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Why Personal Finance is Like Cross Dressing

This is a very special post dedicated to my friend JT McGee at Money Mamba, who is not a cross dresser (as far as I know). Please visit his site, where he will be linking to this post, very reluctantly I’m sure, in every post roundup for the foreseeable future. (Bwahahahaha!) He also blogs about cool stuff like economics, money, and politics.

Disclaimer: I am not in any way trashing transgendered people or those who cross dress. I’m a psychotherapist and member of PFLAG, not a hater. If you are offended, I truly apologize.

I’ll be honest – this post started out as a joke about earning Klout and driving traffic to my site. But the more I thought about it, I realized that personal finance can be compared to just about anything. Other bloggers have compared personal finance to potty training, fantasy baseball, religious evangelism, and even puberty, so I thought, Why not cross dressing? If blogging has done nothing else for me, it’s given me confidence that I can write about the weirdest, most random crap ever and someone will read it. (They may not enjoy it, but they’ll read it.) In order to prove that point, I will provide you with five safe-for-work reasons why personal finance is like cross dressing.

1. Personal finance is a taboo subject.

There’s a reason so many of us blog anonymously – we are deathly afraid that our friends or family will discover all the details we post about our finances. Money is a fine topic as long as no one starts using real numbers or talking about their bank balances. People are reluctant to admit and deal with their financial problems, which is part of why the United States is falling apart right now. How many news stories have we seen where someone committed suicide because s/he was in debt and didn’t know how to find a way out?

Compare this to the people I’ve known and/or treated who cross dress, and it’s much the same. They spend way too much energy concealing a big part of themselves from their loved ones. They suffer tremendous anxiety, stress, and depression due to feeling like there is no solution. They torture themselves wishing things were different.

2. Personal finance involves hard work but can also be rewarding.

It sucks to sit down and actually look at all your bills and expenses. It’s not always fun. In fact, the #1 reason people tell me they don’t budget is “I don’t want to know how bad it is.” But if you get through it, you can make changes and end up with a far better future.

Similarly, the act of cross dressing takes considerable time and effort. Ever been to a drag show? (If not, ever watched Mrs. Doubtfire?) The transformation from male to female, or vice versa, takes a lot of time. You get sweaty and uncomfortable. You get frustrated. And in the end, the results make you sit back and marvel at how different things have become.

3. Personal finance is misunderstood.

A select few of my friends know I blog about my finances, and they all say the same thing. “Yuck, I could never do that! You mean you actually tell people when you screw up and spend money? I’d never be able to quit posting!” People think of personal finance as some torture chamber where Dave Ramsey takes your car away and Suze Orman screams “DENIED!” in your face. They put off making change because they don’t understand what it means to take control of their finances.

Think about how the average person responds when they hear “cross dressing.” (I can only imagine what some of you thought when you saw this post!) When someone wants to wear clothes made for the opposite gender, people just freak out. They assume it means the person is gay. They make comments ending in “unnatural.” They cover their children’s eyes. If any of those people would ever calm down and just talk to someone who cross dresses, they would see that their assumptions don’t have anything to do with the way it actually works.

4. Personal finance is diverse.

Don’t believe me? Just look at some of my fellow bloggers’ websites. There’s personal finance advice for parents, single people, college students, retirees, investors, people with debt, people out of debt, broke people, rich people, kids, teenagers, ninjas, health nuts, coupon clippers….

The cross dressing world is also diverse. There are people who cross dress for theater. There are people who are transgendered and awaiting reassignment surgery. There are bank presidents who wear women’s lingerie under their $300 suits just because they get a kick out of it. One size does NOT fit all (see what I did there?).

5. Personal finance is none of your business. Or mine.

With all the time we spend writing about money, none of us PF bloggers can tell you how to live your financial life. We have opinions, but ultimately, you’re the one who knows what’s best for you. You know what your expenses are and what works for you and your family. If you want to write about your finances here on the interwebs, I’ll personally do what I can to help you get started. If you don’t, no one is going to hunt you down. Personal finance is different for each of us, and that’s what makes it possible for people like me to tell my story without worrying about whether people are going to judge me.

Cross dressing is also a very personal thing. If my guy friends want to borrow my mascara or my girl friends want to shop for lumberjack boots, it’s really none of my business what reasons they have for doing so. My opinion doesn’t amount to a hill of beans because it’s not my life. If you found this post through a web search for cross dressing, you’re probably leaving disappointed please don’t let other people tell you how to be who you are. Take the information that works and leave the rest.

If you’re interested in learning more about cross dressing or transgender issues (but not their relationship to personal finance, unfortunately), consider reading my favorite book on the subject, She’s Not There: A Life in Two Genders (not an affiliate link). The book tells the true story of a college professor who made the brave decision to stop living a lie. It’s well written and provides SO much good information on the subject. 

About Andrea Whitmer

Andrea is a freelance web developer and mom trying to maintain a sense of humor in an otherwise chaotic world. She blogs in hopes of helping others avoid the same mistakes she made in the past. Join in the discussion here on So Over This, or connect on Twitter, Pinterest, Instagram, or Google Plus. You can also subscribe to new posts via RSS so you never miss out!


  1. Hahahaha.. I feel lucky that I saw this bet being formed on Twitter.  Sorry JT.  It's actually a really good article and JT is lucky to have to link to it from now on.  🙂

  2. this. is. awesome.

  3. Very well written and high quality post. Personal finance, for what ever it is, a very rewarding almost always if its laws are followed.

  4. Love it!  When I read your lead in I was thinking how in the h… is she ever going to find comparisons – but you did!!

  5. Anonymous says:

    Brilliant post. Hoping this gets a lot views.

  6. Nailed it!  This is truly amazing. Great job.

  7. That was a good book. It was especially interesting to reflect on it when one of my college professors was going through transition last year. I wasn't in the class, but I heard all of the hateful comments made by my fellow students who were.
    I hope, for the professor at my university, that as she gets new students, they won't see anything "scary" about her. It's too bad that dealing with someone *else's* transition seemed so traumatic for my peers 😉

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