The second XOXO Festival — upbeat, exciting, inspiring, amazing — ended yesterday in Portland, and I’m on the flight back, and I and can’t stop thinking about failure. Disastrous, merciless, unrelenting failure.

XOXO is the distillation of everything that’s right about indie and maker culture. You can’t possibly be interested in what’s going on in those communities and come away not ready to dedicate (or re-dedicate) yourself to them. XOXO is a perfect place to be who you are, who you want to be, who you are becoming.

And, in one way or another, I’ve failed at each of those things, which is what makes me want to talk about it. Tech culture — and to a lesser degree, the indie community that comes out of it — does not, and desperately must.

It sounds both massively cynical and relentlessly despairing to come away from a wildly inspirational conference like XOXO, filled with people who are both successful and happy, and be most interested in the other side of the equation. I firmly believe that XOXO is perfect as it is — it achieves its goals brilliantly, almost magically — but indie culture at large (and I count myself as part of that culture) needs to be able to have open conversations about the risks, consequences and costs of pursuing your dreams… and failing. Not just business failure, not just financial failure, but personal and emotional failure as well. The decisions our dreams inspire have consequences, and if we imperfectly understand those consequences, the results can be devastating.

This is about how we evaluate risks, gauge costs, and — ultimately — accept and move on from the failure to achieve what we set out to. We cannot be whole unless we acknowledge, discuss and internalize the sometimes shattering consequences of taking a leap and plummeting straight into the ground. We’ve got the conversation about success down pretty well — probably too well, in fact, to where the topic almost automatically evokes the standard storyline of passion, struggle, victory. But until we can talk just as freely about failure, the story of indie culture remains a Disneyfied fairy tale — based on reality, but without the occasionally ugly ending.

Do you love your dream enough to sacrifice your life’s savings? Your marriage? Your oldest friendship? Your mental heath? In more than a handful of cases, your life? These are real-world consequences of failure. But if and when they are discussed, it’s over beers, quietly, in the back-channel. When the topic gains a wider audience, it’s almost mercifully in regards to a single, sad incident — Aaron Swartz dreamed big dreams, for all of us, and however you trace the lines, they ultimately cost him his life.

There are hints of a wider conversation out there. At XOXO, Cabel Sasser spoke movingly about what sounded to my untrained ear like clinical depression, even in the face of inspirational material success and iconoclastic freedom. Marco Arment called his talk a therapy session, and detailed how he moved from grinding fear, through personal understanding, to a new approach to his career. Jack Conte charted the collapse of his self confidence in the wake of a hit.

But how many people looking for investment can openly talk about their anxiety? How many people who are financially successful can discuss the end of their marriage? How many people have seen their dreams collapse to dust in front of them and are expected to pick themselves up and get back to it?

This is not about putting together a conference about failure (FailCon 2013 — sign up now, loser!), or adding a handful of cold-water speakers at existing conventions, or opening up the mic for five-minute stories about lessons learned. It’s about doing the deeply hard work of removing the failure taboo from our culture, allowing the human beings who try — and try hard — and don’t make it to not have to keep the fucking grin plastered to their face, for fear that they’ll be treated as damaged goods.

There is a term in statistics called “survivor bias.” If all you look at are the survivors of a particular population over time, you’ll come away with a mistaken understanding of the probabilities of success. Which pretty well describes the vast majority of public conversation in indie culture. We rightly celebrate the people who have taken chances, found audiences, and secured their financial and emotional success. So much so that it’s become (at best) rare and (at worst) scandalous to even publicly mention failure or crisis or fear, except as a stumbling block to overcome. Failure is temporary, an opportunity, a lesson. Pivot! On to the next thing! Upward and onward!

Which only serves to make true failure — real, lasting failure — feel that much worse. Sometimes failure is not something you bounce back from. Sometimes, it’s something you grow around. Sometimes, it’s something that you seal away and try to forget. Sometimes, it’s something that stays with you every second of every goddamned day.

XOXO was a place where conversations like these took place — both on stage and among the attendees — and it must continue. A cultural norm that requires relentless optimism — that mocks or derides or even just tries to ignore failures, be they economic or emotional — cannot survive. We are made of people, and unless each of us can speak, grow, and even fail as people — as complete people — we will never have a culture that can sustain itself beyond the enthusiasm that will inevitably sour into hype.

There are people who are telling these stories, and the more who do, the better it will be, for everyone.