#12: Hassan is writing books & creating courses on the side, making 5 figure income

Have you ever wanted to write a book? Books are a timeless form of expression that's rewarding. But writing books has historically been challenging. Now, thanks to technological advancement and ease of distribution, today, anyone can start the book writing side hustle. Our hustler, Hassan, has been writing books on the side for 16 years!

🤯 Published 16 books on Amazon in four different genres

🤩 Published 11 courses on Udemy with 250K+ students

🏆 Received Amazon Best Selling Author recognition

Becoming Amazon bestselling Author by writing books on the side

Hassan Osman is a Director at Cisco, where he leads program management teams. (All the views he shares are his own, not those of Cisco). Along with a very demanding full-time job, he has been writing books on the side since 2007 and publishing Udemy courses since 2013.

A slow start, with a lot of learning

Hassan always had an entrepreneurial spirit in him. After his master's from Carnegie Mellon University in Information Security, he joined E&Y as a manager. And after two years in his job, he started his first side hustle, a magazine about photojournalism and documentaries. But with a huge scope and heavy logistics, he could not sustain it.

In the next few years, he gathered knowledge and expertise in information security. It was a fascinating topic, and he thought of sharing it with the world. So he started documenting everything in a book. He did not have a publishing company, and self-publishing a paperback was a lot of investment. Thanks to technology, ebooks were becoming popular, and Amazon self-publishing came to his rescue.

It took about six months for him to finish the book and publish it, titled ‘Securing Your Information in an Insecure World’. At that time, he believed that writing a book was 95% of the work and marketing was 5%. But the sales and reception of the book proved otherwise. While the book got good reviews and a few companies also bought it, it was not a success by any metrics.

It made him think that he needed to approach writing books differently. Even though writing the book takes most of the time, success depends on marketing & distribution.

Seven years wait for the next book

In 2010, Hassan moved to Cisco and enrolled for an ALM, General Management, at Harvard University. With university and a job, he pushed book writing on the back burner. Even though his first book was not a success, Hassan realized that he enjoyed writing and sharing his knowledge. He also learnt the importance of understanding and serving market needs. So he actively analyzed trends, read book reviews and kept observing people's needs. He wanted to reverse-engineer his next book.

In 2013, virtual teams emerged as a concept, and only a few companies were practising it. Hassan was one of the few managers to manage a virtual team dispersed across time zones. He had self-learned and gained knowledge from his education at Harvard to manage teams. He observed that many people wanted to learn more about managing virtual teams. So, he started a blog called the ‘Couch Manager’ to share his learnings.

His blog got good traction, 5-6 articles went viral and were syndicated by top media publications. He decided to write a book to help managers work with virtual teams. He researched Google and Amazon search results and other books on the same topic. Armed with all this data, he decided to keep his book short and insight-driven.

In 2014, with the help of Amazon Kindle Direct Publishing, he published his second book titled Influencing Virtual Teams. It became Amazon's Best Selling book and got media attention. The topic was new and gaining traction, so Hassan was contacted whenever there was an article on remote work or virtual teams. He got mentions in publications like the Wall Street Journal, Entrepreneur and more.

From Books to courses: creating a playbook to be consistent

The success of Influencing Virtual Teams boosted Hassan's confidence. Even without a traditional publisher, he became a bestseller based on his content. He wanted to explore more of his interest in sharing and teaching about his experiences.

He learned about Udemy, a platform to upload a course and get students without explicitly working on marketing. He already had the content from his book, he decided to repurpose it into a course. He started recording his videos and published them. The Udemy course too got good traction and he created one more income source on the side.

After a few months, he observed another paid point- emails. Many people need help with writing effective emails. And as a PMO manager, he had the experience of writing effective emails, and he decided to write a book titled Don't Reply All. He also converted the book into a Udemy course.

Since then, he has established a playbook for coming up with ideas, writing a book and then creating a course. He now has 16 books and 11 courses. Some of the topics that his books are based on are- team management, travelling in Europe with kids, and how to write and publish on the side while working a full-time job. These topics do seem diverse, but all these topics have always been at an intersection of his interest, knowledge and market trends.

Another exciting part of his playbook is that his topics are mostly evergreen and related to his job. He believes that books should not have a short shelf life. The topic should be relevant for extended periods and should not need constant updates. And writing for topics related to his job helps him grow in his career. People see him as an expert; over time, he has built a reputation because of this side hustle. And in terms of financial benefits, he generates four-figure revenue from books and five-figure from his courses.

The secret behind his consistency

Hassan has written a book and produced courses consistently over the years. He has also written a book and made a course on how anyone can become an author on the side. A significant enabler of his success is the process he has built. To complete a book, it takes him 6 months, with writing 30 minutes five days a week. His first course took four months, but now he has templatized his course creation process and reduced the time to two months. Building a course and book includes many parts, from selecting a topic to creating the cover image.

You can get Hassan’s book on how to write a book on the side for free here.

What has kept Hassan going for so many years is the fact that writing feels like therapy to him. Book writing for him started as a way to share his knowledge, and now he views it as leaving a legacy behind him.

"I absolutely love teaching. Your book can be read by anyone. The feeling of someone from a foreign country that you've never heard of, reading your book and sending you an email saying, 'This is great, or Thank you’ is unparalleled. I wish everyone could experience that."

The side hustle has also given him financial security. Be it an economic recession, a bad boss or not liking the work, he can always take a step back and have a security blanket. With his books, Hassan has also created a small audience for himself on Twitter. His network has now been expanded to prolific authors and creators.

Hustlers Insights of the Week

Hassan is an inspiration for us to start building a side hustle in our interest area. Books can be challenging, but he found a way to succeed.

Learn from your failures: The first hustle you start may not become a success. But it will teach you some lessons that can prepare you for your next hustle. Don't take failure as the end of it all; learn from it, iterate, and you will find success.

Build your own playbook: Books can be written on any topic and in any genre. You should research and identify your own space. Then build a playbook to come up with topics and get distribution for them. It should be at the intersection of your knowledge, interest and market demand. Hassan has been following this formula to create successful books.

Understand the market: Finding book readers or course students can take time and effort. Hassan could crack this without having a massive audience because of his thorough understanding of the market. He researched topics and keywords people were searching on Google and Amazon and adapted his content accordingly.

If you want to learn more about writing a book and creating a course, Hassan has built a playbook that you can buy.

Did you learn something new about side hustles reading this? If yes, share it with a friend to increase the surface area of knowledge so that more people can know how to make money.

Also, know anyone (who is making money from their side hustle while having a full-time job) we should feature? Let us know by replying, and we will get chatting!

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