17 questions for creatives: Brainstorming boosters for creative business owners

By Brittany Taylor

brainstorming

17 business brainstorming questions for bosses

to help you get clear on your creative business


by Brittany Taylor

published April 10, 2018

updated May 27, 2018


There’s more to spring than daffodils and dandelions. It’s the season of new beginnings, and to celebrate, I’m sharing a slew of questions to help you think about growing your creative brand in thoughtful, purposeful ways.

As April showers morph into May flowers, keeps these Qs on the backburner. If intentional growth is on your agenda this spring, there’s nothing better to keep you on-track than these spring questions for creatives.

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What these questions can help you accomplish as a creative business owner

Whether you’re a fine artist or photographer, graphic designer or web developer, a writer like me or a maker with hands that can’t sit still, I know we all have something in common: a desire to evolve our creativity.

We all want to sink deeper into the well that inspires us. We all want to grow as dreamers, makers, and doers. We all want to be doing something different next year, in 5 years, in 15.

That’s exactly what these questions for creatives are for. They’re inspired by spring—the season of new beginnings—to help you discover ways you can grow as a creative person and a creative business owner this year.

These questions can help you:
  • Finesse your creative process
  • Motivate yourself to make new things
  • Dig deeper into your business brand
  • Figure out who you are as an artist
  • Decide where to focus your time and energy

  • Come up with new content or products
  • Determine what areas in business and creative life are your pain points

How to use these brainstorming questions

The great thing about brainstorming is that everyone is wired differently. What a question means to me might be completely different from what it means to you—and that’s wonderful!

Go with the thought process that feels best for you. My go-to brainstorming technique is word association. Learn more about how that works here.

To help you along, each question is followed by tidbits that will shape your thinking. Feel free to use these extras as you see fit—or not. If you’re feeling a little “meh” about a brainstorm Q, the additional context and questions might give you something more to work with. But don’t push it. If you’re still running on empty after a minute or two of contemplation, move on! This exercise is meant to inspire you on your creative journey, not stymie you.

Ready for the questions? Read on!
#1. What about your work wakes you up?

In Greek mythology, spring is the season when Earth comes out of morning after the loss of Persephone to Hades, god of the Underworld. That’s why everything is bright and new and fresh once the weather begins to warm: It’s the natural world’s way of celebrating the return of its favorite daughter.

If Persephone can awaken Mother Earth after a long winter away, what about your creative work wakes you up? What catches your attention? What makes you want to grow your ambitions, your talents, your skillset? What inspires you to do the work?

#2. How do you envision your brand growing in the future?

For some plants, every spring is a blank slate. Come winter, they’re dead and gone. Once spring returns, the seedling stretches into a stem, into leaves, into a flower or a tree, a bush or a vine.

For others, spring is like hitting a natural “play” button on the remote of life. Winter put growth on pause, but with the changing of the seasons, the perennial is back in action, ready to grow bigger and stronger and more vibrant than it was the year before.

#3. What parts of your work have you cut back in the past so they can grow big in the coming months?

I live in South Carolina, and we’re awash in crepe myrtle trees. Late in the fall, these beautiful specimens are pruned way, way back. Then, it looks like a shame to cut away so much growth.

When spring comes around, though, these trees come back better than ever. Their flowers are lush, their limbs strong. Without the pruning, this sort of return would be impossible because some of the plant’s energy resources would be diverted to support less-healthy branches.

#4. What has informed your ideas of creative beauty?

Creative inspiration doesn’t come from nowhere. There’s a museum in Baltimore, the American Visionary Art Museum. All of the work it shows is created by untrained artists, many of whom are inspired by dreams or visions. Others are inspired by nature, by mentors, by history, by other works of art.

What has shaped what you think is beautiful and worth creating? It could be an experience you lived through, a lesson you learned, an artist you admire, or something else entirely.

#5. In what way are you blossoming right now?

When I think of a person who is blossoming, I think of someone who is coming into their own in some way. Often, the imagery is used for adolescents and pregnant people, individuals who are going through periods of significant change.  in their bodies and their minds.

So, what’s blossoming inside of you? Remember, it’s not about coming to your peak creativity or even your prime. Blossoming is about moving into a different stage of creation or existence. Consider any revelations you’ve had, any big changes you’ve made in your business, and any emotional or spiritual work that has inspired your current work.

#6. Why have you gone through the pain of this creative labor?

The pain of childbirth is unique. So is the pain of creative birth, and only those people who have experienced them both can compare the two (and that’s not me).

Think about what your creativity has cost you. Have you sacrificed time with family? Have you risked your health? Are you putting other work or opportunities on the line?

#7. When will you feel safe enough to open your petals?

