Doing Hard Things FI Edition: Selling Shares I had a fascinating conversation with my friend, Kim, in NYC earlier this month: Kim reached FI and left her job literally two days before I saw her. She’s going to live off selling shares of index funds, and she mentioned all the talk recently in the community about FI potentially “not working” because people would be too scared to sell shares when the time came. While she said it did feel a little odd to finally need to sell shares after so many years of diligent savings, her brilliant point was as follows: It will only feel weird the very first time. Once that’s done, selling shares is just what she’ll do as part of life. We concluded that it’s just like any other hard thing in life. You do it precisely because you know it’s the right thing to do, and that once you’re on the other side of that initial discomfort, it’ll be a cakewalk.…