Discover the Paradox of Happiness: Understanding Why Joy Can Lead to Sadness – A Comprehensive Insight

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Happiness. Chase.
All you wanted. Chase.
You thought you had it. Chase.
All those things you want to wear, drive, eat, and drink. Chase.
Those things you want to be observed having, people seen with, ways perceived as. Chase.
Filling empty hearts with clicks and taps. Chase.
That workout routine you plan to start, that silver bullet diet you won’t cheat on, and that dream you set in the corner that always gets pushed to tomorrow. Chase, chase, chase.

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Seeing as we’ve never been more connected and informed than today, you would think we’d be a few thumb taps away from contentment at any given moment, right? Considering the vastness and variety of fibers that stitch together the internet it seems we would have the key to unlock what everyone so desperately wants….. HAPPINESS.

Instead, the truth is we follow caricatures to envy, use online shopping carts to fill the craters in our souls, and coach algorithms to feed us a buffet of outrage.

With the emergence of social media, many of us search for happiness by endlessly peering into the black mirror abyss. We sit hunch necked, absorbing a constant stream of dopamine soaked LED light waves. Relentlessly thumbing through the infinite scroll of influencer burn-in smiles, wax figure couples, self-proclaimed guru renaissance men, biohack charlatans, and multi-platform niche archeologists.

But why are we so focused on achieving happiness? Why “HAPPY”? What does it mean to be HAPPY?

Well, the dictionary tells us happiness is “Feeling or showing pleasure or contentment”. Let’s say that’s exactly what we’re searching for. And if we consider our species’ unrelenting pursuit, then it seems we are striving for a hypnotic, starry eyed stupor with a limitless IV drip of pleasure to keep our faces permanently stretched in a smiling position. If that’s the case, then we should each stand up one after another, working our way around the folding chair circle, state our names out loud, and confess our happiness addiction.

Pursuing happiness is like trying to grasp and keep a handful of oxygen. It’s an everlasting path to emptiness. Instead of searching outward for others’ approval, material possessions, lofty goals, or whatever else we think will make us happy, perhaps it’s time to turn the flashlight inward. Imagine if we were to illuminate from within, casting light on a new path and shifting our focus from needing to be happy to becoming PROUD.


“Happy” is a strange word. It seems to mean something different to each person who attempts to describe it. Think about it, how do we feel when someone randomly asks us… “Are you happy?”. If you’re not Patrick Bateman or Joe Davola then it probably feels awkward and difficult to answer. Even if you were to mutter an unsure “Umm….yeah” it would likely be an effort of social etiquette to keep the conversation pleasant.

If happiness is what we are all chasing, but proves to be an elusive criminal, stealing our time and attention, yet we continue to make zero progress, then where do we go from here?

First, we stop trying to catch lightning in a bottle and instead shift our focus to discovering and growing what’s already in the bottle. And we do that with PRIDE.

Like any endeavor we assume, we must identify a worthy direction in which to aim our focused attention. When we pivot our focal point from the need to become happy, to spotlighting what makes us proud, we enable ourselves to become increasingly specific and intentional.

So how do we set about highlighting our pride? We recalibrate the aperture of the microscope and inspect our days for PROUD MOMENTS. Seems simple, right? Well……actually…..with a little organization… is.

On a recent episode of the Modern Wisdom podcast, show host, Chris Williamson shared an insight the seems quite fitting for the idea discussed here:

“You want to permanently be on the lookout for as many reasons to feel good about yourself as possible. Because Lord fucking knows there’s enough reasons to feel like shit about yourself and everybody has that.” — Chris Williamson, Modern Wisdom Podcast, Episode #718

“Permanently” being the key word here. Discovering, spotlighting, and experiencing the moments in which you should be proud of yourself is a perpetual practice. It is a cognitive frame shift that requires continual focus until it becomes muscle memory of the mind. A new neural pathway.

For a moment, imagine you have a dreamcatcher in your brain. With this dreamcatcher, you have full control over the 70,000 plus thoughts that occur each day. You decide which thoughts flow through the web and which thoughts deserve your attention and are captured. Now suppose you’ve optimized this dreamcatcher to catch any moment during the day in which you should be proud of yourself.

For example, maybe you were proud you made it to the gym today. Maybe you read a chapter in that book that’s been sitting in the backseat of your car for the better part of a year. Maybe you chose not to pick up fast food, or spent more time with your children, or reacted calmly to something that normally upsets you, and so on. There are so many moments to find pride in yourself each day. All you need to do is start searching for them.

At first you will likely find pride in the bigger things, after all they are the easiest to identify in the beginning. However, as you start to build momentum with consistency you will begin to find pride at the atomic level.

