CUT YOUR TEETH is for the creators who sit at the intersection of taste, ambition, and business—because no one told you it's okay to be all three.
When everything falls apart (over and over and over again) you have no choice but to look back.
The first thing I smell is laundry detergent.
I taste it in the air. Coffee lingers underneath.
My dad is here. Walking barefoot in the living room. He’s pacing, steps loud and heavy on the wooden floor.
He has this look on him that won’t change for another twenty years:
Eyebrow scrunched, lips pressed into a thin line, a mist glazing over his eyes, his mind somewhere far, far away.
He never told me when things were wrong. He didn’t have to. I always felt it. My mom was somewhere else, her bones made of steel, heart soft as a cloud. I feel her presence even when she’s not here.
My dad doesn’t seem to notice me. Not at first. I’m always lingering in our house like a ghost with pictures to draw, and ideas to share. Little daydreams captured in misspelled letters and half-finished worlds. He’s the first one I go to, always.
The sight of his face makes my smile fall.
My sister, still a baby, still cocooned in her favorite pink blanket, is fast asleep somewhere, but I don’t know where. Part of me wants to find her, hold her tiny hand in my clenched fist, before I ask the question that shatters my whole world.
I don’t know why I know.
I don’t know why I ask the question.
“Daddy, are we broke?”
It climbs up before I can stop it.
Once it slips into the air, my dad finally manages to look at me. There’s a hollowness to his cheeks I hadn’t seen before. The urge to ask what’s wrong, what did I do, can I fix it burdens me deeper than the truth I already know.
“Yeah.” He sighs, then looks torn between sitting on the couch and running his free hand through his hair.
Eyes lost and distant, wandering through the mist once again.
“We are.”
Before you know you’re falling, your fingers are already grasping on the cliff. You hear the ocean below. You smell the air. You have nowhere to go but down.
I was younger than ten, but older than five—old enough to understand the gravity of what was happening, but too young to really grasp the magnitude of it all—when my parents lost everything in the stock market crash of 2008.
My dad is a self-made man. Not the Kylie Jenner kind. He scrapped his way to building a business that he sold for millions. He’d been in the same room with Steve Jobs, and said no to him, too. He’d been through the fires of entrepreneurship. The falls. The highs. The addictive magic that comes with it.
In those early days, he was passionate, insanely creative, and pioneered taste with function. He led through example. I sat on the floor of his office, bows in my hair, while he talked with his employees in-between meetings. I was in my own world, drawing unicorns with magic marker all over his whiteboard. He never erased them.
My mom worked herself to the bone, a fixture of the woman who loved being a mother but loved the ingrained adrenaline of corporate culture. She’s the type with eyes like a deer, soft and brown and warm, though full of maternal protectiveness if pushed too far. She carries herself with the subtle reminder of teeth, if you push her too far.
(That, we share)
Most of all, I don’t know anyone who knows how to love better than her.
To this day, she tells my sister and I she loves us almost every day. Unprompted and without expectation. I am very grateful to have someone like that, when so many people don’t have a mother who loves them, or have a mother at all.
While my dad taught me how to lean into my passions, my interests, and what lit the little fire inside, my mom taught me how to love unconditionally, to choose kindness before animosity, and to be generous when you can.
They both taught me work ethic, respect, and gratitude.
They had their faults. They’re not perfect. No one learns anything from perfect. Unfortunately, I can’t recall as much as I would like to. I want to remember what it was like, living in the house they earned before it all crashed and burned.
We had neighbors. Other affluent families. I’m not sure who was born into old money or who established their own legacies. My parents were hard workers, and I learned so much from observing them. I learned not to be entitled at a very young age. It followed me everywhere, and for that, I’m grateful.
I do remember always worrying.
Born anxious, my dad’s friends would joke. I was so hyper-aware I would look for fire escapes in hotel lobbies. I could tell when my parents were upset before they had to say anything. I hated disturbing the peace so much, that I was disciplined only once, and did whatever I could to completely avoid causing problems ever again.
