Meet Bailey Dahlgren | Artist & Entrepreneur

We had the good fortune of connecting with Bailey Dahlgren and we’ve shared our conversation below.

Hi Bailey, why did you pursue a creative career?
I distinctly remember being in kindergarten and being asked by my teacher to fill out an info sheet where my classmates and I could then learn a bit more about each other and what our little six year old hopes and dreams were. I wrote ‘Performer’. We were supposed to pin it up on this large, daunting cork board and I remember feeling so nervous to admit that. And about 5 minutes into my answer being on display for the entire classroom, I quickly jumped up with my pencil, crossed out the word ‘Performer’, and put ‘Doctor’. Looking back on that, I laugh because how silly was I not to completely erase it? If I didn’t want anyone to know, why let it sit there as proof that I wanted it, but would instead pretend to dream up something else? That internal debate came up for me multiple times over the next two decades. I went to college for musical theater and visual arts. And again, during my junior year – I made the switch over to Pre-Med. Graduating with a degree I had no business putting as much time and energy into as I had. You could tell though, the artistry would not let my fear win. During my undergrad, I sold paintings/murals on the side, I wrote short poems and comedic pieces that I uploaded to WordPress, I audited acting classes, I sang covers and participated in outside plays, I even had a nice little side business of writing peoples’ college essays for them. What can I say? When you have a talent, make it your hustle. 😉 This creative livelihood was there, always pursuing me, I was the one being stubborn. Finally, as I was studying for the MCAT, prepared to apply for MD/PhD programs – I saw the future and it was grim if I continued to deny the part of me that could not be buried no matter how hard I tried. So, I moved to Los Angeles, wound up as a celebrity assistant, studied improv and stand up, invested in a vocal coach who was more like my long-lost therapist. Meanwhile, at my job – I was growing within the production company. Within 4 years, I had now started and was running the company’s unscripted slate of TV/Film projects. Then in a post-pandemic, dating-app-fatigued world, my sisters, best friend, and I started a speed dating company on a whim. We were aiming to build a community that highlighted the need for human connection in all its varied forms, whether be it a friend or flame, which conveniently, is our company’s name and a pursuit that is still building strong today! The yearning to dig into my art and stop reasoning with myself out of pursuing creativity seemed to be the choice every day. I’ve since left the production company, moved to New York City to pursue music/comedy, and continue to work on this company that my sisters/bsf and I care so deeply about. I answer at length when asked ‘why art?’, because it’s not a simple answer just like what defines art and what defines creativity are not simple definitions. Perhaps even defining a creative or an artist is hell itself. The honor for me in staying loyal to a career in the arts is to know that it can look like so many things and I now welcome and validate that. Meanwhile, there is an opportunity every day for me to settle for less than all that art can bring me. Settle for the money. For the ego. For the title. For the career prospects. For the external understanding. But no form of settling feels as meaningful, intentional, and in tune with my childhood self/my person as a whole as when I trust that my hunger for more only comes when I don’t feed myself with art & creativity in the first place. I guess you could say the short answer is: I keep pursuing it because I can’t seem to get rid of the damned thing. I hope, for my lucky self, that never changes.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I think my art mimics how I tend to walk through ordinary life. Usually a bit obliviously, but always interested (& susceptible) to any of life’s extra-ness. Its curveballs. And usually those unexpected moments were the most moving to me. The reason I’d want to make something, to create something in response. I think in the unintended, I found my playing field. It came into fruition usually like, I felt this ‘thing’, I then made this other ‘thing’ out of sheer response to feeling this ‘thing’, and now others are telling me they also have known or felt this ‘thing’ too. Don’t get me wrong – this isn’t anything new. As artists, I think we are all taught to make things that relate to others; otherwise, how would we ‘sell it’ to the masses for consumption. But how often do we acknowledge the profound nature of those relatable moments and how rarely they are planned? And that’s what I’ve always appreciated about making art of any kind. In whatever format. It was always a learning journey for me as I continued through the daily ups/downs of life. A tool in which I grew more into my own understanding of my place in this world as I learned that the story I was telling was something someone else understood or could empathize with. I was suddenly not alone. Whether in the bliss or in the dull and bleak.

