Why do you keep choosing things that don’t make you happy?

Why do we keep choosing things that don't make us happy

Read on to learn 27 fascinating psychological reasons why you might choose things that don’t make you happy – and grab 8 tips to finally stop.

Ah, the common conundrum: Why do you keep choosing things that don’t make you happy?

Why do you cling to the painful familiar like a security blanket made of sandpaper?

It’s not just you.

Each of us humans seem to have developed a twisted love affair with melancholy, like a moth to the flame of our own angst.

It seems we find a sweetness in the sorrow, a familiarity in the ache.

Well, coming up I’m going to explain why people might choose things that don’t make them happy. Plus I will offer strategies to break this negative pattern.

I’m sharing about this topic because I am leading behavioral change expert and bestselling author – as well as a columnist for both Oprah and Psychology.

I’m also the founder of the therapist recommended program The Tweak a Week Online Course – where I share small do-able habits that can improve your life in big ways.

I’ve spent the last few decades writing books and designing courses all about what motivates people’s behavior.

So I put together this article all about why you might choose unhappiness.

And so you can become motivated to stop sabotaging yourself!

27 Reasons Why You Keep Choosing Things That Don’t Make You Happy

It’s time to understand why you might be stuck in self sabotaging patterns – so you can more bravely start choosing things that make you feel happier.

if it does not make you happy why do you keep choosing it1. Masochistic Equilibrium

We’ve all been there. Standing in line for the world’s most disappointing rollercoaster – you know, the one called “Choices That Make Us Miserable.

You’d think we would’ve learned our lesson after the first ride.

But nope, we’re season pass holders.

The thing is, humans are creatures of habit. The familiarity of a bad situation can often feel safer than the uncertainty of a good one.

It’s like choosing to keep wearing a pair of shoes that give you blisters because at least you know where the blisters will be. 

2. The Comfortable Discomfort Theory

Have you ever noticed that your comfy couch has a dent in it? That’s you, my friend. You’ve sat in that spot for so long that it’s shaped like your butt.

Similarly, we humans have emotional couches. We sit in our emotional discomfort because it’s shaped like us, and we’re used to it.

Trying out a new chair seems risky – what if it’s too firm, or worse, what if it doesn’t have enough lumbar support?

3. Sunk Cost Fallacy 

Imagine you’ve bought tickets to the “Sunk Cost Fallacy” fiesta. You’re there, the music is terrible, the guacamole has gone bad, and someone’s uncle is doing the worm.

But you stay because you’ve invested in those tickets, and you’re determined to get your money’s worth, even if it costs you your sanity.

Similarly, we often keep choosing happiness-draining activities, relationships, or jobs – because we’ve already invested so much into them.

It’s like eating a bad meal because you paid for it. Sure, it tastes like cardboard with a side of sadness, but your wallet remembers.

4. Fear of Missing Out

We humans have a fear of missing out. And not just on parties or social events, but on our own life choices. We often stick with the bad because we’re afraid that as soon as we let go, it will turn into the best thing ever.

It’s like keeping a banana in the fruit bowl even as it turns black, just on the off chance it might suddenly become a gourmet dessert.

5. The I’ll Fix It Fantasy

Some of us are fixers. We see a dumpster fire, and we think, “I can make that into a cozy campfire.”

We stick with bad choices because we believe in our magical ability to turn them around.

It’s a bit like thinking you can make a healthy smoothie out of pizza and donuts. Optimistic, but nutritionally dubious.

6. Comfort in Commiseration

There’s a strange comfort in commiseration. We bond over shared misery, like everyone complaining about how bad the coffee is at the office yet continuing to drink it.

It’s terrible, but it’s OUR terrible coffee. And we’ll moan about it together.

Sometimes, shared unhappiness is a group activity, like synchronized swimming, but with frowns.

7. The “What If I Deserve This?” Wormhole

choosing unhappinessThen there’s the guilt. Some part of us believes that we deserve the unhappiness.

It’s the “what if I’m a terrible person and this is my punishment?” line of thinking.

We become martyrs of our own self-doubt, like someone who apologizes to furniture after bumping into it.

8. The “But I’m Learning” Loop

We love to justify our bad choices by saying we’re learning from them.

And sure, learning is great.

But if you keep touching a hot stove, maybe you’re not learning the right lesson.

It’s like repeating kindergarten – because you really want to get that finger painting down.

9. The “I’ve Seen This Movie Before” Syndrome

We’re drawn to outcomes we’ve experienced before, even bad ones, because they’re predictable.