The thought of my parents in pain—my sister, too, once she got older—was so, so much worse than any of the suffering I could endure.
So, when my parents lost their home, their wealth, and their collective sanity—losing everything you’ve built from the ground up can do that to you—my only thought was to try and make things as easy for them as possible.
I didn’t like seeing them cry. I didn’t like seeing them in pain. I didn’t want my sister to see me suffer. She needed someone to show up for her. If they couldn’t, I would.
I wish I could blame everything on the stock market crashing.
My parents’ marriage fell apart, for reasons I can’t share. I’m still only now picking up the pieces from that fallout, like sifting through the ashes of a nuclear aftermath.
I remember my dad tearfully looking me in the eye, wearing a suit, his cologne pungent and hair combed, his briefcase left forgotten on the floor while my mother stood in the background as a grand barricade of protection.
I’ll never forget that look on his face.
The way he looked at my sister behind me.
The way he looked like the entire world was caving under his feet.
Maybe it was.
“We love you both so much. This isn’t your fault.”
I believed he believed his own words.
I didn’t think they were true.
I only recently realized that this is where the cycle began.
There are chains of iron and chains of gold. What you choose—yes, it is a choice—depends on what held you close as a child, from first breath and first loves to first failures and first devastations. The goal isn’t to focus on iron, or gold—it’s to learn how to be free. Period.
I know someone else—even if it’s just one person—is resting on the other side of this letter who might know this cycle all too well. Perhaps even better than me.
You could be the ambitious overachiever who hated following else’s rules, destined to make your own. You could be the creative who struggled to pay attention in school, but could spend hours of uninterrupted bliss drawing, writing, sculpting, or doing whatever you wanted. You could be the survivor that learned speaking up punished you, and you forgot that you never had to ask permission to feel. You could be the artist, the builder, the thinker who’s always yearned, but never jumped.
You could be a combination of every one of them.
You could be one or two.
You could be none—but then again, you wouldn’t be here if that were true, now would you?
Unknowingly, what happened in the fractured portrait of my childhood planted the seeds that would sprout into trees of problems upon problems upon problems.
Problems that manifested in stomach ulcers, the fear of being seen, the constant pressure of being watched, the unshakeable personal expectations of achieving what felt impossible.
I’m as allergic to excuses as I am to coddling.
This created an unconscious craving to be recognized, to be understood, to be loved.
Not by others. By myself.
For example, my love of writing opened up avenues for my imagination to spread its wings; even back then, I favored writing over reading, and used reading as an ember to light the fire within me to get started. I was so addicted to creating—still am—that entering the worlds of others made me feel stilted and restless.
I didn’t know how to be jealous, to be envious.
I was so ready to embark on my personal vision, my tastes, my dreams, that what others’ built simply didn’t matter. Every creation I admired left a handprint on my brain and heart that I would then use as creative leverage, in some way or another.
Just, not in a literal sense.
Some people struggle with coming up with their own ideas. This is an affliction, and a very unfortunate one to see. There should never be any reason at all that the human brain lacks for original thinking, original ideas, and imagination in any capacity.
This type of person suffers out of frustration, trying to brute-force their way through artistic limitations, and constant comparison to other people.
I was never one of those people.
I have other problems, however, that can be just as destructive when unchecked—just a lot more dazzling to the naked eye. Problems where I’m overflowing with so many ideas that I start a dozen or so projects every week, and struggle to finish them. Problems where I’m committed with manic energy to one or two at a time, then lose interest in them within a 72-hour period.
This is the case with brands, businesses, skills, and even some of the fictional stories I’ve written over the years.
Since I was little, I’ve captured thousands upon thousands of fleeting ideas—characters, worlds, concepts, abstracts, spaces—across spare notes on my phone, the margins of math and science homework,
That doesn’t even scratch the hundreds of unfinished snippets of stories that will never see the light of day.
The most devastating part about this whole thing?
None of it matters.
Because none of those pieces have ever been finished.
Keeping your work invisible is a crime. Showing work you made that you only created for someone else—while putting what you crafted with soul on the shelf—is even worse. This is the true cycle of self-betrayal for creator-operators (founders, builders, and makers).
