We Didn't Plan This

The Podcast for People Who Ditched Their Five-Year Plan

About

Two doctors walk into a lunch. There’s no punchline — this is literally how we started the We Didn’t Plan This podcast.

We’d both spent years inside systems that are very good at telling you who to be and considerably less helpful once you start wondering if that’s actually what you want. We had the credentials. We had plans (or at least we thought we did).

What we didn’t have was a single honest conversation about what it cost. This podcast is us finally having it — with each other, with guests, and with anyone who’s ever hit every milestone and still felt quietly off-script.

MEET YOUR HOSTS

Faith Nadine Choo

Faith is a doctor (NUS Medicine ’21) who broke her public healthcare bond to become a freelance General Practitioner, and started writing honestly about the system she left behind — and then couldn’t stop.

Her blog, Chasing Faith and Love, has been running since 2016 and covers everything from med school admissions to burnout to how she’s building a less conventional life. She helps prospective students navigate medical school applications, and supports doctors figuring out what comes after the public sector.

She’s currently on a Barista FIRE journey — working 20 hours a week as a locum GP and filling the rest of her time with side quests (@faithisaunicorn, @drfaithnadinechoo): drawing anti-work comics (@theantiworkers), studying languages, baking, singing, and generally refusing to pick just one hobby.

Check out and subscribe to her YouTube channel here → The Side Quest Doctor

Isaac Ong

Isaac took the scenic route: law first, then medicine (Duke-NUS Medicine ’25), where he’s currently serving in the public healthcare sector. Outside of work, he’s an avid scuba diver, adventure lover and certified PADI instructor.

Somewhere along the way, he founded Summit Education (@summiteducation.info) to support students from their schooling years through early adulthood find direction, build confidence, and navigate everything from DSA to Ivy League applications. His students have gone on to Oxford, Cambridge, Penn, Cornell, and beyond.

He’s spent years inside institutions built on credentials and compliance, which makes him exactly the right person to co-host a podcast about questioning all of it. He believes mentorship is a relationship, not a product — and that identity should come before achievement. (The podcast is, in many ways, an extension of that.)

Catch up on his adventures on Instagram @twoyellowshoes.

WHY WE CREATED THIS

We’ve both spent a lot of time inside systems that reward compliance and punish detours. Systems that hand you a script early, tell you to follow it, and don’t leave much room for the question but what if I don’t want this?

The We Didn’t Plan This podcast is what happens when we stop pretending that’s fine.

If you’ve ever hit every milestone and still felt off — this podcast is for you. And thanks for joining us on this journey.