Once a forlorn business major, 26-year-old Portland-based singer songwriter Haley Heynderickx now takes customary instrumentation and storylines and amplifies them unexpectedly.

When a friend sent me her Tiny Desk submission of “The Bug Collector” two years ago, Heynderickx’s acute self-reflection channelled through idiosyncratic metaphors made me cling to the video like an otter toting its favorite rock. In the recording, Heynderickx holds her guitar upright, the body of it in her lap. She deftly fingerpicks her way through the observations of an unreliable spectator being stalked by a naked centipede (unlike the typical clothed ones), a vengeful priest from a past life reincarnating as a praying mantis, and a vindictive millipede.

Flora, fauna, and humans permeate Heynderickx’s 2018 debut album, I Need To Start A Garden. They are employed to capture a truth about both vegetation and the human condition: a lot of alluring stuff is wild, its growth uncontrollable and dense. As of early December, Heydenerickx is back on tour and will be playing at Boot and Saddle on December 10th.

The Key: I wanted to ask you a little bit about your experience becoming acquainted with singing. I read that you started teaching music classes, many of which were spent convincing kids that they could sing. You said that some people can’t handle the embarrassment that comes with learning how to sing but you just kept singing, not knowing if you were good or bad. What encouraged you to keep singing when you were detached from the concept of being a good or bad singer?

Haley Heynderickx: Hm, how do I answer that with elegance? I think singing is something that naturally is a joyful eruption in you and you can’t help doing it whether you’re in the shower or when you’re alone. It’s proof that you have inklings of wanting to find your voice. And if you know that it’s an inkling that you have, then it is allowing yourself to give space to find your comfort zone and singing alone.

When I was a kid, my parents and I lived in a mobile home and I was too shy for my parents to hear me sing. So I thought just putting a blanket over my head would prevent anyone from hearing me sing, even though that doesn’t really barricade what’s actually going on. But that felt like enough privacy to continue and obviously the church and choir and starting little singing groups with friends during recess. But it’s different if you’re an adult wanting to learn how to sing than when you’re a kid. So my answer was all over the place and I’m already losing the root of the question cause it was juicy and I’m spinning in circles.

TK: I have a follow-up question! What did it look like to become good at singing when your intention was not necessarily to be a good singer?

HH: What does it look like? It looks very embarrassing. Like voice breaks at open mics, but still that relief and excitement you feel as you share. It wasn’t perfect. It feels really good to be around people and share this part of myself that feels like enough and that’s why I still go to open mics—to share that moment of relief with each other of, wow, we can share our voices in this cluttered world even if it’s for this one random hour a week of what we’re going through.

TK: I believe that you wanted to study music during college and like many people in the arts, ended up graduating with a business degree because maybe there were some fears and projections of other people that deterred you. What steered you away from business and back into music?

HH: I unfortunately remember the tipping point very clearly, because it involves crying at a little kid’s birthday party. My mom attends many Filippino parties. And in that circle of friends you just end up going to a stranger’s birthday where it’s a friend of a friend or a mom’s, auntie’s, friend’s kid. It was my second year of college and I felt like my soul was a little lobster in a pot of boiling water. A random dad walked up to me, whom I didn’t know well. They, said “how are you doing?” And I gave him the traditional college speech of “just, just getting through it, in my last accounting classes.” He just looked at me cause I think my face was shaking. He said, “how are you really doing?” And then I just cried on a random dad at this little kid’s birthday party. And I realized that I had a problem.

Some people are damn good at accounting and very fluent when it comes to numbers and can have a relationship with business. But for me, I really just didn’t know what I wanted in my life. I had to wait for messages that loud to know my intuition was in place and then take the steps to follow. So I knew that was the right path from right there—to take a break and to see what music meant to me. But sometimes I get scared.

The songs I’m writing now are a bit cheesy and I wonder if it’s still applicable to others. Who knows, maybe I will take my accounting job in five to ten years or five months. I say these things, hopefully satirically, but you never know. So I take all these, each of these days with gratitude, but also a grain of salt.

TK: Yes. I think people are afraid to be absorbed in a creative profession, whether it’s music or art, because it’s like, what if I lose myself in this and it doesn’t work out and I don’t know how to get “back”? There’s nothing wrong with holding opportunities that feel more practical or stable in our field of vision, so long as we don’t let them prevent us from walking the right path, as you say. This conversation makes me think of your lyrics in “Slow Talkin’” when you sing “Don’t be twisting your inhibition / Don’t go drop, kick your intuition.” How do you get in touch with your intuition, especially amid a system that discourages pursuing a non-normative career?

