| Achievement | How to unlock
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| - Survive for two years without losing.
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| - Purchase five unique items in one game.
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- All That Schoolin' Paid Off!
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- And I Could Walk 500 Miles
| - Walk for 500 seconds in one game.
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| - Hoard $100,000 in Cash in one game.
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| - Buy 100 cookie jars in one game.
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| - Purchase twenty unique items in one game.
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| - Purchase twenty-five unique items in one game.
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| - Purchase all thirty-five items in one game.
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| - Survive for one year without losing.
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| - Hoard $50,000 in Cash in one game.
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| - Start ten jobs in one game.
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- It's Not An Addiction, I Swear!
| - Spend $1000 on lottery scratch cards.
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| - Buy all education talents in one game.
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| - Get fired from 10 jobs in one game.
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- Midlife Existential Crisis
| - Get fired from 20 jobs in one game.
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| - Purchase ten unique items in one game.
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| - Make $1,000,000 in Cash in one game.
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| - Survive for five years without losing.
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| - Make $250,000 in Cash in one game.
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| - Survive for three years without losing.
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| - Spend $5000 on lottery scratch cards.
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| - Purchase fifteen unique items in one game.
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| - Buy 30 Grandfather Clocks in one game.
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- Worthy Viewer of Viewingne
| - Watch the credits until the end.
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| - Purchase thirty unique items in one game.
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| - Try to finance more than six items at once.
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| - Survive for four years without losing.
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