In my twenties, I would have considered this unhinged.

Back then, I had it all figured out. I was following The Code of Very Important Chronological Life Events with grace and precision:

I got a degree from a prestigious East Coast college. Check.

I got a job in advertising on Madison Avenue. Check.

I got promoted. Check.

I got engaged after a year of dating. Check.

I got promoted again. Check.

I got married. In a castle. Check.

I was on track to being Very Successful and Important. Then, I took a detour. I quit my well-paid Madison Avenue ad agency job to become a full-time yoga teacher in Denver, certain I had discovered my true self. I glowed in my rebellion against the traditional path. I was raging against the machine! I was bohemian! I was vegan!

But beneath the surface, the yoga mat, and the vegan tofu scramble, The Code of Very Important Chronological Life Events marched on:

I bought a house.

I had a baby.

I bought a bigger house.

And then, less than two years later, I checked another item off of the list:

I got a divorce.

Check.

Suddenly, The Code was scrambled. Selling the house and my belongings while caring for my baby, I faced an uncomfortable possibility.

Perhaps I didn’t have it all figured out after all.

For as long as I can remember, I’ve climbed. In middle school, I was thinking about college, touring schools during Spring Breaks and family trips. During an Amherst college tour, the admissions host asked prospective students to raise their hand according to their current grade level. I was the only eighth grader in the room. In high school, I pored over new releases of the U.S. News and World Report Top Colleges, prioritizing my college applications first on the school’s ranking, then on their fit for my interests. My first husband and I started dating while he was in law school. I was certain that we needed to get married in the month-long break between his semesters, which obviously meant he needed to propose at least eleven months ahead so we had sufficient time to plan. The night before our wedding, I remember lying awake at the tingle of a question in the back of my mind. Was this all happening the way it ought to? Was I moving too fast? I closed my eyes and went to bed. I had a wedding to get to tomorrow.

In all of the striving, I left little room to pause. To question. To ruminate.

My divorce exposed the price of my clipped, tidy trajectory. I wasn’t ahead of my peers anymore. I was behind. With baggage. I celebrated my two best friends’ weddings while finalizing my divorce. I watched friends start and grow their families while staying up alone at night with my only child. I saw friends graduate from doctorate programs while I hunkered down in a toxic job that paid the bills. I watched colleagues getting promoted as I was getting fired.

When my husband and I started dating, we had each veered off the typical path. In the rearview mirror, we each carried a divorce, a child, and a wake of financial decisions born of stress and desperation. In initial efforts to impress each other, we coolly professed we were electing a different course, all the wiser from our experiences. After his teenage son graduated, he was going to defect to Nicaragua and open a beach bar. I was… well, I was going to raise a three-year-old and “keep kicking ass” at my job… you know, the one I was barely surviving. We told ourselves, and each other, we were choosing something bold and brave. In reality, we were threadbare and short on options.

Having launched, skyrocketed and fumbled The Code of Very Important Chronological Life Events, we started making it up as we went along. We co-authored a relationship contract. After drafting it in Word, we printed it out and cracked open a bottle of champagne to celebrate our commitment. Who needs marriage? Been there, done that, have the scars to prove it.

On schedule, friends asked when we were going to have kids. We considered it. We wrote out a two-by-two matrix: Have Kids, Don’t Have Kids: Pros and Cons. It didn’t reveal a clear answer. We decided to write a different kind of familial story, one that prioritized our two children and room for ourselves. We drafted an estate plan, legally bonding our family in life and legacy. Never mind that we barely had two pennies to rub together.

Years later during the pandemic, we were on a casual stroll through the park. We wondered aloud, “Well, we’ve survived the zombie apocalypse together. Why not get married?” By the end of the walk we had picked a date and booked a venue.

“Just propose to me in enough time so that we can invite people,” I told him. He agreed.

None of it—the family, the vineyard, the marriage, the house—would exist if we insisted on the proper order of things.

It doesn’t mean I’m inoculated against The Code of Very Important Chronological Life Events. I still take inventory. My career. My belongings. My travels. My 401k. Are they enough? Am I on track? What comes next?

But no life is tidy. And we wildly overestimate our control over it.

You can do everything right. You can get into the right college. Get the right job. Get married. Get the house. Have the baby. Get the promotion. You can execute perfectly. And it still might not matter.

Because life just doesn’t work like that. We’re much smaller than we think. As we all do, I just keep cycling through the realization of my smallness— the embarrassment, the shame, the grace, the acceptance, and all the way back again.

Agency. Surrender. Repeat.

This morning, I neglected my well-worn meditation cushion. I shuffled to my office, ready to start my work day. I swiveled into my chair, firing up my computer.

Then, in a flash second, I decided to ignore it all for a moment.

I swiveled away from the computer. I placed my bare feet on the cold tile floor. I set a timer to ensure I wouldn’t be late to a meeting. I closed my eyes.

Things proceeded as usual. Racing thoughts. To do lists. Checking things done and undone. But, for one exquisite nanosecond, I felt something else. In one tiny micro-moment: peace, joy, belonging, and the thrill of recognizing that I felt it in the first place.

The moment was interrupted by the realization of the moment. Then, as any bad meditator would do, I checked my timer. I still had five minutes left.

Last year, I meditated my ass off. Like years past, I set my annual goal to meditate for 108 hours. A nearly daily regimen of 20-minute meditation sessions and a 10-day silent meditation retreat skyrocketed me to 158 hours (9,480 minutes to be exact). I really nailed it. Zen: check.

This year, as I’ve sought to unwind my obsession with goals, I’ve stopped counting. And, I’ve meditated far less.

In fact, I’ve just done a lot less in general.

I told myself that setting down goals was an invitation towards curiosity. An invitation towards openness. An invitation towards play. But, in practice, I’ve met my own invitation with paralysis and, sometimes, boredom.

Turns out, well-worn habits are hard to change.

After checking my timer, I padded across the cold tile floor, compelled to pick up a book I hadn’t touched in more than fifteen years: Meditation for the Love of It, by Sally Kempton.

Sixteen years ago, I bought Kempton’s book on the heels of my full-tilt revolt against a corporate career. A newly-minted certified yoga teacher, I had quit my New York ad agency job and moved to Colorado to teach yoga full-time. I met Kempton, and her book, on an extended yoga retreat in Estes Park.

I opened the book to the first, dusty dog-ear with no knowledge of what to expect.

Despite twenty years of deep meditation experience, Kempton opened with her own reckoning with her practice. She realized she was “using [her] spiritual practice as Band-Aids or perhaps as tonics—nourishing techniques that [she] employed to keep [herself] in good working order.”

Seeing myself in her words, I read on.

As she sought to reinvigorate and evolve her practice, Kempton admitted that she wanted meditation to retain the joy and dynamism it held in her early practice. But, as an experienced meditator, she knew that “meditation can’t always be fun.” She decided to reengage her practice from a beginner’s mindset, approaching each session as an experiment and as play:

“ I would give myself permission to bring an element of lightness and spontaneity to my meditation. I would let myself play. In fact, each time I sat to meditate, I would consciously remind myself, ‘It’s okay to be playful.’”

A faint, fifteen-year-old highlighter mark streaked across this passage. I closed the book. I went to work.

I began my Substack with no goal in mind. I just felt like writing. I lightly set an intention to write on a weekly basis. In “The Artist’s Way,” Julia Cameron advocated for this style of creative discipline. Setting aside time or intention on a daily or weekly basis to explore and create. Unwittingly, I carved a similar discipline into this Substack. By committing to writing something each week, I committed to having something to say. A small “c” commitment, built on the spirit of creativity and expression, not expectation.

But this week, I had nothing to say. I told myself I’d forgo the writing, and in doing so, I’d further break a relentless pattern of setting big “C” commitments in small “c” practices—goal wolves in sheep’s clothing. Goalless enlightenment: check.

Then, this morning happened. The cool tile under closed eyes and grounded feet. The serendipitously dog-eared page. The faint highlighter mark of Kats gone by.

And as I wrapped my workday, taking an evening stroll around the park, I felt inspired to write.

Which came first? The commitment? Or its surrender?

In Zen Buddhism, koans are paradoxes upon which to meditate:

“Two hands clap and there is a sound. What is the sound of one hand?”

When logic fails, practitioners must sit with the question versus seeking immediate solutions. In some traditions, a practitioner ruminates on a single koan for an entire lifetime. A well-considered answer matters; but, reflection matters more.

I don’t have the answers to my own riddles. But my relationship to the riddle itself changes. In one moment: softness. Cold tile, calm breaths, serendipity. In another: rigidity. The timer, the schedule, the discipline.

Both are always true. And maybe always will be.

When I got a divorce, I was very close with my ex-husband’s family. In the separation, I not only lost a partner; I lost a set of parents and siblings. Tension coursed through the years that followed. New boundaries were constructed. But eventually, we forged a path. In our own individual ways, we each stepped forward into a new relationship. Not the same shape as before, but rooted in a steadfast love of my son. More than a decade later, my relationship with my once in-laws has bloomed into something deep and beautiful. It’s not a perfect family tree. It has its knots. But, it is strong and resilient. It’s weathered many storms.

Another storm is raging now, as illness rips through part of the family. The details aren’t mine to share. But the stress is palpable. I might be on the outskirts, but I feel the reverberations nonetheless.

