Wednesday, April 30, 2025

8 Questions Every Creative Should Ask Themselves at Least Once a Year

Creative pursuits like writing, art, or music aren't just things we do. For a lot of us, creativity is an entire lifestyle, a way of existing and taking up space in the world around us. 

But if you're anything like me, it's all too easy to lose your way, especially if your creativity is also how you earn a living. Life gets busy. Stress levels rise and inspiration becomes ever harder to come by. Sometimes it's really easy to forget why you even wanted to be creative in the first place.

Although it took me years to really get the memo, it's essential to pause, recalibrate, and check in with yourself once in a while. Not from a critical angle but from one of genuine curiosity and self-compassion. 

Admittedly, I'm guilty of not doing this anywhere near as often as I know I should, but I'm working on it. Asking myself some simple questions once or twice a year and exploring those answers in whatever way makes sense at the time has helped. So, if you're someone who ever creates something out of nothing and calls it art, these eight questions are for you.

1. What do I create when no one is watching?


I don't know about you, but I create very differently when I'm doing it for personal expression and sheer joy than I do when I'm hoping to "get somewhere" with whatever it is I'm making. And it's only natural to care what other people think about what you make, even essential if you count on creative earnings as part of your living. 

But asking myself this question now and then brings me back to the truest version of my creative self, the version that doesn't really care if something I want to create makes me money or earns me new clients. I'm constantly reminding myself to make enough room for creativity that honors that version of me. If I don't, burnout can become a problem.

2. What have I made this year that felt the most like me?


Sometimes you luck out and your answer to this question is something that got a ton of likes or made you some cash. In the summer of 2020, I published the most successful piece of writing I've ever put out there for public consumption –– a Medium piece called 8 Life Lessons I've Learned at 40-Something That I Wish I'd Known at 20-Something

That piece was a Sunday afternoon one-off that happened to resonate with a ton of people and go viral. I wrote it from the heart expecting nothing, and life decided to pleasantly surprise me for a change. But my most heartfelt, authentic piece during a given year is rarely the one that made me the most money or helped me attract a readership.

Some years it's something I jotted down in my private journal that no one ever sees but me. Or something that didn't quite resonate with others the way I would have liked but that I loved anyway. Last year, it was the bumper crop of fresh tomatoes I grew in my back garden. You get the picture.

3. What am I afraid to make and why?


Every creative person has one –– a project they've been thinking about for years but never quite start. Or maybe it's a topic that's a little too personal. A big idea that almost makes you feel like you're overreaching. You dream of taking it on year after year but ultimately decide not to do so out of fear.

Over the years, I've realized fear makes an interesting compass. In a lot of cases, it points to exactly the work I need to be doing more of. I'm not here to tell you to get over your fear or push ahead tomorrow if you're not ready. But I am going to encourage you to sit with it and explore it a little. Scratch out an outline just because or talk to someone else about it. See what happens.

4. What am I no longer interested in creating?


It's OK to outgrow things when it comes to your creative life. It happens to the best of us. We do things a certain way over and over again, first because it works for us and then because we're simply used to doing things that way. People start to expect it of us, and maybe we decide sticking to something that doesn't quite do it for us anymore is safer than taking a chance on something else.

That's when stagnation starts to set in. That's when you run the risk of falling out of love with creativity altogether. It's happened to me. It's not pretty or easy to come back from. In the long run, it's a lot easier and less damaging to just let yourself evolve.

5. What rituals and habits actually support my creativity?


I'm not talking about the ones every other creative you know swears by or the ones you wish did the job. I'm talking about the ones that actually help you and make it easier to keep on creating. For me, it's little rituals like starting my day with a short walk in my garden or by setting an intention for my day by pulling a tarot card.

Whatever you do doesn't have to make sense to anyone else. It only has to work for you. I don't know about you. But I've wasted a lot of time trying to force habits that sounded better on paper than they actually worked for me in practice when I should have just been pulling the damn tarot cards.

6. When do I feel most connected to my voice?


Your creative voice isn't just how you sound when you show up to write, paint, bake, and so forth. It's your essence as a creator, and it often makes itself known in ways you don't expect. You know it when you feel it.

Think about when you feel the most "on fire" creatively and find it easiest to do amazing work that just flows. Is it first thing in the morning at sunrise or late at night after everyone else is in bed? Does that feeling have a way of finding you when you're spending time out in nature or meditating? I know for me, the most electric side of my creative self loves to show up when I'm reading or watching movies.

The more you know about the specific environments that get your creativity flowing, the easier it becomes to coax your muse into showing up when you really need her.

7. What do I secretly wish someone would ask me about my work?


This is a question I don't ask myself as often as I should, and I'm convinced a lot of other creatives are the same. I often create things that dance around what I really mean without spelling it all the way out in plain English, especially when I make art. And I'm fine with people simply appreciating those creations on a surface level.

But I'd be lying if I said I didn't secretly wish someone would get curious enough to ask me about some of the more ambiguous things I create. "Why did you write this exactly this way?" "What does this symbol really mean and why is it important to you?" 

Maybe someone will ask me those things one day. But those questions still serve an important purpose even if it never happens. I don't have to wait for someone to ask. I can talk about the answer in another medium. And I can incorporate part of what answering that question myself taught me into my next piece.

8. What would it mean for me to feel creatively fulfilled this year?


And yes, I do mean "fulfilled" outside of the typical milestones like getting published, having something go viral, or selling a piece. What does it mean to you outside of those things? Maybe it means finally writing that one thing that both scares you and excites you. Maybe it means creating consistently for an entire month or establishing a routine that truly serves you.

Holding space to define creative fulfillment on my own terms keeps me free as a creator, because it's so easy not to be when you also create for a living and have clients to satisfy. It reminds me that creative fulfilment isn't about being chosen by others so much as it's about choosing myself. 

Over the years, I've found asking questions like these is about more than just touching base with myself from a practical standpoint. It's also about coming home to the part of myself that has always created for joy and personal expression, not algorithms, popularity, or even money. That matters.


* This reflection is part of The Feast of the Wandering Pen, a month-long return to voice, ritual, and intentional writing.

2 comments:

  1. Awesome advice! So many creatives need to hear this. Thanks for sharing your insights!

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    1. Yay, thanks! It's tough to remember to re-center, especially when you leverage your creativity for professional purposes. But it's worth it.

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