Mid-life Transition Pillows

Add a touch of humor and comfort to their space with pillows that celebrate mid-life transitions. A cozy reminder that new beginnings can be both fun and supportive.

All Products Prints T-Shirts Mugs Pillows

Strange Aftertaste birthday cards. mockup

Strange Aftertaste birthday cards.

from $19.00

"I'm coloring it a little bit at a time, so it won't be noticeable."

"I'm coloring it a little bit at a time, so it won't be noticeable." mockup

"I'm coloring it a little bit at a time, so it won't be noticeable."

from $19.00

The fate of the emigrant

from $19.00

'For your information, I am engaging the energy of change and complexity to create the future I desire.'

'For your information, I am engaging the energy of change and complexity to create the future I desire.' mockup

'For your information, I am engaging the energy of change and complexity to create the future I desire.'

from $19.00

He kept up his guitar practise... mockup

He kept up his guitar practise...

from $19.00

"Your contents have shifted."

from $19.00

Mister Mid-Life Crisis

from $19.00

"I’ve settled comfortably into middle-age while Barry has settled comfortably into Middle Earth."

"I’ve settled comfortably into middle-age while Barry has settled comfortably into Middle Earth." mockup

"I’ve settled comfortably into middle-age while Barry has settled comfortably into Middle Earth."

from $19.00

'See? You call my look 'a midlife crisis' but for these guys it's a major TV series.'

'See? You call my look 'a midlife crisis' but for these guys it's a major TV series.' mockup

'See? You call my look 'a midlife crisis' but for these guys it's a major TV series.'

from $19.00

"More quarters! For God's sake, more quarters!!"

"More quarters! For God's sake, more quarters!!" mockup

"More quarters! For God's sake, more quarters!!"

from $19.00

"Some mid-life crisis that turned out to be."

"Some mid-life crisis that turned out to be." mockup

"Some mid-life crisis that turned out to be."

from $19.00

"Follow that dream!" (man boarding taxi)

"Follow that dream!" (man boarding taxi) mockup

"Follow that dream!" (man boarding taxi)

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

"Colin kept the bar fairly low."

from $19.00

Middle Age: When you finally get your head together, and your body starts to fall apart!

Middle Age: When you finally get your head together, and your body starts to fall apart! mockup

Middle Age: When you finally get your head together, and your body starts to fall apart!

from $19.00

'I refuse to relinquish the title, 'Top Young Exec'.'

'I refuse to relinquish the title, 'Top Young Exec'.' mockup

'I refuse to relinquish the title, 'Top Young Exec'.'

from $19.00

"I'm here for the hair."

from $19.00

The Gingerbread Man Hits 50.

from $19.00

"Good news, honey - seventy is the new fifty."

"Good news, honey - seventy is the new fifty." mockup

"Good news, honey - seventy is the new fifty."

from $19.00

"This old bike of mine has sure lost some if its speed over the years."

"This old bike of mine has sure lost some if its speed over the years." mockup

"This old bike of mine has sure lost some if its speed over the years."

from $19.00

"I'm 59 and they say I'm middle aged. Just how many people do you know who are 118?"

"I'm 59 and they say I'm middle aged. Just how many people do you know who are 118?" mockup

"I'm 59 and they say I'm middle aged. Just how many people do you know who are 118?"

from $19.00

'Chicken soup for dummies who don't sweat the small stuff.'

'Chicken soup for dummies who don't sweat the small stuff.' mockup

'Chicken soup for dummies who don't sweat the small stuff.'

from $19.00

'Where Are They Now?'

from $19.00

'I've used up all my eligibilities' mockup

'I've used up all my eligibilities'

from $19.00

'You again? You know it's called a mid-life crisis, not mid-week!'

'You again? You know it's called a mid-life crisis, not mid-week!' mockup

'You again? You know it's called a mid-life crisis, not mid-week!'

from $19.00

We micro-grafted all the hairs from the back of your head to the top and now we've completely covered your bald spot.'

We micro-grafted all the hairs from the back of your head to the top and now we've completely covered your bald spot.' mockup

We micro-grafted all the hairs from the back of your head to the top and now we've completely covered your bald spot.'

from $19.00

"I just don't want to be 'that' waffle."

"I just don't want to be 'that' waffle." mockup

"I just don't want to be 'that' waffle."

from $19.00

Speedo Limit: 21 Years

from $19.00

'Here's your chance to become a legend.'

'Here's your chance to become a legend.' mockup

'Here's your chance to become a legend.'

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

"You've come to a fork in the road – age-defying or age-appropriate?"

"You've come to a fork in the road – age-defying or age-appropriate?" mockup

"You've come to a fork in the road – age-defying or age-appropriate?"

from $19.00

"Hon, I'm taking your advice and starting a new chapter."

"Hon, I'm taking your advice and starting a new chapter." mockup

"Hon, I'm taking your advice and starting a new chapter."

from $19.00

"My once perky chicken breasts hang like flapjacks, I don't lay eggs anymore, I'm burning up with hot flashes, I'm...."

"My once perky chicken breasts hang like flapjacks, I don't lay eggs anymore, I'm burning up with hot flashes, I'm...." mockup

"My once perky chicken breasts hang like flapjacks, I don't lay eggs anymore, I'm burning up with hot flashes, I'm...."

from $19.00

"Just when I’ve reconciled the fact that I’m in my 40s, my 50th birthday shows up."

"Just when I’ve reconciled the fact that I’m in my 40s, my 50th birthday shows up." mockup

"Just when I’ve reconciled the fact that I’m in my 40s, my 50th birthday shows up."

from $19.00

"The nest may be empty, but our drinks are full."

"The nest may be empty, but our drinks are full." mockup

"The nest may be empty, but our drinks are full."

from $19.00

Mid-life Transition Pillows Collection

Mid-life Transition Mugs

Explore our collection of mugs celebrating mid-life transitions—perfect for morning coffee or tea with a humorous or heartfelt message.

Mid-life Transition Prints

Find inspiring prints that beautifully capture the essence of mid-life change—great for motivating and uplifting every day.

Mid-life Transition T-Shirts

Check out our mid-life transition t-shirts—wear your new chapter with pride and a bit of wit to start every day right.