The hundreds of thousands of words I wrote, dashed, and spilled over the years? Those novels, stories, concepts, business plans, poems, and imaginary scribblings that came from the dome and had nowhere to go but anywhere I could find?
No one has ever seen them.
No one has ever read them.
No one has ripped them apart or learned to love them. No one has taken them from fleeting idea to full-fleshed story.
No one has looked in the eye of Perfectionism the Unbreakable Knight—in his stupid godforsaken Armor of Weak Falsities—and won the Secret War of All Creativity.
(Someday I’ll put all these flesh-and-blood abstract metaphors into a philosophical novel for your hopefully-non-reluctant perusal…)
Let’s be clear, that I’m not counting the work I wrote as an English Literature major. I wrote a 25,000-word fictional story for my senior thesis in three days—while recovering from a concussion and suffering major depressive episodes—and I can safely call that a piece of work that was, quite deservedly, ripped to shreds.
In my early teen years, I wrote fanfiction. I was a popular writer for several specific fandoms. I left that life a long time ago, but it did teach me how to receive and carry constructive criticism. It also taught me how soul-sucking it was to write for ideas that were never truly mine.
So, what I’m talking about now—these spare phrases, stories, and worlds that I can truly call mine and only mine—were the only ones hidden. I was afraid of being seen. I didn’t know this at the time, but it’s quite obvious in hindsight.
What these pieces of work became, was nothing.
They’re now figments of another time, another memory, another version of myself that I’ve long since abandoned, lost in the sea of “What Could’ve Been,” and that’s the most terrible fate indeed.
A tragic fate most creators face, if they don’t wise the fuck up.
You might think:
“Well, Taylor, that sounds brilliant! I love creating, too. How did you get into a toxic cycle if you recognized you loved making things for yourself so young?”
You’re asking this because you already know the answer to this.
You’re asking because you’ve already been affected by it.
You’re asking because you know the hard truth.
Whether you identity with one, two, or all three of these…
I don’t have the perfect answer for everyone, but I may have the perfect answer for you:
“To recognize what you love most—to create for yourself in a specific or multiple vocations—is to recognize the inner fire that only you can burn. It’s to look at what inspires you, not your neighbor. It’s to see the uniqueness of your brain, heart, soul, and experiences, and use those paints to craft a portrait only you can make. To recognize the one or many things you love to create for yourself, is to recognize what you’ve been placed on this earth to do. To ignore it is to deny yourself. To ignore it is to deny a higher power (if one such exists). To ignore it is to betray the person you are. You must do whatever you can to avoid betraying what you’re meant to do, and lean into the fires that flicker inside.”
This is pleasant to think about on a philosophical level.
But what about turning it into actionable advice?
We’ll get into that next…
Create for others first, and you lose what makes you a diamond buried within the coals. Create for yourself first, and it becomes impossible to be ignored. Create for yourself while breaking the cycle of survival and turning it into a furnace for business, art, and taste—that’s the unbreakable move. The move of real creators.
I’ve made a lot of mistakes since this cycle of self-betrayal began.
It started with working in one of the family businesses. I was a self-taught copywriter, ready to take on a scrappy marketing role to earn my stripes.
I will keep identities hidden, as I don’t want specific people mentioned. These are not flattering stories, and the people involved have not been in my orbit for the last ten years or so. They’re not here to defend themselves, and while this is my personal story—and I have protected these people on a public scale for a long, long time—I have no interest in bringing attention to old demons.
What you need to know is that, during this period, I went through:
Crippling anxiety, depression, and gaslighting. I was clinically depressed for over a decade. I just wasn’t diagnosed until my early twenties. I lost twenty pounds of muscle, woke up with heart palpitations every day, and had panic attacks in the bathroom at least once a week.
