The Unlikely Success Of The Great Discontent’s Long-Form Musings On Failure

Ryan and Tina Essmaker, the married duo behind The Great Discontent, share what they’ve learned by going deep with people who’ve seen the dark side of creative risk.

Dissatisfaction fuels action–or, as Benjamin Franklin quipped, “The discontented man finds no easy chair.”


Ryan and Tina Essmaker, the married duo behind The Great Discontent, wholeheartedly agree. They launched TGD as a side project in August 2011, publishing online Q&As every Tuesday with creative types like Barathunde Thurston, Maria Popova and Paula Scher. As the site’s name suggests, TGD interviews focus on the darker side of creativity: risks taken, asses burnt, false starts. This lends an unusually intimate feel to their conversations. With a readable, visually lush site mixing diverse content forms, TGD is madly popular in design circles, yet almost unknown outside of them.

Tina and Ryan Essmaker

Recently, the Essmakers quit their day jobs and fired up a Kickstarter campaign to launch TGD as a print magazine–itself a gigantic risk. Fast Company caught up with the Essmakers to talk about what they’ve learned from their years exploring creative risk, and how they’re applying those lessons to their own venture.

FAST COMPANY: When did you decide to go full-time with TGD?


RYAN ESSMAKER: We had been doing TGD as a side gig, and it’s a lot of work. Initially we had week-to-week sponsors for individual interviews, but recently we switched focus to four official partners per year. We lined up two of the four–MailChimp and Adobe Typekit–so that gave us some runway to initiate this transition. But it’s still risky: we really need four partners to make this work.

Why do you think honest explorations of failure resonate with your readers?

RYAN: People who make things, we all experience failure but we don’t talk about it. You read a lot of success stories, but our curiosity wasn’t there. Success is never as cut and dried as it seems; it’s never all skipping through a field of tulips. Talking about those darker times gives readers hope. It also makes our interviewees more human.


Why is the Internet suddenly so taken with long-form journalism?

TINA ESSMAKER: From the beginning, we planned to do long-form interviews, hoping people would consider the content valuable enough to spend time on. People spend time reading books, watching movies, et cetera, so we hoped they would also spend time reading TGD. And they did!

RYAN: We also think people are starting to see online content as more valuable than before. High-quality journalism demands more words. Also, page count is not a factor online. We don’t have to fit our stories into two to three pages or whatever an editor outlines. We can tell the story the way we want and, as long as the content is intriguing (and well-written), people read it.


What can you do with TGD in print form that you can’t do online?

RYAN: Print preserves the content in a way that’s more tangible. It’ll allow us to curate the interviews; we can revisit interviewees and see where they are now. [Print] also makes TGD more gift-able.


What have you learned about risk from TGD?

RYAN: One of our most recent surprises was Elle Luna. We interviewed her on a whim–we had mutual friends in common. We keep going back to that one.

TINA: She started her career at Ideo and went on to work with teams to design and build Mailbox’s iPhone app (later acquired by Dropbox), and help redesign Uber’s iOS app and scale the storytelling platform Medium. Now she’s an artist who paints and works with textiles.


RYAN: We use a quote from her interview in TGD’s pitch deck: “It’s scary to say goodbye to the structure and systems and prizes that keep us afloat in good times and in bad, and say hello to that potential abandonment, fear, and humiliation…It takes a great deal to choose to do that…But…if we can encourage people to do this heart-led, soul-led work, then it will be unbelievable.”

TINA: Ryan interviewed Elle alone, and I transcribed it. I do that all by hand; I don’t use any software or service. We had just decided to go out on our own, and I thought, She’s speaking directly to us. Lots of our interviews feel like that: wow, this interview is just for me.

You interview creatives, yet your subject lends itself naturally to entrepreneurs. What can TGD teach people starting a new business?


TINA: There’s no right time to start something. If you wait until the timing is perfect, you’ll never do it. That’s relevant to almost all the business people we’ve interviewed. Scott Belsky from Behance told us his entire executive team was unqualified, including himself. They developed each other along the way to become successful.

Or Jane Ní Dhulchaointigh, who invented this product called sugru, which is the Irish word for play. It’s this self-setting rubber you can mold to fix, modify, and improve your stuff. It’s waterproof and really versatile. She paid a contract laboratory to do three experiments, but when the results told her nothing she decided to figure it out herself. It took her six years and 8,000 lab hours to perfect sugru’s properties, but she did it.

Starting a business is hard and, like Jane, many of us have figured it out along the way after putting in many, many hours and resources. The stories on TGD teach that if you’re willing to work hard, you can do anything you want, whether or not you feel qualified. You learn as you go.


You’ve started making short films, like Two Minutes with TGD. Tell us about that.

TINA: We filmed 138 interviews in three days at Brooklyn Beta. They were really brief, just two minutes long, and we asked everyone three questions: Are you creatively satisfied? What would you say to your 18-year-old self? And what would you say to your future self?

How would you answer those three questions yourselves? Let’s start with whether you’re creatively satisfied.


RYAN: I have this perpetual feeling of dissatisfaction, and the only thing that quells it is pushing myself to try new things. TGD is fulfilling because it involves a large range of creative disciplines. Dissatisfaction is what drives you forward. It’s an essential part of the creative process.

TINA: Ryan summed it up for me.

What advice would you give your 18-year-old selves?


RYAN: Move out of Michigan soon and do anything other than what you’re doing right now.

TINA: Those risks you’re thinking about aren’t as risky as they seem. Take them.

That’s tougher advice to accept when you’re older. Have you interviewed any more experienced folks who heeded it?


TINA: I think of Lisa Congdon. She worked in education until her early 40s, then transitioned into being a full-time artist. That’s inspiring for me, to think it’s never too late.

What would you tell your future self?

TINA: Don’t get comfortable. Don’t fall into habit or ritual. Remember your priorities.


RYAN: I wouldn’t say anything to my future self. I’d just observe Old Man Ryan and see if I’m happy or a miserable old man. I hope I’m still working too, and not just playing golf.

Let’s close with a TGD-style question. What scares you most, and how do you combat that fear?

RYAN: My biggest fear is not being able to work on the things I’m most excited about. That’s a reason for taking this leap [with TGD]. Something inside me dies when that happens.

TINA: A lot of things I’m doing now, I’m not formally trained in. My background is in social work; I worked with homeless youth for 12 years in Michigan. So I’m afraid of being unqualified. But you don’t have to be totally fearless to do something. Even when fear is present, I do it anyway. And it’s never actually as scary as it seemed.


About the author

I write about design and culture for Slate, Business Week, The Believer, Fast Company, GOOD, I.D. - oh, I'll stop