Jocelyn K. Glei on Ideation and Being Accountable in Your Projects

When inspiration strikes the heart, it’s our role as makers to give it form. Choosing a medium is part of the process and it influences the way we engage with the people we seek to change. What if instead of a podcast it was a video series or vice versa? What if you have to learn an entirely new skill to convey your idea? Is there a right answer?

We spoke to Jocelyn K. Glei, the curious mind behind the insightful podcast, Hurry Slowly. She was also the founding editor of 99u and creator of their best-selling book series, which includes Manage Your Day-to-Day and Make Your Mark. She’s also the author of Unsubscribe and gives talks on how we can find more meaning and creativity in our daily work. Her body of work spans various mediums and yet her message, the change she seeks to create, shares a common theme around creativity and productivity.

Jocelyn shares her process for transmuting inspiration into tangible work that impacts people.

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Your work is always thoughtful, polished, well-researched, and fills an important gap. Do you have a checklist of sorts for your projects? How do you ensure that what you’re shipping is at the quality you desire?

Jocelyn:  I’m driven by intuition more than reason or research. I also tend to have a million ideas. For instance, in my Evernote, there are about 30+ notebooks, each tracking notes for a different idea. Some have only one little note, just that initial kernel of an idea. Others have 65-90 notes. By jotting down each idea and putting them in one place, I can see which ones are ripening. That is, which ideas I am returning to again and again, and fleshing out. This helps me recognize which ideas have legs, and which ones were just passing fancies that won’t hold my attention.

As for quality, an innate and relentless perfectionism seems to do the trick. I get extremely obsessed about every single detail of anything I make. So for the 99U Conference, which I ran for 6 years, I’d rigorously vet the speakers, but I’d also make the music mixes that would play during the breaks. For my book Unsubscribe, I wrote and self-edited all the content, but also hired the illustrator, collaborated with him, and designed the layout of the book. For my new podcast, Hurry Slowly, I curate all the interviews and write all the commentary, but I also worked with a composer to create an original theme song and collaborate with my producer on every single edit. I’m not saying this is entirely healthy, but it is — for better or worse — my process.

I strongly believe that the amount of love and care you put into a project is always apparent. Even if people are not conscious of it, they can sense when you have paid attention to every little detail. The typographer Erik Spiekermann wrote a really beautiful blog post about this.

Ideas are fun to play with because of their flexibility and potential. When an idea excites you, at what point do you start developing strategies and actions to bring it to life? What’s one of the first things you do when you commit?

Jocelyn: When I feel like I am consistently fascinated by an idea, which usually means over the course of many months or even years, and it seems to have the right level of ripeness, then I explore it in more depth.

So, in this scenario, step one would be idle thinking or passive thinking. I wait and see if an idea comes back to me again and again, and I listen and take notes. Then when it feels ripe, step two happens, which is active or purposeful thinking. Asking: What would this idea look like? How would you execute it? How would you package it?

If I can come up with viable answers to those questions, then I’ll consider moving forward with an idea. But there are other factors as well: Do I have the bandwidth to execute the project? Am I willing to devote my time to it for however long it will take? And most importantly: Does it feel like now is the time? At the end of the day, deciding to pull the trigger is really just a feeling.

Once I commit, the biggest step is to create some accountability. Either by: Announcing the project publicly, or by bringing collaborators on board to get invested in it. Ideally, both! Without accountability, it’s very easy for my attention to drift and glom onto another shiny new idea.

I strongly believe that the amount of love and care you put into a project is always apparent. Even if people are not conscious of it, they can sense when you have paid attention to every little detail.

On the outside, it looks like you ship your work and don’t look back. With your book Unsubscribe, you gave talks and wrote essays that were featured on various publications. Then boom, a podcast, not directly about email, but on the same frequency of creativity and productivity. How do you decide when to move onto the next thing and how do you decide what that’ll be?

Jocelyn: In Greg McKeown’s book Essentialism, he has this one little paragraph I was really struck by. It’s a piece of advice that Peter Drucker gave to Jim Collins, who’s the author of a bunch of bestselling business books, including Good to Great. What Drucker told him was: You can build a great company or you can build great ideas but not both. That quote really resonated with me. Particularly because I read it at a moment when I was thinking about starting a new business with someone.

And I thought to myself: “You know what? I’m not interested in building a big, lasting organizational structure, I’m interested in building ideas.”

