Welcome to Side Hustle School

We talk about why proposing an anchor date makes it easier to set plans with friends. We also include answers from Questioners about why they don’t like to answer questions—and how to get them to answer questions. Plus helpful ideas for grappling with grief. Resources & links rel ... Show More

Listening to Lady Gaga sing the theme song of iconic children’s TV show “Mister Rogers’ Neighborhood” made me pay attention to the song’s familiar words. I get choked up every time I hear them. Resources & links related to this episode: Get in touch: podcast@gretchenrubin.com Vis ... Show More

We discuss whether we might be expecting too much these days from the workplace, from marriage, from schools, from family. We also talk about the challenge of tackling a big project—and actually getting it done. Resources & links related to this episode: Listen to the Since You A ... Show More

A busy college student discovers a way to create his own schedule and make $2,000 a month by walking dogs.  Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challeng ... Show More

This listener needs help discovering his skills! In this episode, we discuss how ANYONE can identify and develop skills for a successful side hustle.Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin ... Show More

What does money really mean to you? In this episode, I break down the hidden truths about money—what it actually is, where it came from, and how it controls most of our lives without us even realizing it. This isn’t about getting rich—this is about freedom, peace, and purpose. Fe ... Show More

In this week’s “Failure Friday” segment, we hear from a tech professional who started offering design and development services as a side hustle. As the business grew, balancing it with a full-time job and personal life becomes overwhelming, leading to stress and performance issue ... Show More

In this episode, we discuss how to diversify your freelance income to create a more resilient business or side hustle.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 sho ... Show More

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: developing your skills as a “connector.” Side Hustle School features a ... Show More

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 efficientl ... Show More

In this episode, we'll explore the key milestones and financial targets that can signal when it's time to transition your side hustle into a full-time business.Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money with ... Show More

Do you feel like money always slips through your fingers? In this episode, I dive deep into the emotional and strategic foundations of building real wealth. If you’re ready to completely transform your mindset, habits, and life, I’m launching something powerful — and I want you ... Show More

A freelance graphic designer, is struggling to keep his side hustle going amid global upheavals. What strategies can help you maintain momentum even when it feels like the world is falling apart?Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ... Show More