Why You’re Pursuing Happiness All Wrong

I was sitting around the table with a bunch of people who had “made it”. They were experts in their respective fields, six-figure earners, and successful entrepreneurs who’d worked with famous celebrities and politicians.

By all accounts, they were the kind of people that so many of us can’t help but envy.

As the night went on, however, a different story unfolded. Thanks to some interesting question cards, we all started to reveal a similar journey we were going through.

We all spent years pursuing what we believed would make us happy — money, status, influence, women. All of us achieved those goals and then realized, “Now what?”

We weren’t suddenly happier. In fact, some of us were left unfulfilled and disappointed. We’d invested energy, time, and emotion chasing our dreams — often at the expense of personal values and relationships.

We didn’t take for granted what we had, but we also were forced to see that those accomplishments didn’t provide lasting fulfillment.

And because of this, we were all starting to discover what made us really happy in life. Things like…

  • Moving across the country to an area with open-minded people that resonated with who they were.
  • Reconnecting with and building a relationship with a brother.
  • Traveling the world alone and having to be vulnerable, outspoken, and able to connect with strangers.
  • Choosing to use a marketing career to help individuals and not just make corporations more money because it’s more personally rewarding.

We were all chasing false ideals in the pursuit of happiness. And there’s a good chance you are, too. It’s not your fault because as Harvard Psychologist Daniel Gilbert has shown — we’re terrible at predicting what makes us fulfilled.

All we can rely on is our own trial and error combined with guidance from other people who’ve found their happiness. After years of searching for the answers myself and helping others do the same — hopefully I can help you find what won’t make you happy and what will.

The Money Myth

Since childhood, you’re told by just about everyone to study hard so you can get a lucrative career. And it makes perfect sense — money influences every aspect of our lives.

Anyone who’s struggled with poverty can tell you how miserable it feels trying to figure out how you’re going to pay your rent for the month.

Because of this, money becomes most people’s #1 measure of happiness.

When we’re feeling unfulfilled, we believe that more cash will fix all our problems. But I can tell you with certainty that it won’t.

I work daily with six and seven-figure clients who hate waking up in the morning.

People in wealthier neighborhoods tend to have the highest rates of suicide.

Some of the poorest countries in the world have the highest rates of happiness.

My friend coaches millionaire entrepreneurs who battle depression and constant self-criticism.

Don’t get me wrong, money sure makes things a hell of a lot easier. But for the vast majority, once you get to the point where you have some comfort and aren’t worried about your next meal, you’re satisfied. That range is around $60,000-$100,000 per year depending on where you live.

If you disagree, why not test it out? Money is not the scarce resource we are led to believe. There are more opportunities to immediately make money than ever.

You could…

Become an Uber or Lyft Driver. Teach English or music lessons. Self-publish a book or guide. Rent out a room or your entire place on Airbnb. Create a Udemy course. Host local paid Meetups on a subject you have expertise in. Deliver packages for Amazon.

All these can easily provide $500-$1000 per month or more if you’re willing to invest the effort. But you’ll likely find yourself in the same position and wondering…

What am I missing?

The “If I Just Get This One More Thing…” Misconception

Many of you have likely made good money and realized it didn’t change your world. Others never cared for money in the first place.

So your next logical step is to think…if money isn’t the answer, then there must be something else. And we listen to the world around us for guidance.

Unfortunately, we’re being marketed to constantly. Drink more, fuck more, buy more, and look better. Surely one of those things is what I need!

We then believe there’s just one missing piece in our lives that will solve everything. Something tangible. Something we can obtain.

So you try to find happiness through…

  • Lots of sexual conquests.
  • A big house, a huge fenced in-yard, and all the gadgets you could dream of.
  • Designer clothes and high-end makeup.
  • Illicit drugs and prescription anti-depressants.
  • Attracting that one girl you’ve been putting on a pedestal.

All of these give rushes of satisfaction and pleasure. They feel great. They can provide a sense of accomplishment. And they all seems to work at making you happy — at least for a while.

But eventually, those positive feelings go and you’re left empty-handed again, maybe even moreso than before. You start to see that those ideas weren’t a long term solution.

I used to think sleeping with women was what I needed. I studied “pickup” for years, got laid a lot, and then had a major breakdown after realizing no one knew or loved the real me. It didn’t make me feel more like a man, it made me feel hollow. Neil Strauss wrote about the same struggles in his new book, The Truth.

Cameron Russell gave a great TED talk about how some of the most beautiful women who are top models in the world have the lowest self-esteem and are disgusted with themselves.

I know people who’ve been on Xanax, Zoloft, Prozac, Lexapro and every other antidepressant. And guess what, those alone don’t cure their depression.

Some men come to me miserable and obsessed with getting this “one perfect girl“. And sometimes they do end up dating that girl. Unfortunately, they are never suddenly transformed into a confident, self-loving person. In fact, their neediness hurts the relationship and they end up alone, even more miserable than before.

Now I have nothing against consumerism or indulgence. I’ve got a high-end smartphone. I bought a new Subaru. I’m getting an Oculus Rift or Vive (I haven’t decided which yet).

But, I’m fully aware that these are a source of temporary enjoyment and pleasure, not lasting happiness.

Because anytime you’re seeking a fast, permanent fix from the external in this world, you will never find true fulfillment. You’re thinking about this the wrong way.

What Actually Makes Us Happy

True happiness doesn’t come quickly. It’s not something you can just throw money at or consume. It is a daily practice to cultivate and appreciate meaningful personal experiences. Experiences which challenge us, make us grow, teach us lessons, or show us how we’re improving the lives of others.

By definition, meaningful personal experiences are subjective. They can be small, everyday choices or life-changing decisions. They are somewhat unique to you and they are insanely hard to predict. The only way to know for sure is to stop speculating about all the things you need to obtain to make you happy and instead, seek fulfillment through living in the moment.

Yes, you can get a guideline of what will make you happy by figuring what makes other people happy. Of course, you’ll still need to test it out for yourself.

I will tell you that for most people, those fulfilling experiences almost always revolve around feeling more connected to your core self and to others. I mean human connection is why we’re all on this planet anyway, right?

Here are some of the moments where I and people I work with have been happiest:

  • Reading more to broaden your critical thinking skills and develop your emotional intelligence.
  • Providing value and giving back to the people closest to you, to strangers, and to the community.
  • Putting yourself in situations that force you to work through your anxieties and inner demons.
  • Having the hard talk with your family about how they raised you so that you can build a healthier relationship going forward.
  • Hosting a dinner that brings all sorts of friends together.
  • Exploring the world and connecting with nature and new cultures.
  • Going to a cooking, dancing, or painting class with your partner.
  • Taking a trip with a friend, family member, or aging parent.
  • Joining an athletic group or sports meetup and discovering your passion for Ultimate Frisbee or Whirleyball.
  • Journaling for self-reflection, self-understanding, and self-acceptance.
  • Moving to a new location that aligns more with your values and has similar minded people.
  • Taking a psychedelic drug to expand your mind or have a life-altering experience. Not to just numb the pain.
  • Bringing a young family member to a museum for the first time and teaching them new ideas.
  • Developing a mobile application or self-publishing a book you’ve been putting off.
  • Going to events and trying new hobbies which challenge your comfort zone and build your social circle.

People’s deepest regrets on their deathbed are never about making more money or buying more things. It’s always about human connection and significant experiences.

But you will only find happiness by truly valuing these experiences. Work towards cultivating more meaningful moments each and every day and be grateful for them.