Venture into the gray with me

It’s been a year, to the day, since I quit my job to pursue Pearl Music full time. I highly enjoy being a founder. It feels like a role I was always supposed to step into, it was just always a matter of when. I am more myself than I have ever been & I feel like people talk about how entrepreneurship is a constant state of personal development & one of the most intuitive things you can do. I could not agree with that more. You have to be willing to take risks, sit with a lot of uncertainty, & be extremely self-motivated. All of this while remaining calm & clear-headed so you can keep moving forward & building with clarity.

With getting to build my own structure in the way that suits how I work & create, I have had to reflect on other systems I have been in. Both the good & the bad, in order to understand what pieces I would want to integrate & which ones I would want to learn from & do differently. Maybe bad is the wrong term for it, because for that place, it may not have been bad… but it did not suit me.

I’ve always had this rebellious side to me. It is like this devil on my shoulder that says “you only live once, why not?” I actually think that is a requirement for being a founder because inherently you are trying to ignite change, which is essentially “delinquent.” You need to be okay with going against the status quo or else you will just end up creating something that feels very safe or has already been done before.

I felt a lot of shame & guilt over the years about my rebellious side. At times, I didn’t always know how to harness that energy correctly… it would manifest in reckless ways. It was never malicious. It was just a devil on my shoulder saying “let’s fucking send it.” Not always the most mature way to handle things, but it has also made for a life where I have experienced a lot of different things. Turns out when you mature a bit & can utilize it in a healthy way, it becomes a super valuable trait because you will do things that others wouldn’t dare to do.

Like I said, I have had to grow into this because it has gotten me into trouble in the past. Obviously nothing that was too detrimental to my future or ever done with malicious intent, although at the time it felt like the end of the world. This is where the shame & guilt built up over time. I really had to unpack that layer because it started to impact how I moved through life. I stopped trusting that side of me & got drilled into my head that I was the problem. I ended up in this state of perpetual guilt & self-reflection. It made me feel really small. Like at that point, I couldn’t take up space or have an opinion that went against the status quo because it would just be me “being me” again… & that had always seemed to end with me getting in trouble or being misunderstood.

The complicated part is that I am actually highly disciplined & self-motivated. I always have been since I was a young kid. I have been in sports, done well academically, & pursued a stable career. My rebellious streak made it so people often couldn’t reconcile those things existing together in the same person. The people closest to me usually understood both sides at once, which I think is why people trust me. I take risks, but I am also deeply self-aware & know how to analyze risk to a certain extent. I am never going to drive anyone off a cliff, but I will push you out of your comfort zone… safely.

I grew up around a family of storytellers who maybe also knew how to rebel a bit. It made me want to try things for myself & build my own repertoire of stories one day.

An example I think about is high school. I think it was my freshman year. We were in gym class & gym class at my high school was goofy. We had to wear heart rate monitors & be in a certain “zone” for a set amount of time every class. This was pre-Apple Watch or Fitbit, so we had to wear these monitors around our stomachs with this disgusting gel on them. I remember one time we had a fire drill during gym class & my P.E. teacher was one of the varsity football coaches… a guy you would not want to fuck with, but he had a soft spot. During the fire drill I asked “& if there is a fire, do we need to be in our heart rate zone the whole time too?” That isn’t the actual story, but just how my mind works.

We had different activities we could choose from & one was biking around the park across the street from our high school. Another girl in my class & I realized you could pretty easily sneak off the path with the bikes & go do whatever you wanted. We thought it would be hilarious if we ditched class in the middle of the bike ride & then popped back in right before it ended. We planned it to the T. It wasn’t even that wild… we were going to bike to the ice cream stand in downtown Grayslake, get ice cream, eat it, & come back. We just wanted to prove we could do it.

So one day, we did. We got ahead of everyone else in the class, veered off the path, hid the bikes behind some trees, & ran to the ice cream stand. We were still in our gym uniforms with these fucking heart rate monitors on. We actually ran into seniors there because they could leave campus for lunch & they were like “are you kidding me?” They respected it & thought it was hilarious.

We ate our ice cream, ran back, got on the bikes, & merged back onto the path. One girl saw us & we were like “SSHHHH.” We made it back just in time. It was truly harmless, but obviously we could have gotten into a lot of trouble. It was for the story & honestly, it was such an adrenaline rush.

I wanted to make sure I never left a stone unturned in my younger years because you never get that time back. But as I got older, I started to feel a lot more shame around this side of myself… like if I didn’t follow the rules better, I wouldn’t be successful in adulthood. It wasn’t really high school that made me feel this way though. It was college. More specifically, being in a sorority.

This actually shocks a lot of people now that I was in a sorority because it feels so unlike me. My experience in a sorority is not black & white. The truth of it exists in the gray area. I gained many of my closest college friendships from that experience & I am still friends with some of those people today. That is why people join sororities in the first place… for community. Making friends in a new environment is hard.

