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Back in 2012 I had to choose between a steady office job or a commission-only sales gig
I took the safe route and went with the office job at a property management firm in Austin. It paid $38k a year with benefits but man I was bored out of my mind after 18 months. Meanwhile my buddy took the sales role and within 3 years he was pulling in six figures but also had some terrible lean months. Looking back I wonder if I should have rolled the dice - has anyone here made a similar call and regretted it either way?
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jenniferwells25d agoMost Upvoted
The thing nobody mentions is that boring jobs sometimes come with boring coworkers who teach you boring but useful stuff. Like how to understand property tax assessments or negotiate with contractors. Meanwhile sales guys learn hustle but miss out on that institutional knowledge that keeps things stable later. I've seen both paths and the real regret usually isn't about money, it's about whether you picked something that taught you skills you'd still use ten years down the road.
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