A couple of years ago, my husband and I landed a pair of tickets to The Tonight Show, an event so meticulously orchestrated by Jimmy Fallon and crew that we left feeling we’d had an experience of a lifetime. A particularly memorable part of the afternoon was a private concert by The Roots, a band I was certainly familiar with as a child of the 80s but to which I hadn’t given much thought since jamming to Things Fall Apart nearly two decades prior.
The Roots seem to have mastered the ability to reinvent themselves. Which is why I was so intrigued to read drummer Questlove’s new book about creativity.
Creative Quest is Questlove’s third title (following a memoir and a book about food and the people who make it), and the jacket refers to him as “a cultural omnivore”—based on the variety of stories shared throughout these 275 pages, that title seems legit. He draws on his three decades of experience making music and interacting with some of the world’s most creative rappers, musicians, chefs, and comedians.
Questlove’s overarching theory is that creativity shouldn’t be over-thought. In fact, it tends to happen to people who are engaged in a creative process and aware of moments of creative responsibility within it. The rest of the book offers tactics for pursuing a creative process that lasts a lifetime.
At times, the book speaks squarely to a creative in the more traditional sense: someone who makes art, music, or films. But many of the themes are certainly relevant to a creator of technology products, and in fact, they support the idea that any creative person should consume them. Five ideas, in particular, stuck out:
Collaborate Over Compete
Competition is referenced throughout this book, and Questlove is passionate about the topic. He shares stories of discomfort as he learned to embrace opportunities to work with artists he considered different (i.e. more commercial) like Jay-Z and Usher. He explains how his mind opened to the idea of copying or riffing on a competitor’s work as a way of showing respect and creating something new from something already great.
He also details how he approaches emerging musicians as both a mentor with experience to lend and an apprentice to the unique perspective they bring to the field. Questlove is clear that competition fuels his creative journey. These ideas are probably familiar to many PMs – letting go of biases, coaching others to work collaboratively, and trying to influence instead of control, are all hallmarks of the craft.
Curate the Creative World
Questlove spends a lot of time in the book reflecting on the influence of technology on his industry, and on the creative process. He describes the human brain as transforming from a container of information to a retriever of it. In many ways, it enables musicians to do their work more effectively—any song, sound, word or story is within reach. And yet, it gives us unlimited ways to become distracted and paralyzed by options.
The inclination of some creatives is to block out everything that is happening around them while creating. But Questlove argues that learning to process all of the creativity happening around you is part of being creative yourself. He suggests thinking like a museum director curating an art exhibit—figuratively hang all the words or images or bits of information as a sort of show that you curate from when it’s time to create.
For Questlove, the outcome of a perfectly curated DJ set invokes the following: “You want the crowd to be moved spiritually and psychologically and physically all at the same time, and for an idea to start to form around the idea of that movement.” That sounds a lot like the experience we’re trying to inspire as technologists.
Embrace Restlessness
Any creative person desires to stay sharp at the craft while also improving upon it. And yet, our nature is to keep doing what works or what people love about what we’ve already created. In technology fields, we often use Agile to finetune the things that are working and address and improve upon those that aren’t. Questlove seems to affirm this by explaining how each album by The Roots uses a different approach or process to improve upon the last. The key is to preserve a sense of original mission and continue coming back to it.
One way of staying restless, Questlove says, is by finding a creative outlet outside your creative outlet. Depart, Questlove says. This seems appropriate coming from a guy who co-leads a band that performs five days a week, while also authoring books, performing DJ sets, hosting chef events and producing records. In tech, we often refer to “getting out of the building” to find inspiration. For creatives, that means making in unique ways.
Set Limits to Ensure Creative Output
A healthy creative process means making decisions. As product people, we don’t have the luxury of open-ended creativity. There are limits set on time and target market because our products must see the light of day. Questlove brings up the valid point that these constraints don’t mean less creativity. They instead force us to “distill and discipline our creative impulses”. The decisions we make about the products we build are part of the creativity required to bring them to life.
Think of Failure as Nourishment
Questlove dedicates an entire chapter to success and failure toward the end of the book, sharing specific stories of albums that didn’t turn out how the band expected or moments when he felt ashamed by what he had created. Engaging in creative work over a lifetime means that failure is bound to happen. But Questlove argues that failure can nourish a creative person in ways success can’t. Success feels good, it validates. But it can also narrow focus, make us play it safe and avoid risks and experimentation. Creatives must first accept failure, and then let it liberate versus debilitate their creative process.
There’s a sense of romanticism in Questlove’s description of a fruitful creative life. I think there’s a lot more pain and suffering than he describes. But the idea of creativity as a fluid activity that is inspired differently throughout life is most certainly valid and applicable to our discipline of product.