Career Guidance from Artists

In the last two months, I attended both my 15th business school reunion and my 20th college reunion. At both reunions, it was interesting to see how many of my peers are in the midst of reconsidering what they want to do with their careers. The questions vary—e.g., I’ve got 10-15 years left in my career; what do I want to do with them? What is “success” for me now?—but the common factor is a yearning to find something authentically meaningful to them. 

Coincidentally, I recently read The Work of Art, in which Adam Moss interviews 43 artists to understand how they find inspiration and the ability to create novel works. Many of their insights are relevant to those career questions.

Interest v. Talent

For example, Moss asked the writer Michael Cunningham whether interest or talent was more important in art. Cunningham then described his realization as a young man that he should abandon painting for writing. “[My peers] never got tired of trying to paint. And I started writing and realized that I felt that way about writing. [...] The fundamental question, Can you do some sort of justice to life using only words and ink? was endlessly interesting to me.” 

He continued: “My sense of my ability to write still comes and goes. It depends on the day. But I don’t know if I’ve ever in all these years lost that fundamental interest in the proposition: here’s ink, paper, words in a dictionary.”

I found his point insightful because part of my peers’ exploration of new paths was that they made their initial career choices based on talents, and their interest in those areas has run its course. Cunningham’s insight suggests that the next phase of our careers should be powered by answering, What topics have interested me endlessly?

Validation Sources

For the book, Moss interviewed New York Times editors Dean Baquet and Tom Bodkin about how they designed the front of the newspaper, which is both a technical question of design and a philosophical question about the function of a “front page” when most consume news through digital means. The conversation made Moss reflect on his efforts while working at the Times to reshape the weekend magazine. He said:

“When I became the magazine’s editor, I became more aggressive in testing the New York Times’s boundaries, which made me both allies and enemies at the paper. In retrospect, I realize that I felt freer to experiment than my colleagues because the validation I sought was from outside the paper—I wanted to impress my old magazine crowd more than the newsroom. I’ve come to see that where you direct your need for approval has a lot to do with the kind of work that you do.”

This point struck me because I’ve seen people gain the courage to shift careers only after they’ve reached the point where they care little about the opinions of others. Of course, that choice runs counter to the socialization we receive throughout our lives. But Moss suggests another path to finding the courage to step into more meaningful pursuits—simply surround yourself with people whose validations push you in the direction you want to go.

Leadership Wisdom 

“It’s only by making a volume of work that you’ll be forced to confront what it is that you don’t know how to do, and learn to do it. Oh, and the other thing is, you need to show your work to other people and have them tell you what they don’t like. There was a period when I would pay this guy fifty bucks to tell me what I was doing wrong.” 

— Ira Glass, host of This American Life, as quoted in The Work of Art