069: Start Your Teacher Side Hustle in 2025

How to Use Live Challenges to Grow Your Online Business

Are you looking for a powerful way to launch your course, membership, or digital product? Or maybe you’re a teacher looking to start selling your own resources on Teachers Pay Teachers? In this episode, I’m diving deep into live challenges—why they work, how to structure them, and how you can use them to grow your business. Plus, I’m sharing all the details about my upcoming FREE 3-Day Teacher Resource Challenge happening this March!

In this episode, we’ll discuss:

1. What is a Live Challenge & Why They Work

How hosting a free (or paid) multi-day challenge can help you connect with your audience and sell your offers.

2. How I Run My 3-Day Teacher Resource Challenge

A breakdown of my challenge format, including engagement strategies, action steps, and how I nurture participants.

3. Live vs. Pre-Recorded Challenges

The pros and cons of each format and why I prefer pre-recorded content for my trainings.

4. How to Use Challenges to Sell Your Course or Membership

The strategy behind transitioning from free challenge content to opening doors for your paid program.

5. Exclusive Details on My Upcoming Challenge

What you’ll learn in my FREE 3-Day Teacher Resource Challenge (March 14-16), and how you can sign up!

Resources Mentioned:

Connect with Lindsay:

You may also like:

Former teacher Lindsay Bowden, standing and holding a teacher resource, helping educators learn how to sell on TPT

About Lindsay

Former teacher Lindsay Bowden, standing and holding a teacher resource, helping educators learn how to sell on TPT
Lindsay is a former high school math teacher turned full time online biz owner. She has earned over $320K in revenue from Teachers Pay Teachers.

Free trainings

Check them out here!

Recent Episodes

Use a podcast to grow your TPT store text overlay on a bright modern office workspace with desks, chairs, and natural lighting, representing podcasting and Teachers Pay Teachers business growth
TPT SEO Tools Are Actually Worth It text overlay on a soft neutral workspace with a coffee cup and minimal aesthetic, representing Teachers Pay Teachers SEO tools and keyword strategy for sellers
Teachers Pay Teachers keyword research made simple text overlay on a bright, modern living room with neutral decor, white furniture, and soft natural lighting
How to use TPT SEO and data to grow your store faster text overlay on a clean, neutral workspace with a desk, laptop, flowers, and minimal decor

About Lindsay

Meet your go-to math resource gal

Lindsay has been creating math resources for over 10 years and now helps other teachers and moms create and sell their own digital products. Shop my resources or learn how to monetize your skills!
100 ways to make money on TPT as a teacher

100+ Profitable Teacher Resource Ideas

Find your perfect, profitable, TPT product idea, and start building an online business that runs on autopilot! 🎉