The creative process is an emotional one. Putting your emotions and your art on display makes you vulnerable. To do that, many of us creatives wait until we’re in a safe physical, mental, and/or emotional place.

Maybe we’ve come to terms with a heart-wrenching event. Maybe we’ve become more secure, financially. Maybe we’re recovering from a mental illness or from a period of self-doubt. What is it that makes you feel shy about sharing your creativity with a wider audience?

#8. What have you learned from the winter seasons of your work?

Winter is often associated with death and dying, but those aren’t the only images it brings to mind. Winter is also a time of hibernation, of peace, of internal meditation and self-care.

Maybe this winter has been a time of death for you, but maybe it hasn’t. What has the literal winter season—the months of December, January, and February, in the Northern Hemisphere—brought you? Or, if you’ve weathered a metaphorical winter, what has that time been like? What have you learned about yourself, your life, and your work?

#9. Who is the sort of person you can see admiring the garden you’re growing?

Sometimes, we create work for ourselves. Other times, we create for other people. Regardless, our art tends to draw attention, whether we intend for it to or not.

Regardless of who you’re creating for—yourself or others—what kinds of people do you think would appreciate the work you’re doing right now? Who needs it? Who could be helped by it? Who could you envision collecting it, and what kinds of characteristics does that person possess?

#10. How do you feed your creativity?

For your creative work to evolve, you have to expose yourself to new material. Otherwise, your work will stagnate. Without inspiration, you’ll create the same thing over and over...and you’ll get tired of it and lose your will to create.

What are a few recent bits of inspiration you can remember? They could be anything! New foods, new brands, different points of view, a quote, a movie, a book, a song, a painting, a sculpture, a piece of furniture, a dance piece—anything!

#11. Do you think your creative spirit has been fully birthed yet?

Do you feel “there”? Do you feel like you’ve peaked? Do you feel like you’ve reached a personal best?

Or, conversely, is there more to be done? Is there further to go right now? Do you envision future creativity that exceeds the work that you’re doing now? What would you like to do in the future? What sort of creativity do you wish for yourself? And what would help you get there?

#12. When do you see yourself reaching out for help to tend your creative work?

Some forms of creativity require a team effort, while others are more commonly undertaken as a solo venture. What do you think the advantages and disadvantages are to either type, or to the type of creativity that calls to you?

If you work independently, what would it take for you to ask somebody else for help, either with the creative work itself or with managing the business of it? And if you work collaboratively, what would it take for you to strike out on your own?

#13. Why did you plant the seeds you chose?

Creative people are often multi-hyphenates, regardless of whether or not they make a living from their creative work. We tend to favor multiple genres rather than sticking with or appreciating just one, even if we’re not skilled or talented in all of the areas we’re interested in.

What is it about your specialty that made you choose it over every other option? Can you see yourself exploring another avenue in the future?

#14. Who has been your midwife as you’ve worked to build you creative business?

Before there were doctors and obstetricians, there were midwives. It was these midwives, these miracle women, who birthed children and cared for pregnant and postpartum mothers in the Old World.

Every birth is different, and so is the birth of every creative work. Some require more assistance, others require less. Is there someone who supported you? Who checked in and made sure you were making progress? Is there someone who stood by from beginning to end, ready to step in if you made a wrong turn? Is there someone you called for when you were worried, despairing, or lost?

That person is your creative midwife. Consider what that person has brought to your work, and what it is you need most from someone in a support position.

#15. What words of praise do you want to be showered with?

Have you heard about the five love languages? A love language is the way you prefer others to show they love you. The languages are gifts, quality time, words, acts of service, and physical intimacy.

If you value words, what types of words do you want people to use to describe you and the work you do? If you prefer another form of appreciation—purchases, followers, hugs, disciples—what does that appreciation look like, and why does it matter to you?

#16. How does your work march us toward a better future?

I believe every bit of creativity has the power to evoke positive change, even if that change is making someone smile. Your creativity could be huge, inspiring some sort of international public activism. It could be small, a tiny product you can tape to your wall.

Whatever it is, how do you want people to use it? How do you think it inspires other people? And what do you want your work to inspire other people to do themselves?

#17. What brands or bosses are the perfect partner for your work?

One thing I’ve learned as I’ve grown in my creative business is this: There is always enough success to go around. In the spirit of that, I’ve pulled my creative community close to me for mutual support, inspiration, and friendship.

There are some brands and bosses that I see being very close to my own work, both spiritually, in terms of beliefs and values, and physically, in terms of what the end product looks like and does in the world. Are there any that come to mind when you think about your creative business?

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About me

Brittany Taylor

My name is Brittany, but my friends and clients call me "Britt." Online small business owners hire me to create content strategies and write their blog posts, email newsletters, and social media updates. I work with bosses around the world from the marshes of Charleston, S.C.

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