Over Christmas break, Cora and Drew were looking to earn some money on their own. Cora wanted to repay a friend’s kindness by taking her out for a cupcake and juice. Drew has his eye on a Batman toy.

We had recently read the Tuttle Twins series, about twins that learn life lessons about economics, entrepreneurship, and the law.

For this week’s letter, I asked a couple of clients that work in tech security what are the most important practical steps the average person can take to protect their financial data online.

Budgeting can be counter-productive and leave us feeling worse than when we started. We’ll go through a period where we feel “spending shame.” We’ll get motivated to create a budget and stick to it. There are some people that can thrive on a budget. Others will stick to it for a few months and gradually stop. The last group will just outright rebel.

There is a better way to look at spending that can help you avoid the spend, shame, budget, repeat, cycle.

As many of you know, 10 years ago, I was coaching Texas High School football and teaching 8th grade social studies. My schedule was brutal. I worked until 7 most nights and until 10 on Thursdays and past midnight on Fridays. Saturdays were spent in the film room and Sundays were for grading papers and player performances.

In college, when I waited tables, I would get these nightmares where I had dozens of tables at once. We called them “Chili-mares.” Even though there were certain aspects of teaching I loved, I would have similar dreams.