Chicago’s Substack

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Chicago’s Substack
Chicago’s Substack
Inside Chicago Southsider: How We Landed Our First Intern (Step-by-Step)

Inside Chicago Southsider: How We Landed Our First Intern (Step-by-Step)

Behind the scenes of our first internship — the wins, the lessons, and the responsibility of shaping future leaders.

Jul 09, 2025
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Chicago’s Substack
Chicago’s Substack
Inside Chicago Southsider: How We Landed Our First Intern (Step-by-Step)
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Photo by Sam Balye on Unsplash

Hey Chicago Southsiders,

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Let me say this loud and clear:

Running a news organization is not a solo sport.

When I started Chicago Southsider, I was on a mission — to tell the stories about the people and places that make the South Side an essential part of our country’s history.

A place where forgotten history runs deep, where culture still breathes through murals, music, and memory, and where people are working every day to make this community better than they found it.

But trying to do all of that with a lean team and budget?

It’s not for the faint of heart.

Then one day, a friend casually mentioned something that stuck with me:

“Why not work with interns?”

Game-changer.

Chicago’s Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.


🍽️ Before we get into the meat and potatoes...

Let me say this: no one gave me a roadmap.

I didn’t have a guidebook, a template, or a contact list. I didn’t know which departments to reach out to, how to make the pitch, or what interns actually need in order to succeed.

So I learned the hard way. I figured it out through trial, error, and a lot of late nights. But now? I’m saving you time.

Whether you're thinking about bringing on an intern, curious about how we do it behind the scenes at Chicago Southsider, or just want to understand how to grow your mission with limited resources — this step-by-step guide is for you.

Keep reading to unlock the full post and get:

  • The exact department I contacted to land our first intern

  • How to structure a job description (and an example of the one I submitted)

  • What I’ve learned about working with Gen Z (and what to avoid)

  • Why this one step could change the future of your mission

Become a paid subscriber to unlock the full guide.

Chicago’s Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

You’ll get instant access to this post and future editions that take you behind the scenes of building legacy, leadership, and local media on the South Side.

👣 Step-by-Step: How We Landed Our First Intern (and How You Can Too)

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