Additionally, by allowing myself the freedom to create in any capacity, I gained the opportunity to respond to it as if I am the audience as well because I’d made no assumptions on what the outcome was supposed to be. I like to think that that is a very common part of artistry and that all artists I admire or respect approach art similarly. To describe it with less abstraction, I never wrote a song knowing that it’d help me overcome a trauma. I never joined a documentary project to find accolades or make sure an audience learned that piece of content. Even with Friend or Flame, I never organized the first event with an aim to embark on a business venture with my close friends/family. I just did because it excited me or felt necessary in my moments of real life and it became what it was organically. Now I can sift through these doings to see what feels right to continue as an art form.

I laughingly attribute this process to the fact that I sometimes think I’m so self-absorbed that I can’t look past my own feelings or experiences in the moment long enough to think outside of what’s going on in the present. So when I create, I have nothing in my brain thinking of an outcome or beyond. I’m in the here and now, with a subtle peace in the piece, and actually hoping it just gets out of me so it no longer takes up so much headspace. Me and my brain have always had some beef, if I’m being honest.

I think it actually goes back to my inner turmoil as an artist; as someone who doesn’t feel I sit in one lane. I constantly debate what path is the right one. Which one will make me happy. What if I’m taking up too much time and energy on the wrong one. Will it ever make sense to me? Yet, it’s what has my attention in the now. It is real and apparent in the moment, because I’m actually experiencing it. How can I abandon that? I can’t. So why not create from it? I’ll continue to hold all of my dreams and future creations and projects and entrepreneurial endeavors with a loose grip. Knowing that it could all hit me different tomorrow and out of respect and trust that the act of clenching it too tightly will be my deterrent, I’ll stay open to where it wants to take me. And in that admittance, I’m ultimately proud and also very excited to see what else comes out of me and any collaborations I’m fortunate enough to be included in down the road.

If there is one thing I want people to know about my brand or story, it is that I practice what I preach. And that is – that the unpredictable is scary as hell and also one of the best places to find the extraordinaries of life. Whether creatively or just in the act of living itself. These extraordinaries of living- we should all, I hope, know well.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
Oh boy. The places we could go in LA alone!! My itinerary would likely be all over the place. I am impulsive and a lackadaisical planner. This means, my suggestions will be all across LA and not at all conducive to a one day itinerary when considering traffic and drive times :). But, I’d definitely make sure we grabbed a burrito from Tacos Por Favor in Santa Monica and don’t punish me for this, but a black coffee from 7-11. (There’s one right by my sister’s apartment in Glendale and the way we are avid users of 7-11 Rewards will show to you our loyalty to the franchise). Next, we’d have to make our way to the Goodwill in Pasadena. I don’t think you understand how many $7 pairs of boots and beautiful glassware I’ve gotten from there. Every time I go back to LA, we make our way, and I always end up buying a suitcase there too so I can lug the treasures back to NY with me. (:

We’ll also obviously need to find a dancing outfit there for what I have planned for the evening. Occasionally I’ll hit up a Crossroads instead for one-of-a-kind pieces, but those Buffalo Exchange and Crossroads prices can f right off. Pardon my french.

We’ll then traipse throughout LA. Perhaps hit up Olvera Street – where you can see the oldest building still standing in LA. Grab a masterful vegan donut from Donut Friend once we get hungry (Polar Berry Club is a personal fave), stop by the taco stand in front of the Target in Eagle Rock for the best street tacos I have ever had. (Shoutout to Angel’s Tijuana Tacos) and then I’ll write here that we’ll go home to wash our newly thrifted outfits for the night’s festivities. This is, of course, a lie. I prefer a spritz of Goodwill upon first wear and won’t be shamed!!

Next – take a nap, duh. And then get dressed in your finest duds, please don’t skimp on the ‘i’m hot af’ mantras you’ll tell yourself as you walk out the door. You better be wearing comfortable shoes. Looking hot has nothing to do with long legs. It has everything to do with being able to bring the heat on the dance floor, imho. Closed-toed shoes are my personal advice though. I’ve had to venmo some extra $$ to the security guys at the door when my little piggies were showing. Maybe I’m just a sucker….shit.

