Growing an online teaching business can feel overwhelming. One minute you’re motivated, the next you’re wondering if you’re even doing the right things.
If you’ve ever asked, “What should I be doing each week to move forward?”—this post is for you.
Inside Teacher Boss Society, we give you a clear plan, ongoing support, and real-time coaching to help you stay on track and grow your business with less stress.
Weekly Coaching That Moves You Forward
Every Thursday at 10:30 AM EST, we meet live for a one-hour group coaching session. These calls are not passive webinars—they’re real conversations.
We talk about what’s working, what’s not, and brainstorm solutions together. Whether you’re stuck on pricing, struggling to find students, or trying to scale, this is where clarity happens.
All calls are recorded, so if you can’t attend live, you can catch the replay anytime.
Monthly Business-Growth Challenges
At the end of each month, we host a challenge to help you take focused, strategic action. These challenges are released on Monday, Wednesday, and Friday, and they’re short and to the point.
Each one is designed to:
- Get you results fast
- Help you stay accountable
- Push you to take action that matters
You can go through the challenge content on your own time, so it fits your schedule.
Trainings That Build Your Business Skills
Once a month, we run a live training focused on an important area of your teaching business.
Here are a few of the trainings we’ve done recently:
- Once a month, we run a live training focused on an important area of your teaching business.
- Here are a few of the actual trainings we’ve done recently:
- Enroll & Grow Challenge: Trial & Conversion (February 2025)
- Visual Branding (March 2025)
- Website Revamp (April 2025)
- High Converting Freebie (May 2025)
- Email Sequence (June 2025)
Missed the live? No problem—every training replay is saved for you in your member portal.
Daily Support + Private Community
Need help between calls? Our private Facebook group is open 24/7.
You’ll get:
- Fast answers from Jillian and the community
- Encouragement and accountability
- A space to ask questions, share wins, and troubleshoot problems
This group is often the first place members turn when they need clarity, support, or just a little motivation to keep going.
A Peek at a Typical Week
Here’s what a regular week might look like inside Teacher Boss Society:
| Day | What’s Happening |
|---|---|
| Monday | Work through challenge content (during challenge week) |
| Tuesday | Ask questions or share updates in the group |
| Wednesday | Continue challenge content (if applicable) |
| Thursday | Live coaching call @ 10:30 AM EST (or catch the replay) |
| Friday | Wrap up challenge task (if applicable) |
| Anytime | Watch trainings, catch up on coaching replays, engage in group |
What’s Next?
If you’re looking for real progress—not just more advice—Teacher Boss Society is your next step.
You’ll get the roadmap, the support, and the accountability you’ve been missing.
🧡 Start your journey with us today. Coaching calls happen every Thursday—your seat is waiting.
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