Can You Learn to Be Creative?

Or Maybe a Better Question: Do You Already Know How to Be Creative?

Life on the road in a camper van
Photo by Kevin Schmid on Unsplash

A Case Study: Erin’s Story:

Erin spends her WorkLife on the road being creative. For several years that has been as a writer, more recently she’s begun to give talks and now teaches on the subject of creativity.

A Woman, A Camper Van, and a WorkLife on the Road Being Creative

You can’t teach creativity – so what am I doing here?

I’m here to show you that you already know how to be creative.

Every time you tell a story or a joke or make an excuse to get out of something, you’re being creative.

Those were the first words Erin spoke to a classroom of students who had signed up for her Creativity class. Her first class and her first time teaching on the subject of creativity being critical for success for freelancers of the 21st century.

Continuing, Erin said:

My WorkLife on the road began straight out of college. When wanting to fulfil my dream to travel the world, I set out to do just that. 

My first stop was Australia. Having gotten a one-year working holiday visa, I wanted to see as much of the country as possible. I figured the best way to do that was to hire a camper van to give me the freedom to travel where and when I wanted. 

To enable this freedom and to cover the costs of my travel and my stay in the country, I needed to get creative. 

That was when I started a practice of what I believe to be insightful self-question and effective self-feedback.

I asked myself:

What have I got by way of experience, knowledge and skills?

Being straight out of college, I didn’t have much experience. My degree was in history – so that was my area of knowledge. As for skills, because of my lack of experience, I wasn’t really clear on that. 

Then I asked myself:

What can I do with my knowledge of history to fund my travels?

That question didn’t immediately bring up any answers, so I parked it.

Next, I asked myself:

Does my love of history and my desire to travel have anything in common?

The feedback that this question brought about reminded me of why I studied history and what I loved about it.  

I loved going back in time and building knowledge of interesting people, places and events and their impact on society. I loved the journeys my reading took me on and the discoveries I made along the way.

I realised my desire to travel was starting from the same place my desire to study history had begun from.

But what did that mean in the context of wanting to find a way to fund my travels?

To discover the answer to that question, I rephrased the question I’d parked: What can I do with my knowledge of history to fund my travels? To: In what way can I do this? 

The answer that came to me was that I could change the journeys my reading took me on to real-life journeys – journeys around Australia, going back in time and building knowledge of interesting people, places and events and their impact on society.

I liked that answer. But I needed to go deeper to get more clarity. So, again, I asked myself:

In what way can I do this?

I thought I could write stories about my discoveries, exactly as I’d done in my history essays – stories of interesting people, places and events and their impact on society.

I needed to go deeper still to understand how doing this could give me the financial independence I needed to travel freely. So, again, I asked myself:

In what way can I do this?

This helped me realise I needed to figure out who would pay for this and why?

Mulling this over brought me back to my love of researching and how in preparing for my journey around Australia, I’d read the Lonely Planet Australia – a book that was in every traveller’s backpack. The books were a great guide to learn about places of interest to visit, to then go deeper on arrival to learn even more. I thought maybe that’s where I could come in. I could tell those deeper stories. Because that’s where I saw the gap – the gap from the overview given in the book to the more detailed facts bringing history and current-day together. 

But I still needed to figure out who would pay for this and why?

I knew it wasn’t going to be travellers because I didn’t have any way of getting this information to them. I was only beginning my travels, and even if I had wanted to write a book – which I didn’t at that point – I didn’t have anything much to write about yet, and even if I did, I had no way of publishing it. This was the late 90s, and self-publishing wasn’t on my radar, nor was blogging.

I went back to mulling it over. I thought about where I went for up to date information whenever I travelled. Back then, it was always to the tourist board when I was planning a trip and the local tourist office when I arrived at my destination.

Then I asked myself my favourite type of questions – What If? Questions.

What if I wrote about the stories I’d discovered in Sydney – the city I’d landed in and the starting point of my road trip.

That’s exactly what I did, and when I’d finished writing the stories, I approached the tourist offices around the city, asking if they thought they would be helpful to visitors. They liked them and said yes, but they didn’t have a budget to pay me for them. I was OK with that because, really, I just wanted to get a sense of whether they liked what I had written and if they were open to distributing them. As they were, I said they could have them for free and asked if I could get in touch in a couple of weeks to get feedback on whether people visited the places I’d written about. 

I knew they would get feedback from these places because I’d connected with people everywhere I’d visited and collected their contact details – names and phone numbers. Then when I had written the stories, I called to ask if it would be OK to send copies. They were, and so I printed them off and popped them in the mail (email hadn’t really taken off then either). Then I followed up with a call to check they’d received them and to get their feedback. Everybody really liked what I had written and said they would give feedback to the tourist offices in Sydney – which is where people would travel from, to encourage the offices to distribute them.