Of course, the big things are significant moments to be proud of and offer solid ground in which to start building this mental muscle. Nevertheless, as you become increasingly consistent in the practice of highlighting proud moments throughout the day, things will start to become more granular. And this is where it gets interesting.

For instance, let’s say last Monday you woke up early, got out of bed, and went to the gym. You acknowledged the moment, allowed yourself to feel proud of getting a much needed workout done and planned to follow the same training schedule the following week.

The next week comes and things don’t quite feel the same. You did not want to get out of bed and it took every ounce of energy to convince yourself into lacing up your shoes and getting out the door.

Now, when you look back on this moment at the end of the day, will you be most proud of going to the gym (like the week prior) or finding the willpower to work through the moment that got you out the door in the first place? Likely the latter. Next thing you know, the day will come when you find that you’re proud that you no longer allow those types of thoughts to enter your cognitive sphere.

Your consistency will plant momentum. Momentum will sprout discipline. And discipline will grow pride. And you will illuminate each step along the way to becoming PROUD.


So now we understand that in order to slowly build our self-pride we must pay close attention and highlight each choice or moment. But how do we go about organizing and capturing these moments so that we are able to expose them to ourselves consistently?

Much like anything else we want to remember or document…..we write it down. The last thing we want is to find at the end of the day is that we’ve forgotten to take a moment to recognize the many moments in which we are deserving of pride. This means we need to create a new habit.

Understanding that creating new habits can be quite difficult, we must keep it as simple as possible to ensure we are taking action and not just simply in motion.

“We are so focused on figuring out the best approach that we never get around to taking action… Action… is the type of behavior that will deliver results.” — James Clear, Atomic Habits, p. 142–143

“When you’re in motion, you’re planning and strategizing and learning…Motion makes you feel like you’re getting things done. But really, you’re just preparing to get something done.” — James Clear, Atomic Habits, p. 142–143

We’ve all started to-do or task lists to help keep us productive and we’ve all seen them stack like a jenga tower. The tower of tasks becomes overwhelming and we start to remove pieces based on time and effort. Looking back at the end of the day realizing the tower had crumbled again. This leads to the opposite of pride. We become upset that we’ve seemingly made no progress and discouragement sets it.

Let’s avoid this by making things as simple as possible.

Whether you’re scratching pen to paper in your journal or tapping 1s and 0s into Apple Notes, decide what will take the least effort and promote maximum consistency. Once that’s established, we start with 3.

Each morning write the following sentence and follow-up with 3 answers:

Today I will be PROUD of myself when…

Then, each evening do the same for the following:

Today I am PROUD I…

If the journaling habit is already in your arsenal then this may prove to become more of a Habit Stacking practice. For those of us who’ve yet to etch the journaling habit into our neural pathways, this painless daily exercise may serve as a launching point.

To prevent this practice from turning into another to-do list, the morning and evening proud lists must remain separate. In fact, it may be wise to not even look back at the morning list ever again. Whether or not you had a chance to complete the list of 3 from the morning is irrelevant.

The point is to put yourself into a mind frame that will set you in the direction of making yourself proud each morning. You will continue to find more and more moments to be proud of when you sit down to write your evening list. The proud moments you start to write about in the evenings will begin to surprise you.

What I’ve found through this practice and am betting you will likely discover as well, is the list in the evening will start to grow from 3 to 5 to 10,11,12 and so on. This is great! We’re finding more and more things to be proud of.

Next thing you know, you’ll be asking “Why?”.

Sure, you’re proud of number 4 on the list. But WHY? And why did you notice that today? What makes you so proud of that specific thing? As you write these answers out the journaling will begin and you will find you’ve begun a daily habit of writing about how proud of yourself you really are.

There is so much for each of us to be proud of. Feverishly search for every opportunity to recognize it in yourself. Once this becomes a daily practice, you will be proud of yourself everyday and will no longer allow the search for happiness to lead you to disappointment and sadness. You will have found your PRIDE.

Be PROUD of sending the text you were anxiously ruminating on for days prior.
Be PROUD of going to the gym and choosing to cook at home rather than picking up fast food
Be PROUD that you were slower to anger, and when you weren’t able to slow down be PROUD you apologized quicker than usual.
Be PROUD that you didn’t hit the snooze button.
Be PROUD you tried your best.
Be PROUD you complained less today than yesterday.
Be PROUD you tiptoed outside your comfort zone.
Be PROUD that your children are kind
Be PROUD you played an instrument, or followed along to a Bob Ross video to learn to paint
Be PROUD that you’re trying to do one of the most difficult things anyone can do, to change
Be PROUD you did the work when nobody was watching
Be PROUD you proved them wrong
Be PROUD you asked for help
Be PROUD you had patience

Thank you for reading!

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