Taxes and optimizations

By my early estimates, I’ll owe between 5k and 7k in taxes come April due to some oversight of mine throughout the year. I’m frustrated not that I owe more taxes, but that I didn’t plan appropriately to space that out over the year. I believe I receive ample return on the taxes I pay and could arguably pay more and still be happy.

For a few years now I’ve wondered if I would be paying less taxes if I had a CPA do my taxes for me – primarily due to my (now two) rental properties. I’ve contemplated if it would be worth having the CPA refile my taxes for the past several years.

It was this morning at the gym that I realized I had two contradictory mindsets about this. If I believe I receive great value for my current taxes, why do I feel the need to optimize the amount of taxes I pay? Because I love optimizing things – it’s why I love performance work – I’m OCD like that. This instance, however, is ridiculous. It’s not worth my time if I’m already happy with the current state.

One could view this as a sort of self-awakening, a realization of the bigger picture. While that’d be nice, it’s wrong. In reality this is just more actualization of my optimizing OCD. In this case I’m just optimizing my global time utilization instead of the more localized tax payment!

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I'm a gay geek living in Seattle, WA.

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