If creativity is self-expression, then every idea is a chance to move deeper into yourself. And that’s the journey I’m interested in. So each project, whatever it is — a book, a conference, a podcast, a movie — just feels like a new opportunity to learn, to explore, and to play. Of course, you have to spend some time on marketing and PR and those sorts of things if you want the project to reach an audience, but for me the real joy is in the journey from idea to reality. And once the project is shipped, the question is: “What do I want to explore next?” The through-line from this project to that one, from Unsubscribe to Hurry Slowly, is simple — it’s me and my interests.

And anything else you try to build up to make that through-line more clear — a personal brand, a job title, etc — can just as easily end up holding you back in my opinion. No one likes to be put in a box, but it’s easy to choose to put yourself in a box. In my mind, I call it “the allure of competence.” You get used to doing the things that you know how to do. And so you keep doing those things. I’m trying rather hard not to keep doing the same things, but it’s a difficult habit to break!

What are your thoughts on the importance of medium vs. the content? What do you personally care more about in this creative process?

Jocelyn: I would never say that I care about medium more than content or vice versa. They’re inextricably linked. But I will also admit that deciding what medium to present a new idea in is a constant struggle for me. I’ve created websites, events, magazines, books, podcasts — and I’ve enjoyed working in every single one of these mediums. So deciding how to package an idea is always difficult.

But I think the final decision always comes down to two things.

The first factor is: What experience do you want people to have? Because the equation is basically “medium + content = experience.” I also like thinking about a book or a conference or a podcast in terms of experience because it gives you an awareness of how important every single detail is. It makes you ask: How do I want someone to feel when they listen to this podcast? Or when they open this book? Or when they walk into this auditorium?

The second factor is: Where is the most challenge? For instance, I was recently thinking about doing a new video project, and the prospect made me highly uncomfortable. Which made me feel like I really need to do it, because I’ll have absolutely no idea what I’m doing. For me, half of the fun is figuring out the medium.

No one likes to be put in a box, but it’s easy to choose to put yourself in a box.

In a world where everyone seems to be an ideas person, you seem to have mastered the art of execution. How do you decide which ideas are worth moving forward with, and how do you start them?

Jocelyn: I certainly wouldn’t say I’ve mastered the art of execution! In my opinion, mastery is a recipe for complacency. I interviewed this wonderful Slovenian philosopher Renata Salecl for the Hurry Slowly podcast and she said, “You have to be dissatisfied, in a way, to do something in your life.”

In other words, creativity doesn’t come out of happiness, or a sense of mastery, it comes out dissatisfaction — the feeling that something is missing. And for better or worse, I am very good at feeling like something is missing (haha), which keeps me motivated to make stuff.

As for how I decide which ideas to act on, there are two elements: ripeness and intuition.

As mentioned above, I track all of my ideas in Evernote, so I can see which ideas are ripening. If there are a lot of notes, that means I’ve been circling back to that idea again and again. And when ideas are persistent, when you just keep getting little pings of inspiration about them, that usually means there’s something of value there.

Once you know the idea has staying power, there’s the question of intuition, which I think of as a strange mixture of gut and readiness. Gut is your primal feeling about whether or not the idea will resonate with people. Readiness is about how prepared you are to do this thing.

It often happens that you are persistently drawn to an idea, and that you know intuitively that it will resonate with people, but you’re just not prepared to execute on it yet. You’re too afraid, you haven’t mastered the skills, you need to refine your style — there’s any number of reasons why this might be the case. Of course, you have to weigh those doubts against the fact that no one is ever really “ready” to do anything that counts.

Creativity doesn’t come out of happiness, or a sense of mastery, it comes out dissatisfaction — the feeling that something is missing.

Have you ever walked away from a work in progress? What was missing, how did you know it was the right time to put it down?

Jocelyn: If there is accountability on the table, I don’t think I’ve ever walked away from a project. If I’ve told someone I’ll do something, generally speaking, I do it. I will say there have definitely been projects that I have not walked away from that maybe I should have. Suffice to say: Don’t put anything out into the world that you don’t 100% believe in.

As for projects where I lacked accountability, I can’t tell you how many I haven’t finished.

The answer is lots.

If I’m not beholden to someone, I am probably not going to finish that project. I wish it were different, but the guilt of disappointing someone is a huge motivator for me! The good news is, that once you know that about yourself, you can always find accountability hacks to keep yourself engaged.

How much do you dive into learning everything there is to know about a new medium, and how much do you own your own super powers and outsource the rest?

Jocelyn: My approach is pretty much just to commit to a project, dive in, and figure it out. What’s most important to me is to have a super-clear vision for the project going in.

