For the past year, my life has been a whirlwind of building, creating, and pushing forward in ways I never thought possible.
I’ve been deep in the trenches—building websites, writing e-book resources for prospective online teachers, creating reading comprehension blog posts for English learners, and developing task-based, interactive courses for adults who want more than just grammar drills.
Every day, between teaching Russian corporate professionals online, managing household duties, playing chauffeur for my family, grooming my cat, and being a husband, I carve out time to write, design, and create.
I’m not just teaching English lessons anymore. I’m building a teacherpreneurial venture from scratch—an independent, one-man business designed to help learners thrive and to show other teachers how to do the same.
The Long Road Here
I’m a 52-year-old white South African male. That fact, in itself, has shaped my life in ways many people outside South Africa will never understand.
Over the past 30 years, my professional path has been stunted and scarred by systemic barriers: Affirmative Action and BEE (Black Economic Empowerment) policies, age discrimination, and entrenched reverse racism that has left highly qualified individuals like me shut out of opportunities.
I hold three postgraduate degrees—in Law, Education, and Development Studies. And yet, in three decades, I have only once managed to secure permanent employment in South Africa for two years. The rest has been a revolving door of under-employment, unemployment, and frustration.
Despite my qualifications, intellect, and experience, the message was always clear: there was no space for me.
So I turned to TEFL. For decades, I taught English abroad—in places like Somalia, Sudan, Oman, Saudi Arabia, Iraq, and China. These weren’t easy countries. These were challenging contexts, often unstable, politically volatile, and culturally difficult. But they gave me what South Africa never did: work, dignity, and a way to support myself.
Returning to South Africa to care for my aging parents, I had no choice but to reinvent myself once again—this time as an online English teacher. Like Matthew McConaughey once typecast in RomComs, I became typecast as an EFL teacher. No-one is able to see me outside of TEFL, even though I have so many transferrable skills that is supposed to give me opportunities outside teaching.
Why Teacherpreneurship?
For me, entrepreneurship isn’t a luxury. It’s survival. I’ve seen first-hand the limitations of Online Teaching Platforms (OTPs) and Online Teaching Marketplaces (OTMs). They are useful, but they come with ceilings—fixed rates, limited flexibility, and little real freedom.
By contrast, building my own Online Teaching Business (OTB) puts me in control. I decide the direction, the content, and the clients I want to serve. I can create eBooks, courses, and digital resources. I can reach learners directly, without middlemen dictating the terms.
It’s not easy. It’s not safe. And it certainly doesn’t come with a fixed salary. But it is a way forward.
The Skills Gained Along the Way
This journey has forced me to learn—and fast. Beyond teaching, I’ve become:
A web designer, building functional sites to showcase lessons and resources.
A writer, producing eBooks and blog posts that help both learners and teachers.
A course creator, designing structured, interactive lessons for adults worldwide.
A marketer, figuring out SEO, funnels, and how to actually reach an audience.
A bookkeeper, tracking income and expenses in a world without fixed salaries.
A project manager, juggling multiple roles and deadlines while still teaching daily lessons.
The Pros and Cons of Solopreneurship
Like any honest reflection, I need to admit: this path isn’t perfect.
The Benefits:
Freedom to choose my own direction and clients.
The chance to build long-term assets (eBooks, courses, blog posts).
A life not dictated by employers or governments.
The ability to work anywhere, anytime.
The satisfaction of knowing that I, together with God, have built something to be proud of.
The Challenges:
No fixed salary—income can be unpredictable.
The weight of responsibility for every part of the business.
Long hours, often eating into personal time.
Constant learning curves: from tech to marketing to sales.
Isolation—no colleagues to lean on, only yourself, depending on GOD.
Why Keep Fighting?
South Africa today has one of the highest unemployment rates in the world—over 63% in some estimates. Corporations are fleeing, crime is rampant, governance is corrupt, and opportunities are shrinking by the day.
For people like me, who’ve been shut out of the system for decades, waiting for a job is no longer an option. The only real option is to fight back—to carve out a space that no one can take away.
And so I get up every day. I create. I teach. I write. I build. I rely on God’s strength to keep going, even when everything in the system seems designed to crush people like me.
I may not have a “career” in the traditional sense. But I have resilience. I have global experience. And now, I have built a teacherpreneurial venture that allows me to stand free.
Final Thoughts
Teacherpreneurship is not the easy road. It is not the safe road. But it is the only road left for many of us who have been blocked, sidelined, and written off.
If you are reading this and you feel the same way—that you’ve been told “no” one too many times—then take this as your encouragement: you don’t have to wait for permission. You don’t have to wait for an employer to decide you’re worth it.
You can build your own.
And I’m proof that even in the toughest climates, it’s possible to survive—and maybe even thrive—when you take control of your own future. With God's help anything is possible.
I often think of a line from the movie Bridge of Spies, where Soviet spy Rudolf Abel is asked by Tom hank's character if he’s worried about his fate. His reply? “Would it help?” That has stayed with me. Complaining, lying down, or worrying about circumstances I cannot control won’t change them. What helps is action—getting up every day, putting one foot in front of the other, and building something that is mine, with God’s help.
So yes, I may not have the safety of a fixed salary or the recognition of a traditional career. But I do have freedom, resilience, and a venture I am building one word, one lesson, one course at a time.
📘 Ready to Start Your Own Journey?
If my story resonates with you—if you’re an aspiring online teacher or someone looking to build an independent career—you don’t have to do it alone.
I’ve put everything I’ve learned into my book, Teaching Without Borders, a complete guide to getting started as an online English teacher.
Inside, you’ll discover:
✅ How to break into the online teaching world
✅ Practical strategies to find students and secure work
✅ Tools, tips, and roadmaps to launch your own teaching career
👉 Click here to get your copy of Teaching Without Borders and start building the freedom you deserve today.
© 2025 Henry English Hub. All rights reserved.
HEY, I’M HENRY
Hi, I’m Henry Lilienfield, a TEFL veteran with teaching experience across China, Taiwan, Oman, Saudi Arabia, Iraq, South Africa, and online. With a law degree, two post-grad qualifications in Education Management and Development Studies, and a Level 5 TEFL Diploma, I bring deep knowledge and a practical approach to everything I teach—whether it’s English lessons or how to start your own online teaching business.
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