It’s time to revisit the stigma surrounding debt

I argued that a lot of the advice we're seeing online these days is "built for the internet". In other words, the guidance is full of fixed and definitive rules of thumb and lacking in nuance. At one point in the conversation, I asked Kevin if he thought the abundance of information was causing people to overthink their financial decisions or oversimplify them.

His answer? "It depends."

A spirited conversation followed. We exchanged our controversial takes and I even admitted my own
shortcomings and highlighted where I tend to oversimplify as a recovering perfectionist. Even though I know better, I find myself still holding on to a nagging belief that my financial milestones have to be
achieved in an orderly, logical fashion.

I cannot even begin to tell you how much this flawed logic has cost me over the years. It is, by far, my
most expensive trait.

I built my life around this arbitrary list and then spent years telling myself that I couldn’t do anything
additional until I completed the thing before it perfectly. This kind of narrow "all or nothing" thinking
caused me to delay investing because I believed I needed to be completely debt-free before I started. I wasted so much time believing that I was making a principled decision when I was really suffocating
under the weight of my own perfectionism.

I'm obviously not trying to encourage anyone to ignore their debt or treat it with reckless abandonment. But I am suggesting that we need to stop talking about debt as if the only thing to do is avoid it.