HH: I have a quote that I’m going to steal from Jenny Slate, who I just saw share her poetry at Revolution Hall a week ago. And she said, “I do not feel qualified to answer such deep questions, but I love answering questions. So I’m going to try.” I have a moment of feeling a bit naive. I’m just a weirdo in my twenties. I study my weird books and my weird friends and I’ve been lucky to meet wise women and fortune tellers at the right times at the right places who encouraged me to study the little details and feel synchronicities.

Oh, you’re pretty much asking, how do you feed the soul? Because once the soul feels more fulfilled and heavy, I believe the intuition gets sharper. Feeding the soul could be as tiny as investing in those friendships that make you feel full and inspired. It could be reading a letter to someone you really love or yourself. It could be reading, taking the time to read the books that mess you up internally and externally and make you question everything. Oh, there’s so many ways to sharpen the intuition, but it’s still a mystery to me. But I hope I can giggle in my sixties or seventies and say, ah, I found my answers but maybe, I still don’t know, but I’ll feel much wiser answering that then than I do now.

TK: I really love that you said intuition is sharper when the soul is fed. That it’s sort of a prerequisite  to a sharp intuition.

HH: The language is so tricky because it’s so quick to be written office cheesy.

TK: I know. Yeah.

HH: I’d like to attempt to find my language and talk about the things between the lines.

TK: Oh, I love that. There’s a really fine line between something that’s cliche and profound and I think the conversation around intuition exists in that liminal space. I really love when you sing, “I am humbled by breaking down” in “Show You a Body.”

HH: No one points out these lyrics that you’re pointing out! It makes me feel warm and fuzzy.

TK: I may have had two glasses of wine last night and listened to all your music and wrote down all the lyrics that made me feel some type of way away, you know?

HH: Thank you for those Spotify plays.

TK: Oh, of course. What is your relationship to songwriting when you are broken down?

HH: Oof, damn. Juicy question! My relationship to songwriting when I am broken down. It’s frantic. When I feel really down, I am so relieved that I have some weird outlet to attempt to describe where I’m at for the sake of feeling better. And sometimes, well at the beginning for me, that meant just covering songs I really love. It’s that cathartic feeling when you put on a tune that you can just scream along too. When I was younger, something clicked where I realized I felt more in my body when singing along to a song with the artist. I don’t know when that transferred to “and now I want to play it my own way.”

But it’s dangerous because it’s kind of addictive when it goes well, then you want to allow yourself to be in that dark place to really feel it out even more and to try to write from there. But that tortured artist will run out eventually and then you realize that sometimes you can sabotage yourself and trick yourself into being down more often. So you can write from that place and then your friends say, well, you’re not fun to hang out with anymore you’re keeping in a cloud and then you have to admit, okay, I’ve moved through the emotion. I should stop milking it. I can live my life not needing to feel that intensely emotional all the time. There are definitely seasons for allowing yourself to feel it out, but to be brave enough to walk through that emotion to a new plane, the greater plane of thinking that makes it clear.

TK: That’s really insightful. Emotions are energy to be worked with and to move through us. And if we cling to one as fuel, especially suffering, then we forget how to access inspiration from other emotions.

HH: Yeah, you get it. You know this stuff. I know I sound cliche, but I can’t help it. It’s just, it fascinates me that you are, you being those who have listened to the music, you’ve changed my life and you’ve helped me through the dark periods. And it’s weird reading from a place of being okay now. And knowing that a lot of those songs are written as my therapy songs and needing to process a lot, getting home from work and break up and new chapters of adulthood.

So I’m kind of feeling floundary right now, but I’m still trying to figure out what place I’m writing through, because I’d still like to be shared. I’m wondering what to write about when you’re feeling okay and how do you celebrate feeling okay. And who wants to listen to songs about feeling okay? I hope people like the songs about feeling okay. I do. But I’m feeling kind of shy right now. I’m in a new chapter because of all of you, which I’m grateful for.

TK: I have another emotions-y question if that’s okay.

HH: Okay. Bring it on.

TK: You’ve said that “Om Sha La La” is about being embarrassed and seeing how much you can get away with when embarrassed. Is there an embarrassing performance-related story of yours that stands out to you? Like the kind that reappears vividly when you’re trying to fall asleep.

HH: Could you reword that? I got lost when you started talking about Dreamland stuff.

TK: Yes. When you’re falling asleep, is there an embarrassing moment on stage that barges into your brain? For example, when I’m falling asleep, sometimes an intrusive embarrassing memory emerges, like when I slid through a wet floor sign in middle school.

