Ep 22: For When You're Bad with Money (with Cait Flanders)

Ep 22: For When You're Bad with Money (with Cait Flanders)

Scroll down to stream the episode here and for show notes. Or, click the buttons below to listen on your favorite platform.

I’ve wanted to do a money episode for a while, but I didn’t think I was qualified, so I didn’t. Which pretty much sums up everything.


From being scolded for my (many) spending mistakes as a growing consumer to a perpetual cycle of feeling powerless and incapable of handling money into my adulthood, I’ve come to live in a constant state of panic about my finances. I think about money 95% of the time, and usually not in a “I’m such a money magnet!” type of way. It’s more of a cycle of going from getting paid (“Woo! I’m rich, bitch.”) to spending mindlessly (“Eh, I don’t know if I need this but I just got paid and it’s not that much and I’ve felt restricted for so long fuck it!”) to feeling guilty (“Wow you’re an asshole and you’re going to pay—literally—for that later!”) to realizing I have bills coming (“Oh, did you forget about us? Yes, Adult, you have a phone and electricity and insurance and credit card debt, but funny how you forgot when you bought that third Voluspa candle. Asshole.” – Bills) to spiraling because pay day isn’t for another week (“Oh no, I’m going to run out of money, how did I get here again, am I going to Money Jail?!”) to PAY DAY!

Any attempt to turn it around would eventually plummet right back in the cycle.

Yeah, so, how could I possibly do an episode on it?

Because—I realized—a lot of other people feel like that, too. And we believe it will always be that way, because that's the way it's always been.

And that thinking influences every money-related moment: spending, paying off debt, getting a loan, asking for a raise. The list goes on.


I used to think that if I made more money, found $10,000 on the street, paid off some debt and got things like “assets” then the cycle would dissolve on its own. But then a lot of those things happened (except the $10,000 on the street, but that’s why I always look down) and my relationship with money didn’t really change. I would find myself in the same panic approaching pay day, in the same shame-cycle that I’d spent too much and saved too little, that I was doomed to a bleak financial future.

So, if more money, more savings, and less debt weren’t the solution, what was? 

(Hint: It's in this week's episode.)

I was introduced to this week’s guest by my friend, Ann, a fellow Worrier of Money. She told me she knew this Wall Street Journal best-selling author, personal finance blogger and former in-a-shitload-of-debt-er, Cait Flanders, and we just had to talk.

Like I said, I’d wanted to do this episode for a looooooong time, and when I read Cait’s blog, book and her email to me saying “Yes, I’ll be on the show,” I knew she was the right person to do this episode with.

Because even though the details of our stories are a little different, the same underlying theme was the same:

We were telling ourselves we were powerless to money. And that that’s the way it was always going to be.

But then Cait embarked on The Year of Less, in which she stopped shopping, gave away most of her stuff, and challenged everything she believed about herself and money. She talks about getting out of debt, budgeting, mental traps she’d find herself in with money, and how she completely changed her relationship with it.

And how that’s possible for all of us, too.


Cait's Book

Debt Free Forever book

Cait's Blog

Money-saving Apps that have worked well for me like Acorns and Qapital


Ep 23: For When Everything Hurts (AKA Managing Stress & Pain)

Ep 23: For When Everything Hurts (AKA Managing Stress & Pain)

Ep 21: For When You Don't Know (Part 2)

Ep 21: For When You Don't Know (Part 2)