Undiagnosed ADHD, OCD, and a cocktail of other mental issues that I didn’t realize I had until it was almost too late. Alongside my depression and anxiety diagnoses, my therapist made it very clear to me that I had been functioning miraculously despite a plethora of internal and psychological issues. (We’re much better now)
Financial trauma. One morning, on the way to work, I stopped at a gas station with two miles left in the tank, and had to rifle through my car to find a few dollar bills I could use to make sure I made it to work. My bank account was overdrawn, and I had five dollars left in my pocket. I was in tears the entire week. My relationship with money was already horrible. What my parents went through was awful, and it affected my sister and I deeply. However, the stress battled at this place was far worse than anything else.
Destruction of the body, heart, and soul. The company went under. A family member involved that I greatly treasure became suicidial. I insisted they live with me, while the people who crashed and burned with the company used verbal abuse to mask their own trauma. I lost my confidence, sense of self, and believed my skills were negligible, that I was an awful writer, and that somehow, the destruction that followed was entirely my fault.
A paranoid boss made applying for jobs very difficult. While the company was suffering, I had to sneak away into closed rooms to update my LinkedIn profile and apply for jobs. I was terrified of this person knowing what I was doing, that they would scream, threaten, or unleash. When they were angry, they were terrifying. One afternoon, they passive-aggressively mentioned that I shouldn’t list my freelancing as the most recent position on my profile, because “it looks like you have another gig.” I’ll never forget that exchange.
It’s difficult rehashing these events. I could write multiple hours-long television dramas just recapping what happened in specific, painful detail. If I wanted to.
Thankfully, I don’t.
This is the softest version of the truth I can present, and I hope you don’t take that for granted as someone who may have gone through something similar.
Now, these experiences worsened the cycle of self-betrayal. It contorted my self-perception in ways that damaged how I approached work, clients, and my creativity for years. I stopped believing in myself, but I pushed anyway. I started a consulting business, charged pennies for copywriting work for B2B startups, and slowly began to build something for myself.
Then, I felt the pressure again. I took full-time roles. I joined the marketing team at the USTA. Got laid off in seven months. I landed a contract job at Nike after teaching myself the art and science of UX writing and content design. (You can figure most things—if not everything—out if you put yourself in a corner on purpose). I moved on from Nike to another full-time role at Meta. I got laid off again, along with thousands of other unsuspecting, talented workers, within eight months.
I hated working in corporate. I hated working for other people. The pay was good, of course, but that didn’t matter to me. I used that as motivation to stay, to pay my bills and be responsible. But I was frustrated with the limitations, this box I had placed around myself. I had to drag my feet to serve clients work I didn’t like making. I was putting my vision on the back burner. I was scared, but didn’t realize it. I was unknowingly falling victim to a cycle of my own design. I didn’t see it for ten years.
As expected, the cycle continued.
I did good work at Revolut.
Burnt out. Hated it. Got sick. Moved on.
I did good work at a biotech startup—probably the worst corporate experience I’ve had in my entire life—while wrangling with a Machiavellian boss, crippling self-doubt, and writing admittedly awful copy with the pay of one person at the time and expectations of a full team.
Burnt out. Hated it. Got sick, mentally and physically. Moved on.
Started a ghostwriting business. Personal branding for venture capitalists. Changed the niche at least eight times. (Loved a lot of industries, you know). I was able to actually help these investors tell honest stories and connect with others on their platform.
Burnt out. Hated it. Had a mental breakdown. Moved on.
There are blips in the story. Ones I may share another day.
But for today…
Here we are.
Cutting my—our—teeth once again, so to speak.
On a mission to identify, regain, and become the creative self I was always meant to be—while embracing the hustle of entrepreneurship, the beauty of taste, and acknowledging I’m a fucking ambitious person who loves slow mornings and moving lightning-fast in the same breath.
Today, you and I are embracing the perspective of a novice opening up the heart and soul and eyes once again to the identity you had sacrificed to become passable, to become ideal, to become sought-after in traditional work.
You are worth more than that.
You are more than that.
You are more.
For ten years, I created for others, first.
I abandoned my dreams, what made me uniquely powerful as a storytelling expert in startups. I had ignored my growing confidence and chose to suffer, instead. I had grown so unconsciously used to suffering and silencing myself that I believed it was simply where I was meant to be.
