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Side Hustle School

Ep. 3425 - First $1,000: The Med School “Decision Doctor”

Side Hustle School

Chris Guillebeau

Entrepreneurship, Entrepreneurship,, Careers, Small Business, Business, Side Hustle

4.73.3K Ratings

🗓️ 18 May 2026

⏱️ 6 minutes

🧾️ Download transcript

Summary

In this week’s First $1,000 segment, we hear from a medical resident working in Chicago who has a side hustle as the med school “decision doctor,” helping students and interns navigate crucial decisions.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.


Show notes: SideHustleSchool.com

Email: team@sidehustleschool.com

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Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com


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Transcript

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0:00.0

The Med School Decision Doctor.

0:10.2

Hey friends, what's up?

0:11.4

Welcome back to Side Hustle School.

0:13.3

It's Chris Gillebeau, your host.

0:14.7

In this week's first $1,000 segment, we're going to hear from a medical resident working in Chicago

0:19.6

who has a side hustle as the

0:21.7

med school decision doctor. He helps students and interns navigate crucial decisions. This is a big

0:28.0

market. All kinds of people are going through the med school process. And the stakes can be high in this

0:33.5

process because some of the choices that you make in terms of your study plans, in terms of

0:38.0

applying to different schools, in terms of selecting a specialty and so on, I'm sure there's more to

0:42.9

it, but there are a lot of different decisions you make that can affect the rest of your life

0:47.8

in this world. So Clarissa, this medical resident, she has found a way, you know, because it's not enough to be a doctor. She's got plenty of extra time in her life, apparently. She has this side hustle and she's making good money with it, helping people. So let's look at how she made her first $1,000. And what might this mean for you? Perhaps there's something you can do as well. That's the whole point of our podcast.

1:15.1

I'm going to bring you Clarissa's update. Well, her story, I should say, I'll come back at the end with a few words of wrap up.

1:26.6

In the world of medical education, I, Dr. Clarice Reynolds, a senior attending at a hospital in Chicago, found a side hustle opportunity that hit close to home.

1:37.3

My experience navigating the convoluted path of med school and residency sparked a desire to guide others through this journey. I remembered

1:45.8

the countless nights I spent fretting over major decisions such as choosing a specialty, ranking

1:51.0

residency programs, and deciding on fellowships. Each decision carried a weight that could

1:55.6

shape my entire career. It was during a late-night discussion with fellow doctors reminiscing about

2:00.1

our early years that I had my eureka moment.

2:02.9

The realization that many students and first-year residents grapple with the same decisions we once did was a calling.

2:09.3

I could use my experience and insights to make a difference, and so my side hustle was born.

2:14.6

I set out to offer decision-making consultations for those at the crossroads of their medical journey.

...

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