Optimizing Your Finances (and Taxes!) in 2022

(GCC: I am often asked, “Do you know any good CPAs?” and “What are some good tools for doing my taxes?” I never thought both questions could share a common answer – Kathryn from Making Your Money Matter is a CPA (who gets it) who has developed some very cool tools for doing taxes (and more) that cost less than an hour with a CPA. Disclaimer: links in this post are affiliate links.)

I remember the first time I found Go Curry Cracker and read one of Jeremy’s blog posts going through his tax return in detail. It covered his then-recently filed 2015 tax return, with over six figures of income and still no income tax due (only a small amount of self-employment taxes).

I’d like to say that I—a CPA—was intuitively able to do a quick review of the numbers and figure out pretty fast how this worked out. However, I had to pull out a pen and paper and calculate it by hand just to make sure it made sense.

Each spring since, I’ve looked forward to the annual tax return reveal. (GCC: 2021 tax return coming soon!)

If you have ever wondered, How can I optimize my taxes in the same way… without all the hassle of becoming a tax nerd first, well… have I got a tool for you.

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The Obamacare Tick-Tock

Thanks to the Affordable Care Act aka Obamacare, the health insurance options available to us are standardized. It definitely makes it easier to compare and contrast.

And thanks to a series of somewhat dated yet excellent blog posts (e.g. Obamacare Optimization in Early Retirement and Obamacare Optimization vs Tax Minimization) I have a clear understanding of how to balance costs and benefits.

Unfortunately, that balance seems to require either a cheap plan with insanely high deductibles (just pay the first $13,000 of medical needs out of pocket, good times) or an OK plan with decent benefits but restrictive income challenges.

So which did I choose? Both.

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Earning an Easy $250+ with Uber Eats

I recently read a post on Frequent Miler about a deal where you can earn $250 or more by becoming an UberEats delivery person and completing a single order. Though I don’t usually bother with low-reward, high-effort deals anymore (like gift card arbitrage), this one piqued my interest so I decided to give it a go – and it was easier than expected!

Definitely a good way to get a $250 Christmas Bonus. Would do again.

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