The depth of one’s love doesn’t always align with the framework it lives within. My love for my once in-laws swells beyond tidy boundaries. I yearn to demonstrate that love in action, but that doesn’t mean it’s my place or my time.

Effusively, I’ve offered to help in any way, big or small. I’d move mountains. I’d take care of the dogs. I’d go to the hospital. I’d run errands. I’d do anything. I’ve wrung my hands and wracked my brain, wondering how I can support. Repeatedly, I’ve asked if there is anything I can do to help.

“People in crisis can’t answer that question,” my husband said. “You need to stop. You’ll know when it’s your time to help.”

As is often the case, he’s right. As is often the case, there’s also more to the story.

How do you know when it’s time to step forward, despite the framework of well-worn boundaries? And how do you decide, when you can never be sure what lies on the other side of your efforts?

I’ve grappled with this question for decades.

My biological father and I haven’t spoken for more than twenty years. It’s a story that could consume an autobiography.

My dad and I had many ups and downs. In my late twenties, I reached out. I cracked the door open ever so slightly, offering my contact information and an invitation to step forward together. No response.

After becoming a parent, I reached out again. I sought the advice of a private investigator. I tracked down his likely address. I wrote, offering new routes to connect. No response.

As I calculated my father’s advanced years, I tried again, harboring the worry that the next time I heard of my father might be through his death. Pulse racing, I called him. Voicemail—on the other side, his recorded voice as clear as if I had heard it yesterday. I left a message. No response.

The next year, I tried again.

No response.

As a parent myself, I couldn’t fathom it. My love for my child runs so deep that there is no slight, no offense, no divide too great to cross for that love. It is boundless. It is the greatest gift of my life.

But, I have no clue what’s on my dad’s side of the door.

As hurtful and confusing as his choice has been, it is his. I’ve knocked. I’ve cracked the door open. I’ve wedged a foot in the door frame. And it sits there, awkwardly unanswered.

There’s nothing I can do to change it. But, it has changed me.

I approach these thresholds with caution. Countless years of therapy have taught me principles and healthy habits on codependence and boundaries. Through decades of practice and failure, I’ve learned to spot when I’m barging through a threshold too eagerly, alone, or when I’m advancing bravely, with a tenderhearted, genuine desire to build a bridge.

Regardless, I have zero control of what occurs on the other side.

On occasion, though, I’ve reaped the rewards of honoring that brave voice.

When my former sister-in-law sent me an offhanded text about a crazy opportunity to buy a vineyard in Argentina, I barged through the door. I felt the goosebumps on my arms. “We should do this,” I told her. Years later, we own a wine business together. Our friendship bloomed into new, unexpected territories alongside our partners.

When my adult stepson experienced a medical emergency, I didn’t hesitate. I’d spent years treating our relationship delicately, careful not to overstep my role. Heart racing, I booked flights and packed bags. My husband and I were by his side within hours. I didn’t ask for permission. Our relationship grew to new depths as a result.

I walked through those doors unannounced. Not entirely unwelcome, but unbeckoned nonetheless. The goosebumps and the adrenaline weren’t mystic signs. They were intuition. The deep knowing that, regardless of the outcome, I had to do this.

In those cases, I was rewarded. With my father, not so much.

Sometimes, I know. I know the fine line between respecting boundaries and accepting an opaque threshold. Other times, I don’t. I guess. Or, I move forward because I have to. Whether it’s received or rejected, I do it for myself. But, the rejections create more hesitation at the threshold. More questions. More self doubt. More wondering whether I’ve done enough, been enough, said enough, tried enough.

Today, I sit in the discomfort, standing in the placeless place. Knocking. Not knowing if I’ll ever know whether to open the door and barge through. Not knowing what truly sits on the other side—of a well of worry, grief, and love in which my emotions are just a drop in the ocean.

And I never will. Sometimes, I just get lucky.

Its facade is a product of its history. World War I spared Berlin’s buildings, but left it economically fragile. World War II destroyed 90% of Berlin’s buildings, not to mention the Holocaust’s far greater toll in human lives. After 1945, much of Berlin was in ruins. The Cold War created new scars through the wall and the Death Strip.

But, Berlin is a city that reveals its character by keeping its history visible. Instead of hiding its scars, Berlin preserves them and builds with them. This past week in Berlin, I visited ZK/U, a center for art and urbanism built upon the remains of an abandoned cargo railway station. A glass roof rests on top of the original brick walls; an artist’s living quarters occupy a former cargo hold; a garden grows over the site of the rail lines.

I also visited The Fotografiska Museum, whose building was once an artists’ commune, a Nazi prison, and a high-end department store. The artists’ commune of Tacheles was born from creatives protesting the building’s demolition after the Cold War. They stayed for more than twenty years. When I first visited Berlin in my twenties, I explored the artists’ open rooms and stairwells, finding colorful graffiti and sculpture at every turn. When I visited last week, I explored the photography museum’s sleek exhibit halls, but admired the original graffiti-soaked stairwells and hallways.

Like countless others in Berlin, these buildings express the city’s commitment to building transparently alongside history, never forgetting. Memorials to the darkest parts of Berlin’s past stand beside new construction. Portions of the wall stand beside a riverside park. Berlin reveals its past and its present together, unabashedly.

My husband always jokes that I’m a Kat with nine lives.

Growing up, I moved frequently. Each time, as I mourned the loss of moving on, my parents reframed it as a fresh start, a chance to be whoever I wanted to be. I took the advice and ran with it. I even changed my name. From Katie to Katherine to Kat.

Over the years, I reinvented myself countless times. From prep school A+ student to small town artist goth. From Bozeman High School to Vassar College. From sober, studious college student to senior year rager. From actor to ad agency account executive. From corporate hustle to vegan yoga teacher and back again. From married to divorced to remarried.

As I tried on new identities, I left the previous ones behind. In each of my nine lives, I demolished the previous.

In the process, I grew. But at a cost.

My approach to rebuilding was a wrecking ball. I razed the past to the ground. With it, I leveled far more than prior identities. I flattened friendships. I shed witnesses to my prior selves like a snake sheds its skin. I obliterated memories. Inadvertently, as I tore down connections to the past, I tore down the scaffolding of memory.

The foundation of my approach rested on something immovable: a deep desire to avoid mistakes and missteps. My drive for the facade of perfection was painfully staked into the ground. I constantly plastered over the rough edges of myself, presenting instead a shiny and smooth wall to the world around me. For more years than I can count, this blueprint guided how I navigated the world. I engineered gleaming new structures of identity, discarding the broken bits instead of building upon them.

Now, I’m tired of the wrecking ball. Tired of the force that propels it. Tired of the cost of demolition.

Instead, I’m architecting a new form of reinvention. One that isn’t so much about the renovations themselves as the principles that guide their design.

I’m learning to take a more careful approach, one that remodels with caution instead of destruction. Rather than starting each year with an overly ambitious new laundry list of goals, I’m taking time to listen and simply take the best next step. Rather than cultivating all-or-nothing friendships to align with the entirety of who I am, I’m giving grace and space for friendships that fulfill parts of me, not all. Rather than charging off to accomplish some grand new feat, I’m staying in place. Observing the space around me to understand what’s true and enduring.

I’m learning to honor and preserve the past as part of this redesign. In prior lives, I never shared my deepest failures. Now, I offer them more freely. Surviving my twenties. Getting fired. Losing friendships. Struggling as a single mom. Grappling with my career. I fight the instinct to slap a fresh coat of paint over the graffiti. Instead, I’m letting the graffiti speak.

It’s a work in progress.

Last week in Berlin, I considered reaching out to an old friend, one of my closest friends in my early twenties. During that time, I was stumbling through life in New York, trying to find myself; she appeared to be on the fast-track to success. Her career as a curator took off, catapulting her into the public eye and high-end art scene. From where I stood, she seemed to have it all figured out. We were on vastly different paths. We lost touch. When I recently discovered she was living in Berlin, leading a well-known art residency she founded, I was compelled to reach out.

I didn’t.

When I asked myself why, a simple answer emerged. As much as I’m trying to reclaim and embrace my eight prior lives, there’s still a little piece of me that is embarrassed. Embarrassed by how many selves I’ve tried on. Embarrassed by my messes. Embarrassed by friendships I neglected. Embarrassed by the disparity between who I was then and who I am now. Even if I’m not razing the building anymore, I’m still hesitant to put the construction site on display.

But, learning new ways of building takes time. A demolition crew doesn’t adopt historical preservation skills overnight. Those skills are formed through patience, humor, compassion, and a whole hell of a lot of mistakes. I have a long way to go before I can pick up the little pieces of rubble and hold each one up to the light.

Berlin kept its scars so as to not forget itself.

I’m late.

I’m imperfect.

But, I’m trying.

My grandma always cared deeply about her appearance. And it showed. For as long as I can remember, my MeMaw never looked anything less than a million bucks. Everyone who knew her has memories of her incredible style. When my mom was in college, MeMaw dropped jaws rolling onto campus in a powder blue Cadillac with a matching powder blue suit. She busted out her collection of full-length furs regularly. At 70, with crimson hair and bright red lipstick, she was still turning heads as she’d walk through a room in a matching red leather mini skirt. She slayed.

