Episode Description

Trevor and Joe sit down with Caroline Lupini, freelancer extraordinaire, to discuss how she got into full time writing, her life as a digital nomad, what her parents thought of all of this and more. We also discuss some of her favorite countries and her wildly variable accommodations while out of the country.

In our Patreon only Final Boarding Call segment, we discuss applying for credit cards while abroad, why she mains the Chase Sapphire Reserve despite other cards catching up, and ask – “Sup with Citi?”.

Interested in listening to the bonus segment? Find out more about subscribing on our Patreon page

Episode Notes 

2:45 – Introducing Caroline

3:47 – How she got into travel writing 

7:20 – What does the life of a freelancer look like?

13:08 – Where she’s been, how she pays for her travel (when miles, when cash?) 

16:17 – Mitigating risk and things to think about when staying at AirBnBs

19:23 – Country counting 

21:28 – Experiences in Iran and Cambodia

25:00 – Caroline’s planning process before and during travel, her experience staying in hostels regularly (Trevor faints)

29:29 – Do you think you’ll stay on the road forever? Could Joe or Trevor do this?

33:27 – What her family thought of the whole travel all the time idea, and what they think now 

37:23 – How do you earn miles and apply for credit cards while traveling all the time (Patreon only) 

41:43 – Why the Chase Sapphire Reserve is Caroline’s go to card (Patreon only) 

46:13 – Sup with Citi? (Patreon only)

Find all the places Caroline writes on her website.

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Music: “Ten Hundred Years” by Poly Action, “Feet Gone Soft” by Monplaisir, and “Feet Gone Wild” by Monplaisir