It’s like watching a movie you hate over and over.

10. Stuck in The Cogs of Cognitive Dissonance

This is the mental discomfort that occurs when our actions are not in harmony with our beliefs. So we tell ourselves stories to justify our choices. “I must love my job,” we say, “otherwise, why would I do it?”

We’re narrative creatures, and sometimes our stories are less about the truth – and more about comfort.

11. A Chummy Devil is Better Than a Stranger Devil

They say the devil you know is better than the devil you don’t. It’s why we cling to a crummy job, a withering relationship, or a dead-end habit with the tenacity of a barnacle.

Because the unknown abyss of change is too daunting. So, we choose the same old, same old – even when it’s the same old misery.

12. Society Made Me Do it

We’re social animals, and we crave acceptance. Sometimes we keep choosing the unjoyful path because it’s what’s expected of us.

It’s like wearing uncomfortable and ugly shoes – because someone said they’re stylish.

13. Paradox of Choice Stops Us From Choosing

Psychologist Barry Schwartz was the first to discuss a concept called “Paradox of Choice,” which suggests that having too many options can lead to decision paralysis – which then leads to less happiness.

It’s like standing at the cereal aisle – looking at the abundance of choices – and feeling overwhelmed.

As a result, we grab the same boring box of cereal we always do – because choosing a new option feels too hard.

14. Limitations of Self-awareness

woman hugging cactusWe don’t always know what will make us happy. Like that time you thought you wanted a pet snake, only to discover that you’re actually terrified of snakes.

Our wants are often out of sync with our needs, and figuring out the difference requires a level of introspection that can feel as elusive as a shadow in the dark.

15. Misguided Quest for Perfection: The Unicorn Chase

We often stick with the wrong choices because we’re waiting for them to magically transform into unicorns.

We think, “If I just work harder, stay longer, or twist myself into a human pretzel, this miserable relationship/job/pair of jeans will suddenly become perfect.”

Spoiler alert: Unicorns are hard to find because they’re fictional.

And so is the idea that a bad choice will become a good one if you just bleed enough glitter.

16. Drama Addiction

Some of us are addicted to drama.

We say we want peace and happiness. But then we’re bored by the second episode of “Tranquil Valley.”

We crave the roller coaster, the rush of the crisis, the adrenaline of the argument.

It’s not that we enjoy being unhappy. But we do enjoy feeling something.

And even unhappiness proves we’re alive and kicking. (Often, literally kicking.)

17. The Identity Crisis: “I’m the Guy Who Hates His Job, Right?”

Unhappiness can become a part of our identity. If Carl has complained about his job every day for the last ten years, who is he if he’s not complaining? The thought of being “Carl, the guy who’s content with his work” is more daunting than dealing with the existential dread his cubicle inspires.

Identity is a powerful thing. And sometimes, it’s tightly woven with the fabric of our discontent.

18. Hope Springs Eternal: The Gambler’s Dilemma

Then there’s hope. It springs eternal, especially when we’re making bad choices.

It’s the gambler’s dilemma: “Maybe this time it will be different.

So we stick with the unhappy choice because of that tiny, nagging possibility that maybe, just maybe, this will be the time the slot machine pays out. And sometimes it does, which reinforces the whole cycle.

19. Overthinking Ourselves into a Corner

Why do you keep choosing things that don't make you happy?We overthink. Analyze. Make pro and con lists until we’ve got enough content to publish a book titled “The Comprehensive Guide to My Indecision.”

We get so wrapped up in thinking about next steps – that we stay stuck in the unhappy choice – because making any new move feels like stepping onto a minefield.

20. The Rebellion: “You Can’t Tell Me What Makes Me Happy!”

Let’s not forget our rebellious streak. Sometimes, we stick with the unhappy choice just to prove a point. It’s like a two-year-old refusing to eat broccoli.

21. The Myth of Suffering for Success

There’s this glorified narrative that you must slog through a swamp of suffering to reach the promised land of success and happiness.

We’re told that pain is a rite of passage, a necessary evil on the road to achievement.

So, we persist in choices that make us miserable, believing that it’s just the price of admission to the big show of “Making It.”

22. The Ego’s Sticky Fingers

Our egos have the adhesive quality of industrial-strength glue when it comes to our identities.

Admitting that we don’t like something we’ve chosen means admitting we were wrong. And who likes to be wrong? No one, that’s who.

We’d rather stick with an unfortunate choice – than face the ego-bruising reality that we might have goofed.

23. Illusion of Permanence

Here’s a fun fact: nothing is permanent. Yet we operate under the illusion that our current state is as fixed as the North Star.

