Ambitious Underdogs Gifts

Looking for a gift that honors the ambition of underdogs eager to make their mark? Our curated collection celebrates resilience, courage, and the drive to succeed against all odds. Whether they’re climbing career ladders or pursuing personal passions, these unique items add a humorous and hopeful touch to their journey. Show your support and inspire the doers and dreamers in your life with thoughtful, creative presents that speak to their unstoppable spirit.

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Cleaner in front of interview panel - 'So what makes you want to apply for the job of Equity Fund Manager?'

Cleaner in front of interview panel - 'So what makes you want to apply for the job of Equity Fund Manager?' mockup

Cleaner in front of interview panel - 'So what makes you want to apply for the job of Equity Fund Manager?'

from $19.00

The trauma of losing.

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"When I grow up, I want to become president and eventually the subject of a groundbreaking, critically-acclaimed Broadway musical."

"When I grow up, I want to become president and eventually the subject of a groundbreaking, critically-acclaimed Broadway musical." mockup

"When I grow up, I want to become president and eventually the subject of a groundbreaking, critically-acclaimed Broadway musical."

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"He wants to be a plastic surgeon when he grows up."

"He wants to be a plastic surgeon when he grows up." mockup

"He wants to be a plastic surgeon when he grows up."

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Gifts from the House of Low Goals. mockup

Gifts from the House of Low Goals.

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'When I grow up I want to join the SWAT team!'

'When I grow up I want to join the SWAT team!' mockup

'When I grow up I want to join the SWAT team!'

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'Hey guys?. . . Help us think what Dale could do for his '15 minutes of fame.''

'Hey guys?. . . Help us think what Dale could do for his '15 minutes of fame.'' mockup

'Hey guys?. . . Help us think what Dale could do for his '15 minutes of fame.''

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"Remember—we're not Eagles fans or Patriots fans. We're Tom Brady Somehow Gets Humiliated fans."

"Remember—we're not Eagles fans or Patriots fans. We're Tom Brady Somehow Gets Humiliated fans." mockup

"Remember—we're not Eagles fans or Patriots fans. We're Tom Brady Somehow Gets Humiliated fans."

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"If we only use 10% of our brains, how am I supposed to get passing grades?"

"If we only use 10% of our brains, how am I supposed to get passing grades?" mockup

"If we only use 10% of our brains, how am I supposed to get passing grades?"

from $19.00

Well, wish me luck. Mom and dad can handle an 'A' and two 'B's, but I've REAL-L-L-L-Y got to spin the 'D' in math!

Well, wish me luck. Mom and dad can handle an 'A' and two 'B's, but I've REAL-L-L-L-Y got to spin the 'D' in math! mockup

Well, wish me luck. Mom and dad can handle an 'A' and two 'B's, but I've REAL-L-L-L-Y got to spin the 'D' in math!

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'This game is going to be a character-building experience.'

'This game is going to be a character-building experience.' mockup

'This game is going to be a character-building experience.'

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'I can't figure out whether I'm a secretary or an executive - I do executive work, but get secretarial pay.'

'I can't figure out whether I'm a secretary or an executive - I do executive work, but get secretarial pay.' mockup

'I can't figure out whether I'm a secretary or an executive - I do executive work, but get secretarial pay.'

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"Someday, I'm gonna be president of the United States."

"Someday, I'm gonna be president of the United States." mockup

"Someday, I'm gonna be president of the United States."

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"I promised myself I would never let this happen to me."

"I promised myself I would never let this happen to me." mockup

"I promised myself I would never let this happen to me."

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"Like many attorneys I was the runt of the litter."

"Like many attorneys I was the runt of the litter." mockup

"Like many attorneys I was the runt of the litter."

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'If hired, where do you see yourself with the company in five years?'

'If hired, where do you see yourself with the company in five years?' mockup

'If hired, where do you see yourself with the company in five years?'

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Balloons vs. Rockets

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"Baldo, you're smart, but you should study more. Don't you worry about your future?"

"Baldo, you're smart, but you should study more. Don't you worry about your future?" mockup

"Baldo, you're smart, but you should study more. Don't you worry about your future?"

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Masochistic Soccer Fan

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"The new position not only comes with a bump in salary, but allows me to extend my reach into areas where I'm not qualified."

"The new position not only comes with a bump in salary, but allows me to extend my reach into areas where I'm not qualified." mockup

"The new position not only comes with a bump in salary, but allows me to extend my reach into areas where I'm not qualified."

from $19.00

'I understand the school has a policy of promoting from within, so I'd like to be considered for your job when you retire.'

'I understand the school has a policy of promoting from within, so I'd like to be considered for your job when you retire.' mockup

'I understand the school has a policy of promoting from within, so I'd like to be considered for your job when you retire.'

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"The name's Bond. Duane Bond."

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The forgotten Grimm brother

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80 Million Euros for a football player. mockup

80 Million Euros for a football player.

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Second, third and fourth effort!

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A boxer refuses to give up after he has lost the fight.

A boxer refuses to give up after he has lost the fight. mockup

A boxer refuses to give up after he has lost the fight.

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Maps to the Hovels of Would Be Stars. mockup

Maps to the Hovels of Would Be Stars.

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"Baldo, have you given any thought to your future?"

"Baldo, have you given any thought to your future?" mockup

"Baldo, have you given any thought to your future?"

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"Misses 100% of the shots he does take. Still loves hockey."

"Misses 100% of the shots he does take. Still loves hockey." mockup

"Misses 100% of the shots he does take. Still loves hockey."

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I'm only a part time waiter, I'm really an actor...You may have seen me at the movies. Maybe, where do you sit?

I'm only a part time waiter, I'm really an actor...You may have seen me at the movies. Maybe, where do you sit? mockup

I'm only a part time waiter, I'm really an actor...You may have seen me at the movies. Maybe, where do you sit?

from $19.00

Say it loud! We suck and we're proud! mockup

Say it loud! We suck and we're proud!

from $19.00

Ambitious Underdogs Gifts Collection

Ambitious Underdogs Mugs

Explore our mugs for ambitious underdogs—perfect for daily motivation and a smile at the start of their day.

Ambitious Underdogs Pillows

Discover pillows for ambitious underdogs—comfort and inspiration combined for their living space.

Ambitious Underdogs Prints

Browse prints for ambitious underdogs—bring motivation and personality into their home or office.

Ambitious Underdogs T-Shirts

Check out our t-shirts for ambitious underdogs—wear your aspirations and humor with style and confidence.