Her obsession with looking good wasn’t all for vanity’s sake. Growing up very poor in rural Kansas and with little education, my grandmother’s beauty was her way out. Her striking looks turned heads and brought many a man to his knees to propose. She married six times, with two marriages spanning more than 30 years each. As a young woman, Frieda’s beauty was her currency and her passport: from Kansas to Beverly Hills to Texas and beyond.

MeMaw instilled her attention to outward appearance in my mom and in me. The best compliment you could earn from my grandma was that you looked “pretty.” From her lens, beauty and style were more than a fashion choice. It was a key to survival. It mattered to her more than it does to most… because it had to.

My grandmother’s story, though, is not my own. Thanks in part to her struggles, and to my mom’s, I’ve lived a very different life. I distinctly remember my grandmother’s pride as she watched me graduate from Vassar College. The trip across the country was difficult for her and her husband, but she did it anyway.

My education and career have offered me far more choices than Frieda had. Nevertheless, my love of self-expression and style remains. I cherish my grandmother’s lessons that celebrate beauty as an outward expression of self worth. I abandon beauty as a projection of worth. I keep the inherited joy in style. I ditch appearance as a full-time job.

In my 40s, self-expression and style are not a catwalk, but a tightrope. I’m surrounded by cultural messaging that coaches me to disappear. Vast palettes of muted beige, grey, black, and white, in large, billowing, shapeless formats litter my Instagram feed. On the surface, this imagery is sold as elegance; underneath, it’s an invitation to fade into the background. Women in their 40s and beyond are subtly encouraged to step backwards towards irrelevancy. As we’re guided towards fifty shades of beige, we’re guided towards a bigger message: Be less noticeable. Be less loud. Be less.

No thanks.

In my teens, 20s, and 30s, my style took many shapes. I bounced from gothic teenage rage, to edgy New Yorker, to playful professional. But, the styles that marked those years don’t resonate for me in my 40s. Cheerful little dresses and sky high stilettos feel forced and uncomfortable. Over the years, my body has changed, but more importantly, I have changed. I am more self-possessed. I am more self-confident. I am more self-aware. I am less interested in projecting an image or in turning heads. But, I’m no less interested in expressing myself.

And I know I’m not alone. Women in their 40s and beyond are craving and creating their own forms of expressive style. My hairstylist shares her fashion Pinterest board with me as she cuts my platinum blonde pixie into a faux-mohawk-mullet. My trainer winks with a lid covered in mauve glitter eyeshadow as she shows me the silver lamé pants she just purchased. The nurse at my doctor’s office smiles through her pierced lips as she abandons the iPad medical forms to show me the Nike Tabis she just bought in three colors.

Each of us, in our own way, is offering a graceful “fuck that” to the pervasive messaging requesting we step back. We’re refusing the script, tearing it up into little pieces, and casting them into the air with a wild laugh. Women in beige might wonder what the hell is wrong with us. And to that we say: we don’t care.

For me, it’s a work in progress. I’m still discovering what makes me feel beautiful, strong, confident, alive. The more I explore, the more I realize how many forms of self-expression live within me. A white t-shirt, jeans, and kickass sneakers, paired with a luxuriously sexy perfume. A vintage suit that fits like it was tailored just for me. A dress that makes me feel as strong as I am. Style takes countless forms. For me, it’s about attuning to what makes me feel happy, hot, poised, and playful, from the inside out, not the outside in.

If I’m lucky enough to live into my 90s like MeMaw, I have a long way to go before the lights go down. I want to live those years taking up more space, not less. I want to be that woman rocking the red leather mini skirt. My grandma taught me the currency of style and beauty. Now, I’m learning where I actually want to invest: in myself, unapologetically.

This week, waiting to board a plane home from a work trip, I read an article in The New Yorker, “Can A.I. Produce Writing That We Actually Want to Read?” The author, Jay Caspian Kang, created an experiment: train AI on the voice of several famous authors; ask it to produce texts in the style of those authors; then ask humans to parse out the originals from the counterfeits. At first, AI fakes were easy to spot. AI-generated characters “apart from fidgeting… mostly did nothing.” When Kang pushed Claude to produce more decisive characters, Claude took it too far. Every character sprang into action, jumping on horses, delivering urgent messages, or running. As Kang’s experiment continued, the fakes improved, ultimately with as little as 17% of testers discerning the difference between real Bram Stoker and AI Bram Stoker.

Kang concluded by drawing a parallel between the writer’s relationship with technology and that of grandmaster chess players. Computers have reliably beaten humans at chess for decades; yet, humans still pursue the game. Humans play chess because they value the cognitive process of the game, even if computers can smoke us. Kang argues that writing is the same. People will still choose to write as a mechanism for synthesizing thought and communicating with others.

The article’s algorithmic arrival at the top of my newsfeed was timely. Like so many, I’m fatigued by receiving and parsing AI-written memos—rife with overly ambitious word choices, em dashes, uncharacteristic cheer, and the most annoying telltale marker of all: “it’s not X; it’s Y.” My brain is tired. Increasingly, I find myself drawn toward two co-existing poles: transparency in the use of AI, and the raw beauty of messy, human authorship. Kang’s article touched on a topic I’d been circling for weeks. I wanted to learn more, but wasn’t sure where to start.

So, I turned to Claude.

I asked for additional article recommendations. Claude replied with a few strong contenders, including academic papers and Substack authors I had never heard of. I spent the better part of my plane ride reading additional perspectives.

When I came home, I told my husband about the articles. He responded by sharing a few more.

Among many authors, a central theme persisted: the human process of writing is best left unassisted by AI. João Batalheiro Ferreira expressed skepticism towards leveraging AI in the brainstorming or revision process. Allan Reeder referenced his experience as a writing coach who guides college applicants in essay authorship, arguing for the precious value of slowing down to wait for original, true insight and “what we call voice.” Eve Fairbanks lauded the inefficient hang-ups and backtracking of the writing process as “a feature of human thought process, not a bug.”

I’ve known many writers obsessed with the process. My ex-husband—a fantastic writer, gifted with skill, smarts, and three college degrees—used to insist he could only write in a room with hardwood floors. Everyone has their thing. In many writers’ eyes, the blank page is a solemn rite of passage. A mountain every author must climb.

But here’s the thing: the page was never sacred.

Of all the articles I read, the most fascinating was one Claude suggested, an academic paper by Jon Ippolito. Ippolito argues that authentic voice—that elusive, uniquely human, deep soul truth—has been augmented for thousands of years. Those who argue that AI is offloading a cognitive process aren’t wrong; but, they are missing the many historic inventions that progressively altered the cognitive process of expression. The alphabet shifted traditions of carrying stories through song, oration, and memory. The Gutenberg press shifted the perception of calligraphy as essential to expressing personality. Word processors shifted the editorial process, offering a digital means of revising the written word. “Perhaps the loss of authorial personality predates AI-generated prose; perhaps the slippage began the moment the alphabet separated the speaker from what is spoken, and the gap has been widening with every introduction of a new writing medium.”

Ippolito acknowledged those who valorize the writing process as a mode of self-discovery and cognition. But, he argued that we might be on the precipice of a new evolution of human expression, a new split: between discursive, oral, or embodied personal communication and compact, machine-readable, impersonal communication.

I see traces of Ippolito’s argument in my own process, which I began well before reading these articles. I’ll cut to the chase: my process includes AI. It does offload certain forms of cognition. But, perhaps not where you’d expect it.

Here’s how it works:

• Step 1: Wind aimlessly around ideas spinning in my brain. Question the worth of said ideas.

• Step 2: Sit alone in a quiet room or parking lot. Record voice memos, as if talking to my closest friend. Gesticulate. Sigh. Pause. Wander. Stop the recording. Get back to life.

• Step 3: Upload voice memos to Claude. Ask Claude to interview me. Answer Claude’s questions in writing or voice.

• Step 4: Ask Claude to stop blowing smoke up my ass when it tells me I’ve hit on an insight “nobody but you could have thought of.”

• Step 5: Read Claude’s observations of patterns and connections. Correct misunderstandings. Request a suggested outline. Discard half of it.

• Step 6: Draft, in my own words, outside of Claude.

• Step 7: Upload a draft to Claude. Remind it (again) to stop being a sycophant. Ask for input on what’s structurally sound or weak.

• Step 8. Go back to my draft. Revise. Revise again. Revise again. Revise again.

• Step 9: Feed my final draft to Claude. Request input on fact checks and grammatical errors.

• Step 10: Fix. Publish.

My process doesn’t begin with a blank page. It doesn’t include a writing coach. It doesn’t include an editor or a publishing house. It doesn’t require hardwood floors.

But, it does take time. Time borrowed in between the competing demands of everyday life. Hours spent typing away in a bathrobe on a Sunday morning. Stepping away, coming back. Reconsidering. Restructuring. Ruminating. Resolving. It’s not a diamond mined from the earth. It’s grown in a lab of voice, written word, an overly eager, unpaid AI writing coach, and more espresso shots than I care to enumerate. But it’s a diamond nonetheless.

Some might say I’m skipping the necessary friction. I disagree. The friction remains. It just lives elsewhere. It lives in the part of me that questioned starting a Substack. It lives in the moments when I criticize the value and worth of my ideas. It lives in the hours spent writing and rewriting. It lives in the pernicious voice under the surface when I hit publish, asking whether it’s “good enough.”

