What Would I Have to Accomplish to Finally Feel Good Enough?: The Oreo Math That Erases Every Win

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Do you ever feel like one mistake cancels out everything good you’ve done?

I was sitting with that question early one morning, before anyone else in my house was up. I expected to answer with a number in my bank account, a title or a goal weight. Instead my brain went straight to failure. I couldn’t tell you what good enough looks like for me, but I could list every single thing that knocks me out of it.

In this episode, I share what I call the Oreo math. There was a time when I tracked every calorie. I’d spend two hours at the gym, burn 300 calories, then come home and eat three Oreos at 75 calories each, and in my head the whole workout was gone. Once I noticed it, I started seeing that same math everywhere.

At work, I turned a struggling client relationship around and got caught on video being called “such a joy to work with.” Then they disabled our product with no warning, and one loss felt like it erased every win before it. With money, I earn six figures in a career I built without a college degree, and I’m still in debt. In my head, the debt cancels out the whole thing.

I don’t have this figured out. I’m still in debt, and I still feel it in my chest when a client leaves. But I’m practicing letting the good stuff count at least as much as the hard stuff.

If you grew up with not much money and not much backup, you may have learned early that one mistake could cost you a lot. This conversation is about checking that voice’s math before you take its word for it.

In this episode:

• The question that sent my brain straight to my failures.
• What the Oreo math is, and how one slip can feel like starting over at zero.
• The client I lost after turning the relationship around, and why one loss can feel like evidence you don’t belong.
• How the Oreo math shows up with money after a career glow-up.
• Why I built my own system so the good column gets to count.
• Why keeping track of your wins is a skill some of us were never handed.

Something to consider this week:

The next time you think “well, that ruins everything,” do the math out loud. Write down exactly what you think the mistake just canceled out, then ask yourself whether that math is actually true. Then write down one thing in the good column. It doesn’t have to be big. It just has to still count.

Discover your perfectionism pattern

Take the free Perfection Hangover Archetype Quiz to explore the patterns that may be showing up in your decisions. It can help you put words to why one loss feels so much heavier than ten wins. My result is The Prover. What resonates with you?

If a friend came to mind while you listened, send her this episode. It might start a conversation you both need.