Embracing My Flaws in 2016

Photo: Charleston TheDigitel / Flickr

I’m the kind of person who doesn’t learn without making mistakes and making those same mistakes repeatedly. In 2016, I’m afraid that, for my own good, I’m going to have to keep making some financial missteps.

For most of my adult working life, I worked full-time jobs with great health and 401(k) plans. I signed forms that HR told me to and didn’t think much about the real cost of things. Then I quit my full-time job in the summer of 2014, and have had my eyes opened.

In 2015, I went to an ear, nose and throat doctor to find out that when they put a camera up your nose, it’s called an endoscopy and it costs about $850. With old health plans, these kinds of visits were covered. But, under my new plan, since I hadn’t hit my deductible, I was responsible for all of it, plus the cost of the visit. I actually found myself getting nostalgic for copays and flexible spending accounts. Who does that?

But do you know what I’ll never forget? What a deductible is in a health care plan.

I used my father’s accountant for my tax return for years, and she charged $1,200, then $1,500. This year I used TurboTax. Next year I’ll be using a local accountant who specializes in freelancers who will charge a few hundred dollars.

Now I’m keeping every single receipt and measuring the dimensions of my desk for the home office deduction.

I inherited a car from my father and kept it in Brooklyn for a few years. I could teach a master class in getting parking tickets from the classic “parking too close to a hydrant” to “having expired registration and inspection stickers.” I learned how much new brakes, brake lines, new tires and a new door handle for a 1998 Toyota Tercel cost. I gave the car to charity so, I learned that a beat up used car will probably only get you a five hundred dollar tax write-off, not its Blue Book value.

So: Whenever I find myself in a nice car, I appreciate the hell out of it. I’m sure by next year I’ll have screwed up my Zipcar account somehow.

Among my other genius moves, I kept a gym membership that I didn’t use, I continue to use Time Warner cable, and I refuse to calculate how much I spent on Starbucks this year. I’ll save that until next year.

These things may sound like lessons that a 38-year-old should have already learned, but I never had that crappy job phase in my twenties where I scraped things together.

I was fortunate, but everything about my money felt automated—hidden behind some curtain. I worked and received insurance cards and biweekly pay stubs with a list of numbers, and I just assumed everything was going along as planned. I didn’t know the inner workings, but that’s changing.

Now I know where every single dollar goes. I’m sure I’m going to keep wasting some, but I know that each of those decision is mine.

Tom Stoppard said, “Age is a very high price to pay for maturity.” So is cash. But if it helps you avoid the same mistakes in the future, it’s not a bad investment.

This article is part of The Billfold’s 2015 end-of-year series, “Our Best Selves in the Coming Year.”

Rob Penty is an improviser, storyteller, writer, and web developer living in Brooklyn. Check out his blog.

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