Although there was no conversation about being paid for my stories at this point, I was OK with that. After all, I had no experience doing what I was proposing. I was drawing on my knowledge of writing history essays, but to write stories, I needed to develop my skills in more of a creative writing style way. My single objective at this point was to raise awareness to my idea and my stories. 

On the road, I wrote more stories and followed the same process to distribute them to tourist offices and the locations I’d visited, then followed up with calls to get feedback. As people in the tourist offices got to know me through my follow up calls, they began to suggest they let their local tourist board know what I was doing and send my stories on to them. This is exactly what I was hoping for, I had tried contacting them directly myself, but I wasn’t getting anywhere with that. Now I was able to ask for introductions from the people I was building relationships with, who were happy to oblige. Together with the forwarded stories and the feedback about my work from several sources, these introductions allowed me to get past the gatekeepers who had previously screened out my calls to now connecting me to the people I had been introduced to, simply because they now recognised my name and were familiar with my work.

Once that happened, things started to happen quite rapidly. The tourist boards asked if they could distribute my stories to their offices throughout the world. To make my stories available to people who were planning their trip to Australia. Exactly what I was hoping for, and of course, I said yes. That was the point I went from writing free stories to getting paid for them. 

It wasn’t a lot of money, to begin with, but I was OK with that. I was operating on a backpackers budget, so I didn’t need a big income from my writing. I just needed enough money to fund my travels and what had become an accidental WorkLife on the road. 


Since then, the only looking back I’ve done has been through the rearview mirror of my camper van every time I hit the road for a new destination in search of my next story.

Had I taught myself to be creative, or did I already know how to be creative?

Words of Wisdom

On reflection, I think I taught myself the process of how to be creative in my thinking by establishing the practice of insightful self-questions and effective self-feedback. Every time I wrote a new story, I was being creative. I was being creative by doing.

You can do the same.

Nature and Nurture Creativity Assignment 

For your first assignment, I want you to think about a dream you have – your equivalent to my dream of wanting the travel the world.

Think about what you need to be able to achieve this – your equivalent of my needing to cover the costs of my travel and my stay in the country.

Now it’s your turn to get creative and to start your practice of insightful self-question and effective self-feedback.

Draw on the questions I asked of myself to get started and modify them to get to your most insightful questions to elicit your most effective feedback. 

Be open to reframing your questions. My reframed question: In what way can I do this? It became one of the most insightful and powerful questions I continue to ask myself.

That, in turn, led to my favourite type of question: What If …?

I believe this assignment will enable you to recognise how a process can guide and grow the creativity you already have within yourself. The creativity that is critical for success for freelancers of the 21st century.


As a WorkLife Learning Practitioner and Writer, I create learning programmes and resources to help people manage, develop and transition their WorkLives in good, challenging and bad times. 

The focus of my work begins by helping people identify a WorkLife path that’s true to their core values, purpose, and motivation. This is followed through by creating meaningful short and long-term WorkLife plans while enabling self-coaching, self-directing, and self-leadership to drive these plans.

I bring you stories created from questions and answers drawn from WorkLife lessons. What I’m trying to do is to highlight different solutions, to provide you with a pathway so that even if a particular story doesn’t apply to you, you understand there is a path to follow. 

Whatever you want to do, there is a clear path to it, and once you understand those steps, it becomes much more intuitive, and hopefully, it motivates you to get started. Because that’s what you need most, the motivation to get started. The motivation to follow your vision.

I created The School Of WorkLife book series to help people continuously fine-tune their learning, development and growth in the areas most important to them. Click on the series to see all the books available and previews of what’s inside each book. 

How To Be Creative In Your Thinking is book 15 in the series. Click on the title to see a preview of what’s inside the book.  


Currently, I’m writing stories for series two of The School Of WorkLife book collection. In celebration of this, each week, I create a 50% discount offer on the corresponding book from series one.

Here’s a link to How To Be Creative In Your Thinking in my Shopify Store. The discount will automatically be applied when you add the book to your shopping cart.

The book is reduced from £3.99 to £2

Please note your email address is the required Contact information to enable the e-books to be emailed to you. Your download will be available immediately in the Shopify store, and you will also receive an email with download links for your digital purchases. 

Published by Carmel O' Reilly

Carmel O’ Reilly: WorkLife Learning Practitioner & Writer Author of WorkLife Book Club, Your WorkLife Your Way and The School of WorkLife book series. Created to help you manage your WorkLife Learning. Blogger & Podcaster: Telling people’s powerful stories about WorkLife challenges & successes Founder of My guiding statement is to help people pursue their WorkLives with greater clarity, passion, purpose and pride by creating continuous WorkLife learning programmes that are accessible to everyone.