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Book Summary: Art Thinking – How to Carve Out Creative Space in a World of Schedules, Budgets, and Bosses by Amy Whitaker

Educator and writer Amy Whitaker combine her talents in art and business to explain how they serve one another. She proposes using a mind-set she calls “art thinking” to harness the joy and creative thought of making art in tandem with the structure and organization of the business. Each chapter addresses one aspect of the creative process, from development to making financial decisions to producing your project. Whitaker offers activities to spur creative thinking and provides a step-by-step guide for allocating project resources. Her grounded business approach provides a path to creative work that won’t break the bank. Creative people will benefit from her manual, which we also suggest to managers who lead creative people but must maintain productive constraints.


  • “Art thinking” fuels the realization that art and business serve one another.
  • It defines art as a process of “inventing point B,” not just going from A to B.
  • Everyone is an artist, and any field can benefit from art thinking.
  • Identify your “lighthouse question” to uncover your true interests and values.
  • Being “in the weeds” refers to the vulnerability and uncertainty of exploring a big question before you know how to answer it.
  • Use “portfolio thinking” to line up sources of support and income to support the big picture, so that you can dare to self-invest in riskier projects that might fail.
  • Claim your “ownership stakes” of the value in what you create; reflect on its potential for risk and reward.
  • Art thinking includes understanding how markets and business relate to your work, and how business modeling and project management are also creative processes.
  • Combining art and business means working across fields, being able to ask questions in any field even if you can only answer them in one.
  • Connect with people in other areas, or read a magazine out of your area of specialty.

Art Thinking - How to Carve Out Creative Space in a World of Schedules, Budgets, and Bosses by Amy Whitaker


The “Art Thinking” Framework

Art thinking fuels the realization that art and business serve one another. It uses art as a guide to engaging in a process and adopts business as a system in which creativity can operate. Art thinking is a mind-set that forges a partnership between the creative excitement of exploration and the structure and organization of the business. Art is the exploration of “inventing point B”, that is, creating “something new in the world that changes the world” instead of just going from A to B. Long-term business success depends on inventing point B, but short-term performance pressures make it hard to carve out space to do that. Art thinking combines “mind-sets of art” and “tools of business” to move forward in any field with MBA-MFA thinking.

“Aerial View”

Taking a wide view of your work allows you to establish guideposts and benchmarks. In their book The Power of Full Engagement, collaborators Jim Loehr and Tony Schwartz described four types of energy: “mental, emotional, spiritual and physical.” Elite athletes, for example, don’t work with just one energy source; they switch among all four to allow each one to rest.

“Art thinking is a framework and set of habits to protect space for inquiry.”

Rest allows new ideas to surface. Setting aside “studio time” without a specific project enables the process of discovery. You can find creative work in all areas of life, including the “social, organizational, civic, analytic, spiritual, kinesthetic, aesthetic, physical/material, narrative” (storytelling) and “harmonic,” which is “the domain of rhythm and cadence.” Explore these areas.

“In the Weeds”

Being in the weeds refers to the vulnerability of being in the middle of a project, not yet able to see the solution. There is a bias in perception because we see other people’s work from the outside when it is done, but they navigated the same uncertainty to get there. Use mindful practices to allow the process itself to govern the outcome. Keep three things in mind:

  1. “Judgment versus discernment”: Defer judgment and “embrace discernment.” Judgment means labeling as good or bad. An expectation of excellence can deter creative risktaking. Discernment means observing what is working and what can be better.
  2. Define a “grace period”: Even for urgent and important projects, there is usually a window before you truly have to know the answer. Give yourself this grace period before you have to know the answer, to give yourself more space for exploration.
  3. Stay in the moment: Looking ahead to completion shifts focus away from the process.

Your “Lighthouse Question”

Art thinking calls for asking questions and discovering new ways of thinking. Rather than focusing on SMART (specific, measurable, achievable, realistic, and time-bound) targets, identify a project’s Major Dramatic Question (MDQ), or lighthouse question. In a screenplay, the MDQ is the core issue that the film poses. The MDQ isn’t the plot question – how will Harry Potter overcome Lord Voldemort? – but rather something deeper, such as whether Harry can be both extraordinary and ordinary at the same time.

