courtney osborne on writting & social media coaching

This is COURTNEY. A home-schooled, writer and entreprenuer. She’s the creator of CLO (facebook page), cofounder of The Hustle Hamilton and a Social Media Coach. She’s also in the process of writing a book on the background works of the wedding industry.



 Did you know what you wanted to do when you finished schooling? 

I Desperately wanted to write books for a living not long before I finished school, and having been put off the Film industry by my older brother (who worked in it for many years) I can definitely say I felt lost.

There was a lot of pressure from my parents to study something. I very nearly studied to become a Teacher (which would have been a disaster… the students wouldn’t have liked it either). I would say the main difference between me and the path that many people my age took was that – I refused to study if I didn’t know what I wanted to do. Which resulted in an ultimatum from my parents, study or find a job.

How did you know how to go about writing a book/start a business? Where did you find resources around this side of things?

For the book I picked the brains of a few published authors I knew, they were all so helpful + I read a lot on publishing.

For the business, I got an amazing accountant. I knew I had to get one because I get all uncomfortable around money stuff  (something I am working on changing). Because I started (and still am) quite small, its easy enough to learn as you go. There are plenty of resources online, and most people are happy to give you advice or understanding if you are humble and honest about where you are at.

Where did the ideas of CLO, your book, hustle Hamilton and your online business come from? 


The Dear Me Letters that I publish on CLO Facebook page are fairly recent venture for me, and in a way the most personal exposure of my writing to date. The letters themselves I have been writing them since I was about nineteen. I read a few of them to close friends, but never really thought they would apply to a wider audience until recently.

The book I’m writing ( attempting to anyways) I got the idea for while working in the Wedding Industry and observing all the amazing people that make up the “Machine” that runs the Industry. There are so many of their stories to be told, a lot of understanding that needs to be gained by hearing what goes on in the background of peoples special day.

My Coaching Business I began by total accident. People kept asking me to help them with their SM business accounts, then they started referring me to other people ( total strangers) who wanted to pay me and get my business card and quote them… suffice it to say I was no prepared for any of that! But a few months of hustle and now I am doing ok! Still 100% learning as I teach.

What motivated you to start writing a book & start an online business?

I spent a lot of time waiting for the perfect opportunity to come along. Then one day (at an Entrepreneurship conference in Auckland that I attended almost by accident) I realized that by choosing to wait for the “perfect circumstances” I was actively saying No to many future options that I might have taken up. It was the first time I had felt like I was in a room full of “My People” – except I wasn’t living like they were.

I told my boss the next day that I couldn’t do that anymore and while there was still a transitional time between working for someone else to myself, I can honestly say I have never looked back. I should have done this years ago. But I was busy playing it safe.

Writing a book has been on my bucket list since a very young age (it was up there next to Attend the Oscars and learn the Piano). However I can’t write when I’m stressed or tired, unfortunately I’ve spent a large part of my life being stressed and tired.  So when I said I would write a book I was really committing to a healthier lifestyle as well.


How did you fund the startup of your idea? (or were there no costs)

Coaching didn’t take a whole lot of funding, and most of the material I needed (laptop, bank account, internet) were things I already had.

However I will say that without the support of my (angelically patient) husband I would have really struggled to take the leap and back myself through the beginning stages of establishing a business.

Do you have a day job or do you fund yourself through your own business?

Between my book, other writing and my clients I keep pretty busy and the money is getting better. I’m in a very fortunate situation where I have a supportive Husband (with a full time job) and a house. These two factors make it a lot easier for me that for other people starting out.

This is an amazing blessing, but I also feel the weight of huge responsibility to use this opportunity to the best of my ability. 

What was the toughest part of starting out?

In the beginning it was the nearly crippling self doubt. Which surprised me because I’m don’t tend to have confidence issues. But I soon realized that I was completely comfortable living up to ( and exceeding) other peoples expectations, I just had zero coping skills for my own absurd expectations. I had spent most of my life prioritizing my job or my relationships over my own goals and aspirations so working on them in the form of my business 24/7 was a struggle at first. 

What’s the best habit you’ve picked up? 

To always question “why” –at a really early age my mother would say: “If you know how to flick a switch you can turn a light on, and that’s great. Lots of people go through life just turning lights. But if you understand electricity you can still turn a light on – you could also change the world. Always strive to understand what is going on behind the scenes.”

Knowing that there was always more to everything ( people, circumstances, life) has given me a curiosity that I am so grateful for, more than once it has saved me from making ” pack-mentality” decisions I would have regretted.

What fears come up for you around your craft (writing)?

For a while it was the fear of vulnerability. I had become very good at controlling people’s perception of me, but writing was my therapy so I couldn’t fake anything. 

After that it was the thought of others judging me. Things like “ What do you know about life?” “ Who died and made you the expert.” Above all the fear of people assuming that I understood or had some kind of “special” insight into life that they didn’t have. That stopped me from publishing the Dear Me Letters for a really long time!


What’s something you know now that you wish you knew when you were starting out  post schooling?

I would tell myself to stop trying to control everything (myself included). I’m a natural organizer, and the urge to customize and perfect most things in my life was strong when was young.

My brother knew me well and he once said something that I found troubling for many years: 

“Courtney, one day you will realize that you control very little in life and  when you do, things will get much easier to deal with.”

I completely get what he was saying now, but it was a few hard knocks to my reality before I understood how letting go of control could be a nice (even preferable) idea.

Intrigued for more and want to stay tuned?

INSTAGRAM: @co_osborne or @colauren


Anddd if you’re a young creative/entrepreneur located Hamilton get in touch and come along to the weekly meet ups.


Dan & Prils


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