Playful Businessperson Pillows

Add a cozy, humorous touch to their workspace or home with pillows that showcase their playful business attitude—comfort and humor all in one.

All Products Prints T-Shirts Mugs Pillows

LEMONADE 50 CENTS, NOW HIRING, 'Okay, you're hired -- now, I want you to forget everything you learned in pre-school.'

LEMONADE 50 CENTS, NOW HIRING, 'Okay, you're hired -- now, I want you to forget everything you learned in pre-school.' mockup

LEMONADE 50 CENTS, NOW HIRING, 'Okay, you're hired -- now, I want you to forget everything you learned in pre-school.'

from $19.00

Ice Cream Surgeon

from $19.00

Ice Cream And Summer Rentals

from $19.00

Perks Featured in Vacancy at Toy Company

Perks Featured in Vacancy at Toy Company mockup

Perks Featured in Vacancy at Toy Company

from $19.00

"The new revenue stream is finally kicking in."

"The new revenue stream is finally kicking in." mockup

"The new revenue stream is finally kicking in."

from $19.00

"Sorry, stock-market jitters."

from $19.00

"Actually, I used them as collateral for a loan."

"Actually, I used them as collateral for a loan." mockup

"Actually, I used them as collateral for a loan."

from $19.00

"The jury didn't buy my defense that CEOs just want to have fun."

"The jury didn't buy my defense that CEOs just want to have fun." mockup

"The jury didn't buy my defense that CEOs just want to have fun."

from $19.00

Boy in toy car talking on phone.

from $19.00

Office Park

from $19.00

Young Doctor, Young Nurse, Young Undertaker

Young Doctor, Young Nurse, Young Undertaker mockup

Young Doctor, Young Nurse, Young Undertaker

from $19.00

"Recess is over, Your Honor."

from $19.00

'Interesting. At first, I didn't pick her as dominant.' - Child chairs meeting at Toys Inc.

'Interesting. At first, I didn't pick her as dominant.' - Child chairs meeting at Toys Inc. mockup

'Interesting. At first, I didn't pick her as dominant.' - Child chairs meeting at Toys Inc.

from $19.00

Melvin likes to indulge his inner child.

Melvin likes to indulge his inner child. mockup

Melvin likes to indulge his inner child.

from $19.00

"So how long have you been working the business?"

"So how long have you been working the business?" mockup

"So how long have you been working the business?"

from $19.00

'Court is recessed until the big hand is on the three.'

'Court is recessed until the big hand is on the three.' mockup

'Court is recessed until the big hand is on the three.'

from $19.00

Just a little heads up!

from $19.00

'ok, who threw that?'

from $19.00

'The action next week is going to be in bird seed, but if you quote me, I'll deny I said it.'

'The action next week is going to be in bird seed, but if you quote me, I'll deny I said it.' mockup

'The action next week is going to be in bird seed, but if you quote me, I'll deny I said it.'

from $19.00

"I've built this business up from scratch. . . "

"I've built this business up from scratch. . . " mockup

"I've built this business up from scratch. . . "

from $19.00

"Excuse me...but there are hairs in my soup. I think we should be supportive when our friends open a business. But sometimes I wonder...what are they thinking?"

"Excuse me...but there are hairs in my soup. I think we should be supportive when our friends open a business. But sometimes I wonder...what are they thinking?"

from $19.00

"Alfresco Plumbing & Hardware Supplies" mockup

"Alfresco Plumbing & Hardware Supplies"

from $19.00

"In this office we work hard and we play hard, Timpkins"

"In this office we work hard and we play hard, Timpkins" mockup

"In this office we work hard and we play hard, Timpkins"

from $19.00

'Sales has challenged us to a snowball fight.'

'Sales has challenged us to a snowball fight.' mockup

'Sales has challenged us to a snowball fight.'

from $19.00

Man at important looking desk lined with quill pens gets ready to shoot one at a dartboard on his wall.

Man at important looking desk lined with quill pens gets ready to shoot one at a dartboard on his wall. mockup

Man at important looking desk lined with quill pens gets ready to shoot one at a dartboard on his wall.

from $19.00

"My records show we sent your bonus. Have you looked on your roof?"

"My records show we sent your bonus. Have you looked on your roof?" mockup

"My records show we sent your bonus. Have you looked on your roof?"

from $19.00

'Good luck with the presentation dear and I still think it would be better without the hat.'

'Good luck with the presentation dear and I still think it would be better without the hat.' mockup

'Good luck with the presentation dear and I still think it would be better without the hat.'

from $19.00

"Why can't you ever be serious?"

from $19.00

"Damn it, Bershire, I've told you to never call me when I'm in my executive ball pit!"

"Damn it, Bershire, I've told you to never call me when I'm in my executive ball pit!" mockup

"Damn it, Bershire, I've told you to never call me when I'm in my executive ball pit!"

from $19.00

I see from this you were very good at organising office parties.

I see from this you were very good at organising office parties. mockup

I see from this you were very good at organising office parties.

from $19.00

"Our founder was a real joker. That's the first silver dollar he ever glued to the floor."

"Our founder was a real joker. That's the first silver dollar he ever glued to the floor." mockup

"Our founder was a real joker. That's the first silver dollar he ever glued to the floor."

from $19.00

Attorney-at-play

from $19.00

'The Dorvil people feel that the merger was a mistake. They want out, they want half the company's assets and they want child support.'

'The Dorvil people feel that the merger was a mistake. They want out, they want half the company's assets and they want child support.' mockup

'The Dorvil people feel that the merger was a mistake. They want out, they want half the company's assets and they want child support.'

from $19.00

'You dropped the ball. You're being paid to throw it.'

'You dropped the ball. You're being paid to throw it.' mockup

'You dropped the ball. You're being paid to throw it.'

from $19.00

Playful Businessperson Pillows Collection

Playful Businessperson Mugs

Explore our range of mugs designed for playful entrepreneurs and creative professionals—bring humor and style to their daily coffee break.

Playful Businessperson Prints

Choose prints that showcase their lively spirit—adding a touch of humor and creativity to any workspace or home.

Playful Businessperson T-Shirts

Find t-shirts that celebrate the playful businessperson’s vibrant personality—perfect for casual office wear or weekend fun.