“Building your own metaphor means becoming authentic and original by adding together areas that interest you and becoming larger than the sum of your parts.”

The MDQ is akin to a person’s pivotal lighthouse question that guides you forward in life and work. To uncover your true interests and values, ask questions like: If money were no object, what would you do? Or ask, “Wouldn’t it be cool if…” or “How could this be better… ” and complete the sentence.

“Build a Boat”

Your lighthouse question must work within the “structure of your financial ecosystem.” Using “portfolio thinking” and identifying your “ownership stakes” let you pursue your project while maintaining balance in life and developing value.

“The act of inviting people into other fields is one of kindness and graciousness as much as one of education.”

Portfolio thinking means making sure you have other sources of support and income in case your creative project fails. When your lighthouse question requires an investment of time or money, portfolio thinking helps you decide wisely. Establish an “income portfolio” and an “investment portfolio.” Your income portfolio is made up of the tasks in one job or, if you are a freelancer, within assorted gigs. Your investment portfolio holds the tasks or gigs that pay you later.

“Instead of motivating people with praise and criticism, aim simply to make them feel truly seen and heard.”

Claiming an ownership stake in what you create aligns the risks you are taking with the reward potential of your work and its value. Whether through royalties, resale rights, or fractional or general ownership, maintaining a financial interest in your work is a long-term investment in yourself. Ownership stakes are important because early-stage creative work is hard to value.

“Wanting to skip past observation to judgment is a form of racing to the end instead of staying in the weeds.”

Bruce Henderson of the Boston Consulting Group sorts a business into four areas: “dogs, cash cows, questions or stars,” and urges balance among them. Stars have a big, growing market share. Cash cows have great market share but aren’t growing. Dogs have neither earnings nor growth. Question marks are the home of art thinking: growth and sales are possibilities that are not yet realized. Apply these designations to the life skills that contribute to or detract from your success. Art thinking is aligned most with turning question marks into stars.

Managing the Creative Process

Being the manager of creative projects poses certain challenges. Managers have to understand that doing creative work leaves the practitioner vulnerable. Even idealistic and deeply audacious visions still have to meet goals as well as expectations inside an organizational structure. The concept that applies best to manage the creative process may be a term psychoanalyst Donald Woods Winnicott coined, the “Good Enough Mother,” except the “good enough manager.” As a mother nurtures a baby into independence, the good-enough manager helps bring a project from being a vulnerable new idea to becoming a viable market entry.

“Excellence is the steady base of humanizing patience that comes from having trekked through weeds to the front of the pack.”

Project Oxygen at Google identified eight characteristics of good managers, many of which map onto the “good enough manager”: being able to coach well; having an empowering personality; being interested in the group’s overall happiness; being “productive and results-oriented”; exercising excellent communication skills; cultivating careers; providing a “clear vision and strategy”; and having the technical skills to guide the team.

“Creative work in any field asks you to risk offering something first.”

The manager of a creative project should allow time for exploration and discovery and can cultivate three roles, for the manager or members of the team: guides, colleague-friends, and producers. Guides offer constructive support in the face of possible failure. Different from gurus, they are teachers more than experts. Colleague-friends are fellow travelers who share both workplace knowledge as well as the trust, rigor, candor, warmth, and generosity of friendship. A producer takes on the secondary creative work of making an idea commercially viable.

“The more you are yourself, the better chance you have to make your own contribution and to create your own life and work.”

Pitfalls of creative work include the “soufflé problem,” the “pretending-to-be-a-writer problem” and the “never-fallen-off-the-bike problem.” The soufflé problem is one of excessive monitoring. Checking on a cooking soufflé too often makes it fall. A creative project is just as delicate in its formative stage. The pretending-to-be-a-writer problem is one of hiding behind the formlessness of creative processes and not doing any work. The never-fallen-off-the-bike problem is the liability of past success, self-identification as intelligent, or lack of experience with failure, all of which can signal a lack of resilience. If you have never fallen off a bike, you don’t have confidence and self-trust about being able to get back on.