My process has removed the fear of trying.

Embodied in voice, hands, words on page, my process is my own.

My process isn’t perfect. But it’s no less true.

In a world oversaturated with cheery, tidy, AI-written prose, I want to hear the words and voices of other humans. I want to hear the messy thoughts. The half-baked ideas. The unresolved questions. I want to hear those thoughts regardless of where they began—a terrifyingly blank page, a static-laced microphone, a tentative dance step, or a ten-word AI outline. No matter their genesis, these expressions are brave. It takes courage to share the ideas living within you.

My Substack has given me a place to write, create, explore, reveal—with no goal attached. It gives me a place to let my thoughts breathe. Sometimes, I find out that it resonates with others. I get an email, a text, or a Teams chat from someone who read a post and felt compelled to reach out. They say they felt seen. These messages are authentic. They forge unexpected bonds and connection points. Often, these are some of the most deeply human moments in my week.

They say to trust the process. I will trust mine.

My son graduated from middle school this week. His school hosted a series of celebrations and closures to mark this rite of passage. In a Closing Circle, classmates gathered in their homeroom groups—a collection of students spanning three grades, all who shared the same advisors throughout middle school. One by one, each eighth grader sat in the center of a circle comprised of their peers. The students surrounding the eighth grader each shared their favorite memories and takeaways about the person in the middle.

Then came the graduation speeches. The night before graduation, in a room of 150 people, each advisor stood on stage with their advisee, delivering a speech tailored to that specific child—who they are and what makes them extraordinary. Each student stood beside their advisor, quietly receiving all of it: the praise, the kindness, and the attention of a full gymnasium.

On graduation day, each eighth grader delivered a speech of their own to the entire commencement audience. As they exited the stage with their diplomas, each child walked through one last closing circle, comprised of every faculty member. Each teacher shook their hand, looking them in the eye with pure joy, and ushering them forward.

I cried. Multiple times. So did Leo.

Driving home from the graduation festivities, Leo and I reflected on how moving it was. He said he found himself crying during the advisor speeches, but not in the moments he expected.

“I wasn’t crying for any specific person,” he said. “Even the kids that I’m not friends with, or that I didn’t really hang out with… we are all going through the same thing, at the same time, together. I think we all know that. We’re all going through something big. And it feels like we’re there for each other, no matter what.”

Like every eighth grader, Leo is excited and scared about high school, all at once. Like every eighth grader, he sees one chapter ending and another beginning. Like every eighth grader, he’s holding memories of what went well, what didn’t, and who he’s become as a result. As the graduation speeches unfolded, each story was unique, but each contained a similar arc—of individuals growing into themselves through the power of experience, perseverance, and self-acceptance.

On stage in front of his community, or in the quiet moments in the car with his mom, Leo—like his fellow eighth graders—was choosing to stay open despite his fears. He was remaining attuned to a bigger truth: that his experience, while uniquely his own, is cut from the same cloth as his peers.

The Wind on the Mountain

Last year, I went on a 10-day silent meditation retreat. The retreat had extensive guidelines to shape the experience. No talking. No cell phones. No reading. No music. No eye contact. No passed notes. Just me and 100 silent retreatants living in monastic quarters, following a consistent daily regimen: rising at dawn to the meditation bell’s gong; seated meditation; moving meditation; silent meals; sleep. The container was set. Teachers provided daily spoken guidance. Each day, we sat in a large circle, receiving their instruction in silence.

From the outside looking in, it sounds pretty damn weird.

But, something magical happens in a setting like this. When you are no longer concerned about being “liked,” you slowly set down the performance of your personality. Over the course of days, you unwind the need to be regarded. The energy you typically hurl outwards—projecting who you are and why people should care—that energy recalibrates. You become a vessel. An open container to receive.

Towards the end of the retreat, I hiked into the hills behind the meditation center. The smell of wild sage permeated the air. The crunch of dirt beneath my shoes pattered softly in my ear, keeping rhythm with my strides. I reached an overlook where I could see far outwards, towards a foggy California ocean bay many miles away. As I stood on the lookout, the wind blew softly. In that moment, I felt the wind blowing through me. I felt myself as the wind. As the dirt. As the sage. As the bay. As one small, inextricably interconnected microcosm in the macrocosm of the universe. Tears rolled down my face as I stood, palms open, arms outstretched, feeling.

Constricted Apertures

In my daily life, the vista and the horizon are harder to see. At work, my colleagues and I engage in back-to-back meetings, hosted in the high definition 2D frame of a Teams screen. Thousands of us sit, in our individual office chairs at our individual laptops, typing away to respond to emails and pings, to author perspectives, to build and implement new solutions for data, technology, and AI. Full-fledged adults, broadcasting to the world who we are, what our expertise provides, and how we deliver impact.

In this setting, the aperture tightens. We project labels: our expertise; our years of experience; our accolades; our ambitions. Usually, these broadcasts are recorded in the language of “me”, not we. Each person pushes to be heard. Interrupts to get a word in. Steers toward their own needs rather than the whole.

It’s exhausting.

We are operating from a place of high demand, high expectation, and—let’s be honest —fear and scarcity. Fear that there isn’t enough for all of us. Fear that we can’t achieve the objectives unless we focus on our own goals. Fear that the standards are impossible to achieve.

It’s no wonder that we contract. Our vision narrows to a pinpoint: ourselves. I see it happen daily in my colleagues, and I see it happen in me. I know I’m seeing through a narrow lens when my patience runs thin and my tone gets sharp. When I find myself clamoring to interject in a meeting of vocal leaders, each expounding the importance of their individual objectives. When I end the day depleted, feeling like some kind of lone wolf despite being surrounded by countless smart, capable, kind people.

Creating the Container

Graduating eighth graders feel their fear in their bones. But, they also admit they’re in an active mode of self-discovery. They are just beginning to form who they are, working it out in real-time, before our eyes. That freshness, mixed with the simultaneous acknowledgement of their wisdom and all they’ve yet to learn—that keeps them open.

As adults, we’re encouraged to project something different, more self-possessed, more self-confident. We’re encouraged to appear as if we know ourselves fully; as if we’ve crystallized an elegant personal value proposition. We pose before a zoomed in lens, ready to take the world by storm and to show everyone what we’re all about.

But let’s be real: we don’t have it figured out.

Eighth graders are early in the journey of self-discovery, but adults are also perpetually in self-discovery, whether we acknowledge it or not. Acknowledgement hinges on humility and vulnerability, on dropping the facade of having it all figured out. The meditation retreat crafted a container where every adult acknowledged this implicitly, simply by showing up. The eighth grader circle, the meditation circle—these places invite, encourage, and celebrate us living inside the messy state of becoming instead of the tidy state of knowing.

When the fabric of modern life is geared towards individualized optimization, striving, and outcomes, how do you create the container for openness? How do you create the space for discovery?

It’s hard. I don’t have all the answers.

But I know it’s a space I long for—for myself and others. I want to create the conditions that break the pinpoint focus of striving and self-promotion, and widen the aperture towards the bigger picture, the interconnected vista. I want to cultivate spaces that honor the individual, the child, the wild sagebrush, just as much as the collective, the circle, the distant bay.

For me, it means listening more than I speak. Staying curious about who people are still becoming. Attuning to what’s happening for all of us, not just what’s happening for me. And catching myself when I bristle—asking what fear lies beneath, within me as much as within others.

Even when this is my deepest intention, I still stumble. The wind on the mountaintop isn’t blowing through me in a Tuesday afternoon leadership meeting.

But I can leave the window open to feel the breeze.

And the truth is: I’m bored as fuck.

At the beginning of this year, I made an uncomfortable decision to set down my relentless pursuit of goals. I put down the ruler that charted out my annual, quarterly, monthly, and weekly goals and focus areas. I abandoned the symbol-coded bullet journaling. I gave my rainbow colored pens a sabbatical. I decided to pursue my worth as inherent, not earned.

Seemed like a great idea.

Then I had another great idea: let me catalogue my insights and progress! I spent a Saturday afternoon building a GPT based on my journals, my prior goal structure, and my new commitment. In hours of robe-adorned, coffee-fueled GPT vibing, I created a methodology for weekly reflection. I restructured my handwritten note-taking style to a digital format that my GPT could easily analyze. I created a complete phygital system (part physical, part digital): a digital notebook for tasks, a physical notebook for journaling. I diligently wrote weekly journal entries. I listed what I was noticing, what I was letting go, and what I was living in. I shared my journal entries and digital logs with my GPT, mining further insights and reflections. I definitely made sure to do this every Sunday.

Wait a minute.

You see where this is going.

Somehow, even in the absence of rigorously structured goals, my goal orientation crept back in. I was architecting a new, elaborate framework by which I could continue to evolve, grow, learn, and gain insights in my goal-less endeavor.

Once again, I set down the structure.

But I still needed something. Some form of accounting for what the hell I’m actually doing or need to remember. After reading Oliver Burkeman’s Meditations for Mortals, I settled on a compromise: logging a simple, unstructured, unfiltered list of to-dos to quiet my monkey brain on a Sunday night; logging a simple, unceremonious list of things I had done throughout the week. Less glamour and revelation, more facts and humility.

