Job Pessimist Pillows

Add a touch of humor to their workspace or home with our playful pillows, featuring funny quotes perfect for the job pessimist who loves a good laugh about work life.

All Products Prints T-Shirts Mugs Pillows

Insecurity Guards

from $19.00

"Son, the world is full of disappointments. About 7.7 billion of them."

"Son, the world is full of disappointments. About 7.7 billion of them." mockup

"Son, the world is full of disappointments. About 7.7 billion of them."

from $19.00

Pessimists v Optimists.

from $19.00

"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!"

"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!"

from $19.00

'There, Mr Optimist. Now how full is it?'

'There, Mr Optimist. Now how full is it?' mockup

'There, Mr Optimist. Now how full is it?'

from $19.00

'I make certain all my clients are pessimists...they don't expect to win.'

'I make certain all my clients are pessimists...they don't expect to win.' mockup

'I make certain all my clients are pessimists...they don't expect to win.'

from $19.00

Tom's last day.

from $19.00

"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day."

"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day." mockup

"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day."

from $19.00

The End is Near art gallery opening. mockup

The End is Near art gallery opening.

from $19.00

"I see fleeting moments of happiness in between extended periods of boredom and stress."

"I see fleeting moments of happiness in between extended periods of boredom and stress." mockup

"I see fleeting moments of happiness in between extended periods of boredom and stress."

from $19.00

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!'

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!'

from $19.00

"Maybe you should be depressed, your life isn't that great."

"Maybe you should be depressed, your life isn't that great." mockup

"Maybe you should be depressed, your life isn't that great."

from $19.00

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!'

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!' mockup

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!'

from $19.00

'Barnhill from Marketing will present our economic projections.'

'Barnhill from Marketing will present our economic projections.' mockup

'Barnhill from Marketing will present our economic projections.'

from $19.00

"Let's save some time, shall we?... Yes, no, for about five years, since I was a small boy, yes, I can start on Monday. Thanks, bye."

"Let's save some time, shall we?... Yes, no, for about five years, since I was a small boy, yes, I can start on Monday. Thanks, bye." mockup

"Let's save some time, shall we?... Yes, no, for about five years, since I was a small boy, yes, I can start on Monday. Thanks, bye."

from $19.00

"Die alone"

from $19.00

'Some see the glass as half empty, some see it as half full -- I see it as taxable!'

'Some see the glass as half empty, some see it as half full -- I see it as taxable!' mockup

'Some see the glass as half empty, some see it as half full -- I see it as taxable!'

from $19.00

"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment."

"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment." mockup

"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment."

from $19.00

Half Empty/Half Full/I'm Still On Vacation!!!

Half Empty/Half Full/I'm Still On Vacation!!! mockup

Half Empty/Half Full/I'm Still On Vacation!!!

from $19.00

'Taking guard' 'The pessimist'

from $19.00

Gonna Suck

from $19.00

'Would you say this glass is half empty or half full?'

'Would you say this glass is half empty or half full?' mockup

'Would you say this glass is half empty or half full?'

from $19.00

Y2K Solutions Inc.

from $19.00

'Turned out nice again.'

from $19.00

"Ambitions... to be proved wrong." mockup

"Ambitions... to be proved wrong."

from $19.00

This will be a banner day for you! mockup

This will be a banner day for you!

from $19.00

'You know, that Lenny is a real 'glass half empty' kind of guy...!'

'You know, that Lenny is a real 'glass half empty' kind of guy...!' mockup

'You know, that Lenny is a real 'glass half empty' kind of guy...!'

from $19.00

'So when I couldn't pay the mortgage, the bank offered me this rescue package!'

'So when I couldn't pay the mortgage, the bank offered me this rescue package!' mockup

'So when I couldn't pay the mortgage, the bank offered me this rescue package!'

from $19.00

Things are never as bad as they seem - they're usually much, much worse.

Things are never as bad as they seem - they're usually much, much worse. mockup

Things are never as bad as they seem - they're usually much, much worse.

from $19.00

"I don't like hearing happy stories." mockup

"I don't like hearing happy stories."

from $19.00

"We've got a vacancy for a church mouse, if you're interested?"

"We've got a vacancy for a church mouse, if you're interested?" mockup

"We've got a vacancy for a church mouse, if you're interested?"

from $19.00

"This feels like the start of something that will eventually break one of our hearts."

"This feels like the start of something that will eventually break one of our hearts." mockup

"This feels like the start of something that will eventually break one of our hearts."

from $19.00

Job Pessimist Pillows Collection

Job Pessimist Mugs

Browse our collection of funny mugs that perfectly capture the job pessimist’s candid humor—great for a daily dose of laughter with their morning coffee.

Job Pessimist Prints

Discover funny and relatable prints that celebrate the job pessimist’s perspective, perfect for decorating their office or home with a humorous touch.

Job Pessimist T-Shirts

Check out our collection of witty t-shirts designed for the job pessimist—ideal for expressing their honest attitude towards work with style and humor.