In 2015, Kevin Durant left his team of nine years to join the best basketball team in the world. In the NBA, great players like Durant are judged based on whether or not they win championships. This undoubtedly influenced his decision to join the team with the best chance to achieve that goal.

Except when he ended up winning a title, he didn’t find what he expected. His friend Steve Nash reflected on Durant’s confusing emotions that summer:

“He didn’t have a great summer,” Nash told me last year. “He was searching for what it all meant. He thought a championship would change everything and found out it doesn’t. He was not fulfilled.”

Kevin Durant not happy after winning a championship quote

The realization that achieving a goal will often not fundamentally improve your overall well-being can be a challenging moment for people.

It is also a moment where people can choose to orient in a new direction or double down on the same path. This seems like an easy decision to make, but over and over again, people continue back down the same path.

Goals work extremely well early in our lives, but then we get lost

graduation hats

Early in our lives and careers goals are more achievable. It’s easy to get promoted from analyst to senior analyst, get a certain grade in a class, land your first job and get into grad school.

Around 25 or 26 years old many people start searching for goals outside of work. This is when people commit to running their first marathon, learning a new skill or even committing to a career change.

A few days after reaching these kind of goals, the glow of accomplishment fades away and we are left with the burden to decide on the next goal.

After achieving a series of goals or after achieving a more challenging goal such as landing your dream job, making a ceremonial amount (e.g. $50,000, $100,000) for the first time, getting awarded a certain title or getting accepted into your dream school, we may not want to pick any more goals.

We may just find ourselves feeling a bit hopeless and sad.

We all need something to orient our lives towards. At a certain point in your life, the simple goals stop working and you either have to keep raising the stakes or change your orientation.

Reaching a WTF?! Moment

second chapter of success or similar to the second mountain idea from david brooks

In my experience talking to hundreds of people who have navigated life transitions, many people seem to reach a “wtf” moment where they start to question their current conception of success and what makes them happy.

This can be a devastating moment as they lose connection with a narrative of their life that has made sense and suddenly find themselves a bit lost. Depression is not uncommon and is something I faced in my own journey.

The “wtf” moment can creep up on you slowly or it can be the result of a clear crisis -a health crisis or getting fired from a job.

It is inevitable that many WeWork employees hit this point when their company status went from an exciting $47 billion IPO to potentially worthless company within a few short weeks.

Andrew Taggart identified two ways this moment of waking up can happen:

  • The way of loss: Something or someone of the utmost importance has been taken from me.
  • The way of wonderment: I marvel when in the presence of the incomprehensible.

Andrew Luck was by all means successful when he decided to retire as Quarterback of the Indianapolis Colts before the season started in 2019.

Yet if you read closely, he likely experienced the “way of the loss” four years prior to that decision.

In 2015, he was injured and for the first time in his life and had to “sit on the sidelines” literally and figuratively. It was the first time he didn’t dedicate every waking moment to football:

“I’ll say it right now—I think it was a blessing in disguise,” Luck said. “Absolutely. It forced me to reevaluate many, many things in my life. And the result has been … yeah, really positive. And I shudder to think of not having that. I don’t think I’m married if that had not happened. I think I eff that up. I truly do. I truly do.”

He had found that the default metrics of success of the football world weren’t enough for him:

I’d put way too much of my self-worth directly into how I was performing on the football field,” Luck said. “And then I wasn’t on the football field and I felt quite empty. It was very unhealthy, first for me, second for the relationship with my now-wife, and my other relationships.

While the circumstances of Luck’s decision, namely the fact that he’s walking away from one of the most desirable and high-paying jobs in the world, make his decision seem crazy – the same type of decision is being made around the world every day.

Those people are deciding to rearrange their lives – often in bold ways – to reclaim what gives them meaning in their life.

A Brief Detour To Grapple With Happiness

Perhaps you have been reading this post and thinking to yourself, “this is very simple Paul, people really just want to be happy.”

Many people have told me this is the key to life but I think they are missing something profound from this statement.

I could divert the article right now and go down a deep rabbit hole exploring what makes people happy, whether or not we can properly define happiness and what role money has to do with happiness, but I’ll spare you.

