliance are birds of a feather depending on who the messenger is.

This is something my mother and I experience with my dad. Sometime last Christmas he decided to purchase a rather large family portrait and hang it above the fireplace. My mother hated it, asked him to take it down and he refused.

I agreed with my mother, but the majority doesn’t rule in my family. My sister does. A few weeks later, she came home for the holidays. When she saw the picture she said, “Wow, that’s huge. Dad, we’re not the Trumps. You should move it.”

The next morning it was gone. Now, my mother and I have learned that if we really want my dad to do something, we just ask my sister to tell him.

If you’re a parent and ask a teenage boy to do his homework, he might throw a fit, turn in a late assignment, and argue with you. But get him an attractive female tutor and he’ll start to behave like a straight-A student.

If a kid gets some advice from his parents, it falls on deaf ears. But if a friend gives him that same advice, he’ll listen.

If you piss off a girl you’re dating, send her best friend on your behalf and your chances of make-up sex go up a lot.

When you’re having trouble persuading someone to do something, don’t shoot the messenger (yourself). Try sending a different one.

One other note on this: don’t overlook the value of a message because you hate the messenger. I’m pretty liberal and you’ll never find me watching Fox News. But Roger Aile’s book is among those on my shelf.

Why? He built a massive audience for his content. There’s probably something important I can learn from that. Just because you disagree with someone’s message, it doesn’t mean you can’t find value in what they say. Seeking out viewpoints you disagree with is an antidote to cognitive biases.

8. Hitting a low point gives you power that is hard to access at any other time in your life

Do you feel comfortable with how your life is going at the moment? At some point in our lives, we all establish ourselves in a rhythm, a routine, and a way of life that we never question.

We get comfortable and content. But there’s one exception: rock bottom.

Think back to all the moments in your life when you hit rock bottom.

  • A relationship ends
  • You lose your job
  • Someone near you dies
  • As an athlete, you have an injury that ends your career

These moments are so confusing that you feel you will never recover.

But these are often the moments that lead to radical change, progress, and personal growth. Paradoxically, there is nowhere to go then but up.

These moments make you more bulletproof than ever. When you have nothing to lose and everything to gain, you tap into a power that is difficult to access at any other time in your life.

These moments teach you to turn adversity into an advantage and to move from the lowest point to the highest point in your life.

9. Clinging to an outcome beyond our control undermines our work

When it comes to creative work, nothing holds you back more than the attachment to results that are out of your control, and almost every result is out of your control. You have no idea how a critic will react or whether your work will resonate with the audience. Your job as an artist is to focus on the process, not the prize.

This not only undermines our work, but it also undermines every aspect of our lives. The more expectations that are placed on a situation or another person, the more likely we are to be disappointed. If you don’t expect anything, everything comes to you.

10. No matter how good you have it, you will always want more

In a twisted way, the same brain chemical that enables us to achieve extraordinary things makes us wired for dissatisfaction. When we are unaware of this, we spend our lives chasing false horizons and wondering why we are so miserable.

It rewards you when you obey it and makes you suffer when you don’t. It is the source of creativity, and further along the spectrum, of madness; it is the key to addiction and the path to recovery; it is the bit of biology that makes an ambitious executive sacrifice everything in pursuit of success, that makes successful actors and entrepreneurs and artists work long after they have all the money and fame they ever dreamed of; and that makes a satisfied husband or wife risk everything for the thrill of someone else.

This is the curse of dopamine, also known as the molecule of more. The only antidote to the disease of more is a personal definition of enough.

11. Do not underestimate the power of audacity

Molly Fletcher is a sports agent who has been called Jerry Maguire. When she started her career, she slept on a friend’s couch in Atlanta because she couldn’t afford the rent.

When she learned that the tennis pro had quit his job in an apartment complex, she asked the manager for the job, but with one bold caveat. She asked the manager to let her live there without paying rent.

Thanks to her audacity, she lived rent-free for many years.

12. Sometimes you can turn your greatest weakness into your greatest strength

In the fourth grade, I was failing reading. So my teacher called my parents to a parent-teacher conference. She told them that I might have a learning disability. But my parents thought she was just a shitty teacher. Ironically, I became an author.

Joze Piranian has a bad stutter. And today he is a sought-after speaker and comedian. He made a career. Perception can turn a weakness into a strength and vice versa.

