Essays & Confessions

How To Ask Your Most Embarrassing Questions About Money (Or Life)

By | Monday, February 01, 2016

Ask Chelsea Anything_Graphic_title card_v2

Over the past few months, I’ve received a lot of questions. Most of them have been emails asking for advice on life situations (usually involving finance to some degree), but a lot of them have been more to the point: when are you going to start an advice column? Apparently, I have deceived you all into thinking that I have a modicum of perspective on life — mine or others’ — and that this is something I should be sharing. And while I feel strongly that I am a sizzling hot mess who is not capable of doing much for anyone besides semi-regularly feeding her dog, I have made a lot of mistakes in life. Like, a lot. And I suppose what might set me apart in that regard is that, mostly on this blog, I really force myself to confront those mistakes as much as I can. It’s not a perfect system, but it sure as hell makes me feel accountable for something, and has resulted in a lot of tangible improvement.

So I’ve decided it’s finally, probably time to start this dang column, because after over a year of doing a lot of confronting my own bad habits and past mistakes (financial and otherwise), I feel a lot more qualified to share what I’ve learned.

To help me, I’ll be consulting experts and people much smarter/more accomplished than me to guide us all on the path to independence, fulfillment, and balance. Sure, there will be some things that I can answer myself (and I’m guessing that nine out of 10 of those answers will be “dump him”), but it’s a good chance for us all to learn a little more, myself included. So even those really down-and-dirty money questions, send away, because I’ll do my part to find the right person to answer it.

And if your question is just about life, don’t be shy, either, because TFD is not just about money. It’s about living better in every way you can, and sometimes “deleting certain people from your phone” is just as essential as “saving your emergency fund.” No question is too silly, and no mistake is too big. (Trust me, I’ve probably made all of them, and probably in a more embarrassing/public way.)

So ask me your questions, and I’ll do my best to answer them here on TFD, once a week. Send them to

I’m waiting to hear from you.

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