top of page

The Pursuit of Happiness

“When I have a car, I’ll finally be happy!”

“When I go to college, I’ll finally be happy!”

“When I get a girlfriend, I’ll finally be happy!”

“When I buy a house, I’ll finally be happy!”

“When I am a principal, I’ll finally be happy!”

“When I earn my PhD, I’ll finally be happy!”

“When I get married, I’ll finally be happy!”

“When I write a book, I’ll finally be happy!”

These have been my thoughts throughout life. I assume when a certain goal is accomplished or milestone is reached, life will be complete.

Each goal listed above has been achieved. And while clearing each hurdle produced brief bursts of enjoyment … those moments were short lived.

I’m not alone in my thinking. We assume when we get a promotion, date the right person, make more money - life will be good. Yet in most cases, we return to our natural level of well-being shortly after reaching our destination.

This begs the question: Why does true happiness feel so fleeting?

First Car: Nothing better than rolling around in the 1990 Ford Tempo blasting some Nelly!


One my favorite books about the psychology of happiness is Happier by Tal Ben-Shahar. In his book, Ben-Shahar outlines four distinct happiness archetypes, which are default attitudes towards happiness that all humans possess. Those archetypes are Hedonism, Rat Race, Nihilism, and Happiness.

While Ben-Shahar’s research is outstanding, his terminology is a bit academic. To assist with comprehension, I've translated his archetypes into four happiness “mindsets:”

Self-Indulgence Mindset: Do you focus on immediate pleasure while completely ignoring the future consequences of your actions? True accomplishment takes time, yet humans are conditioned to forego future benefits in exchange for quick hits of satisfaction in the form of objects, food, activities, and entertainment. Like Veruca Salt in the classic "I want it now!" scene from Willy Wonka & the Chocolate Factory, today's instant gratification culture reinforces the hedonist mindset.

Rat Race Mindset: Do you choose to suffer during the present for the purpose of anticipated gains in the future? Many people believe true happiness is found later in life, only after decades of hard work and sacrifice. Rather than be thankful for what we already have, society tells that personal contentment comes after we have more money, power, and possessions than our peers.

Woe Is Me Mindset: Do you struggle enjoying the present moment while also lacking a sense of future purpose? If self-indulgence describes living in the present, and rat-race describes living for the future, woe is me describes living in the past. Rather than believe they control their destiny, many people stubbornly blame past circumstances for their lack of personal and professional advancement.

Fulfillment Mindset: Do you participate in activities that bring you present enjoyment while also leading to a fulfilling future? To feel optimal levels of happiness, people should identify and engage in actions that provide both present enjoyment and future gains. According to Ben-Shahar, people who embed these activities into their daily and weekly routines live the happiest lives.

To be clear, constant happiness through the "fulfillment mindset" is impossible as not every activity can provide present enjoyment and future benefit. Sometimes we must focus on the present - such as taking a day off from work to rejuvenate our mind. Alternately, sometimes we must focus on the future - such as skipping a night out with friends to complete a graduate class assignment.

Also, understand these are mindsets - not actual people. To varying degrees, we all possess characteristics of all four mindsets. For example, many educational leaders (myself included) get stuck in the rat race mindset: "When I reach the next level of leadership - I'll finally be happy!" they say. However, three months into their "dream job," they discover their general happiness is no different than before.


“I already know what makes me happy,” some readers may be thinking. “I don't need to change anything!"

Unfortunately, humans are bad at predicting future happiness. In Stumbling on Happiness, Dan Gilbert suggests that we are bad at predicting our future emotional states because we rarely reflect on the emotions that accompany recent experiences. Whereas we assume a particular activity will produce happiness, these predictions are often inaccurate.

For example, people regularly associate passive relaxation with happiness. "I can't wait to lay around and do nothing on Saturday!" is a statement we have all made. However - after a day of laying on the couch, watching television, eating junk food, and scrolling through our phones – we often feel fatigued and anxious as opposed to refreshed and peaceful.

Another common mistake is overestimating the enjoyment of a special event. "New Year’s Eve is going to be epic!" people predict as they plan an evening of fine dining and limitless cocktails. While some experiences meet expectations, in many cases NYE ends up being a huge let down. Combine spending too much money with a terrible hangover ... are we are likely to feel worse on January 1st than most days of the year!

Alternately, say you are part of a community organization. In these clubs, you are often asked to volunteer time to assist with local projects. When the sign-up form reaches your table, you smile at the sheet while secretly thinking, "How am I going to get out of this without looking like a jerk?" Little do we realize that volunteering is one activity that produces the highest levels of happiness.

So how do we identify the specific actions that will bring us happiness? Here are four ideas to consider:

Reflect: Given that feelings of happiness depend on the individual, careful attention must be given to the feelings produced by everyday actions. Use a notebook or electronic document to record your daily tasks and evaluate them according to how happy each makes you feel. Devoting a few minutes to this practice when your memory is fresh will provide valuable insight into your preferences for genuine enjoyment.

Daily Gratitudes: One surefire method for improving happiness is keeping a daily gratitude journal. Each night before bed, write down at least three things for which you are grateful. Examples could be as small as the morning sunrise or as big as a relationship with a spouse. While writing your ideas, consider the feeling each detail brings. What emotions are associated with these items? Focusing on positives before bed not only leads to better rest, it increases the likelihood that life’s bright spots are remembered.

House Money: The term “playing with house money” is a psychological phenomenon where gambling one's winnings (typically at casinos) feels less risky than gambling the money that was brought from the outside. In education, a similar phenomenon happens when teachers realize they don’t have to work because a snow day has been called. During these unexpected days off, small pleasures – such as sipping on coffee or reading a book - are magnified and trivial anxieties vanish. Training your brain to approach each day as a “snow day” can create optimal levels of happiness.

Fulfillment Mindset: In Atomic Habits, James Clear suggests that we “engage in actions that contribute toward our desired identity.” When I read this line back in 2018, I couldn’t help but think about all the time I was wasting: “Does scrolling through social media and watching sports really make me happy?” I wondered. When I replaced those trivial activities with more meaningful work – such as reading and writing – my happiness skyrocketed while my anxiety decreased (more on this in the next chapter). I have found that investing in myself is one of the best ways to embrace Ben-Shahar’s fulfillment mindset.

My ex-wife didn't leave much when she moved out ... but she did leave this sign. Was she trying to tell me something?


When I get a promotion, I will have peace.

When I make enough money, I will relax.

When I have more power, I will be content.

We have all made these comments.

However, I challenge you to do this: Imagine going back five years ago and being told you would have all of the “things” that you have today: the job, the possessions, the money, the relationships. Odds are, you would be insanely jealous of your future self.

Although prolonged bliss often feels allusive, understanding the psychology of happiness and identifying our personal conditions for joy helps us get one step closer to living a fulfilling life.


If you liked this article, you'll love my book Learning Curve!

Learning Curve is 360 pages and PACKED with useful ideas on leadership, education, and personal growth.



bottom of page