growing a teaching business and a family - jennifer-2

Growing a Teaching Business and a Family: Interview with Jennifer from English Outside the Box

I’ve got a great interview for you today.

Jennifer (English Outside the Box) and I discuss growing a teaching business while also growing a family, how to go from one-to-one lessons to online courses, and her tips for those getting started.

We get into the different platforms that you can use to host your courses, favorite social media platforms, the biggest frustration in the early days and much more.



Jennifer moved to Brazil with her husband and that’s when she started teaching English.

After three years of teaching in language schools, she wanted to have more independence. One night, started on a teaching platform before creating a website and profiles on Facebook and Instagram.

The biggest frustration at the beginning was managing student expectations and finding the balance between helping learners for free and creating an income.

Jennifer found students through Facebook in the beginning. She started with an old student who she used to teach and got many referrals from this initial student.

When I asked about her favorite social media platform, you’ll notice that this has changed. At first, it was Facebook, then Instagram, and she is currently coming up with a new strategy.

We then talked about YouTube and why she stopped giving a live lesson at the same time every week. She has seen growth since stopping this.


Jennifer started by putting her online courses on Udemy, then on to her own site, before going with Teachable.

Here is a break down of these platforms:

Udemy (affiliate link):

  • they host and sell your online course
  • marketplace for students
  • less control over your customer information and pricing

Selz (affiliate link)

  • digital product payments and delivery
  • no marketplace for students (market your own courses)
  • no online course templates

Teachable (affiliate link)

  • best all-in-one solution
  • not as much control than hosting it on your site

Own Website

  • most control
  • can be difficult to set up

Jennifer spent her evenings and weekends creating her first courses; like a side hustle.


Jennifer thought about maternity leave in advance.

She collaborated with other teachers so she had content to post for the first few weeks after giving birth.

She also decided to work asynchronously with her learners where she gave them feedback on their speaking and writing.

Routines are constantly changing. She worked while her son was napping. Boundaries are important.

She wants to improve the courses she has now and start doing live events.

Learn more about her company here.



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