How I make money, points, and miles paying off student loans

I have two theoretically competing goals right now: paying off giant student loans and traveling around the world to experience the best in beauty, in person. Those goals don’t have to be in conflict. I’m about to wordvomit every tip and trick I’ve picked up along the way for creatively paying off student loans and snatching cash, points, and miles while doing it. I’m doing to my student loans what Accutane did to my acne. And lower back.

There are plenty of sites that can give you the student loan payoff 101 — I’m not here to cover that well-trod ground. Instead, I want you to just walk away from this post more engaged with your money in some way. I also want to encourage readers with student loans to think creatively about how their loan payoff strategy can pay off in ways that make life bigger.

Disclaimer: I’m not a certified financial anything. I’m just a Renaissance historian who hates debt and loves free, fancy travel.

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Hot Take: Inside the Norwegian Bliss Spa Thermal Suite

Edit on 210519: ok, so this hasn’t aged well hahaha. You and I probably won’t be going to the Bliss spa any time soon, and I’m getting an antibody test later this week to try to determine if the weird mystery illness I got after our cruise was COVID, so maybe stick to a sheet mask?


It was announced earlier this month that Gwyneth Paltrow’s lifestyle brand goop is heading to sea with Celebrity Cruises. I’m not a goop person at all (it seems like a very vagina-focused brand, while I see fanserviced as more pussy-adjacent), but I’m a bit delighted that someone with a lot of Treat Yo’ Self-Care cultural power is recognizing that cruises can offer more than children playing in the adult pool and norovirus-vector buffets.

It turns out that goop at sea isn’t so much a whole chartered cruise (groups ranging from Weight Watchers to furries have chartered private and semi-private cruises before) as a single goop day on the yet-to-launch Celebrity Apex with some goopified accents throughout the sailing. goop at Sea (oh god, that’s the real name) is available only to people who book in the suite category and pay an additional $750 per person for a ticket, so prepare to pay up if you want to take part. When I quickly estimated the cost for two people to sail with goop, the price was just over $10,000 — and that’s not including flights to and from Barcelona or any extras. I seriously wonder if anyone other than journalists looking to blow their legacy publication’s travel budget for the year are going to book this.

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