My workdays are often long and chaotic. On a typical day, I might lead 10-15 meetings. I am in a perpetual state of context switching. In an hour, I might go from: business development mode → admin mode → problem solving mode → wine biz mode → client deliverable mode → mom mode, all compressed into two 30-minute meetings, endless Teams chats and text messages in the background, and the slight breath between it all.

At the end of days like this, my brain feels like a hard-boiled egg. Dense, hot, and stubbornly unwilling to yield the protective shield around it. Even as I move through the daily rituals of unwinding – taking a walk, making dinner, convening over a meal with my family, reading a book, turning the lights out early – I feel my brain cooking, racing to catch up with whatever actually happened in that jet-fueled window from 8 am to 6 pm.

On weeknights, I wait for my brain to unfurl according to a schedule. On weekends, the opposite occurs. I indulge in two days of quiet, agenda-less living. I rest. I make food. I walk. I connect with friends and family. I’ve spent so much of my life in a loop that demands constant striving, hustle, go, go, go. My work day still models that mindset. But, outside of that context, I find myself slowing down dramatically. Observing my plants. Taking a stroll. Running little errands. Planning dinner. Making dinner.

I am so excruciatingly bored.

Whether the weekday grind or the weekend respite, I arrive in the same space: restless ennui.

Old me would have a simple fix to this problem. Take on a new project! Set a new goal! Become fluent in Japanese! I’ve gotten better at spotting the telltale signs, but I still struggle to lay down this habit. In the course of twenty minutes of Saturday couch lounging, I will entertain any number of exciting future realities: community theater, visual arts, a new wine degree, mahjong mastery, reading the complete works of Shakespeare, taking up rollerskating.

I haven’t acted on a single one.

My mental urge to “solve” my boredom doesn’t seem to dissipate. I want so badly to extricate myself from my restlessness. But, deep down I believe I’m here for a reason.

The more I sit with my listlessness, and the more I sit with my passing fancies, the more I realize they’re a cover for something else entirely.

In a moment of frustration and self-quandary, I went back to my non-goal goal-GPT for input.

Annoyingly, the robot had thoughts.

“Are you too afraid to fail that you aren’t willing to try anything?”

Annoyingly, the robot wasn’t wrong.

Side note: this was also the moment when I completely disengaged from further interaction with the GPT, as it bordered on psychotherapy. Kernels of truth are best delivered by humans, not robots.

Because I have been so historically goal-oriented, I struggle to pursue anything without:

• An endgame

• Confidence that I’ll excel

• A gold star

My flights of fancy lack the characteristics for unlocking gold-star-level achievement. They aren’t nearly sexy or public enough. And, they might turn out to be things I objectively suck at. I’m pretty miserable at riding a bicycle, as an example; do I really want to rollerskate?! That could be… bad.

Beyond the fear of failure or fear of not being “the best”, there’s something more. Something bigger that’s holding me back.

I don’t want to pursue for the sake of pursuing. I want to feel something. I want to feel the spark in my veins that signals I’m on the right track. I want to feel that thrill of inspiration, that twinkle in my eye, that sense of possibility mixed with apprehension.

And right now, I don’t feel it.

Maybe, just maybe, that boredom is the fine edge of terror. Terror in failure. Terror in a lack of vitality. Terror in not knowing what you actually want or where to go from here.

And maybe, just maybe, that’s the whole damn point.

Maybe the most terrifying idea of all is: this is just life.

In midlife, you weigh two polar realities: you aren’t going to be and do everything; the version of you who was going to do it all has invested in their 401k and is planning toward retirement. You aren’t gazing upon endless potential futures ahead. The window of possibility has narrowed – not closed, but narrowed.

Yet, you still want more: more growth, more mystery, more self-discovery, more adventure, more evolution. The wanting is subtler now, and the pull toward it requires more bravery.

As I approach this year’s squishy, non-number birthday, I am living inside this messy middle. Of letting go, of giving everything, of mourning what isn’t, of celebrating what is, and of relishing and questioning who I am, who I am not, and who I have yet to become.

Maybe that’s the strange, awkward wisdom of midlife in full bloom. Maybe the wisdom is in accepting that perhaps there isn’t a bigger point. Maybe it’s always both. Maybe it always has been.

I don’t know. Ask me next year.

“How are you feeling?” I asked.

“Anxious,” Leo replied.

“That makes sense,” I responded, “Tell me why.”

He let out a sigh. “More independence. It’s the thing I’m most excited about and the thing I’m most nervous about.”

Leo was en route to a big adventure. Each year, his middle school sends its graduating eighth graders on a trip to England, honoring their heritage as a British primary school, and celebrating the culmination of their primary school experience. Nine brave teachers chaperone fifty eager fourteen-year-olds through London and beyond for an action-packed, week-long itinerary with no parents, no cell phones, and no homework awaiting their mutual return for the last week of school.

“I can understand why you’re feeling nervous,” I said as we pulled into the parking lot.

I helped him hoist his bag out of the car. “And you are ready for this! You’ve gone on shorter school trips without your parents. You’ve gone on international trips with us. This is just a little bit bigger, and with more responsibility.”

He nodded.

“I am so excited for you! This is going to be the trip of a lifetime. If there’s any small piece of advice I can offer, it’s this: take it all in. Try your best to be in the moment and to savor it.”

He looked into my eyes. “I’ll try.”

We strode to check-in, queuing up beside teachers and students buzzing with excitement. The Head of School attempted to strike up a conversation. Leo offered single-word replies, his eyes darting towards the ground and towards me.

We checked in. Leo found his friends and began to settle in, relaxing into a smile. I took a few pictures. I chatted with a few moms.

I said goodbye. “Have an awesome time!”

The Parking Lot

Alone, I walked out of the temperate airport, back to the hot asphalt parking lot, a catch in my throat. Buckling in, I turned the music up, ready to move on.

I paused. Maybe I ought to take my own advice. I turned off the sound.

I burst into tears. I cried the whole way home.

The tears rolling down my face were a sweet and salty mixture—of joy, pride, sadness, love, letting go, all at once. A complex brew of emotions, aged slowly and gently over fourteen years of motherhood. The bright notes of happiness, reveling in my son’s adventures. The undertones of mourning, sensing a chapter of parenthood beginning to close. The bold notes of pride, watching Leo step bravely into bigger experiences, even when feeling uncertain. The crushing depth of my love, my heart expanding beyond my body, beating not just within myself, but within my son.

The weight, the beauty, the power of it all feels like more than I can handle.

And yet, I do.

My parenting is beginning to shift its shape from nurturing and safeguarding a child, through shepherding and growing a young boy, towards celebrating and witnessing a young man. Young parents often hear older parents say, “The days are long, but the years fly by.” Trite as it seems, the adage is true. The evolution is slow, until it isn’t.

Moments like the airport drop-off arise now and then, offering a poignant reminder. Slowly but surely, I’m releasing my hands cupped around this person that I’ve known and nurtured since before he knew himself. The most important and rewarding effort of my life is changing before my eyes. That change, while exactly as it’s meant to be, is bittersweet. A love and force so vast, so all-consuming, and yet one that requires letting go.

Leo’s own complex mixture of emotions is mirrored in me. He felt anxious and excited for the exact same reason—for the thrill and the worry of independence. In my own way, I was, too. Joyful and bereft over the exact same thing—he is growing up. My heart, living outside my body, navigating on its own.

The Dance Floor

Still carrying the weight of the afternoon, I headed out to meet a friend. LeVon had surprised me with two tickets. “I want to gift you something, but I don’t want to tell you what it is. You just have to say yes.” I did.

Two tickets to “Moms Feelin’ Themselves”.

When I discovered the plan, I gulped down a tinge of dread. Be open to it, Kat.

My friend, Gina, and I met for dinner beforehand. She’d been to this event before. Her eyes met mine across the table. “I’ll be really curious to see what you think of this,” she mused.

We walked up to the entrance. Moms queued up outside, donning their favorite club attire. In broad daylight. At 7:45 pm.

We advanced to the door. Promotional messaging greeted us from the event’s sponsor: Pelvicore Therapeutics.

We stepped inside. The merch booth was already sold out. I had missed my shot at a baseball cap inscribed with “Motherhood is a real job.”

Snaking around the bar, a long line of women waited to pose against a photo booth backdrop bursting with pink plastic flowers.

We grabbed our drinks and headed to the dance floor. First up: Whitney Houston, “I Wanna Dance With Somebody”. Next up: Annie Lennox, “Sweet Dreams”. Next up: Beyoncé, “Girls”. The mom anthem playlist rang on.

I shot Gina a glance. “I can’t handle this.” She nodded.

We were gone in less than thirty minutes.

The Mess

Don’t get me wrong. I’m not here to judge the many women who were clearly loving this. For mothers of young children, in the thick of sustaining human life, with little to no room for anything else, this event probably felt like a safe haven and a release. But for me, and for my stage of parenthood, the whole thing highlighted how small and tidy the spaces for women and mothers are often constructed. We’re given room to celebrate within the singular identity of motherhood. We’re given rallying cries like “Motherhood is a real job.” We’re given a space to connect solely on the commonality of being mothers. I’ve never seen a “Dads Feelin’ Themselves” event. No one hands them a baseball cap and pumps Dad Jams to reinforce their identity. Dads just go do their thing. Partially because they’re encouraged to do so with greater frequency than most mothers. Partially because we don’t hinge their whole identities on fatherhood. Motherhood alone is not enough of a shared identity to forge bonds between women. It’s one note in a complex blend of flavors, experiences, emotions, and perspectives.

