The Debrief: An Online Tutoring Side Hustle

Welcome to The Debrief. This week we interviewed Rachel, a teacher with a side hustle as a tutor. If you didn’t catch it, feel free to check it out here before diving into this edition.

In this mid-week newsletter, we are going to investigate what we covered in our interview and breakdown the key takeaways and share some actionable advice for you to work on in your business venture.

Each debrief is designed to give you something to work on each week based off the advice given by our featured entrepreneur.

Let’s get into it!

Online Tutoring Side Hustle

Key takeaways:

1.  Personalization and Confidence-Building Are the Game Changers
   Rachel’s tutoring approach goes beyond rote learning. By tailoring each session to the student’s needs and learning style, she’s able to turn apprehensive learners into confident communicators. Her focus on building trust and reducing pressure makes her tutoring more effective and fulfilling—for both her and her students.

2. Treat Your Side Hustle Like a Business—From Day One
   Rachel admits she initially underestimated the importance of structure. Setting clear policies, automating reminders, and streamlining client onboarding were all things she wished she had implemented sooner. These systems now save her time and help maintain professional boundaries, which are essential for long-term sustainability.

3. Start with What You Know, Then Market Smartly
   She began by helping a neighbor’s child, then grew her client base largely through referrals. But it wasn’t until she built a simple website and shared educational content on social media that she saw a spike in inquiries. Strategic marketing—paired with a clear niche—turned her small gig into a steady income stream.

How to start this business?

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