Changing my mindset about work

Brandon D. Wilson
5 min readAug 5, 2022

Roughly twenty years ago, I worked for a small, private company that a much larger company acquired. The new company announced that it was paying out everyone’s PTO balance down to just 40 hours. I had about 490 hours of accumulated PTO, the most of anyone in the department and probably top five in the company. That was a nice check, but was it worth the endless weeks and months toiling away without a break?

Some people never met a PTO day they didn’t like. As soon as they accumulate eight hours, they take the day. Good for them. As a manager, I have encouraged team members to take time off. The problem is that historically, I have failed to take my advice. How did I become such a workaholic?

The making of a workaholic

Fifth grade was the first year I brought home straight A’s on my report card. From that point on, my mom expected nothing less. If my report card had all A’s and one B+, she would ask, “What’s with the B+?” If I had all A’s and an A-, she would ask, “What’s with the A-?” If I had three A+’s and the rest A’s, she would ask, “Why aren’t the rest A+’s?” Oh, and forget about taking a day off from school. That was not allowed. I had perfect attendance all four years of high school. These high expectations carried me toward the status of Valedictorian in high school and graduating magna cum laude from college (missed summa by *that* much).

Once I graduated from college, I took the role of a middle school teacher as a 1999 Teach for America corps member. Even though we had plenty of holidays and breaks, I remember many teachers taking “mental health days,” but I took few of them. I thought the class would get behind if I weren’t teaching. I fulfilled my two-year commitment, took the summer off, and figured out what to do next.

I applied to work at the brand new Apple retail store opening up in the Chandler Mall. I didn’t get the job. I tried selling newspapers over the phone. I lasted less than two weeks.

Through a temp agency that realized I had some of the fastest hands in the West (on a keyboard), I started a 20-plus-year career in the healthcare insurance industry. My first role was keying medical claim forms. Despite being the new kid on the block, I still wanted to be the best. I entered into a friendly…

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