Gina and I walked into the cool night air with a sigh of relief and a hearty laugh. She offered to drive me home. As we wound through the city streets of Denver, we talked about our lives: my tears in the parking lot; her family’s summer plans; our careers; our experience of midlife – of wisdom mixed with metamorphosis. The vast, rich, tangled fabric of our identities, with threads of interconnection and sprawling roads to destinations unknown.

There is space for all of it at once.

The free-flowing tears and the cringe. Pride in my work as a mother and insistence on a title beyond “mom”. A love so consuming I’d die for it and a fierce refusal to be solely defined by it.

The polarities belong beside each other. And when we’re brave enough to embrace the grand mess of it all, the fullness of life reveals itself. My heart cracks open wider. And I rediscover its boundlessness.

The dream looks a bit different up close.

We don’t own a winery. Replace grand visions of a sweeping tasting room, production floor and cellar with a single plot of land. We own a vineyard — one acre, nestled in the heart of Argentina’s Uco Valley. It’s stunningly beautiful and surprisingly small.

The answer to the second question, “When can I buy your wine?” is the trickiest question of all.

The Journey

Our Foretold wines have been on a journey. In March, they bid farewell to their Argentine brothers and sisters, traversed the Andes to the Chilean coast, then set sail for America. The journey was long, the accommodations threadbare. Tucked into a shipping container, they laid down for months as they traveled north along the western coast of the Americas.

Today, our wines sit docked at a port in Los Angeles, waiting to clear customs. What happens next hinges on the persistence of four dreamers and the insanities of the three-tier distribution system.

Charting the Course from Textbook to Reality

In the years of study for my WSET Level 4 Diploma, I learned a lot about the three-tier distribution system. During theory exams, I scribbled away frantically in handwritten essays that described the system and its implications in detail. I really knew my stuff. Or so I thought.

On paper, the three-tier distribution system consists of: an importer, a distributor, a retailer. The importer is responsible for navigating the wine’s transition from its country of origin to its destination. The distributor is responsible for selling wine into wine shops and restaurants. The retailer sells wine on premise (read: in a restaurant or bar), off premise (read: at a wine shop or liquor store), or directly to the consumer. Simple, right? Yeah, not so much.

In reality, the system is far more complex. Unique to America, the three-tier system is just one of many global systems to regulate the production, distribution, and sale of wine. Within the American three-tier system, each state has its own rules. Want to buy wine in a grocery store in Utah? Not gonna happen. Want a winery to ship directly to your door? In Rhode Island, only if you’ve physically visited the winery first. Want to buy online? Not in Delaware. State-level nuances abound.

Added layers of challenge arise for small producers like ourselves. What my WSET studies alluded to, but I couldn’t fully appreciate, was just how stacked the odds are for a small, imported brand trying to break through. According to USA Wine Ratings, three companies dominate U.S. wine distribution, and the top ten distributors control over 81% of the market. Large distributors prioritize volume and name recognition over new entrants. Wave after wave of distributor consolidation leaves small producers like ourselves with limited options. As The Drinks Business reported earlier this year, for producers outside the top-volume tier, fewer distributors means fewer options, less leverage, and less likelihood that anyone in the three-tier chain has a financial incentive to tell their story.

As a foreign producer, we also can’t simply walk our wine into a U.S. distributor ourselves. A U.S.-based importer must step in as the legal first-tier entity, taking title to the wine and handling federal registration, including obtaining a Certificate of Label Approval for every label before customs will release a single bottle. That process typically takes up to 15 business days. Hence our impatient wines docked in LA.

As my partners and I began wrapping our heads around these hurdles, we sought input from anyone and everyone that might help. I reached out to every distributor I knew. LeVon pitched our brand to a local restaurant. Nicole dug through her seemingly endless connections (she is known as “the mayor of Los Angeles” in some circles). Bekka and I popped by our local wine shop to sell our wares. We worked all of our angles.

At our local wine shop, I regularly nerd out on wines with Grant, the store manager. His eyes light up when I come in and ask him to surprise me. Once, he hurried down into the cellar to unearth a 30-year-old bottle of Riesling, bounding back up the stairs with effusive commentary. He’s always eager to lean in.

When it came to our wines, he was equally game, offering to sell them in the store once we identified our distributor. He walked us through the pricing structure and the store’s cut.

Nicole’s research led us to a distributor and a DTC shipper, friends of a friend. “Once the mayor, always the mayor,” Bekka noted of her partner’s vast network. Both of Nicole’s contacts were eager to help. Each explained their cut.

Detour: Math

You know how this story ends. Everyone gets a cut. Our little wines begin their journey at the vineyard, where we pay to tend to the vines and make the wines. They end up in the bottle, where costs vary based on bottling and labeling preferences. They trot off to the shipping container, where we pay for freight. They arrive in the states, where the importer takes their cut. The distributor takes their cut. The retailers (on premise, off premise, direct to consumer) take their cuts. And let’s not forget the federal and state taxes along the way.

I’ll spare you the numbers and get down to the sum of it all: by the time our wine reaches your glass, the fraction that finds its way back to Foretold would make you gulp.

Cut back to the dreamy-eyed question I often field: “Are you going to quit your job and do this for a living?” Nope. That math doesn’t math.

Getting Lost in the Details

If I had a dollar for every time my partners or I said “I really don’t understand…” or “I’m not sure how this works…” or “We need more clarity…” or “How exactly are we going to do this…,” I probably could retire off of our wine business.

I’m also not an operator. Vision, brand, taste — those are my strengths. As our logistics have mounted, I’ve often found myself blank-faced and dopey-eyed, wondering how the hell we move forward.

Thankfully, I’m not alone.

I’m surrounded by the strengths of my partners. Bekka: the owner and operator of a multi-generation family art business; a hustler; someone who gets shit done. Nicole: the owner of her own business in TV production and brand integration; a wheeler and dealer; a former accountant with a secret love of Quickbooks. LeVon: the owner of his own consultancy; a CFO; an expert in guiding and growing small businesses.

Each of us brings unique talents to this endeavor, built from decades of experience in our domains.

Walking the Last Mile

When we are this close, with hurdles ahead but the finish line in sight, we keep coming back to one point of focus: trust.

Our whole endeavor was built on this foundation. When I got the first text from Bekka, gently opening the door to the possibility of buying a vineyard, I trusted. I said yes, without hesitation. I leaned forward and said, “We’ve gotta do this.” Countless obstacles existed. Gingerly informing my ex-husband that I was going into business with his sister — a delicate conversation requiring many layers of trust. Sitting down with Bekka, Nicole, LeVon, and a well-paid lawyer to document a formal operating agreement — soberly outlining what happens when things go right and what happens if they don’t. Sitting across the table from each other over a meal and a bottle of wine — openly sharing our individual dreams and fears. Listening intently. Celebrating the places where we agree wholeheartedly while honoring equally the places where we see things differently.

Hours upon hours of deep conversation, partnered problem solving, and shared excitement in our victories big and small have brought us where we are now. We might not know exactly how it’s going to work out, but what we do know is: we’ve got this.

Finding Your Compass

We all have our own “Holy shit, how am I going to figure this out?” moments — whether navigating a complex project, solving today’s mini-crisis, starting a new business, or staring at a blank canvas. Every one of us experiences that moment when we see the stark gap between a gauzy dream and a practical reality. Every one of us feels the knot in the stomach or the furrow in the brow.

The journey with Foretold has taught me how to recalibrate my compass in those moments.

When the going gets tough, I recenter on the true north of this endeavor. The goosebumps I got when the opportunity arose. The tight hugs we shared standing on our land for the first time. The broad smile on LeVon’s face as we planted our first vines. The unbridled joy in Bekka and Nicole’s voices as they FaceTimed us from our fledgling vines. Beyond the details, the hurdles, and the bureaucracy, a stronger pull carries our efforts: joy, vision, love, and the belief in our shared dream.

Whatever your version of this looks like — your dream, your loved ones, your partners, your friends — the principle holds.

That’s the compass. That’s what carries you through the next step, whatever it turns out to be.

The Early Years: Single Motherhood

My first few years as a mom were tough. Leo, my son, was plagued by colic that persisted for a year. He screamed constantly. Severe asthma sent him to the emergency room regularly, his tiny toes and fingers turning blue. He wasn’t a walk in the park. Unfortunately, neither was my first marriage. Leo’s dad and I struggled from the very beginning, not only to stop our son from screaming in public, but to stop ourselves from screaming at each other. It wasn’t pretty. Before Leo’s second birthday, we were in the midst of divorce.

I thrust myself into a new normal as a single mom. I got a demanding new job that I hoped would pay the bills. I rented a third floor walk up apartment, five minutes from the office. I made my life as small and manageable as possible. And yet, it was anything but.

On weekdays, I pushed to prove myself in a private-equity backed, high-growth company. My colleagues were married with children, or young and single. Our executives were exclusively white men in their fifties and sixties. I didn’t fit in. Some of my colleagues made sure to let me know.