This leads to a sort of decision-making inertia, where we assume that the choices we’ve made are as immutable as laws of physics.

The thought that we could just “change something” is as foreign as the concept of a quiet toddler.

24. The Misconception of “Supposed To”

Life comes with a lot of “supposed to’s.” We’re supposed to have a career path, supposed to settle down, supposed to want a bigger house.

These societal scripts can lead us to make choices that align with the “supposed to” – rather than what actually tickles our dopamine receptors.

25. Trying To Dodge Regret

Ah, regret — the party pooper of emotions.

We’re terrified that if we make a change, we’ll regret what we’ve left behind.

It’s like keeping a hideous vase from Aunt Mildred on the mantelpiece because we’re worried we might miss it.

Spoiler: we won’t.

26. Old Fashioned Fear of Failure.

Let’s talk about fear. Not the “there’s a spider in my bathtub” fear. But the “what if I’m not good enough and everyone realizes it” fear. This fear keeps us sticking to choices that don’t make us happy because the unknown is like an endless abyss that’s possibly filled with spiders.

27. Imposter Syndrome

Many of us walking around feeling like a fraud in own life. We think, “Who am I to be happy?” or “Happy people are probably just good at pretending.” So we accept our unhappiness – feeling it’s what we deserve.

How To Stop Choosing Unhappiness: 8 Tips

woman choosing happiness

The following 8 strategies will help you to finally stop the endless cycle of choosing the not-so-happy stuff.

1. Wake The Heck Up

First off, let’s talk about awareness. It’s not just that thing that happens when you realize you’ve been scrolling through your ex’s vacation pics at 3 AM.

It’s about getting real with the why behind your perpetual membership in the “This Sucks” club.

  • Shine a light on the patterns you fall into.
  • Question your choices.
  • Poke at your reasons.
  • Toss the metaphorical salad of your life and see what looks fresh – and what needs to be thrown out.

With this in mind, start a journal.

Write down what you’ve been doing – and how it makes you feel. It’s like being your own personal detective, but instead of solving cool crimes, you’re figuring out why you keep eating ice cream for breakfast.

2. Dare To Be More Daring

Choosing happiness is an act of bravery. It’s acknowledging that the comfort of sorrow is a siren song meant to keep you docked at a familiar shore.

You must decisively and bravely step off the familiar path and endure the discomfort of growth.

It’s not easy. It’s not supposed to be.  True happiness isn’t a prize at the end of the maze. It’s the strength you build as you navigate it.

With this in mind, try something new each week that scares you just a little.

Or at least aim to do something new once a month.

3. Baby Steps Are Still Steps

Change doesn’t have to be as dramatic as moving to Bali to find yourself.

It can be as simple as deciding to choose one thing each day that you know will make you happier.

Even if it’s as minor as swapping out your “meh” breakfast cereal for something that doesn’t taste like cardboard.

Or swapping out watching cat videos at 2 AM for…I don’t know…actually sleeping?

4. Practice Daily Mindfulness

Mindfulness is not just for yogis and people who can pronounce quinoa correctly. It’s for you, too.

Spend a few minutes each day just being with your thoughts, without trying to squish them down with TikTok videos.

You’ll start to notice what truly makes you tick, or what ticks you off, and avoid it.

5. Rewrite Your Story

You’ve got this narrative in your head about who you are. Spoiler alert: It might be full of crap.

Start challenging the “I’m just a person who sucks at life” storyline.

Find evidence that you don’t entirely suck.

8. Be Thankful For The Good Stuff

Practicing gratitude is basically the opposite of wallowing in your own misery. Start a gratitude list.

Every day, write down stuff you’re actually happy about. It’s like making a “not everything sucks” list.

You’ll be surprised how much doesn’t suck when you actually look for it.

Recap: Start Choosing Happiness Over Unhappiness

From now on – as you move through your day – notice when happiness starts to feel elusive – and press that shuffle button on your life. Remember: You can discover new life choices. Be open to embracing the unknown – and open yourself up to a brave new world of happier possibilities.

So, if you’ve found yourself nodding along, recognizing your patterns in the “27 Reasons Why You Keep Choosing Things That Don’t Make You Happy,” or if you’re simply ready to start making choices that align more closely with joy, then my Tweak a Week Online Course might just be the next step you’ve been looking for.

Or if you’re looking for more personalized support, perhaps we should meet up for a 1-on-1 coaching session via Zoom. Learn more about my private coaching sessions here.

Think happier. Think calmer.

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