
'So, how long have you been managing the Department of What Could Possible Go Wrong?'
Looking for a gift for the ultimate pessimist? Our collection celebrates a witty, tongue-in-cheek outlook on life. Perfect for thinkers who prefer to see the downside with a smile. Find humorous mugs, tees, pillows, and prints that embrace the pessimistic perspective while adding a dash of charm to their daily routine.
'So, how long have you been managing the Department of What Could Possible Go Wrong?'
Forlornaments: Tools to drain individual and team spirit
'My pessimism keeps me optimistic.'
"Son, the world is full of disappointments. About 7.7 billion of them."
Platitudes for the hopelessly realistic. When life gives you lemons, get a gift receipt.
The glass is half full. - '' - 'The glass is half empty' - '' - 'Gah!! No clean glasses!!' - '' -
'Satchel, life is like a can of tuna...'
Tom's last day.
"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day."
"I see fleeting moments of happiness in between extended periods of boredom and stress."
The End is Near art gallery opening.
"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment."
"Oh well - same shit, different day. . .!"
'Barnhill from Marketing will present our economic projections.'
"Die alone"
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!'
Half Empty/Half Full/I'm Still On Vacation!!!
"What? You were expecting good news? Expectations are so-o-o-o passe."
'Taking guard' 'The pessimist'
Gonna Suck
"Sometimes, on days like this, I feel like the world is conspiring to make me happy."
'Turned out nice again.'
Y2K Solutions Inc.
"The scariest part is knowing that someday something'll come along that will make us go, 'Even the spider mutants weren't this bad.' "
Your radio show this week was incredible. Buzz off. Who cares what you think? It was angry, vitriolic, sarcastic, mean-spirited, pessimistic. Do you mean that? You really were listening? I'm not giving a compliment. You're less horrifyingly objectionable than usual.
This will be a banner day for you!
"If at first you don't succeed blame somebody."
'I'm afraid things have to get worse before they can get even worse.'
'You know, that Lenny is a real 'glass half empty' kind of guy...!'
"This feels like the start of something that will eventually break one of our hearts."
"Is this worse? Or is this worse?"
DOOM, 'I do love you, Arnie, but you're such a downer!'
All my silver linings have clouds around them.
'Against Joie De Vivre': Meet the author today.
"Oh what a beautiful morning!"
Discover mugs that speak to your inner pessimist—quirky, witty designs perfect for everyday use.
Find pillows that showcase your pessimistic humor—great for adding personality to any living space.
Explore prints that celebrate the art of pessimism—ideal for wall decor that makes a statement.
Browse our collection of t-shirts with clever pessimistic sayings—wear your outlook with humor and style.