One Friday, walking to the office parking lot with a colleague, she brightly chimed in, “Hey! I’m going to be a single mom, too, this weekend! My husband is on a boy’s trip.” Her intention to connect was… ill-phrased at best. A weekend of solo parenting does not a single parent make.

On weekends, I was alone with my toddler. Up in the middle of the night to tend to his cries. Up bleary-eyed in the morning to start the day. Somehow keeping his boundless energy and curiosity entertained until bedtime, then passing out in a heap.

When Monday mornings rolled around, it almost felt like a vacation.

The Breaking Point

One day, slogging away at the office, I got the daycare call: Leo had broken his leg. I rushed there just in time to jump into the ambulance with him and race to the emergency room. Hours later, my then four-year-old and I emerged. Him with an above the knee cast, me with my nerves narrowly intact. I carried him up the three-floor walk up, his body weighed down by the cast, and my spirit weighed down by everything that had happened and everything that lay ahead.

At that time, LeVon (my now husband) and I had just started dating. Leo barely knew him. A protective mom, I was cautious of introducing my son to someone I was dating. LeVon walked through the door with takeout and a hug, and I burst into jagged sobs. He helped carry Leo to his bed, then left with words of encouragement. “You’ve got this and I’m here to help,” he assured. “It’s going to be okay.” I didn’t quite believe him. Even as he watched me fall apart, he had full faith in me. He saw strength in me that I didn’t see in myself.

Of my own volition, the heavy lifting, quite literally, fell on me. I carried my son from his bed to the bathroom. I carried him to the living room. I carried him up and down the stairs. I held him in the night to soothe his pain and fear. I held my worry and sadness alone. Still in his cast, he returned to daycare and the cycle continued. Only now, I shouldered the added burden of my job, with its unreachable expectations. I was carrying everything I could.

Until I couldn’t.

Weeks of carrying the physical weight of my son threw out my back, leaving me in excruciating pain each time I picked him up, and debilitated on the floor thereafter. I could no longer muscle through the experience alone. I called on LeVon for help. He answered without hesitation.

Just as Leo’s cast was being removed, and I began coming to terms with the full financial weight of his injury, a new breaking point emerged.

I got fired. Right before the holidays.

Ten years later, I still vividly remember the uniquely humiliating experience of walking out of my office, flimsy moving box in hand, crying, borderline hyperventilating, and wondering what the hell I was going to do next.

The physical stressors were immediately replaced with financial stressors. I questioned how I’d pay my rent, much less put gifts under the tree from Santa. But, I did as I always had done: buckled down, prepared to bear the weight, and presumed it was all on my shoulders.

Breaking the Facade: The True Face of Resilience

I could no longer pretend I was holding it all together. I clearly wasn’t. My faults, my failures, my weaknesses, my mistakes, my missteps were readily on display. Not my favorite look. I had no choice but to open up and be honest with myself, with LeVon, and with my friends that I was scared, bone-tired, and uncertain of myself.

But here’s the thing: that’s the birthplace of resilience. Resilience is not about toughing it out, pretending you’ve got answers, or racing forward and steeling yourself against what lies ahead. Resilience is about balancing two truths simultaneously: the truth that life can be hard; and the truth that you are strong as fuck.

The months that followed were filled with very low lows, coming face-to-face with humiliation, shame, guilt, fear, self-doubt, and exhaustion all at once. But they were also filled with tenderness – the tenderness born of looking your partner in the eye and admitting you genuinely don’t know what to do, of texting an acquaintance to ask if they know anyone hiring, of graciously accepting a friend’s offer to pay for a meal out. Slowly, I crawled my way up, out of unemployment, out of physical pain, out of debt, and into a new chapter.

There was no magical realization that I’d made it. No light bulb. No sudden awareness of my own strength. Even now, I still question myself, despite everything I’ve clawed my way through. But somewhere along the way, I stopped waiting for the revelation. I started believing in the well of strength I can marshal when the moment requires it.

The Mother’s Day Meal

That first Mother’s Day after Leo’s broken leg and my firing, Leo had just turned five. That year, LeVon taught Leo a new tradition: cooking for me on Mother’s Day.

It started small, with LeVon helping Leo whip up a Mother’s Day brunch. Five years old, Leo beamed with pride as he plated his creations.

A few years went by and Leo expanded his repertoire. Mother’s Day brunch morphed into Mother’s Day brunch and dinner.

A few more years, and the dinners became more elaborate and more independently executed. Roasted chicken with orzo and arugula salad, all crafted by a nine-year-old chef.

Fast forward to last year, when thirteen-year-old Leo sat down to share his Mother’s Day meal with LeVon and me. He flopped into his seat. “Wow, I am exhausted!” he breathed.

I know the feeling, buddy.

The Weight of It All: Carrying More Than You Think You Can

This isn’t just a Mother’s Day post. Everyone carries heavy burdens. Whether you’re a single parent, someone navigating illness or loss, or a person trying to juggle more identities than feels manageable, you know this weight. Mothers carry a particular kind of invisible labor that often goes unnamed and unrecognized. But the experience of simultaneously feeling like too much and not enough is an experience that belongs to all of us.

The strength within you isn’t accessed by shouldering your burdens alone. It’s accessed by admitting to yourself and those you trust that you don’t have it all figured out and that you could use a little help.

That admission is what opens the door. Heartbreak and determination. Exhaustion and strength. Fear and perseverance. When you can hold both, and bravely share the experience with someone you trust – that is resilience.

You contain multitudes. You deserve to live all of them – the good, the bad, the ugly, and the glorious. You just don’t have to carry them alone.

Of the many feminist theory courses I took, this one centered on Donna Haraway’s A Cyborg Manifesto. When Haraway’s 1985 text was assigned to me in 2003, I had no idea I’d be living inside its questions in 2026.

The tl;dr version of Haraway’s thesis: the boundaries between human and machine were dissolving and were bound to happen. The real question was: who would get to decide what the hybrid looked like. Whose body? Whose experience? Whose humanity would be centered in the design? Arnold Schwarzenegger gave us an early answer in The Terminator (which we also screened in this particular class; like I said, this professor was fucking cool).

Today, I’m reflecting on a week spent with my fourteen thousand closest friends at a tech conference: Adobe Summit. More than twenty years later, I’m still sitting with Haraway’s central question.

Big Stage Energy

Every year, Adobe Summit offers an unmatched opportunity to experience inspiring, sophisticated marketing technology evolutions. Agentic AI orchestrating entire personalized customer journeys. Internal workflows compressed from months to moments. On-brand creative iteration at unmatched scale. Complex data and insights surfacing from a single prompt. A marketer’s dream, rendered in high definition on a very large stage.

It’s energizing. It’s also something else, simultaneously.

The opening keynote began with Anil Chakravarthy, President of Adobe’s Customer Experience Orchestration Business — a man — who introduced Adobe CEO Shantanu Narayen — also a man — to deliver his final keynote of his 18-year tenure — who then introduced Jensen Huang, President and CEO of Nvidia — also a man — followed by David Wadhwani, President of Adobe’s Creativity and Productivity Business — also a man — who then introduced two women to run a product demo.

I’m not outlining this chronology to explore a well-worn, painfully true conversation about representation. I’m sharing a different kind of well-worn experience.

As I sat under the dazzling rainbow glow of Adobe’s graphics, I felt something in my body before I could place it in my mind. A tightening, surrounded by a twinge of anger, settling into a familiar discomfort. Women and underrepresented voices know this feeling in their bones. It’s the sensation of sitting inside a space that wasn’t crafted for you or with you, silently questioning whether you belong.

Behind The Curtain

Between sessions, I stumbled across a New York Times article by a fellow Vassar graduate and psychology professor, David DeSteno, titled Anthropic Wants Claude to Be Moral. Is Religion Really the Answer?. DeSteno’s article challenged Anthropic’s approach of leveraging religion to cultivate Claude’s morality. He argued that morality isn’t primarily cognitive, but is, rather, embodied. Religious and ethical practice is felt in the context of ritual, community, or physical experience. DeSteno applauded Anthropic’s intention to infuse morality into Claude, but noted that morality training might ultimately fail because Claude lacks something critical: a body.

Haraway would have had thoughts.

Later in the week, a colleague of mine, a woman driving hard in her career, was preparing to speak at an upcoming tech conference. She asked ChatGPT to help write her bio.

It assumed she was a man.

She pushed back. ChatGPT acknowledged its bias. The moment passed. But when she shared the experience with me, the familiar feeling I experienced in the Adobe keynote returned. The pit in my stomach. The tightening in my chest. I suspect she experienced her own version of these feelings.

The Body as Conductor

Here’s what I’m sitting with: leadership is embodied. Creativity is embodied. Belonging is embodied. It’s not a framework. It’s something you feel before you can name it.

And AI, by definition, doesn’t have a body.

More than that, the bodies that built and educated AI, and that now celebrate its productivity gains on sweeping stages, skew heavily in one direction. So, when we talk about AI learning and leading conversations rooted in morality, judgment, and creativity, whose embodied experience is AI actually learning from?

From the glitzy Adobe stage to the ChatGPT ghostwriter, I see the same embodied experience playing out in real time. These aren’t isolated glitches. They are a reflection of whose humanity has been most legibly absorbed, whose voice has been most codified, whose experience has been most architected into the tools that, so we’re told, are going to orchestrate our productivity, amplify our creativity, and reshape how we work.

