Tell HN: Oops Upwork did it again

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For me, this is a general freelancer market problem. As a freelancer, I have experienced what you’re describing. This is not different than anyone in your company who’s getting swamped in one project and has to drop the ball on everything else. Having said that, as a freelancer, I find it extremely important to be honest and set realistic expectations. If I cannot deliver, you don’t pay. If it starting to take more time, we have to talk before we go further. I do underestimate by nature; everything sounds easy until you start doing, it takes experience to guesstimate correctly.