Welcome to the episode where Caitlin exploits having a podcast with Sara to get Sara to tell her whether or not to sell her house. Does Sara take the bait??

In true Sara fashion, she leans into empowering Caitlin to make her own damn financial decisions, offering a framework to make big one-off financial moves.

Like, how scared are we supposed to be of tax implications? (And what is a capital gain tax and how the hell could it possibly apply to a normal person like me?) And, how can we tell if the stories of our past financial successes are standing in the way of making new decisions that make sense for our future? (Caitlin raises hand.)

Caitlin relishes the power of a “good deal” story, and how maybe those stories are worth their weight in gold (but not helpful in building a future, reality-based investment portfolio, perhaps.) Do you remember the time Caitlin found a Le Creuset dutch oven at a Goodwill in 2007? She does! And she’ll tell you all about it!

Also, along the way, some ins and outs of the consequences of investing in real estate rather than index funds, and the emotional/financial/logistical math that goes along with owning rental properties.

Listeners - what do you think?? Should Caitlin sell her house??

Ask us your dumb investing and finance questions for Season 3 on our Ask Us page!

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This episode was edited by our co-producer Kelly West. Music by Bad Bad Hats and Devmo.