5 ways to become a more positive pessimist

Bonjour, Mon Cheries! Amanda Cherie here: singer, songwriter, business psychology professional and TEDx speaker. Like every kid, I couldn’t decide which I wanted to be when I grew up: a mad scientist, a hippie artist, a model, a GUCCI saleswoman, or a bullheaded corporate businesswoman (#tauruslife).

When you’re a Jill (or Jack) of several trades, you get to perform your music in bold outfits. And you get to use your Industrial-Organizational Psychology graduate studies to help Fortune 150 leaders measure and maximize their performance and bold money moves.

When you’re a Jill (or Jack) of several trades, you get to perform your music in bold outfits. And you get to use your Industrial-Organizational Psychology graduate studies to help Fortune 150 leaders measure and maximize their performance and bold money moves.

You go from speaking to leaders about the art of resilience, to writing and belting a song about it. Most of the time they only cry from the latter. Just kidding, I haven’t gotten a tearfilled standing ovation from a business presentation, yet. *Closes eyes and actually visualizes said response.*

Professionally speaking, I’m basically a power-walking paradox, but I’m also a bit of a contradiction in other ways. When it comes to style, I’m a maximal minimalist. No joke, a friend once referred to my style as “intensely structured chaos.” And when it comes to my vibe, my essence, whatever you want to call it, I’m like a Negative Pollyanna meets a Positive Nancy. Says the woman who studied positive psychology in grad school, I’m kind of a positive pessimist.

Let me explain. “Positive pessimism” means I’m still both a realist and idealist, and I try to use both sides for the good of myself and others.

Think Florence Welch singing about her demons with her angelic voice, or Silver Linings Playbook’s equal parts dark mood and playful banter. Ah, positive pessimism at its finest!

Here are 5 ways you also can become a more positive pessimist:

1. KNOW YOUR DEFAULT MINDSET Some people wake up happy. I am not one of those people. You won’t find me having sing-offs with the birds every morning, nor will you find them dressing me.

My roll-out-of-bed default is Jerry Seinfeld meets Russell Brand-on-a-rough-day. Yes, I just described my natural countenance as two dark-humored, middle-aged men. I love both of them for the record. And, might I add, they’ve both found ways to make a lucrative living from said dark humor.

I’m an artsy night owl with a corporate job for a Fortune 150 enterprise. So being an owl living in a lark world doesn’t exactly help me with the waking up bright and happy concept. I rode the proverbial struggle bus to school every morning when I was a kid. I pictured myself as a positive-minded, productive woman who had figured out how to be a morning person that rolls out bed with a red-lipped smile that stays on until she says otherwise. Hate to break it you, Young Amanda, but you and 6 a.m. still have an on-the-rocks relationship. Sorry not sorry.

With my natural lean toward pessimism - or “realism” as we pessimists like to refer to it - I used to play the “I was born this way” card. But over time I’ve realized the power our mindset has over our success.

I believe in the power of mindset not only because I’ve studied it but because I’ve lived it. I literally lost everything in Hallmark-turned-Lifetime story for another day. But all’s well that inspires a poppin’ first single like “Brand New Empire,” am-I-right?

I literally wrote a song about bouncing back from setback. So I’ve embraced the power we have over our own mindset. And I’ve tried to shift to being a bit more of an optimistic pessimist.

It’s important to be self-aware of your default state of mind. But remember you ultimately have the power to channel your thoughts toward whatever mindset will best serve you.

2. LAUGH AT THE DARK HUMOR. When you hear that inner sarcastic voice, it’s hard not to laugh, or at least raise the corners of your mouth to what others may look a bit devious. Little do they know you’re just enjoying some silent humor in the dark corners of your mind palace. And if appropriate, share it with others who may be as twisted as you are, or who may at least be entertained by it. Disclaimer: condescension isn’t cute. But well-placed dark humor where it is appropriate and welcomed can feel like an oasis. The more vivid the language, the better. No, I’m not referring to kinkiness. Although, if your mind went there, feel free to savor the moment... Okay, I’m talking more along the lines of metaphors.

This isn’t just the pessimism talking. Research shows that metaphorical language can actually help painful emotion feel more bearable. So perhaps consider throwing some metaphor into your sarcastic humor. Take this dark-witted example from The Hunger Games: “I've seen you in the market. You can lift hundred pound bags of flour,” I snap at him. “Yes and I'm sure the arena will be full of bags of flour for me to chuck at people.”

Ah, don’t you love dark, witty wordplay?! It may sound ironic, but sometimes dark humor feels like the brightest part of my day. Not much cheers me up like a black hole of dark-humored memes, a dramatic Marvelous Mrs. Maisel scene, or guiltiest pleasure of all: a Kardashian scream off.

It’s okay to your inner cynic bring dark tidings of comfort and joy. After all, laughter is medicine, Mon Cheries.


Once you’ve gotten a good laugh, press pause. The Mad Hatter headspace is great for mental tea time, but pessimism can quickly spiral down a black hole.

