Mid-life Crisis Pillows

Add comfort and a touch of wit to any space with pillows that acknowledge life's mid-life moments with humor and grace—great for transforming a tough phase into a cozy one.

All Products Prints T-Shirts Mugs Pillows

Speedo Limit: 21 Years

from $19.00

"Take some identification with you in case you die."

"Take some identification with you in case you die." mockup

"Take some identification with you in case you die."

from $19.00

'Yeah, I hate change, too.'

from $19.00

'I worked very hard and finally got to the top of the ladder... only to find that I'd leaned it against the wrong wall.'

'I worked very hard and finally got to the top of the ladder... only to find that I'd leaned it against the wrong wall.' mockup

'I worked very hard and finally got to the top of the ladder... only to find that I'd leaned it against the wrong wall.'

from $19.00

"I'm going to get my old dog, get an old pickup, a double-barrelled shotgun, get my old pink cotton print dress, and get back on Route 66!"

"I'm going to get my old dog, get an old pickup, a double-barrelled shotgun, get my old pink cotton print dress, and get back on Route 66!" mockup

"I'm going to get my old dog, get an old pickup, a double-barrelled shotgun, get my old pink cotton print dress, and get back on Route 66!"

from $19.00

Pants...Before & After

from $19.00

'A spoiler is standard on all sports cars. It helps protect your hair transplant.'

'A spoiler is standard on all sports cars. It helps protect your hair transplant.' mockup

'A spoiler is standard on all sports cars. It helps protect your hair transplant.'

from $19.00

"The only thing that still works well for me is hysteria."

"The only thing that still works well for me is hysteria." mockup

"The only thing that still works well for me is hysteria."

from $19.00

"Can you estimate how much money you'll need for your mid-life crisis?"

"Can you estimate how much money you'll need for your mid-life crisis?" mockup

"Can you estimate how much money you'll need for your mid-life crisis?"

from $19.00

'Suddenly it was apparent where Jack was headed.'

'Suddenly it was apparent where Jack was headed.' mockup

'Suddenly it was apparent where Jack was headed.'

from $19.00

'We only live once. Hope in.'

from $19.00

"There's something wrong with this mirror...every time I look at it, some old fat guy is staring back at me!"

"There's something wrong with this mirror...every time I look at it, some old fat guy is staring back at me!" mockup

"There's something wrong with this mirror...every time I look at it, some old fat guy is staring back at me!"

from $19.00

"It means taking a healthy pay cut, but my dad has decided to stay at home and lock himself in the basement."

"It means taking a healthy pay cut, but my dad has decided to stay at home and lock himself in the basement." mockup

"It means taking a healthy pay cut, but my dad has decided to stay at home and lock himself in the basement."

from $19.00

"And that's when I realized that I much preferred making frothy desserts."

"And that's when I realized that I much preferred making frothy desserts." mockup

"And that's when I realized that I much preferred making frothy desserts."

from $19.00

"It's not so much a minivan as it is a hearse for our youth."

"It's not so much a minivan as it is a hearse for our youth." mockup

"It's not so much a minivan as it is a hearse for our youth."

from $19.00

"Just when did you acquire those tattoos, Warner?"

"Just when did you acquire those tattoos, Warner?" mockup

"Just when did you acquire those tattoos, Warner?"

from $19.00

'I think I am going through a mid-life crises.'

'I think I am going through a mid-life crises.' mockup

'I think I am going through a mid-life crises.'

from $19.00

Truck Introspection Station: 'Am I happy? Does my life have meaning?'

Truck Introspection Station: 'Am I happy? Does my life have meaning?' mockup

Truck Introspection Station: 'Am I happy? Does my life have meaning?'

from $19.00

'I'm finally at one with the universe...but apparently that doesn't include the DOW.'

'I'm finally at one with the universe...but apparently that doesn't include the DOW.' mockup

'I'm finally at one with the universe...but apparently that doesn't include the DOW.'

from $19.00

"If I could take back ninety per cent of the things I say, then I think people would know the real me."

"If I could take back ninety per cent of the things I say, then I think people would know the real me." mockup

"If I could take back ninety per cent of the things I say, then I think people would know the real me."

from $19.00

"Norman still has seventies flashbacks sometimes."

"Norman still has seventies flashbacks sometimes." mockup

"Norman still has seventies flashbacks sometimes."

from $19.00

"I can't believe the things I've heard coming out of his mouth since he started listening to Eminem."

"I can't believe the things I've heard coming out of his mouth since he started listening to Eminem." mockup

"I can't believe the things I've heard coming out of his mouth since he started listening to Eminem."

from $19.00

"My whole life stretches out before me as a series of egg-white omelettes."

"My whole life stretches out before me as a series of egg-white omelettes." mockup

"My whole life stretches out before me as a series of egg-white omelettes."

from $19.00

This is what Fred gets for wishing for more hair.

This is what Fred gets for wishing for more hair. mockup

This is what Fred gets for wishing for more hair.

from $19.00

'It wouldn't be so bad if they were pert and perky.'

'It wouldn't be so bad if they were pert and perky.' mockup

'It wouldn't be so bad if they were pert and perky.'

from $19.00

"You could call it cilia. I prefer to think of it as designer stubble."

"You could call it cilia. I prefer to think of it as designer stubble." mockup

"You could call it cilia. I prefer to think of it as designer stubble."

from $19.00

A mid-lithe crisis.

from $19.00

'Perhaps you're simply scrambling to make up for lost time.'

'Perhaps you're simply scrambling to make up for lost time.' mockup

'Perhaps you're simply scrambling to make up for lost time.'

from $19.00

Tarzan's mid-life crisis.

from $19.00

Sports car colors.

from $19.00

'Are you worried about getting old?' mockup

'Are you worried about getting old?'

from $19.00

'Fred's having his mid-life crisis, Helen -- don't get too close.'

'Fred's having his mid-life crisis, Helen -- don't get too close.' mockup

'Fred's having his mid-life crisis, Helen -- don't get too close.'

from $19.00

'If you're going through your second childhood like Mom says, how come I never see you at school?'

'If you're going through your second childhood like Mom says, how come I never see you at school?' mockup

'If you're going through your second childhood like Mom says, how come I never see you at school?'

from $19.00

'Termites devour my house, the kids devour the hair off my head and taxes devour all my profits... I'm at the bottom of the food chain'!

'Termites devour my house, the kids devour the hair off my head and taxes devour all my profits... I'm at the bottom of the food chain'! mockup

'Termites devour my house, the kids devour the hair off my head and taxes devour all my profits... I'm at the bottom of the food chain'!

from $19.00

Eccentrically dressed husband says to quiet, timid looking wife: 'Now, don't embarrass me!'

Eccentrically dressed husband says to quiet, timid looking wife: 'Now, don't embarrass me!' mockup

Eccentrically dressed husband says to quiet, timid looking wife: 'Now, don't embarrass me!'

from $19.00

Mid-life Crisis Pillows Collection

Mid-life Crisis Mugs

Explore our collection of witty mugs perfect for anyone going through a mid-life crisis—bring humor and comfort to their daily routine with these fun designs.

Mid-life Crisis Prints

Find inspiring prints that celebrate mid-life milestones with humor and positivity. These artworks make meaningful gifts or personal reminders of growth.

Mid-life Crisis T-Shirts

Shop our humorous T-shirts that embrace life's mid-life changes. Great for making light of the moments that challenge and change us, with a fun, personal touch.