There’s a free 20-hour course on the topic that will feed your curiosity better than I can.

What I’m concerned with is the history of the word “happiness” itself.

The word happiness is the ancestor of a Greek word, Eudaimonia, which scholars have suggested would translate to “human flourishing” in today’s terms.

The Greeks thought it was the prime aim of life.

Today we also conceive of happiness as a prime aim of life, but we are left without instructions of how to achieve it.

DIY happiness and everyone is right.

For the Greeks, Eudaimonia was paired with an operating system based on the pursuit of wisdom or virtue. To be happy was to be wise. Yet even in Greek times, people didn’t grok what Socrates and others were trying to convey.

Here is Socrates chastising his fellow Athenians for this confusion:

are you not ashamed of your eagerness to possess as much wealth, reputation, and honors as possible, while you do not care for nor give thought to wisdom or truth or the best possible state of your soul

Hustle all you like, but don’t mistake the money, power and status for what really matters.

Un-pairing achievement and our conception of happiness can be one of the hardest things to do, but perhaps one of the most transformative.

A new conception of happiness could be linking it to the pursuit of “well-being.” Researchers have found that the following factors consistently contribute to day to day well-being:

health, care giving, loneliness, and smoking are relatively stronger predictors of daily emotion

We don’t need to research to tell us this. Just ask your mother or even better, your grandmother.

Help others, find friends and stay healthy. To be wise and ultimately, to be healthy is to pursue well-being.

What About Work?

Fair question.

If achievement won’t make us happy how should we conceive of work?

Early in people’s lives, we grasp after goals that make sense and help us gain confidence in an increasingly complex world.

During that time a lot of the things that drive happiness – relationships, health, being part of communities – happen naturally and people take for granted. Especially for people working in cities.

As we age, our friends move away to build families and we become increasingly isolated. Some people pour themselves into work even more, but find themselves increasingly disconnected from a sense of peace and contentedness.

It is at this pivotal time in our lives when we need to make a choice. Not a choice to make a bold change (thought that may come), but a choice to cultivate a new perspective.

It is a shift from expected outcomes to embracing faith.

Have A Little Faith

alan watts "belief clings, but faith lets go" quote

Faith is about trusting that if you pursue other goals, you will not go broke or be abandoned by your friends or family.

Some people refer to this state as having an abundance mindset and the great thing is that its available to anyone.

Instead of trying to cultivate an abundance mindset, many people mistakenly try to make as much money as possible. I’ve talked to people that tell me “Paul once I have $1 million, everything will be good!”

I return a year later and suddenly they need $1.5 million.

I’m not telling you to stop earning money and to move to a cabin in the woods, starting each morning focusing on manifesting money from the twigs around you.

I’m suggesting that there might be a deeper game worth playing that centers around developing an abundance mindset. At its core, an abundance mindset is about having faith.

Alan Watts said “belief clings, but faith lets go.”

It is our belief in our purpose as a worker that keeps us attached to the outcomes of work. If we have faith that things will be okay we can approach our work and life with a little more lightness, joy and dare I suggest, play.

If you decide to move to a cabin in the woods and start painting pictures of dandelions, that’s up to you.

People look at me a few years into my journey and assume that my new identity as a “freelancer” or “solopreneur” is what brought more joy to my life.

When I reflect, I know that it is about a different mindset.

I’ve embraced faith. Faith that even if I go broke, people won’t leave me to starve. Faith that at the end of the day things will be okay. Faith that exploring this new way of being might bear some fruit.

This doesn’t mean abandoning responsibility.

By having faith, I steal moments from the future in which people help me with open arms, unlocking a genuine feeling of gratitude and love. I literally feel loved.

This orients me towards looking for ways in the here and now to share with and help others. It pushes me to trust the journey. It also helps me connect with and befriend those who are orienting towards the world in a similar way, leading to perhaps the best “proof” that this works.

One of the secrets of the second chapter is that its all about the people.

Faith is about knowing deep down that there are not enough answers in the world that will please your rational brain. It is about owning the inherent uncertainty of life and being grateful for what you have.

Faith is about navigating life without a compass and knowing that following a different path, no matter how scary, is okay.



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