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Making Lemonade #25: Questioning the lemons

How living the questions changes everything

Cross-posted from SubstackView original post.

Hey friends,

Last week I got derailed by the bushfire behind my house, which you can read about here. However, my original plan was to write about big dreams, new beginnings, and how any big change or breakthrough usually starts with a question, and so today we’re going to pick that right back up.

love questions. I was absolutely one of those kids who asked “why?” all the time and drove everyone around me bananas – but so much of the world just didn’t make sense. So much of it still doesn’t, but fortunately these days I’m not reliant on grown-ups for answers to questions they don’t know the answers to either.

I learned, over the years, that some questions have answers, and some don’t.

Some you can go out and find the answers to, e.g. through real-life experimentation. For example, in my mind, I can imagine someone being like, “Oh hey, imagine adding sugar to these lemons. How great would that be?” For some reason I picture them as Roman, but, apparently lemonade was technically invented in Egypt, and lemons were not as commonplace in Rome as all the frescos will have you believe. 

There you go, learn something new every day.


We also have the “why not?” questions, which don’t really have or need answers, like “why not decorate a bike with flowers and a unicorn plushy and call it a fairy bike?” (Amsterdam, 2017)

Others, we can find the answers to because someone else has already found them, researched them, and shared them.

On that note, how good is the Internet?! It took me approximately 0.2 seconds to find the answers to that question. I remember when I had to spend hours sifting through a heavy encyclopedia in the library and hope it had the answers I was looking for. 

My life changed for the better once I discovered Encarta in around… 1998, I think. We had a big boxy Windows 95 PC and I would use it to play Tetris, scroll Encarta, and, eventually, chat to my friends on MSN Messenger after begging my parents to please let me use the phone line. “I’ll be really quick”, I’d say, but then I never was. Though at least it meant I wasn’t asking them endless questions, so I guess that was a win for them.

Anyway, with so many questions in my mind all the time, it’s probably not surprising that I a) have lived a rather unconventional life, as lives go, and b) have ended up being a writer. I remember a few years ago when I first stumbled upon Rilke’s Letters to a Young Poet, and realised I’d spent my life inadvertently living the questions.


“You are so young, so much before all beginning, and I would like to beg you, dear Sir, as well as I can, to have patience with everything unresolved in your heart and to try to love the questions themselves as if they were locked rooms or books written in a very foreign language. Don’t search for the answers, which could not be given to you now, because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps then, someday far in the future, you will gradually, without even noticing it, live your way into the answer.”


Rainer Maria Rilke, Letters to a Young Poet


Living the questions – and questioning everything – has led me from a life I was not at all happy with in the UK, to a life I loved but that was not sustainable, back to a life I didn’t love, and now, into a life that feels more “me” and more enriching and fulfilling and exciting than any of those other lives put together. 

Most of the time. But everything is always in flux, anyway.

For me, asking the questions was like taking the first step to make the changes.

Questions like:

“Why do I need to stay in a job I don’t like?” “Why shouldn’t I travel the world?” “How much money do I actually need to get by on the road?” Led to me packing up my job as a travel agent, saving up around £5000, and booking a one-way flight to Sri Lanka in 2013.


Maybe I’ll title this one “Why shouldn’t I run off into the sunset?” (White Sands, USA, 2018)

“What skills do I have that I can use to make money while I’m travelling?” “Why shouldn’t I be a travel writer?” Led to me starting several different creative businesses over the years, including becoming a travel writer. Read more here and here.

“Should I move to Australia?” speaks for itself. As does “Should I stay in Australia?”.

But then about 18 months ago, some more creeping questions came in like: “Why am I not happy being a travel writer anymore?” and “Why am I forcing this when I know I’m not happy?” 

To counteract this, I invested in a freelance writing mentorship and then, six months in, realised that I really didn’t want to be a full-time writer anymore and went back to the drawing board. On the top of a page in my journal, I wrote “What else could I do with my skills and experience?” “What do I want to do?”

The answer, when it came, surprised me. “Be a creative mentor”, I’d written.

It was funny, because although I hadn’t actually got the results I’d signed up for from working with my mentor, instead, I’d got a lot of clarity and support and felt much more comfortable with who I was and proud of what I’d achieved in my life and creative businesses up until that point.

I’d known even then that I wanted to help others find that same clarity, but I didn’t feel qualified or experienced enough.

In the end, though, I asked myself, “Why shouldn’t I be a creative mentor?” “Why don’t I just give it a go and see what happens?” And so, I did.

I signed up with another mentor who helped me through the process, landed my first clients, got some amazing feedback, and had one of those real light-bulb, stars-aligned moments when it felt like I was actually doing something I loved for the first time in a long time.


That isn’t to say I don’t love writing, because I do – especially writing these – and running writing workshops to help other people discover their creative voices, but being a full-time freelance writer was never really what I wanted to do with my life, either. It just happened.

I mean, don’t get me wrong, I’d have loved to have been the next Pico Iyer or Joan Didion, but writing SEO round-ups about the best places to go in X, or how to get from A to B wasn’t exactly where I saw my life going.

Fortunately, though, now it isn’t. Now it’s going somewhere entirely more exciting, and somewhere intentional, rather than accidental, which is how my travel writing career started anyway.

And, while I don’t regret anything – apart from perhaps how long it took for me to learn to trust myself and the answers to the questions that came through – I’m pretty happy with how things are shaping up, now, too.


Other fun questions like “Why shouldn’t I take my cat on a road trip?” led to some beautiful moments like this and me writing an article I’m actually proud of

I hope that reading this has inspired something in you, too. I wonder if there are any questions you’ve been asking yourself, or any you’ve been avoiding asking yourself (yeah, we’ve all been there), while you try and bury your head in the sand and hope things will get better.

I wish we weren’t all reliant on ourselves so much to make the changes we want to make in our lives, but unfortunately, it all comes back to us. Our happiness is in our hands. It’s a hell of a lot of responsibility, but, truth is, I also wouldn’t want it to be in anyone else’s.

And, if you don’t know what questions to ask, then I suggest asking “Am I happy?” and if the answer is no, ask yourself “What is one tiny thing I could do to make myself happy today, or one thing I could do today to make myself happier in the long term”. It might feel like a big ask, but once we start living the questions, a whole world of possibility opens up.

Okay, love you. Happy Ostara! Sending you all sunny weather and blue skies.

See you next week!

Cassie xx


PS – if you want to know more about my creative mentoring and creative business mentoring services, feel free to drop me a line or check out my mentoring page on my website. I offer free 15-minute discovery calls and one-off sessions as well as ongoing packages to help make all your creative dreams a reality, whether you’re trying to make a business out of it or not!


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