Jennifer Helfand - Online Teacher, Writer and Illustrator

Jennifer Helfand is a creative online teacher, writer, and illustrator. Find out how stopping the vicious inner critic propelled her into the teacherpreneur world and hear her advice for "putting yourself out there". 

1. Thank you for taking the time out of your busy day for this interview. Can you start off by telling us where you teach and how long have you been teaching?

Currently, I teach online. This is my 15th year of teaching.

2. Can you describe a typical day?

At the moment, my days aren’t really typical. When I started teaching online three years ago, I had a regular schedule. I’d teach all day and work on my writing and drawings at night.  Now, aside from teaching, writing, and marketing, I’m setting up an educational/travel program in Spain.

3. Teacher self-care is so important. How do you relax?  

I start my day by reading Rumi poetry and end it with meditation. I try to go for a walk every day. Drawing almost always relaxes me.

4. You took on the tremendous task of writing a book, drawing and teaching online. Can you tell us more?

I found online teaching by accident. After 12 years of classroom teaching, I was completely burned out. I was also finishing my first two books, living in a writer’s cave, and needed to find some way to earn a living. I researched ways to make a living from home and came across online teaching. After a couple of weeks of reading advice from other online teachers, making contacts, setting up a website, posting my information, I dove in. There were a few lines from a movie that kept echoing through my head: “You have to begin before you’re ready. You will never be 100% ready to do anything. If you wait until you think you’re ready, the moment will be over.” I am profoundly grateful that I began way before I was ready. One of my first students wound up becoming one of my best friends. 

Writing my books: That is a much longer story.

5. How did you come up with your teacherpreneur ideas?

In terms of the cartoons for my website, I think it was the end of a long process in which I finally learned how to stop a vicious inner critic from dictating what was worthy and unworthy of being created and shared.

In terms of the educational/travel program I want to start in Spain, it’s been in the back of my mind for years. I’m only now just starting to develop the idea in a much more concrete way.

My children’s book, Nikolas and the Misfit Shapes Find Their Place, is about celebrating what makes us unique. Nikolas was in my head when I woke up one morning: a little shape who didn’t look at all like the perfect circles, squares, and triangles around him.

The idea for The Life of Zerah, an illustrated spiritual allegory for adults and young adults about a seed who wants to become a tree in the hopes that he’ll be loved, came to me one day in a park.  An amazing high school gym teacher had once counseled me: “If you’re ever sad or scared or don’t know what to do, go outside and talk to the trees. Listen to them. Hear what they have to say. They are so much smarter than people.” I don’t remember if I believed that trees truly had advice to give me on the day I went to the park, but it was an extremely bad time in my life, and I was most certainly sad and scared and didn’t know what to do. When I got to the park, I sat down on a bench beneath an enormous tree. I simply started to cry and thought: “This is not what my life was supposed to be.” In that instant, the wind blew a seed onto my lap, and the words I heard inside my heart were these: “Do you think this is the life I wanted? I was supposed to be a great tree!” Zerah was born.

Both books, though not ESOL books, could never have come about without my work in this field and the tremendous opportunities it has given me to meet people from all over the world and travel.

6. Where can we purchase your resources?

The Life of Zerah and Nikolas and the Misfit Shapes Find Their Place are on Amazon in paperback and e-book formats. The paperback version can also be special ordered at bookstores. My books are published under my pen name, Jordana Chana Mayim.  The cartoons are online for free.

7. Where can we find you on social media?




Teaching website:

Writing website:

email: teaching: [email protected]

writing: [email protected]

8. How do you promote or market your books and services? 

I found my first online students through a platform where I’d posted my profile.  Also, I’m starting to figure out how to market my ESOL cartoons and books. I took off backpacking through Europe after the second book was published. I handed out postcards with inspirational messages from my books to people I met during my travels. That has pretty much been the extent of my marketing until now. A few artists and marketers have advised me to try Instagram.

9. What have you had to do outside of your comfort zone as a teacherpreneur?

Pretty much everything. Though I’m extremely outgoing and am fine in front of a classroom, that did not apply to posting even my photo on the Internet. Definitely not videos which I had to do for one of the platforms I registered on before I had any of my own students. I’m not the best with technology and just learning how to screen share on Skype felt like a major hurdle. In my first class, I really felt like I had no idea what I was doing.

Also, I’ve never felt comfortable asking people for reviews, be it for my classes or books. I’d always thought: if people really wanted to review something, they’d offer it, you wouldn’t have to ask. Of course, that’s not the case at all. Once I did whatever it was that I was uncomfortable with, I looked back and said: I was worried about THAT?? Really?

10. I talk to many teachers about their fear or doubt in trying something new or "putting themselves out there".  What advice would you give to these teachers?

These quotes:

 “Everything you’ve ever wanted is on the other side of fear.”

 “In ten years you are going to wish you were the age you are now to do what you are not doing because of fear of what others will say. Learn to live your life and ignore what everyone else says. Don’t let your life pass you by!”

Remember that everything you love: every song, every book, every magnificent work, was created by someone who was most likely afraid to put it out there, at least when they started. They were full of doubts, and self-criticism, and others’ criticism. Imagine how bleak the world would be if they had never risked or been vulnerable and put themselves out there.

11. Is there anything that you would like to add?  

1) When you’re feeling low, watch an uplifting video, listen to an uplifting song, and talk to friends.

2) One more quote. 😊  “What do you think you can’t do? I’ve seen flowers break through concrete.”

Thank you, Patrice, for allowing me to be part of this interview series!


Interested in learning more about transitioning from a teacher to teacherpreneur?  Here are some resources:

1. Read more than 80 inspiring teacherpreneur interviews at

2. Sign up for my free 5-day email course How to Start your Side Hustle

3. Download The Essential Teacher to Teacherpreneur Toolkit - 50 pages packed with information to get you started as a teacherpreneur at 

4. Download 10 Tips to Transition from Teacher to Teacherpreneur

5. Download The Social Media Make-over Checklist for Teacherpreneurs at

6. Connect with other teacherpreneurs by joining my LinkedIn group

7. Set up a private coaching call with me

8. Connect with me on social media. Teacherpreneurs must be on social media.





About Me

My name is Patrice Palmer, M.Ed., M.A., CPP.  I have more than 20 years’ experience as an ESL Teacher, TESL Trainer, and Writer.  I spent seven amazing years teaching in Hong Kong and have taught students from 8 to 80 years in a variety of programs. I now work as a teacherpreneur doing the things that I love such as writing books, courses and teaching materials; coaching teacherpreneurs, travelling at any time of the year and applying the science of positive psychology to all my work ( Contact me at [email protected]




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