Unexpected money mistakes to take charge of now

I've made more money mistakes than I can count. There were $700 wedding shoes and a $26,000 new car. Then, there was the actual wedding that I still haven't blogged about because I don't even know what it cost. A lot. It cost a lot. But these mistakes actually don't bother me. In fact, unlike many people in the personal finance world, I don't actually consider them to the biggest money mistakes I could make.

When it comes to ruining myself financially, Jimmy Choo isn't going to do it. Toyota isn't going to do it. I am. I continue to allow a powerful combination to exist in my life: fear and a lack of information. While I'd like to blame all of the things in my life–and if you've read my blog at all you know there is a lot of stuff–I am my worst money mistake.

MONEY MISTAKE #1 – Benefits
It's open enrollment season. Since we switched to open enrollment maybe two years ago, I've dedicated all of five minutes to weighing my choices. And by weighing my choices, I mean clicking "Accept" twenty times to or so in order to keep things the same. Homeostasis. No change. Nothing to see here. That's a mistake.

I now realize that I might be able to leverage the HDHP/HSA option to my advantage over the PPO plan that has always been the best. There's platinum in the PPO name. Clearly, it's the best. I know. I'm embarrassing myself. The same goes for all the other optional benefits. I've always declined them because I'm young, invincible, and too busy grading 97,000 essays to take the time to educate myself on myself. In an attempt to do things differently this year, I'm spending time with each option. The problem is, I'm not sure I can educate myself in a way where I feel confident before open enrollment ends. As much as I can tell myself to make the jump, I need to be good and ready. And please don't rush me. I'm learning.

MONEY MISTAKE #2 – Investing
If you follow me on Twitter, you know that I have a love-hate relationship with investing. Because it's really scary. I don't care what anybody says. Those overinflated hypothetical situations aren't for me. The truth is investing is a risk, and that's easier to stomach for some people that others. And sometimes it's really exciting, like when my Roth IRA magically turned green after weeks and weeks and weeks of red. Oh, the red! I still don't like it, but I'm starting to get it. Thanks in part to my husband and also people like Des, Maggie, Our Next Life, Emily, and Mr. and Mrs. Groovy.

The next hurdle, though, is figuring out my 403(b). Now that I realize I have the option of investing with Fidelity, money gurus like Ed and Leigh have been really helpful with shedding light on options that will feel similar to Vanguard. For a long time, I felt too stupid to ask questions, especially when there is so much information already written. Just read it, yeah? But people have been beyond helpful now that I'm finding the courage to ask.

When I first started blogging, I set goals for myself. That lasted for exactly one month. I've tried to revisit them several times along the way, but they're just too complicated. It's not that I don't understand SMART goals. Trust me, I've read all the posts on them. And there are a lot.

It's that up until now I haven't realized understood the true obstacles. On some level, the hurdles are optimizing my benefits and reducing my pre-tax income. But my real goal is to feel more confident, to ask more questions, and to be less scared of money. The problem is there really isn't a metric for that. The days when I open my Vanguard account and see an 11.5% year-to-date return make me feel like Warren Buffett. But that's the market, not me, not really. I want to get to the point where I'm confident regardless of what the market, the blogging world, or anyone else says. And how do you write a SMART goal for that?

Money is power. Admitting I don't know something–lots of somethings–makes me feel weak. I joke a lot about people taking away my PF card. It's really not a joke. But maybe if I ask enough questions, if I own up to the fear and the ignorance, maybe we can figure out this money thing together.

So Tell Me...Is there anything you wish you understood better? What do you consider your biggest financial mistake?

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