“Market Structures”

The producer may identify the market for a creative project, or a new market structure or business model may get built as a creative work itself. In the analogy of the letter and the envelope, there are two levels of creative work: writing the letter and designing the envelope. The letter is the creative work itself. The envelope is the structure that supports it. Making the envelope is the art form of business.

“Risking the extraordinary, the failed, the not-yet proven is the way we bring into awareness the next ordinary circumstance.”

Understanding your cost structures helps you negotiate what is possible. A project has “fixed costs,” which remain the same without fluctuations in production, and it has “variable costs” that relate to production. A break-even analysis links these two by identifying the volume of sales required to cover fixed costs. The “unit contribution” is what you net after each sale.

“Art thinking is the process and business is the medium.”

Analyze these numbers to determine whether a creative project or business is financially viable. Use cost structure as the starting point of designing the envelope. Calculate the transaction costs – the expenses of finding, hiring or buying, formatting, and otherwise managing materials and people. Calculate “opportunity costs” of how else you could use resources deployed in one project. Adding up these elements gives you a clear analysis of how to balance “efficiency and invention” for your project.

Characterizing Business as a Design Medium

These models can help you identify “the main artistic limitations of business”:

  • “Imagination problems”: People who must replicate an earlier success hit problems when they count on their vision of what will happen but don’t consider scenarios that have not happened before.
  • “Concentration of interest problems”: These are structural imbalances in which one market actor has a concentrated gain where many actors on the other side of the transaction have a diffuse cost individually that sums collectively to a greater loss.
  • “Externality problems”: Values outside the market are “externalities.” If you’re waiting for a tardy repairman, the repair company saves money by having fewer workers but their gain costs the externality of your time. Price and value are out of alignment.
  • “Political problems”: People with special interests or conflicts of interest may value their interests more than they value the fiscal health of the project.
  • “Character problems”: Technology and the influence of large corporations may lead people to feel they are not responsible for their choices or that their actions don’t matter. A single actor in a corporation may generate the best business solution, but all of those solutions taken together may cause harm.
  • “Common risk problems”: Seemingly unrelated transactions sometimes do relate to each other, unbeknownst to some participants. Information is the key to foreseeing these problems, but people often don’t share data because they fear losing an advantage.
  • “Pervasiveness of capitalism”: Many people, including creative people, don’t understand how the market economy works. That lack of knowledge can keep them in the dark about their available choices.

“Art thinking by its nature is question oriented, not solution based.”

Understanding how market failures and business strategy relate is a part of art thinking or taking a creative approach to how you want to succeed. Some of the solutions to these problems require a collective effort.

“Designing Your Metaphor”

Being asked, “What do you do?” raises complications for those whose jobs don’t reflect the scope of their identity. Consider poignant moments in your life and see if one of those stories leads to an identifier that denotes who you are. Consider unexpected questions, such as: What kind of animal are you? What film character would you be?

“The Connective Tissue in the Body of Knowledge”

As data proliferate and educational pathways become more specialized, working across fields and departments is necessary to business success and to address the great questions of the day. If Leonardo da Vinci were alive today, he would probably not be one person. All of us in conversation would be a collective Leonardo.

“You are looking for ways to dissemble bulky business models to squeeze more efficiency out of them, to build them more nimbly and flexibly, and, more and more, to build a sense of community and purpose that is sustainable and expansive.”

Being able to discuss what you do with others is increasingly important. Connect with people in other areas, or read a magazine out of your area of specialty.

About the Authors

Amy Whitaker is an assistant professor in the Department of Art and Art Professions at New York University. She writes and teaches about the intersection of creativity, business, and life. She holds a Yale MBA and an MFA from the Slade School of Fine Art at University College London.

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