How insane, how awful, how sad.
Yes, yes, yes, woe is me.
(But not really, because we’re not perpetual victims in this house)
Now… we’re changing that.
Because maybe you’re in a similar position.
Maybe you’ve committed a similar act of self-betrayal as a creator, operator, founder, artist, or builder. Maybe you’re sick of falling into the same patterns. Maybe you wish you could identify what makes you truly original in a sea of liars who insist that there’s nothing original anymore. (These people are insecure and too lazy to even try)
Here is my actionable plan to do so, while encouraging you to do the same:
Write this newsletter every week, documenting the progress of building my multi-hyphenate career. CUT YOUR TEETH is small now, but my vision for it to grow it into an unstoppable media brand that spans social, YouTube, and more. My other baby in the works, White Stag, is a narrative design and copy studio for Series A+ consumer startup founders. It’s much more selective, serving as a client engine and private club.
Document the lessons, wins, and failures, and all the stories in-between. Our lives are daily stories. Everything we see, hear, smell, and touch, can all be captured in a narrative worth sharing. This is a challenging journey that will encompass many ups, downs, and revisits. We’ll see how it goes.
The process of writing and self-publishing my first novel. This has gone through many spades, but when you have a vocation that calls louder than the others, you listen. This novel is one of many stories I plan on writing for the rest of my life. I’ll be sharing the progress, what I’m learning from the process, and once it’s available—share it with you.
Financial transparency. I have lofty goals for these ventures. I want to be rich. And so, I will be. I’ll share infrequent, but honest, updates on how these vocations are going, how I’m building streams of income in a way that delights my soul as well as my wallet.
Tell you honestly about what inspires me, milestones I’m planning to reach, the occasional delusional thought, and more. You’ll get the first taste of this at the end of today’s letter, but every week I will recap the former list of thoughts and details in a way that helps you, while affirming my focus.
I’m bullish about individuality in the life of every creator.
You should never feel like you have to diminish yourself for any reason, be it for a job, a path you thought you loved but ended up hating, a partner, your family, or anything else.
You can build the creative path you want—in any way you want.
It doesn’t matter where you come from.
What matters is what you do today.
Create for yourself, first.
Or regret what you could’ve been for the rest of your life.
Work, art, people, and brands that inspired me this week.
+ The book I’m writing. Sounds pretentious, but I promise you this is one of the reasons I’m meant to be on this planet. I’ve wrestled with this story for ten years, and it’s evolved and changed to such a degree that I’ve now accepted it’s taken on a whole new identity.
+ Privileged Few. The stunning media brand crafted by the brilliant and unfiltered Albina Aliyeva. Stumbled across this creation on Instagram, fell in love with the creative direction and branding, and hopped down a rabbit hole (no pun intended) that I think most people across all walks of wealth should investigate.
+ Anything Tobias van Schneider touches. He’s a design leader and maker of many things (doesn’t like the word “entrepreneur”) who’s helmed projects like Carbonmade, Semplice, and my personal favorite—mymind. His dedication to human craft and creativity in this AI-dominated universe we’re wandering (together, yet alone) tickles my bran.
+ What my friend Sasha Cayward is building for founders and venture capitalists in London’s startup ecosystem. I’ve learned a lot from Sasha when it comes to rounding up your ideal people, serving them in a way that delivers real value, and establishing powerful communities. She’s also the Chief Community Officer at Hubble, an online marketplace full of vetted experts, so she (really) knows her stuff. Follow and connect with her on Instagram and LinkedIn.
+ Classical lo-fi. Classical music is my blood type. It’s been my favorite and most-listened-to genre of music since I started taking music seriously around eight or nine years old. Lately, I’ve been loving—and looping—this YouTube video while knee-deep in work, creative writing, and networking.
If you made it this far, you’re a legend.
I feel you. I see you.
Let me know what you’re itching to see from future emails.
This is your world as much as it’s mine.
See you next week, Toothcutter,
Taylor