13. Inherited family trauma shapes who we are more than we realize

In February of this year, I got really sick. I coughed so much that I had to cancel all my interviews. At the age of 42, I realized that getting sick is the way nature tells you to slow the fuck down.

One of the most revealing books I read this year was It Didn’t Start with You: How Inherited Family Trauma Shapes Who We Are and How to End the Cycle. In the two weeks, I was ill, I spent my time doing all the exercises in the book.

These exercises are invaluable, but they also feel like an emotional root canal. Somewhere along the way, I developed a fear that I would die alone. As I am 42 years old and single, I found it hard not to believe that.

The exercises in the book made me realize how many of the men in my family had bad marriages, got divorced, and lost their spouses early in life. I cried a lot that week, but the greatest gift that came from researching the trauma was the realization that my fear was based on their history, not mine.

14. Sometimes it makes you happier to give up your greatest passion

In early 2019, I was planning my escape from San Diego. I hadn’t made many friends and the ones I had were in relationships that took up all their time. But leaving San Diego meant I had to give up surfing, something that had defined my life for more than a decade.

I loved surfing, but I hated my life in San Diego. Every time I traveled for a talk or visited friends in Colorado, I was much happier. I thought I was depressed when I lived there, but I was actually lonely.

When I moved to Boulder with my roommate Matt, everything changed for the better. “There is a basic biological need for connection that must be met to achieve basic health and well-being,” Lydia Denworth writes in her book, Friendship.

Don’t get me wrong. I miss surfing and will always love the water. Luckily, I’m in the mountains. Surfing will always be my first love, but snowboarding is a pretty fantastic mistress. Sometimes, it can make you surprisingly happy to give up what you are most passionate about.

15. Consider the tradeoffs

You may not be the next Steve Jobs, Oprah, or Beyonce. But people in the public eye often become our benchmarks for success. If you want to pursue such wild ambitions, it is important to understand that you have to compromise.

16. Be careful not to worship false gods

Celebrities, billionaires, and cultural icons are our role models for success, so we put them on pedestals without understanding what is really behind their achievements. If you are not willing to have the same level of obsession and commitment to your work, you end up worshiping false gods.

17. It is great to suck at something

The fear that we will not be good keeps us from doing so much in our lives. We forget that everyone sucks when they start.

When most children learn to play musical instruments, it sounds as if they are sacrificing animals in their bedroom. But as parents, you don’t tell the child, “You’re not very good, maybe that’s not for you.” As adults, we do that to ourselves before we even start.

Follow the evolution of some of today’s most famous creators and you’ll see how much they sucked when they started.

  • Seth Godin, the cultural visionary who has written seventeen best-sellers, once wrote a book entitled Email Addresses of Famous People.
  • In Gary Vaynerchuk’s videos of today, he is optimistic, animated, and full of energy. Rumor has it that some of his first videos are dry and boring as hell. He got better with every video.

Do not underestimate how great it is to suck on something. It is the first step to becoming good at something.

18. Stillness is the key to a more rewarding life

The world moves so fast that most of us can’t remember what we ate for lunch yesterday. In the chaos of our daily lives, we underestimate the value of stillness. But stillness allows us to find clarity, to think about the essentials, and to act accordingly.

19. Sometimes fear is useful, sometimes not

No one is completely fearless. If they were, they would cross the road in rush hour traffic without expecting to be hit. They would paddle out into 50 feet of surf without expecting to be drawn. Fear is important for our survival.

There are times when fear protects you and others when it holds you back. Understanding the difference is the key to dealing with your fears.

20. Beware of the over-examined life

We inflict a lot of pain ourselves in the name of spiritual growth and self-improvement. We read books, attend seminars, meditate, etc., in an effort to solve problems and fix what we think is wrong.

Philosophers say the unexamined life is not worth living. But, if we are not careful, we start to live an over-examined life. Instead of examining our lives, we perform autopsies on them. Autopsies are for dead people.

It’s easy to spot problems you don’t actually have. You could easily end up with a bookshelf like mine, with enough self-help books to start a side job as a therapist.

By so desperately trying to raise your level of consciousness, attain enlightenment, or whatever it is you see as the culmination of spiritual growth, you are doing the opposite. Paradoxically, everything changes for the better when you stop trying so hard to change it.

It is true that the unexamined life is not worth living, but the over-examined life is like doing an autopsy on yourself when you’re alive.


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