My issue with sororities was the power dynamics & the rules. It is essentially a bunch of your peers policing each other. Letting things slide for their friends while targeting others within the system. It creates a really weird, toxic dynamic. Girls can be fucking mean & that environment definitely fuels it. I can’t pretend I was perfect in that environment either.

For my sorority specifically, we were at a Big Ten school & in Greek life… the whole thing felt like a giant contradiction. We are going to host mixers & parties with fraternities, but then the second someone got caught doing exactly what everyone else was doing, they would get thrown to the wolves. People acted morally outraged while they, their roommates, or their best friends were literally at the same parties. There was so much righteousness. A lot of girls in my sorority were future teachers & sometimes it felt like they used the sorority as a place to practice teaching… but with people their own age, rather than 8 year olds. I found that piece obnoxious.

At the same time, I genuinely loved my friends & parts of the community… that was what made it so complicated. I could see the ways it benefited me while also recognizing how deeply unseen I felt within it. I found myself in standards meetings more than I should have & I think a lot of people around me decided I was just reckless or rebellious. Meanwhile, I was doing extremely well academically in Computer Science & Engineering. That side of me was mostly invisible in that environment.

I dropped my sorority starting junior year. I had already finished living in the house & then interned in SF the summer after my sophomore year. Once I was in SF, I kind of had this moment of “wait… why am I putting up with all of that back at school?”

It is actually funny, I was also deeply in the closet through most of this. I can’t fully untangle which parts of me were acting out because of that at the time. I just know it was another layer I was desperately trying to suppress. If you think I would have felt safe coming out in that environment… you’re crazy. I didn’t fully come out until right after college when I moved to SF.

I think what hurt most was being part of something that represented community to me while simultaneously feeling unseen, undervalued, & crucified for mistakes that were honestly pretty standard college behavior. I also think that women in their late teens & early twenties can genuinely be one of the scariest archetypes out there… people at that age know exactly how to say something that cuts directly into your soul without blinking. I can’t pretend I never participated in that dynamic either. It was the environment we were all in.

That experience subconsciously shaped how I approached my career afterward. I became obsessed with keeping my personal life completely separate from my work life. Which is funny because I joined a startup in SF right out of college that was actually a pretty chill environment… but I still hid parts of myself out of shame & fear. I put on a mask, even in an environment where I didn’t necessarily have to. I wanted to be taken seriously & respected, & I had learned that when people saw my more rebellious side, it usually came with judgment. When really, most of the time I just wanted to have fun with my friends & fully experience my youth.

I did have to learn that living too much in that mode can subconsciously create emotional unavailability & avoidance though… which can unintentionally hurt people around you.

Did all of this subconsciously influence the women I dated afterward too? Absolutely. Tell me why my first girlfriend came straight out of a sorority & was way more straight-laced than I was. Then later I dated someone who had literally been president of her sorority. Why did I find that attractive? Because I had authority issues from my sorority days. For sure. It is funny how systems & environments can create these subconscious wounds that quietly follow you into other parts of your life.

It is all so messy. None of it is black & white. Was the sorority evil for the things that happened within it? No, a lot of people genuinely had amazing experiences & found real support there. Did parts of it hurt me? Yes. Was I perfect in my reactions or in the ways I pushed against the rules? Also no. Was I a piece of shit for the rules I broke in college that were honestly pretty standard for a college student? Definitely not.

It’s challenging to live in the gray, but god damn is it a lot more open-minded & interesting place to exist. You can actually see your flaws without drowning in shame. You can acknowledge the ways people hurt you without completely villainizing them. It is learning how to separate the actions that hurt you from attacking the entire character of the person who did them. I think that level of nuance makes a lot of people uncomfortable. It has taken a lot of experiences & perspective shifts to be able to stand here & hold this much space in the gray. But I actually like it here a lot more. It keeps me out of shame spirals. It gives me consistent opportunities to learn, see different perspectives, & let people take accountability. It makes me a lot less resentful.

I had to learn that I was never inherently “too much” or always the problem in every environment I was in… even though I started internalizing that after a while. I didn’t need to smooth myself out or lose the parts of me that made me… me. I just needed to learn how to channel those traits in healthier ways.

Now some of that risk-taking energy comes out through things I love to do. I like adrenaline. I have liked to learn how to ski, surf, & sail. I even find that riding the electric assist bikes through downtown SF gives me this weird, similar sense of liberation.

Being a founder is probably the healthiest way I have ever learned to channel this part of myself though. I was willing to take the risk to jump into this life, but every day I am also trying to build something that challenges systems already in place… because I genuinely believe there is a better, more creative solution. What I am building is something most people would never dare take on.

For me though, it makes me feel completely alive.

🔗 https://connoreschrich.substack.com/p/venture-into-the-gray-with-me