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Positive Slope // S.Belsky: The Messy Middle, Killing Elephants, & The State Of Creative Process

Positive Slope // S.Belsky: The Messy Middle, Killing Elephants, & The State Of Creative Process
By Scott Belsky • Issue #4 • View online
My newsletter has been on hiatus, but for good reason. I’ve been in fervent non-stop writing monk-mode to make a deadline for a new book that has been nearly seven years in the making. I’m excited to share the topic below, and I expect the book to be published in mid-2018 (yes, traditional publisher are not known for their lean operations and quick execution times). Suffice to say, I poured myself into this project - and spent hundreds of hours interviewing creative minds and leaders I admire across many industries and geographies. Stay tuned.
I’ve also spent some time the last few months thinking about two other things that I expand upon in this newsletter below:
  1. Killing Elephants In The Room: It is all too easy to ignore them, but if we don’t kill them than they’ll kill us. Especially in big companies or tough moments, we must remember not to aspire for peace as a default.
  2. The State of Creative Tools: As you may know, creative tools, services, and marketplaces are a deep passion of mine (after all, if the tools/process Creatives use to create impact what they create, then the process is pretty damn important). So, I figured I’d share some thoughts along these lines as well. My gut tells me there is much work to be done in empowering creative careers and making creativity more productive and accessible. 

Unpacking The Middle Of A Journey
A project that unofficially started almost seven years ago finally picked up speed in the last couple years and is now in a draft form. It’s all about “the middle” of a venture, when you’re navigating uncertainty, working anonymously, full of self-doubt, yet relentlessly focused on optimizing your product, your team, and your own approach to leadership.
As you know, the myth of a linear journey for any bold creative project or venture is just that - a myth.
In reality, the middle is extraordinarily volatile—a continuous sequence of ups and downs, expansions and contractions. Once the honeymoon period of starting a new journey dissipates, reality hits you. Hard. You’ll feel lost and then you’ll find a new direction; you’ll make progress and then you’ll stumble.
Every advance will reveal a new shortcoming. Major upsets will give rise to new realizations that lead to breakthroughs in progress. At best, you’ll move two steps forward, one step back—at worst, you’ll realize you’ve been walking the wrong path entirely for months. This is what that journey actually looks like.
I’ve come to call the journey of creation one of “relative joy.” Your job is to endure the lows and optimize the highs in order to achieve a positive slope within the jaggedness of real life—where, on average, every low is less low than the one before it, and every subsequent high is a little higher. The best you can do is aspire for a positive slope.
For the book, I chronicled the insights to survive and thrive through the middle, and boiled it all down to “endurance” and “optimization.” To achieve the elusive positive slope, you must endure the downs (the incremental set-backs and struggles) and optimize the ups (everything and anything that seems to be working).
Needless to say, I am really excited for this project to see the light of day. It was very meta to struggle through the middle of my own creative journey writing a book about the middle. I have learned so much about myself from the insights I captured from others and synthesized from my own experiences working with start-ups and big companies. Perhaps my greatest personal realization from the process: I miss operating. I miss building teams, products, and tackling big hairy problems. While I’ll never stop writing and working with early stage companies as an investor or board member, I miss leading a team fixing something important.
The draft is now about 145,000 words and contains over 150 insights for managing the middle, so there is much culling and editing to be done. But at least I have the courage to call it a “book” now, versus a “project on the backburner.” I’ll keep you posted and share some snippets over the coming months…
Eliminating Elephants In The Room
Earlier this year I wrote about the need to tackle organizational debt, which I described as “the accumulation of changes that leaders should have made but didn’t.” But why do leaders shy away from pushing for the most important changes? Why do people sitting around a table keep their doubts to themselves? Much of the hesitation boils down to conflict avoidance and always trying to keep everyone happy.
Your job as a leader is to challenge peace as a default. Create an environment where people can withstand a fight and engage in friction as it arises. Rather than passively surf the whims of peoples’ hesitations to take action, bring the conflict to the surface with questions like:
  • “Let’s debate this out – what is the worst thing that will happen if we launch a bit early? Is scrambling a little bit after launch really worse than punting the project for additional months?”
  • “Who exactly claims we’re not ready to launch this? What, specifically, needs to be done for us to be ready?”
Ultimately, you want a team that values conflict as a means to making bolder decisions and taking the required risks for a more exciting end. Disagreement is great, so long as the team shares conviction when a decision is made.
I like how former RISD president and one of my long-time mentors John Maeda once observed: “A good team does a lot of friendly front-stabbing instead of backstabbing. Issues are resolved by knowing what they are.“ Confrontation tends to be most needed when it is most uncomfortable. It’s the truly tough issues, the ones most likely to advance our potential the most, that we avoid. I am still determined to get a sign someday for my office that simply states, “No Elephants.” To eliminate all “elephants in the room” your team must commit to as much front-stabbing as possible. 
Shortcomings In Creativity: Thoughts
I’ve been spending more time with design teams, and better understanding the modern landscape of tools and services for the creative process. In the process, I keep coming back to a few realizations:
  • Creativity has too much friction. Let’s face it, most people find products like Photoshop, AdobeXD, or Sketch complicated to learn. The sheer number of tools, panels, and options is overwhelming to new users and time intensive for professionals. These applications are also still largely bound to the desktop. Files are too big and cumbersome in a world where more work is done on mobile, tablets, and laptops with less and less storage. The whole notion of “files,” whether they live in your computer or in the cloud, is antiquated. No mainstream creative tool has figured out how to use artificial intelligence and machine learning to speed up the creative process. Especially in a world where labor is increasingly commoditized, creativity needs to be more productive and accessible to everyone. I’ve never met a creative professional that would want to spend three hours doing something that could be done in three minutes.
  • The more tools, the more need for connectivity between them. I love seeing new apps for prototyping like InVision and Principle, new apps for high-performance screen design like Adobe XD (no art board too big!), version tracking like Abstract, and new web, mobile and tablet applications like Figma, Procreate among so many others. If there’s one thing we’ve learned from the past few decades, the greatest breakthroughs come from the intersection of different tools, teams, and industries. So, with the rise of more tools and devices, there is an increasing need for connectivity between them. Creatives are not served well when tools isolate them. With the emergence of all these new tools, I am most excited about the potential of them working together. File format compatibility, assets always at your fingertips no matter what product or device you are using…these “platform values” are what matter most. You shouldn’t have to worry about where your assets live or their version or origin. Your files and assets from the past, alongside those of your peers, are precious resources for your future work. I have long believed that creativity is the world’s greatest recycling program, and the next generation of tools must work together to enable compatibility and flexibility. 
Suffice to say, the creative world - and companies like Adobe that play at the center - have a huge opportunity (and responsibility) to figure this out. There is exciting work to be done.
In Case You Missed It...
Avoiding Organizational Debt – Positive Slope – Medium
Notifications: A Tragedy Of the Digital Commons – Positive Slope – Medium
Give Me A Shout
Well, if you’ve made it this far, feel free to share the newsletter with a friend or give me a shout and let me know what you think. Have a good week and thanks for following along.
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Scott Belsky

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Scott Belsky, NY/SF