HH: That is a good thing to know about yourself. Mine is usually in the morning. I don’t know why. If I drank too much, my brain flirts with all the places I could have been an embarrassing person. But that’s a heavy drink to sip on before you go to sleep. It isn’t like thinking about all of your failures. What do you think about before you go to sleep?

TK: When this otherwise dormant memory appears, I’m not consciously choosing to think about it. It makes me realize how there’s more depth to myself that I can’t always grasp in my wakeful state, as I guess it only surfaces when the subconscious and conscious are particularly engaged.

HH: This is deeply tailored you and I wonder what, what riddle is living behind it. It’s kind of like a portal that’s unique to you.

TK: Ah, it’s definitely a portal!

HH: I wonder what energy it wants of you.

TK: Next time this happens I will ask and I will try and enter the portal forcefully.

HH: Yeah. Your middle school self. I wonder, cause for me, I totally blow through those scenarios and I try not to ever think about them again. But I know that they’re there. Even after the show, I try to meditate and remember things I liked in that hour of sharing time with you. Hopping from show to merch booth scenario and being awkward business woman and person is so vivid that sometimes you forget what happens on stage. I’m so fully intentional for the whole show, I give it my all to be so present everyone there. And when the show is over, I feel so depleted. I can’t really remember the embarrassing times I remember the good times with it. So no juicy memories. I have other friends watching other friends do embarrassing things. But maybe that reveals a lot about myself.

TK: I have another question lyric-related. Well, it’s loosely related, but okay. I think the sentiment, “I need to start a garden” speaks to a desperation for wanting to cultivate tangible growth and change and beauty. What something on your anti bucket list— a thing you know and accept you’ll die not having done?

HH: Wow. Well that was a twist! Hm. I’ve really been getting lost in Jenny Slate’s poetry. And I laugh because she brings up horses a lot, cause she doesn’t understand them. So I might be stealing from her, but I don’t think I’ll ever ride a horse because they intimidate me. They really fascinate me. And I don’t need to ride horses off into the sunset during my life.

TK: What intimidates you about horses?

HH: They’re strong and large. Some they walk on their toenails. It’s, I think, again, I’ve just been listening a lot to Jenny Slate and she will probably scoff with how much I’m quoting her in this interview. I just relate to the things in her brain. But yeah, I’ve always felt like they deserve to be free. They feel us constricting them. They know and their brains are very large and they have this psychic power. They get stuff and may overthrow us one day and I just don’t want to mess with them. I just wish them well, you know.

TK: I totally get it. I have one more question for you. I read that you not only went to college in Portland and currently live in Portland, but that you also grew up in Oregon. What keeps you rooted in Oregon?

HH: As much as I played with the East coast, because I really enjoy it up there, I think it is family. It’s so nice to have a home and roots somewhere. When I travel, I feel like an awkward tumbleweed and it feels really good to get back to my routine. My friends almost forget sometimes that I’ve traveled so much, and we’re back to just talking about the things we usually talk about.

I had a good talk with one of my friends, Old Man Sam, debating, is better to stay in one place, to put your roots really deep or to always be floating around? And he worded it so elegantly. It doesn’t really matter where you go. There will always be good people in the stories you need to study. And I’m tired of torturing my brain with the opportunities and thinking, what if New York feeds me in a completely different way? What if Philly has the best cheesesteaks in the world I don’t need anything else? And the most creative beings to hang out with. It’s all tempting. I don’t think anyone knows what’s best for them really. But it’s, it’s family and friends and my writing desk.

TK: Does touring fulfill your desire to know a lot of different cities without the commitment of putting down roots?

HH: I don’t want to share it too much, but I was in a relationship where we were debating moving. I don’t think I was as present in each town I was in, cause I don’t know, I felt more lost and spinny in my thoughts of what could be the right place. But now that I know that Portland is home, it really does make me take each city more seriously and know that I’m only going to be in your town for a moment and to really take it in. I’m excited to roam around Philly and feel what the air is like out there and hear what the people yell outside their windows.

TK: Probably asthma and expletives but in an endearing way, hopefully? Do you have any specific plans when you’re in Philly besides eating cheesesteaks?

HH: Well, I delete social media when I’m home and when I’m on tour I kind of turn it on and ask whoever checks by Instagram what to do. You guys know your town best and I know so few people there. So I’m kind of excited to turn on social media on Sunday when I started traveling. And hopefully you all will lead me to what’s best.

Haley Heynderickx plays Boot and Saddle on Tuesday, December 10th. Tickets and more information on the show can be found at the XPN Concert Calendar.