There are several key reasons why you might not take the leap into online teaching. Fear is a big one. In this chapter I will show you why your fears are misguided and mistakes are useful.

Lions, Tigers, Bears. Oh My!

Dating girls was always a daunting prospect for me when I was younger. Well, let me be more specific. I was petrified of asking girls out.

Rejection, embarrassment, humiliation… the usual fare. It wasn’t until I was in my late twenties and living in New York when I had a bit of an awakening.

I was out with a group of new found friends with whom I didn’t know too well. Among these new friends was a lovely woman whom I had never met before and with whom I had no real connections. Contrary to the more insular living situations I had been in before, New York City afforded an anonymity that was reassuring. Any kind of embarrassment or rejection would be suffered only once instead of potentially re-living it on a regular basis in a small community. The idea of hiding among 8 million other New Yorkers gave me some confidence.

After some nice conversation, I plucked up some courage and asked her out. She said, “yes” Then, the next day cancelled via text. I could make the story a little longer, but the story is not the point. The point is that after all those years of never asking out someone “cold”, I realized that all the things I had been fearing were really not that bad. I wasn’t shattered; my ego wasn’t destroyed. It was fine. In fact, the feeling that remained was one of regret as I thought back to all the times I could have made the leap but didn’t because I was afraid.

Fear is a funny thing in the modern world. We are still using primitive systems in our brain to decipher what we should be afraid of. Once it was fierce animals, and now it is an attentive audience. The infamous “flight or fight response”, which could have helped us in the jungle, now makes us fearful of public speaking. Fear is also the number one reason you will not undertake online education.

Longwinded segue way? Yes. But performing in public, speaking in public, even asking someone out on a date are common experiences we share. Not so many have found out how un-threatening it is to teach online.

People Aren’t Going To Like What I do

You’re right. People are not going to like what you do. People are also going to love what you do. The vast majority that come across your work simply won’t care.

You need to come to terms with this right now, and furthermore, you need to embrace it. If you try and please everybody, you are going to end up pleasing nobody.

Teach for yourself, teach for your audience and tend to that small group of people who love what you do. It is counter intuitive at first but you are going to be more successful if you embrace your faults and play to your strengths.

I’m Not Good Enough

This is doubtful. I do believe that you should have a strong proficiency in your craft and also have teaching experience but perhaps not as much as you think. It can be a very convenient excuse to get out of teaching online to simply deride ourselves and say that we are not an “expert”.

I was once brought out to the Hamptons in Long Island NY to teach young children on a range of instruments. These were kids, and they were in the beginning stages of learning music. Teaching alongside me was an international conductor. A conductor! These kids didn’t need high level performers to help them at their stage. They needed teachers who were good at teaching music to kids!

Tempting as it may be, bringing in a seasoned expert is not always going to be the best way to help someone. There can be giant gaps of understanding between an artist working at a professional level and a beginner, not to mention the fact that just because you are an expert in your field does not necessarily mean you are an effective teacher. It just doesn’t work like that.

If you have little or no teaching experience, I would recommend getting yourself in amongst some beginners. You will find it surprising what kind of information helps them and what questions they ask. Moreover, you will start to understand your audience by observing the teaching process in a more objective manner.

What kind of questions are being asked? How are they phrased? Are your responses helpful? What order do these questions come in?

To put it bluntly, you only need to be a few steps ahead of someone else in order to help them. The more experience and knowledge you have to offer, the more effective you can be, but don’t let fear get in your way by thinking that you are not good enough.

Mistakes and Failure

To make a mistake signifies that you are trying. You are taking a leap. To fail means that you have the opportunity to do it again and do it better. Both of these should be a positive sign rather than a negative.

Through the I am trying to help people like you navigate through unchartered waters. Around the world there are many other successful entrepreneurs passing on their advice too. However, there is always going to be ground you will have to cover yourself. With the right attitude this foray into the dark will be the most powerful learning experience you will have, even though it might feel like aimless fumbling.

There is something exciting to me about making mistakes. You might find hidden treasure.

Through the process of trial and error, you will discover hidden secrets about yourself, your teaching, your audience and your craft. These hidden truths can only be found via mistakes. Perhaps it is a way to explain a fundamental concept, a series of exercises that teaches more effectively than others, or better yet a way of teaching that synchs with your personality.

If you haven’t realized it yet, I am trying to turn the table on mistakes. They are not to be avoided but celebrated and observed with pride.


Have you ever questioned your title? Painter, singer, guitarist, animator, writer… these titles fit quite well as a student because it takes up the majority of our time. After university, however, our time can be largely occupied by making a living. All of a sudden we draw into question if we are still an artist. If we look at our calendar it seems like we are more of a teacher, barista, waiter, bartender… It can make us do a double take at our own identity.

When I started making an impact online I wondered whether my friends and colleagues would think differently of me. I was hyper sensitive to any criticism and spent too much time checking stats on my website. What became evident over time is that, just like I mentioned before, most people just don’t care. I could spend hours agonizing whether I said the “right” thing in a blog post and when I talked with colleagues, they either thought it was fine or had no idea what I was talking about.

Know that your identity is multifaceted, and it changes over time. To focus on just one aspect of your career, the one that makes you feel like an “artist”, will take you down. The modern creative needs a diverse skill set and you can change hats depending on your given situation.

Nobody cares more about your reputation than you. Remember that.

Round Up

There are other facets of fear we could explore, but really it comes down to an understanding of what the real situation is. The fears you have about teaching online are largely unfounded. They are overwhelming and crippling at the beginning only to subside after several courageous months of lattes and laptop time.

Why not just skip that part and get to helping people?