For instance, if I were making a book, it would be really important to me to have the title, a visual in my mind of the design, a conviction that it would resonate with people, and, of course, an outline of the content. For me, it’s about seeing the big picture of what you want to accomplish in the medium rather than necessarily understanding the medium. Once I have that vision, I trust that the details will fall into place.

As for delegation, I am a bit of a control freak. And because I view every project as a full 360-degree experience — whether it’s a conference, a book, or a podcast — I get very involved in the details. I care about every little aspect, so I usually own as much of the project as I can given my skillset. With the Hurry Slowly podcast for instance, I curate all the guests, do all the booking, conduct all the interviews, select all the musical snippets, write a script for every episode, and decide on all the edits. I also designed and built the website, set up the podcast feed, and write all the show notes. These are all things that play to my skillset.

But I do not handle the audio engineering: I give my producer a script for every show and then he makes the edits, lays in the music, adjusts the levels, and generally beautifies the episode sound-wise. Audio engineering requires a lot of expertise I don’t have, and it’s just way more efficient (and fun) to let someone who knows what they’re doing handle it. Similarly, I came up with the idea for the Hurry Slowly logo — the anchor inside a stopwatch — and then my friend Matias, who is an incredible designer, took the reins and made it a reality: picking a fantastic font for the logotype, streamlining the iconography, and figuring out the right balance for the podcast badge.

I’m happy to delegate things where I can communicate my vision, and have someone else with expertise take it to the next level. But you can’t delegate vision.

What does the future of content look like to you?

Jocelyn: This is the part where I confess that I actively hate the word “content.” Content is a word that was invented by people who want to create boxes that they can sell ads around, and they had to come up with a name for what goes in the box, and that word was “content.” In other words, if you’re using the word “content” that means you really don’t have a vision for what you’re making. Because creating good content requires specificity: it requires a point of view and strong writing and the right package to frame it, to catch someone’s attention, and to inspire trust. This is no easy task.

But to set semantics aside and actually answer your question… The future of content, in my opinion, is all about creating context. We are bombarded with so much information from so many channels every single day, that people crave editorial that can actually help them make sense of everything. We get so much of our “content” in these little bursts now — be it an email, a tweet, a blog post. But it’s always this little bite-sized, isolated bit of information. We rarely understand how it actually fits into our lives.

Given this, I think what’s needed are curators, editors, writers, filmmakers, etc who can really zoom out from that narrow perspective and take the long view. Who can do some of that sense-making for people so that they understand how this political development fits into the long arc of history, or how developing this particular habit will give their life more meaning in the long run. The future of content is about creating a rich, well-thought-out context that makes it possible for people to really process and synthesize ideas in depth — not in this surface-y way we’re all accustomed to now.

In other words, if you’re using the word “content” that means you really don’t have a vision for what you’re making. Because creating good content requires specificity: it requires a point of view and strong writing and the right package to frame it, to catch someone’s attention, and to inspire trust. This is no easy task.

What is your definition of owning your content?

Jocelyn: As my good friend Sean Blanda always says:

(•_•)
<)   )╯Always
/    \

\(•_•)
(   (> Own
/    \

(•_•)
<)   )>  Your platform
/    \

I couldn’t agree more. The Facebooks and the Mediums and the Patreons of the world may or may not last forever. And if you are reliant on them to present your content, or to do business, you are playing by their rules. And they can change the rules any time they want.

I went into business for myself because I don’t want to play by anybody else’s rules. And if you want to set the rules, you have to own your platform.

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This interview was produced in partnership with WordPress.com & CreativeMornings.

Morning people get 15% off their WordPress.com site at wordpress.com/creativemornings.

Interview and photo by Paul Jun. Illustrations by Jeffrey Phillips. ‘Own Your Content’ illustration by Annica Lydenberg.

Recommended CreativeMornings’ talks on ideation:

• Founder of Behance, Scott Belsky, shares how to endure, optimize, and thrive in the middle parts of your creative process—the messy, uncertain moments when you’re bringing an idea to life.
•  Design Justice advocate, Jessica Bellamy, shares ways to leverage your curiosity to drive your creativity.
• Cofounder of Refinery29, Piera Gelardi, delivers an inspiring and actionable talk on living a courageous and creative life.
• Focusing on issue of technology, Jessica Hische explained that even as “just a letterer” she learned how to code for the web and learn new type design applications. In her opinion, learning tech is not only fun, but designers are lazy if they don’t.