
Car insurance, breakdown cover, mobile insurance, home insurance, camera insurance... - 'Life insurance, health insurance, professional indemnity, and tax insurance.' - 'Let the bad times roll... heh, heh!'
For those who see the world through a quirky lens—balancing bright hope with a dash of doubt—our collection captures this paradox perfectly. From witty shirts to inspiring prints, find something that echoes the unique outlook of an optimistic pessimist. It’s a fun way to embrace your creative perspective and share your inner voice with others.
Car insurance, breakdown cover, mobile insurance, home insurance, camera insurance... - 'Life insurance, health insurance, professional indemnity, and tax insurance.' - 'Let the bad times roll... heh, heh!'
"Ambitions... to be proved wrong."
All my silver linings have clouds around them.
'Try and be negative in a positive way.'
'Oh for heaven's sake, you're a cow. Just eat grass and be happy.'
"I feel like that I've been given a unique oppurtunity to speak out on issues."
Six Thinking Hats
"Son, the world is full of disappointments. About 7.7 billion of them."
'Actually, my mom was the first to notice he'd lost that new boyfriend smell!'
'The good news is that from now on I belong to a very rare species. There aren't many personnel managers who create their own pink slip.'
Platitudes for the hopelessly realistic. When life gives you lemons, get a gift receipt.
Doug reasoned that things could be worse...but just how much worse...he wasn't sure??
"Oh, don't mind us... We just want to make sure it's really dead."
Flower growing from a bomb.
Ahhh, spring baseball.
"I call it the The Power of Positive Pessimism. Knowing full well that most of the things I try almost always end in disaster, yet somehow finding enjoyment in every step of the process. It works for me!"
Man replaces tank sign with deer sign
Tom's last day.
"I see fleeting moments of happiness in between extended periods of boredom and stress."
'The key is not to take yourself too seriously: You have to be able to laugh at yourself...'
The End is Near art gallery opening.
"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day."
"Die alone"
Coronovirus dreams
"Oh well - same shit, different day. . .!"
Lent is a real drag this year. - 'Why? What did you give up?' - 'Hope.' - 'I gave up chocolate. Guess what?1' - 'What?' - 'I've made my ideal weight! Yay!'
"Mister, I don't know if the glass is half full or half empty. It's 12 dollars."
Just Because it's Tuesday
'Barnhill from Marketing will present our economic projections.'
"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment."
'I find it difficult not to entertain the occasional negative thought.'
Half Empty/Half Full/I'm Still On Vacation!!!
"There are too many starfish for you to save. How can you possibly hope to make a difference?"
The end is near. The end is nearish. I get this way every spring.
"I can dream, can't I?"
Explore our collection of mugs perfect for optimistic pessimists—witty, inspiring, and designed to start conversations.
Add some humor to your home decor with pillows that celebrate the optimistic pessimist in all of us—comfortable and full of character.
Brighten your space with prints that reflect the quirky, hopeful, and skeptical outlook of an optimistic pessimist—perfect for inspiring your creative environment.
Check out our t-shirts for the creative soul who sees the world differently—funny, clever, and beautifully paradoxical.