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.
So, we have people questioning the validity of the entire concept of Financial Independence because they don’t think you’re adult enough to come up to that point of discomfort and get past it that one initial time.
I look at the FI Community as the most resilient, intelligent, and forward-thinking people I’ve ever seen.
I fully believe you’ll lean into those 5 minutes of discomfort when the time comes..
You’ll log into your brokerage account and you’ll enter the dollar figure you need to live on that month and you’ll hit the sell button.
You’ll breathe a big sigh of relief at how easy that was, and not believe how nervous you were.
Every subsequent month you’ll just sell your shares, because that was the plan you set in place 10-15+ years prior. And it’s working exactly as expected.