Questions and Answers

“Creating is not necessarily about seeking answers, so much as it is about asking many questions until you find an answer you had not yet come to understand.”

Am I cool enough to quote myself yet? I doubt it, but I’m doing it.

I wrote the above in a recent post about creating begetting more creating, where I talked about the answer to your creative problems usually being as simple as starting. But what if you don’t know where to begin?

This is when and why you start asking questions.

Asking yourself questions about the work you want to put out into the world is crucial to creating something meaningful, valuable, and enjoyable.

What do you want to create?

Do you want to paint a masterpiece?

Write a novel?

Drum out a song?

Star in a film?

What about it makes you want it?

Why do you want to create it?

Why does it matter to you?

What problems do you care about solving?

What do you want to give people?

Why does it matter?

Why do you care about it?

Why should other people care about it?

How can you make them care?

These can be big questions. I even struggle to answer these questions for myself sometimes. I couldn’t even come close when I was in art school and supposed to be answering these questions for thesis papers and critiques. It was daunting.

But now, not so much. Now, I find that I enjoy thinking through deep, sometimes philosophical questions like these. Especially when it comes to what I’m creating because it gives my work deeper, and sometimes personal, meaning.

Henry Ford once said, “Thinking is probably the hardest work there is, which is why so few engage in it.”

He’s right. Deep thinking is hard work, but I hope more than a few people are engaging in it! Because letting your mind wander on the things you want to create and why is how you get the creative juices flowing – and it’s a beautiful thing! The human mind, fully engaged.

But the real value is found when you start bringing those thoughts to life through intentional action.

Even if you totally consider it a failure!

I can’t tell you how many times I’ve had an idea for a work of art, executed, and looked at the finished product like… what the f**k?

It happens! Don’t let it discourage you.

If I total hate something I’ve painted, I will paint right over it until I see a piece that aligns with the vision in my head.

And I’ll let you in on a little secret…

That kind of resilience, especially in creative pursuits, comes directly from curiosity, and a strong desire to see the end result.

I’ve said it before, but I’ll say it again, creating is so much more about the process than anything else.

If you can’t enjoy the process, you likely won’t enjoy your destination. And, if you view the process as grueling, painful, and irritating, you’re much less likely to see it through.

(And that can be said for just about any goal you may want to achieve.)

I’ve struggled a lot in the past year or so to enjoy the process. And not the process of art making itself – I always enjoy that – but the process of building an art business. And I can’t tell you how many times I’ve gotten frustrated and uttered (more like shouted, actually) the words, “Why am I not THERE yet?”

Hello, impatience, I see you… Shoo! Shoo!

Like, where the hell is THERE, anyway?

Making millions? Showing in galleries? Selling?

Actually, THERE, for me, is working for myself as a full time artist. Selling my work, showing my work, engaging in philanthropic pursuits, taking two week long vacations someplace tropical. Independent. Living my best life. THERE.

It feels like it’s taking a long time, but that’s because it is. Anything worth while is going to take time and effort. Big dreams don’t come to life over night.

Which is why enjoying the process is so crucial.

But it’s also about feeding your curiosity. Ask more questions. What happens if I switch it up and do this instead? What result will I get if I change this line? This note? This stroke? Those words?

Feeding into that curiosity is part of the process. It’s at the core of “trial and error.”

When you’re asking all of the right questions, and getting curious, and enjoying the process, you’re still going to get some errors. You’re going to fail. Because failing is part of succeeding.

I know you know all of the quotes about getting up after you fall so I’ll leave that on the table. Or rather, I’ll pick it up off of the floor. Here you go: Stop being afraid to fail.

And I’m saying that to myself just as much as I’m saying it to you.

Where am I afraid of failing? Oh honey, where am I not.

I find myself trapped in both the fear of failing, and the fear of succeeding. But I’ll tell you my secret for getting through that too: LEANING IN.

I let my fear guide me as often as I can. I let it tell me where I should go. And not in the way you think.

If my fear is saying go this way and not that way. I’m gonna go that way and not this way. I’m going to do my very best to lean into the fear. Because you know what? That fear is pointing out where my comfort zone stops. It shows me the lines that I should just go ahead and cross. When fear chimes in, I know I’m headed in the right direction, because only when you’re getting out of your comfort zone, do you grow and learn and change.

This worked for me when I was afraid to have a big conversation with my partner, when I was deciding whether or not to take a job, when I was about to be interviewed for a podcast… it’s always scary, like jumping from the tall rock into the river, but it’s always worth it.

(You’re also going to encounter some new input along the road of leaning into fear, and we already know how important input becomes to the creative practice, and to life.)

So follow your fears.

I mean, don’t go down a dark alley at 2AM in a high crime area, and I mean, don’t just go do something dangerous and risk your life for the sake of it. But follow your fears, or at least learn to listen-in when fear strikes.

Fear speaks up in so many areas of our life that aren’t dangerous at all – and those are the moments in which we need to listen and lean.

When all of the fears are telling you not to speak up, speak anyway… when nerves tell you not to hit ‘post’ for fear of what they might think, hit post… when anxiety pipes up and says ‘avoid the event, no one will talk to you’, go to the event… when you think you can’t paint or write or sing or dance, lean into the fear of looking/sounding stupid and do that shit anyway!

Following your fear, and acting on your creative whims are at the very core of sparking innovation. And whether you’re doing your own thing, or you’re working within a company, innovation is the very fuel moving us forward as people and as a society.

It’s the key to growth.

So the next time you find yourself facing a creative problem – or any problem, really – lean in, and start asking questions. Big questions, small questions, simple questions, hard questions.

Questions [almost] always lead to answers, whether they’re the answers you want or not. Especially when they’re not – lean in further and keep on asking. Because people can tell. People can tell when something you’ve created has meaning, offers value, and sparks joy.

So keep going, keep asking questions, keep creating.

You’ll most definitely get there.

Wherever there is.


Happy Questioning,



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