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Art Thinking Your Way to an Encore Career

A chat about using creativity to make a difference and make a living


Part of the Artful Aging Special Report

Amy Whitaker lives at the intersection of two seemingly opposing worlds — art and business. She’s been toggling between teaching artists about economics and coaching business people to think like artists. Her latest book, Art Thinking: How to Carve Out Creative Space in a World of Schedules, Budgets and Bosses, provides a blueprint for all of us to toggle, too, whichever side of the art/business divide we live on.

Whitaker and I chatted over email about how people can use “art thinking” to launch encore careers. It’s something I care a lot about as vice president of marketing and communications at Encore.org.

I’ve been following Whitaker’s work for a long time. Her prior book, Museum Legs, is a gorgeous reflection on the relationship between people and museums. And I had the pleasure of talking with her on many long walks as she was incubating the ideas for the new book.

Art Thinking Author and Book Embed

Still, when I sat down to read Art Thinking, I was stunned. These ideas emerged in a way that creates a new language and framework anyone itching for more creativity could — and should — implement. My guess is that Whitaker’s concepts (studio time, Point B, lighthouse questions and more) will soon become part of the standard lexicon in personal and professional development.

Here’s a bit of our conversation, edited and condensed:

Marci Alboher: Let’s start with some definitions. ‘Design thinking’ is a phrase that’s gotten some traction, but you’ve coined a new phrase: ‘art thinking.’ What are you referring to? How does it differ from design thinking?

Amy Whitaker: Art thinking has some affinities with design thinking, but a key difference. Design thinking is an amazing framework that takes the process of designing a product and generalizes it to solve any problem creatively. Firms like IDEO and frog have pioneered this approach. Design thinking is about finding the best possible answer to a question. Art thinking is about asking, ‘Is this even possible?’

You are not looking for a dreamy Saturday afternoon, but the Venn diagram overlap of meaning and making a living.

— Amy Whitaker, author of 'Art Thinking'

We spend a lot of time in life going from Point A to Point B. Art thinking is about inventing Point B. It is about carving out space for the mindset — over the course of our lives — of staying open to what is new, risking the vulnerability of trying things out and staying true to our highest objectives.

As you know, I’m obsessed with the idea of encore careers — later life work that combines meaning and money — making a difference and making a living. Many people are stuck on how to design that for themselves and there are few organized pathways to help people do that. Any tips on how people can use art thinking to make an encore transition?

I love this question because it’s so honest about the money part, and the creative life adventure part!

The first step is to realize that making a living is part of your creative design challenge. You are not looking for a dreamy Saturday afternoon, but the Venn diagram overlap of meaning and making a living.

The starting point is to focus on what in I call your ‘lighthouse question.’ If you’re inventing Point B, you don’t know the destination when you start. So you need a grounding question to propel you forward. Lighthouse questions often take the form, ‘Wouldn’t it be cool if . . . ?’ or ‘Why is this so broken? Could it be better?’

Once you find your lighthouse question, ask yourself how much time you have to lose working on it. That might be an hour a week, or a half-day a month. Call it your ‘studio time’ project and just get started. It doesn’t matter if you know yet whether you will fail or succeed. It matters that the lighthouse question is what you really want to work on.

As you make progress, figuring out the money side becomes a secondary creative project unto itself. In the book, I use the image of the letter and the envelope. The letter is the project itself and the envelope is the business model or job that fits the project.

Sometimes you can make your mission fit a known envelope. And sometimes you will have to work to design the envelope — to create the job or to design the business model — too. Companies like AirBnB [an online marketplace to rent vacation homes] and [eyewear designer] Warby Parker redesigned the envelope.

Bigger picture, right now, the envelope of how people get paid — in salary or royalties or equity shares — is changing rapidly, so it is an interesting time to be creative with both the mission and money sides.

I was thrilled that your book included some examples of ‘late bloomers‘ like sculptor Louise Bourgeois, who had her first major museum exhibition in her 70s. Do you have any observations about the importance of life trajectory, particularly in this age of longevity?

Yes, absolutely! I’m 42. If you’d met me in my late 20s, I might have seemed like a lost soul. After getting an MBA and an MFA, I ended up with a found-object career — a bloom-where-you’re-planted path of figuring out what I could do with those credentials that would have meaning for me and for others.

Creative paths — including the long arc of life — are so nonlinear and cumulative, that part of designing your way is figuring out how best to carry the past forward toward the frontiers of possibility that you want to embrace.

I’ve been very lucky to have role models in this. My mother moved cities and took a new job in her 60s. My aunt retired and then started a wave of cultural programming in her 70s.

One of my favorite stories in the book is of Louise Florencourt, a first cousin of the writer Flannery O’Connor, who wanted to be an artist but feared a life of poverty and ‘dusting the sarcophagi,’ so she went to work in law instead. Only later in her life, she was called to Milledgeville, Georgia, to take care of the O’Connor estate, which became her driving passion. In the meantime, she had been in one of the first classes of women at Harvard Law School, a groundbreaking, artistic path unto itself.

As a painter, I was trained in oil paint. The thing I love the most about working in oils is that it’s a medium devoted to layering. The richness of the best paintings comes not from the surface, but from the early layers that shine through and come together as a whole. Encore careers seem similarly rich because of their layers.

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