Dessa's a busy person. Between commuting back and forth between New York and Minneapolis, writing an upcoming book of essays, and collaborating with Hamilton creator Lin-Manuel Miranda, she's been making time to work with Lazerbeak (Doomtree) and producer Andy Thompson on a bit of new music. "Quinine" was her first new song since Parts of Speech (2013), and today, she's back with one more.

"Good Grief" continues Dessa's transition from hip-hop to pop, or at least her increasing comfort level in the latter genre. "They say there's good grief/ But how can you tell it from the bad?" she opens, singing over a sustained note. The atmospheric tune is soaked with production by Thompson, Lazerbeak, and fellow Doomtree member Paper Tiger.

Before the release of "Good Grief," Dessa jumped on the phone to talk about her favorite part of the song, what "badass" means to her, and her recent contribution to Puerto Rico relief fundraiser "Almost Like Praying."

Congratulations on the new single! What can you tell us about "Good Grief"?

The first time that we performed it was with the Minnesota Orchestra, so this is one of the first songs of a batch I've been working on. I was really excited to put something out; it had been a long time after focusing on writing and the orchestral show.

Do you have a part of "Good Grief" you're most proud of pulling off?

It's a super hard song to sing. Sometimes there's a tension there: You're aware as a songwriter that some of the choices that you make may pose serious challenges for the singer, and they are both you.

I really like the third verse on this tune. None of us agree what all the parts should be called; I think it's the third verse, and Lazerbeak and Andy think it's the bridge. But [it's] the part that starts with, "Secrets don't like to be kept/ All mine jumped over the fence." I like that section quite a bit -- probably as much for the production as for the lyrics.

The purpose and the service and the merit of grief, and of living transparently -- that resonates a lot with me at this part of my life. Like, "When do we have to hurt, and why?" And I think sometimes in retrospect, we can get a little romantic about previous hurts. Nobody enjoys doing it in real time, but we put a lot of Vaseline on the lens when we look over our shoulder at our past failures and pain. It's easy to sanctify those. But in real time, s-- just hurts.

That reminds me of a thing I've been wondering about for a while. When I look at your older albums and songs like "Fighting Fish" and "Dutch," and compare them to the tone and feeling I get from you now -- more talking about grief, more talking about transparency -- I see the confident Dessa taking a step back. Do you think kickass Dessa will make a return in future music, or have you gotten older and wiser and not so worried about putting on a brave face?

Mm, interesting. To me, I think what's most compelling is the idea of being a badass that acknowledges she does give some f--s. Is there a way to be tough as nails and also open to the world and to life. You know what? When s-- hurts, it doesn't undo me. But I live it fully, like, fingers in the sockets.

In shorthand, I always thought there was two kinds of being tough. There's the boxer who just goes and goes and goes, and never gets hit, and wins everything. That's one kind of tough. And then the other kind of tough that impresses me more sometimes is watching a boxer get hit and stay standing. That's an arresting kind of thing. I remember when I was a teenager, I used to spar with my best friend in the alley. And she just wouldn't really block. She'd just take it on the chin and then come at you, and it was terrifying! [laughs] Absolutely terrifying. I think there's something tougher about a high tolerance for pain than there is about the avoidance of pain completely.

But if the question is, "Are there some battle, bossy jams to come?" Yes. The answer is yes.

Did you renew your lease in New York?

Yes, I did! [sings] I renewed my lease in New York. I'm in Manhattan now, and I'm spending half time in each spot.

I read the Billboard interview where you talked about Puerto Rico and "Almost Like Praying") and everything, and you mentioned that you'd just recorded it in the Atlantic studios. Could we talk about that song a little bit?

Yeah, having the opportunity to play even a small role in a project that's designed to make a big difference for Puerto Rico was something easy to say "yes" to. Lin-Manuel was assembling a cast of Latin artists to create a song that would benefit hurricane relief, which has been really unimpressive in Puerto Rico. People are still hungry and thirsty, and wet from the rain. People are really desperate for tarps, and fuel for their generators, and reliable sources of clean drinking water.

So when Lin texted and asked if I wanted to be part of it, I couldn't text back "yes" fast enough. And in addition to writing a really catchy song, he was able to pull off this small wonder of logistical management. Usually, even as a member of Doomtree at our tiny level, trying to get seven people to do the same thing and to agree on how to get a song out in the world is tricky. Lin-Manuel was able to assemble a small marching army of superstars, from J. Lo to Marc Anthony to Fat Joe to Rita Moreno to Juan Luis Guerra. He really has this star-studded cast. I was really honored to play a small role.

[Editor's note: Watch an NBC special on the making of "Almost Like Praying" here.]

In the U of M commencement speech you gave a few years ago, you talked about how important it is to fail. Could you share one of your more recent failings? I see this as a parallel to "Good Grief" and being real about how much things hurt, but how much you grow from it.

Yeah, I mean, at my Minnesota Orchestra show, I shared the story of a pretty long, ten-year romantic failure. With a lot of sarcasm and a lot of humor, I hope, and a lot of pretty music.

Most recently, I had a studio experience where I was just really nervous! Somebody with a really impressive career walked in to the studio, and I freaked out. I just sang an entire song really, really thoroughly flat. Like on TV, [as bad as] "Elaine can't dance." Comically poorly.

I felt really bummed. I called my mom after all this and I was like, "I'm an idiot." [laughs] I had an opportunity to sing for someone who really knew their stuff, and I just froze and embarrassed myself.

What do you take away from it?

[merry] That'll happen.

I don't think that failure is romantic. I don't think that failure always serves to make you a better person. I think failure is not the stuff of Hallmark greeting cards; I think failure sucks. But it's just that there's no way to avoid doing it in the course of trying to make other awesome things happen. So, nobody hits them all. I've had the opportunity to sing in front of really rad people and done a great job. And that's not what happened this time.

I got bummed out; I drank some beers with friends and made fun of myself. I did a dramatic performance of myself singing badly. You know? Make 'em laugh. And I tried to get over it, knowing I missed a pitch and there'll be other pitches. I'm working on averages here.

Since we last talked, Sims, P.O.S, Paper Tiger, and Lazerbeak have released some new music under the name Shredders. Have you had a chance to listen much to it?

Yeah, absolutely. It's in my car. They have a pretty rad pre-order package, and the fidget spinner is sitting on my kitchen table right now.

How would you contrast Doomtree and Shredders?

Well, Shredders very much seems like the combined efforts of those four dudes. I know them so well as musicians and as homies. It's as playful and aggressive and dancey as those dudes are, as men and musicians.

Yeah. Since Doomtree is playing the Palace Theatre on Nov. 22, I was wondering if you had an opinion on venue news in the Twin Cities. The Triple Rock is closing; Doomtree are playing the Palace. Do you have an attachment to either place?

Yeah, this'll be the first time that I'll have performed at the Palace. I'm really excited; I've heard a lot of really good things about it.

And I was super bummed about the Triple Rock. I sent some blue texts to Lazerbeak and my best friend. Seen a lot of shows there; played a lot of shows that were important to me there. It seemed like such an important beacon for traveling acts, too. A great home for bands on the road.

This interview has been condensed and edited for clarity. Donate to the Hispanic Federation to support Puerto Rico relief efforts here.