We had the good fortune of connecting with Jenn Woolf and we’ve shared our conversation below.
Hi Jenn, every day, we about how much execution matters, but we think ideas matter as well. How did you come up with the idea for your business?
I was working as a writing tutor, and when I arrived at my students’ houses, I would hear things like, “Ughh, the tutor lady’s here” before they opened the door. For additional emphasis, their body language screamed that they would rather be anywhere else. My mission changed from teaching kids how to write to showing them how to be enthusiastic about expressing themselves. Humans are social creatures and we are literally born to communicate. It broke my heart to see kids who either felt self-conscious about their writing or had been convinced that they weren’t very good at it. By focusing on things like figurative language and creative writing, I’ve been able to empower students to trust their own voices and to express themselves. Now, my students are happy to see me, and can’t wait to share their stories!
What should our readers know about your business?
When I first started, I was embarrassed to call myself an entrepreneur. I knew I had a passion for writing and teaching, but I was afraid to put myself out there. I had a major case of imposter syndrome! What I didn’t realize is that by watching my students’ faces light up when they enter my classroom and share their work, I would develop my own confidence along the way. I also didn’t think I could tackle the technical aspects of running an online business myself. After attending online webinars, joining the community of online writers and educators, and persevering, I have now racked up 143 great reviews on Outschool, and feel so lucky that I am able to mentor a new generation of writers. I’ve also learned that tech is fun! I absolutely love designing my own websites and handling the technical aspects of running an online business. I want the world to know that everyone has a story to tell and a gift to share. No matter where you are in your process, don’t doubt yourself. Go for it!
Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
There are so many great spots in Los Angeles. I love being outside, so I would start off surfing at Zuma, and then maybe a hike in the Santa Monica Mountains. Caballero Canyon is one of my favorite hikes. I also love to eat, so I would explore the multi-cultural aspects of our amazing city through cuisine, focusing on the hidden spots like Vinh Loi Tofu in Reseda. It’s a vegan Vietnamese restaurant in a strip shopping mall. Next, I might shift gears and go upscale with Toscana in Brentwood. There are so many great restaurants to explore. LA also has a rocking indie music scene, so I would definitely end the day with a local concert, maybe at the Hi Hat, The Fonda, The Mint, or The Greek. And then maybe we’d have a nightcap at Tramp Stamp Granny’s.
Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
Outschool definitely gets the Shoutout. Even though I run two writing websites (ccwi.net and figurativewriting.com) my students were mostly local. When I started teaching on the Outschool platform in 2019, I was able to reach students all over the world. I now have students in Australia, the UK, Brazil, Canada, and the United States. My young authors get to form communities of like-minded kids from all over the world. Through Outschool, I’ve been able to grow my business, and also to provide my students with a supportive, friendly environment to try out different writing techniques. I love teaching on Outschool so much that I have joined the onboarding team and get to welcome new teachers to the platform.