The turning point from a downward spiral to well-channeled positive pessimism can start with simply a moment to stop and breathe.

Breathe in through your nose slowly and deeply. Breathe out through your mouth slowly and intentionally.

Pausing to breathe will give you time to back out of the black hole. Why, you ask? Breathing intentionally will give your brain a chance to put the places responsible for reflex on a Hulu commercial break, and create space for the places responsible for reasoning.

If you’re going to let your pessimism loose, it’s important to make sure you’re in complete control of it.

Keep that seductively cynical energy under control. As a positive pessimist, you can ride the dark wave like a pro, on a bright a bright yellow “surfboardt.”

Whether pessimism is a smooth ride or a destructive derailer is up to you. Just make sure you’re pressing pause before diving too far into the darkness.


Besides the pure enjoyment of sarcastic thinking, you can actually use positive pessimism for advantages beyond your own mind palace. You can use the energy to step into a creative headspace where you can solve problems and start to take action.

Don’t just take my word for it. Researchers at Harvard, Columbia and European business school professors discovered that sarcasm can lead to higher levels of creativity. So sarcasm can actually have a positive effect on your thinking.

More than that, well-channeled pessimism can help you be more prepared. If you don’t want to ruin your new suede boots (or you want to be prepared just in case the sky legit falls), you’re more likely to check the weather before leaving the house and to pack an umbrella, even if it’s gorgeous outside. Makes sense, right?

Personality science also backs up this logic. Research shows that well-harnessed pessimism can help you feel more confident, be laser-focused on your goals and actually reach them.

So as a positive pessimist, you can actually feel the confidence to anticipate and successfully navigate difficulty.

You can use the energy to step into a creative headspace where you can solve problems and start to take action that can benefit the concrete world. Ain't it fun living in the real world?...sung in my best Hayley-William-from-Paramore voice.


Learn to love your mind for how it works. Be grateful for your brilliantly "brunette" brain for its state-of-the-art humor radar.

While you’re at it, be thankful for whatever crazy situation you’re in that's inspiring your silent sarcasm. Appreciate your creative ability to influence said situation.

You can also celebrate in advance the story you will get out of it.

Think about how comedians see the world. They turn everyday experiences (and outlandish ones) into relatable, laugh-worthy stories. Take comedian Mark Birbiglia’s vivid recollection of a dialogue with his doctor:

Doctor: “If you’re a comedian, then how come you’re not funny now?”

Birbiglia: “What I wanted to say was, ‘I’m going to take this conversation we’re having now and then repeat that to strangers. And then that’s the joke. You’re the joke, later.”

Comedians, writers and musicians - their brains are always scanning the world for a story. They take their twisted observations, experiences and imagination. And they turn them into captivating works of word art for their own entertainment. Then they share it with people.

Similarly, as a positive pessimist you can use your unique mind to seek out the story in the situation. And you can begin to appreciate the value of the story, maybe even more than the value of your own comfort.

You can use positive pessimism to spark your next big idea or craft your next story. Or you may just in it for the comedic therapy. That’s cool too.

Either way, appreciate the multiple benefits of well-channeled sarcasm.

It’s hard to be optimistic sometimes. Duh. But it is possible to be an intentionally positive pessimist.

You can laugh at the dark humor. You can stop, breathe and decide to use your sarcasm for good. Then you can actually use for good. And you can be grateful for the gift of a beautifully offcentered mind that can bring to life fresh solutions, perspectives and (let’s not forget) comedy.

If you have a smile on your face and walk around saying, “I woke up like this,” good for you.

I did not wake up with a glowing grin, but ironically talking about all this positive pessimism has me genuinely happy. You should see the dazzling, devious smile I’m wearing.

For me, every morning is a rebirth. There’s an Amanda Cherie Renaissance from pessimist to positive pessimist. Every. Effing. Day. I work really hard to keep my mindset in a productive sweet spot.

Whether you’re an optimist or a positive pessimist, continuously fill your mind with things that can help you create your own mindset sweet spot. Talk with a friend. Take a walk through nature. Make a power playlist.

Speaking of power playlists, I’ve got something to help you get started with that, Mon Cherie. It’s like candy for your ears and a shot of espresso for your mind.

It’s my first single “Brand New Empire,” a power anthem I wrote about bouncing back from setback.

Whether you need energy to get going in the morning, set the tone for your next workout, or simply boost your mood throughout the day, “Brand New Empire” can help you level up your mindset.

Don’t worry, it’s not bubblegum pop. It’s a bit snarky and saucy. Take the line, “But I hereby dub you King of Con Art, Sir Psychopath.” Total dark humor!

Listen to “Brand New Empire” on Spotify, iTunes, or wherever you listen to your music.

If you want more motivation, plus more bold blends of psychology and not-basic pop songs, let’s stay connected. Sign up now for unlimited candy for your ears and coffee for your mind, on me!

Until next time, may your brain shine just as dark as it does bright, Mon Cherie.


Amanda Cherie

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