Side Hustle School

Chris Guillebeau / Onward Project•sidehustleschool.com

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/

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Episodes

Ep. 3020 - Q&A: “How do I manage last-minute requests without burning out?”

In this episode, we explore how service-based freelancers can manage last-minute client requests without sacrificing quality or burning out. Learn how to build buffer time into your schedule and set clear project boundaries. 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 Emai...

Apr 08, 2025•5 min•Ep. 3020

Ep. 3019 - First $1,000: Miami Divorce Planner Offers “Freedom Celebrations”

In this week’s First $1,000 segment, discover how a former wedding planner in Miami pivoted to organizing “freedom celebrations” for newly divorced clients, landing her first thousand dollars from two high-end events. 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: SideHustleScho...

Apr 07, 2025•7 min•Ep. 3019

Ep. 3018 - Weekend Workshop: Design Your First Workflow

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: creating clear, repeatable systems for running your business efficiently. 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 li...

Apr 06, 2025•7 min•Ep. 3018