Who: Yancey Strickler

Claim To Fame: Yancey Strickler is a writer and entrepreneur. He is the cofounder and former CEO of Kickstarter, the author of This Could Be Our Future: A Manifesto for a More Generous World, and the creator of Bentoism. Yancey is a Distinguished Fellow at the Drucker Institute, a World Economic Forum Young Global Leader, one of Fast Company’s Most Creative People and Fortune’s 40 under 40. He’s spoken at MIT, Stanford, the London School of Economics, the Museum of Modern Art, the Sundance and Tribeca Film Festivals, Web Summit, and startups, nonprofits, and schools around the world. Yancey cofounded the artist resource The Creative Independent, the record label eMusic Selects, and an audio app called Micd. He coaches CEOs, activists, and artists, and advises and invests in startups like Ampled, Hopin, and Wren. Yancey began his career as a music critic in New York City, writing for Pitchfork, Spin, and The Village Voice, and grew up on a farm in Clover Hollow, Virginia. The London Spectator called him “one of the least obnoxious tech evangelists ever.”

Where To Find Yancey: His Website, Amazon, Twitter

Praise For Yancey: “Yancey Strickler is convinced that our value system is broken. In this lucid book, he lays out a vision for how to fix it that’s both audacious and elevating. It’s a thought-provoking read for anyone who knows there’s more to life than accumulating wealth.” — Adam Grant, New York Times bestselling author of Give and Take, Originals, and Option B

Given the above bio and all the projects you’re involved in, the first question has to be: how do you find time to write? Do you have a slotted time or does it vary day to day?

This is the challenge. I keep my schedule open on Mondays and Fridays for writing and other deep work. If I know I’m going to write on a certain day I can do it. But when I’m trying to squeeze it in, or just hope that inspiration makes it happen, it’s much harder. Especially during COVID with a four-year-old at home.

Where do you like to write? What does your ideal work environment look like?

I write in a home office. I use an app called Self-Control to turn off all the websites that like to make their siren calls when the writing process gets especially grueling. I bounce back and forth between paper and screen. I print out things I’m writing. I make outlines on physical paper. I often try storyboarding an essay, chapter, or idea visually as a way to feel the arc of it. At the start of the day my desk is completely clean. By the end it’s covered in books and scraps of paper.

Do you have any pre-writing rituals or habits before you sit down to write?

Not now, but when I was writing the book I tried to consciously cultivate a mood of self-forgiveness each day. I’d tell myself it wasn’t my job to write the best sentence ever or to be the most brilliant author ever, it was simply to build this thing called a book. I almost saw myself as a hired hand.

Early on in the process I would let myself become way too reactive to a particularly “good” or “bad” day of writing. This resulted in me putting a lot of pressure on myself. It didn’t take long to recognize that carrying that mindset every day was not going to result in my best work. So I had to consciously remove that pressure each morning. I still had hard days, but in general the flow was much more natural.

This Could Be Our Future was your first book. Even after years and years of writing, what were you surprised to learn in that process that you wish you knew at the start? Did your writing routine or process differ at all?

What an amazing process outlining is. An outline lets you explore and be creative about structure. It gives you a strong sense of the emotional journey. It shows you the rhythm you can follow or interrupt. The whole time I was writing my book I was writing for a feeling. There was a way I wanted a person reading it to feel – a sense of growing awareness of the world around them, a new knowledge that felt like a secret – that the outlining process helped me tune into.

How I self-edited evolved a lot. Eventually I started printing out everything I’d written for a chapter – the text, my notes, the discard pile, my research – when it felt like things were about 80% there. I’d then spend an entire week marking up these pages, physically cutting out good sentences and paragraphs, using the paper and the walls of my office to better see it. Staying off the computer. It felt like working in the physical space allowed for less rational, more subconscious connections to happen. That space felt more like art.

How do you know if something you’re working on is not worth publishing or not any good? Have you developed any criteria that lets you evaluate your own work?

When I was first shopping my book, I met with a number of literary agents who I liked and who were interested in working together. But there was one agent in particular who I could tell was a bit skeptical of me. I really liked that, and decided to work with them. If I can convince this person that my ideas have merit, I thought, then I’ll know that I’m actually making something worthwhile. 

I continue to use that kind of process. I made sure to have early readers of my book be people who I knew would disagree with it. But I wanted to hear those arguments about what I might have been missing or doing wrong before the book was published, not after! Seeking dissenting opinions early on is so helpful. This is something I do even with blog posts today. 

People often discuss social media’s detrimental impact on things like productivity and personal wellbeing. For writers and creative’s, there’s an interesting tension. Being on platforms like Twitter seems counter-productive, but, having a platform online is one of the biggest assets agents and publishers look for. You’ve written about going dark on the internet a few years ago and then why you began to question that decision. Can you talk about how you utilize social media now? Do you think it’s essential for writers to have a presence there?

Social media is a relationship. Not a love-of-your-life relationship. More like one of those tumultuous, hot-and-cold relationships you had in your twenties.

While writing the book I purposely stayed away from social media as much as possible. There’s such a hivemind of thought and I didn’t want to get caught up in it. What good is a book that reflects the social mood of six months ago – which translates to decades if not centuries of change in historical terms?

I’m semi-active on them. I lurk more than post. There’s value for sure. But it’s mentally dangerous. It fills you up with things that are not you. You live with a mindful of other people’s thoughts. This is how these massive social swings keep happening.

The key is to put it in its proper place in your life. Prioritize real friends first, internet friends second has become my rule of thumb. Too often we ignore emails or texts from our actual friends because we’re scrolling social media or building online brands instead. Like those bad relationships from your twenties, this will not work out in the long run. 

Great writers tend to be voracious readers. What does your reading habit look like? What books or writers have most influenced the way you think and the way you write?

I read all the time. I normally have three or four books going. I finish most things I start but it’s not a rule. My reading has really slowed down during COVID – it’s hard to set aside time for reading when there’s so much else to do, but I’m getting better at it. Influential writers on me… John Higgs (his book on the KLF), EF Schumacher (Small Is Beautiful), Mariana Mazucatto (brilliant economist), Michael Walzer (Spheres of Justice), Milan Kundera (my montage-y style of writing has its roots in a love of Kundera), Liu Cixin (Three Body Problem), the films of Adam Curtis (“Century of the Self”), the song “Parasite (For Buffy)” by Eugene McDaniels.

Any last pieces of advice to aspiring writers?

From childhood my dream was to be a writer, and I’ve been fortunate to do it professionally in a variety of ways (music critic, copyeditor, editor in chief, book author). Ultimately all of these opportunities came because of other things I had learned or was doing – being obsessed with music, the experience of building Kickstarter, etc. In a world where essentially everyone is a writer (if we include social media), it’s critical to have that other thing – an area of expertise, a specific lens or focus, a life experience to share – to stand out. So if you want to be a writer, go live an interesting or obsessive life and take good notes.

Peace.

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