Can you earn Free Rider multiple times?

Can you earn Free Rider multiple times? - Crop skater riding skateboard on asphalt ramp in park

The title is self explanatory. I don't remember exactly how I got it the first time, but I was leaving the game open and alone for at least 10 minutes, and suddenly got it. I've also heard that its a random drop from getting jobs once they turn green, which I focused on for a good 30 minutes but didn't get.

dont-get-fired

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Can you earn Free Rider multiple times? - Side view of crop faceless black man skater in trendy outfit riding skateboard on street near park in sunny day

Can you earn Free Rider multiple times? - Positive young man skateboarding on modern ramp on sunny day

Can you earn Free Rider multiple times? - From above of crop anonymous male opening can of drink standing on sandy beach

What Is the Free Rider Problem?

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