Middle Management Pillows

Add a touch of humor to their workspace or home with pillows that playfully acknowledge the middle manager’s role, blending comfort with a dash of wit.

All Products Prints T-Shirts Mugs Pillows

The Department of Lessons Learned... mockup

The Department of Lessons Learned...

from $19.00

'You are here.'

from $19.00

Another Impromptu Workplace Interaction,

Another Impromptu Workplace Interaction, mockup

Another Impromptu Workplace Interaction,

from $19.00

'A High-pain job? Yes, I believe we have that.'

'A High-pain job? Yes, I believe we have that.' mockup

'A High-pain job? Yes, I believe we have that.'

from $19.00

High Noon at the O.K. Staff Meeting mockup

High Noon at the O.K. Staff Meeting

from $19.00

'Your promotion comes with longer hours with no extra pay. Welcome to middle management.'

'Your promotion comes with longer hours with no extra pay. Welcome to middle management.' mockup

'Your promotion comes with longer hours with no extra pay. Welcome to middle management.'

from $19.00

Minimally Invasive Ethics.

from $19.00

'Does anyone know where they're running the leadership course?'

'Does anyone know where they're running the leadership course?' mockup

'Does anyone know where they're running the leadership course?'

from $19.00

'I have an older brother too, so I know what it's like to be in middle-management.'

'I have an older brother too, so I know what it's like to be in middle-management.' mockup

'I have an older brother too, so I know what it's like to be in middle-management.'

from $19.00

'Well sir, it's just that running this place has always been a real team effort, and. . . you know. . . we're just not sure it's fair for you to go around calling yourself THE Devil.'

'Well sir, it's just that running this place has always been a real team effort, and. . . you know. . . we're just not sure it's fair for you to go around calling yourself THE Devil.'

from $19.00

"Among my fellow second bananas I'm considered top bunch."

"Among my fellow second bananas I'm considered top bunch." mockup

"Among my fellow second bananas I'm considered top bunch."

from $19.00

Office Hierarchy.

from $19.00

'You're my best man, Pomeroy, so I've decided to sell the damn company.'

'You're my best man, Pomeroy, so I've decided to sell the damn company.' mockup

'You're my best man, Pomeroy, so I've decided to sell the damn company.'

from $19.00

Pushing for eternity/Never-ending task. mockup

Pushing for eternity/Never-ending task.

from $19.00

'Sire, we fixed that problem in the sales department.'

'Sire, we fixed that problem in the sales department.' mockup

'Sire, we fixed that problem in the sales department.'

from $19.00

Desk plaque: 'P. Burnside, Upper-Echelon Nincompoop'

Desk plaque: 'P. Burnside, Upper-Echelon Nincompoop' mockup

Desk plaque: 'P. Burnside, Upper-Echelon Nincompoop'

from $19.00

'We've got got 13 line managers and 35 account executives.'

'We've got got 13 line managers and 35 account executives.' mockup

'We've got got 13 line managers and 35 account executives.'

from $19.00

Welcome to middle management. Here's your shield.

Welcome to middle management. Here's your shield. mockup

Welcome to middle management. Here's your shield.

from $19.00

"Excellent point Charles . . . Now if somebody more senior would like to make it."

"Excellent point Charles . . . Now if somebody more senior would like to make it." mockup

"Excellent point Charles . . . Now if somebody more senior would like to make it."

from $19.00

"This position has become very important to the company."

"This position has become very important to the company." mockup

"This position has become very important to the company."

from $19.00

"This is a merit-based organization! Can't you see I’ve hired the very best and most qualified yes-men money can buy?"

"This is a merit-based organization! Can't you see I’ve hired the very best and most qualified yes-men money can buy?" mockup

"This is a merit-based organization! Can't you see I’ve hired the very best and most qualified yes-men money can buy?"

from $19.00

Avoiding bosses on stairs vs. elevator. mockup

Avoiding bosses on stairs vs. elevator.

from $19.00

'You understand, Yomp, it's not me speaking. It's the corporation!'

'You understand, Yomp, it's not me speaking. It's the corporation!' mockup

'You understand, Yomp, it's not me speaking. It's the corporation!'

from $19.00

River of Commerce; FLOW CHART...management ponds, upper, middle, lower...data streams...secretarial pool.

River of Commerce; FLOW CHART...management ponds, upper, middle, lower...data streams...secretarial pool. mockup

River of Commerce; FLOW CHART...management ponds, upper, middle, lower...data streams...secretarial pool.

from $19.00

An infestation of middle managers... mockup

An infestation of middle managers...

from $19.00

'Management no longer thrills Mr. Mossbach, but he's hanging in there.'

'Management no longer thrills Mr. Mossbach, but he's hanging in there.' mockup

'Management no longer thrills Mr. Mossbach, but he's hanging in there.'

from $19.00

'I had the same desires, Beegly...when I was young. Now put that money back in the drawers and get back into your cage.'

'I had the same desires, Beegly...when I was young. Now put that money back in the drawers and get back into your cage.' mockup

'I had the same desires, Beegly...when I was young. Now put that money back in the drawers and get back into your cage.'

from $19.00

Ed Simms - Same location for 20 years mockup

Ed Simms - Same location for 20 years

from $19.00

Suggestion Box

from $19.00

"Care to give to the fund to help save your job?"

"Care to give to the fund to help save your job?" mockup

"Care to give to the fund to help save your job?"

from $19.00

"My God! There goes middle management." mockup

"My God! There goes middle management."

from $19.00

Middle Management

from $19.00

White-Collar Chain Gang

from $19.00

'What bothers me about these meetings is even though it's work, I have the nagging feeling I ought to leave and get back to work.'

'What bothers me about these meetings is even though it's work, I have the nagging feeling I ought to leave and get back to work.' mockup

'What bothers me about these meetings is even though it's work, I have the nagging feeling I ought to leave and get back to work.'

from $19.00

"Looks like we found the issue."

from $19.00

Middle Management Pillows Collection

Middle Management Mugs

Explore our collection of mugs that celebrate middle managers—funny, witty, and perfect for starting their day with a smile.

Middle Management Prints

Browse our humorous prints for middle managers—perfect for decorating office walls or personal spaces with a touch of wit.

Middle Management T-Shirts

Check out our t-shirts designed for middle managers—casual, clever, and ideal for office wear or casual days.