I have a sedentary job, so I was not worried that gaining weight would affect my work.
The biggest challenge for me was getting over the fear of what other people would think or say about me. I was fortunate in that I relocated for a job that moved me away from my friends or family. Yes, some of them would eventually see me as I gained weight, but it was not a daily concern.
I gained weight and, while my co-workers noticed it, they generally said nothing about it. The times I met with old friends and family turned out to be nowhere near as frightening as I thought. Some mentioned my weight gain, but it was more in passing and not a big deal at all.
This emboldened me to really ramp up the weight gain and, thanks to the high turnover rate at my job, we have a lot of new, young employees who have always known me as fat.
I love being fat and have enjoyed the weight gain process. I have zero regrets, but keep in mind that gaining weight is much easier than losing weight. If you're curious, read about set-point theory. For many people, weight gain is a one-way road.
If you're unsure, you can always try gaining a little weight, perhaps 25 pounds or so, just to see how you feel about it. If you like it, you can always gain a little more. If you don't like it, then it's best to stop. If you end up loving it, like I do, you may find yourself going all-in and using heavy whipping cream to rapidly gain weight (think 5+ pounds per week).
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