The Curious Inability To Spend Money On Yourself

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Recently, I hit a major milestone in my journey to overcome what I like to call “frugality disease.” I spent $160 for an hour of private lessons for my two kids. In the past, I would’ve never paid such an amount. I’ve always been the type to teach them things myself, like swimming and bicycling.

But after seeing how much my kids enjoyed their parkour group lessons, I decided this was one of the best ways to decumulate wealth. Nothing makes me happier than seeing my kids happy—nothing. Plus, group lessons are hard to come by on weekends and I don’t have the equipment.

After the private lesson, I didn’t feel too much of the usual agony of “losing” $160. I know they won’t become college athletes with scholarships, let alone go pro, but the joy they experienced was worth it. Still, I couldn’t help but think about how much fresh crab and lobster $160 could buy—at least three pounds worth!

Despite this small victory in spending more money, I realized I still couldn’t bring myself to spend on myself. And that’s where the struggle continues.

The Inability to Spend Money on Myself

I’ve long believed that pain and discipline are necessary to achieve your goals. Being handed things on a silver platter often stifles growth.

Adopting a “broke mindset” can help you get rich, and feeling hunger—both literally and figuratively—keeps you driven. Whether it’s maintaining your weight by remembering those less fortunate or grinding away at a side hustle to escape a bad job, sacrifices are necessary.

So when it comes to spending money on myself, it feels like betraying the sacrifices I’ve made to achieve financial independence since 1999. I’ve been saving and investing for so long that buying things I don’t need feels completely off.

Let me give

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