Anyways….we’ll hit up HomeState in Highland Park for dinner. Make sure to get the frozen margarita. (Big! Life’s too short for little — but if you’re prone to having too much of a good time, be careful. I once ended up at a strip club throwing 50s, all thanks to a little HomeState chug.) Soon prance on over to Gold Line for some vinyl-listening relaxation. Then once you’re good and ready, make your way over to General Lee’s in Chinatown for some rnb and 90s hip hop dancing. People buy tables and thus don’t dance and that is my kryptonite. So, you may have to make sure your crew knows, you’re all there to dance. Then shake some God-fearin’ ass! I once had an amazing matcha gin drink here. That was years ago, but maybe they still have it. If not, I trust their bartenders to cook up something just as good.

Where I always end up for the real dancing is Short Stop. So we’ll obvs have to hit that last. Small cover which goes with the small dance floor, but when you roll in, 8- deep, it’s usually a good time and here – people are more likely to actually enjoy themselves.

By the next morning, everyone will be in need for a MEAL. Millie’s Cafe in Silverlake or Beeps Diner in Van Nuys have that diner food cure for however you’re feeling the morning after a night out. And of course, we all need to be rejuvenated in time for the Friend or Flame event that afternoon. 😉 Yeah, this is the smoothest transition ever seen for a shameless entrepreneurial plug. But seriously – I’d be remiss not to mention people should check out Friend or Flame!! We host speed dating parties throughout Los Angeles and NYC, focused on sparking connection and igniting those in-person friends or flames. We’ve partnered with Alamo Drafthouse, Frogtown Flea Crawl, Loreto, Stache WeHo, JuneShine Santa Monica, Little Ripper, Stay Zero Proof, Moxy Williamsburg, Good Clean Fun, and LA Cha Cha Chá to name a few. So yeah – if my best friend came into the city, they’d 100% be joining me at one of these events. Because who knows, you may spark a match or even better…leave with a new group chat?!

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
My father. Without the guidance, mentorship, openness, and vulnerability of my pops, I would have never been fortunate enough to see the artistry and creativity lived out right in front of my eyes. Both of my parents modeled the act of being a ‘dreamer’. And what I’ve seen in my father as he’s pursued creativity wholeheartedly, with every fiber and detail of himself, is something I attribute my own familiarity to creative evolution with completely. At 28, I decided to depart from my fulfilling and life-giving job in HollyWood at Yoruba Saxon, (shoutout to David Oyelowo for giving me the ample runway to become who I am as a storyteller today, truly) in order to move to New York by myself and pursue the performance dreams that just would not let up. I told my father, and I asked if he’d accompany me as I put on a ‘goodbye recital’ for all my LA friends and family. (it’s giving — ‘it’s Bailey’s world, you’re all just living in it.’ ;)) We rehearsed for a few weeks. I was short, and ornery as I worked through my nerves and imposter syndrome feelings that were erupting, and he was the punching bag. Yet, he practiced with me and gave me surety in myself. As my accompanist/father, he was my focal point of trust. As long as he was the foundation for me on the piano, I felt safe and capable. And the way he tickles those ivories, let me brag on him!!! I try not to cry, but his musical gift is shoutout-worthy all on its own. But beyond that, he also prepared an entire meal for 80 guests. Hors d’oeuvres and cake included! AND he arranged this magnificently beautiful flower arrangement which became the anchor to beautifying my makeshift stage. (Shoutout to the entire Dahlgren family for that evening though, frfr) And during the evening, he got on the mic and practically took the entire group to church with his profound sermon on ‘doing the hard thing’. He is the true definition of multi-hyphenate. I owe my creative wellness to observing his patience with himself throughout his own creative journey. We are now in the process of writing an album together. We meet weekly, I bring the lyrics and a little hum I may have made on a voice memo that week, and over FaceTime we frustratingly power through figuring out the song’s heartbeat, the melody, the story, the tone. And trust me, I recognize how special it is to be creating with my father. And in a way, it kind of feels full circle that we’re now able to make new art together.

Image Credits
Richard Gierman
Crystalyn Human
Gus Olivares
Katie Ring