In 1985, Haraway asked whose body was inside the machine. We’re still answering that question, but the answer I’d give today is not the answer I long for tomorrow.

Let me be clear: this isn’t a post about AI unconscious bias. That conversation is extremely important and is occurring with far more rigor than I can offer. If you want to go deeper, Newsweek’s coverage of AI’s misogyny maintenance hits home, as does Stanford Social Innovation Review’s take on the paradox of the AI gender gap.

I’m talking about something more personal.

My Embodied Truth

Recently, a friend shared an insight stuck with me. In a podcast she listened to, a female somatic psychologist shared this: when something keeps circling in your mind, when you can’t let it go, when it nags at you across days and weeks… that persistence is trauma raising its voice inside your body, asking to be heard.

For years, I’ve ruminated on my place as a woman and a leader in technology and consulting. Many times, I’ve felt the pang that stems from questioning my belonging. In the absence of clear answers, I’ve sought advice and perspective. I’ve sat with senior female leaders in technology, consulting and beyond to hear their stories and seek their counsel. I’ve absorbed their words as salves, as solutions, and as moments of feeling seen. Their perspectives have ranged from uplifting and encouraging to disappointing and subtly devastating. Despite hours of conversation and thought, the question remains.

But here’s what I do know: a deep well of strength resides within me, built from all that I’ve experienced in life. I have endured highs and lows that my body has synthesized into wisdom. The wisdom born of motherhood; of running a marathon; of deep heartache; of climbing fourteeners; of extended silent meditation; of pursuing a dream. The wisdom of these experiences accumulates in this body of mine and makes me who I am.

Yet, I regularly sit in spaces that don’t embody that power or, in the worst cases, actively diminish it. While I’m amazed by the ways marketing and technology are transforming, carving out new productivity gains, orchestrating new experiences, and upending the MarTech ecosystem, I can’t help but consider who these gains benefit most deeply.

I don’t have a tidy answer, but I don’t think I ever will.

Perhaps, just giving voice to the questions is enough. Perhaps, just speaking from what’s true inside myself is enough. Perhaps, in some small way, that physical act alone emboldens others to give voice to what’s true within themselves.

What’s the voice inside you that’s asking to be heard?

So, I began studying with the Wine and Spirit Education Trust (WSET). WSET Level 1 was approachable, teaching me basic pairing principles and key regions. It was fun, so I kept going. Level 2 expanded my knowledge, culminating in mildly nerve-wracking exams that left me with a sense of pride. So, I kept going. In Level 3, things got serious. The material was dense. I sought out a mentor to coach me through tastings and theory. I sat my tasting and written exams, unsure if I’d pass. When I did, I was certain that was enough.

Several years later (perhaps when the amnesia of Level 3 had set in), I enrolled in the WSET Level 4 Diploma, the highest, most rigorous credential offered. The journey that followed consumed the better part of three years of my life.

Every week and weekend, my free time was spent studying: attending lectures, reading dry encyclopedic wine books, drilling flashcards, studying maps, practicing blind tasting, writing wine analyses and tasting notes in timed, exam conditions. My exams were held exclusively in Napa, necessitating flights every few months. “Oooh, Napa! That sounds amazing!” my friends would say. Yeah, no. Think: less vineyards and sunshine, more Hampton Inn conference room in a strip mall. Not exactly a glamorous origin story.

Along the way, I was stressed. I complained. People noticed. “You seem miserable,” friends would ask. “Why are you doing this? What’s your end game?”

My answer was the same every time: I don’t know. I’m just curious. I want to learn. I don’t have an end game, but I’ll never have one if I don’t keep going.

I didn’t have a better answer. And for a long time, it bothered me. Because here’s the honest truth: part of my motivation was the gold star. The achievement of a certification. The A-plus feeling you get when you pass an exam with flying colors. It’s always been engrained in how I operate. I won’t pretend otherwise.

But underneath that was something else. A pull I couldn’t fully explain.

The Art Appraiser, the Argentine Artifacts, and the Art of Inquiry

My ex sister-in-law has been one of my closest friends since middle school. I went on to marry her brother, have a child with him, and get a divorce. Our friendship suffered some hits along the way. But it never broke. Time passed, wounds healed, and as the years went by our friendship blossomed again.

My sister is an art dealer and appraiser. One day, while appraising art in someone’s home, she noticed something unusual: a vast array of Argentine gaucho artifacts. Her curiosity got the best of her. She had to ask.

The owner explained: he acquired his collection over many trips to his vineyard in Argentina’s Uco Valley. He told her about the wines, the people, and the memories forged with family and friends.

“Sounds like a dream,” she responded.

“Is it your dream?” he asked. “Because we’re selling.”

She texted me to share the story. I got chills. The kind that signal you’re on to something.

“We’ve gotta do this.” I said.

And so it began.

A Foretold Destination: The Uco Valley

My sister, her partner, my husband and I flew to Argentina to inspect the land and make a decision. It was a chilly June day, fall in Argentina. We stood on rocky, unplanted earth, gazing out at the snow-capped Andes erupting from the horizon. We looked at each other and said almost simultaneously, “Yep. This is happening.”

So many forces converged to bring us to that moment. A middle-school friendship that outlasted a divorce. A birthday that my sister’s partner and I share. A happenstance appraisal of Argentine artifacts. Years of grueling wine study with no clear destination in sight. It all felt like kismet. It all felt… Foretold.

And so our brand was born: Foretold. Our wine brand represents the vision of four dreamers, brought together by destiny and a touch of magic

The Next Step in a Foretold Journey

Our vines are still young, fledgling Malbec and Chardonnay just beginning to take shoot upwards through the earth. But, that’s not stopping us from bringing our vision to life now. This May, Foretold will release its first wines, sourcing grapes from neighboring growers to produce a rosé, a white blend, and a Cabernet Franc.

We’re still figuring it all out, slogging through the hurdles of import, distribution, and retail. But we’re getting there. And if this journey has taught us anything, it’s that intuition and vision have a way of landing you exactly where you’re meant to be.

The Lessons of Hindsight

If you had told me after my first WSET certification, or in the slog of Diploma studies, that someday I would own a vineyard in Argentina, I would have laughed in your face. If you had told me in the midst of my divorce that my sister-in-law and I would rekindle our friendship and start a business together with our partners, I would have raised an eyebrow. Yet here we are.

In the depths of a challenge, it’s impossible to see beyond what’s right in front of you – whether that’s a wine flashcard, a divorce decree, or a pair of Argentine gaucho chaps. But, sometimes, all you need is that voice within, compelling you to push forward, to ask the next question, to inquire more deeply. It’s not always about seeing the destination. Sometimes, you don’t have a plan. Sometimes, all you have is the chills.

That’s what Foretold is. Not just a wine brand. It’s proof of what becomes possible when you follow your intuition without demanding it justify itself first. Honor the voice that propels you, even when you can’t explain why, even when you seem a little lost to everyone watching.

Sometimes the end game reveals itself only after you’ve arrived.

Foretold wines will drop this May. Once we figure out how the heck we can sell them to you, I’ll let you know. Until then, enjoy the journey.

This year, I abandoned my exam-level conditions. As I began considering my goals and aspirations, I took a step back and thought, “What if I don’t have any goals? What happens then?” The nervousness I felt in posing the question to myself was a cue that I was on the right track. What if, instead of driving towards some well-defined ambition, I simply followed what energizes me, whether in marketing, wine, technology, mindfulness, AI, adventures, or any space in between? This framing felt both terrifying and liberating.

From Goal Obsession To Open-Ended Curiosity

For decades, I treated goal planning like a meticulous process. Color-coded bullet journals, monthly and quarterly check-ins, metrics for everything from revenue targets to personal development milestones. I was suffocating my own capacity for discovery.

As I’ve been pruning my old habits and elaborate frameworks, three insights have emerged thus far.

The Invisible Cost of Complex Goal Systems

Years of intricate goal-setting created tunnel vision I didn’t recognize until I stepped away. When every choice was filtered through predetermined objectives, I missed serendipitous connections and collaborative opportunities. Research shows that curiosity improves leadership effectiveness and team performance. Dropping my relentless goals focus has freed mental space for more nuanced judgment calls, deeper connections, more creativity, and joyful spontaneity that inflexible metrics would have filtered out.

From Proving Worth To Embodying It

During a particularly honest moment of self-reflection, I realized that many of my goals have been architected for the sake of proving my worth to myself and others. Instead, I needed to embody a new truth: that my worth is inherent, not earned. This mindset shift has transformed the rhythm of my daily work and where I choose to point my focus. Instead of checking boxes to validate my competence, I’ve started saying yes to the projects and pursuits that feel genuinely energizing. I’ve started saying no to perceived priorities driven purely by status or optics. As a result, my voice as a leader has grown stronger, more confident, and more self-possessed.

Curiosity As An Operating System For Today’s Landscape

Relinquishing the grip of goals has made more space for curiosity. As I’ve leaned further into this mindset, I’ve begun to see curiosity as a personal operating system advantage, particularly in today’s landscape. From my vantage point as a MarTech leader, AI is fundamentally upending the game. We’re in the midst of a once-in-a-lifetime evolution of digital engagement, data, and technology, and what it means for companies and brands to deliver against consumer expectations. From my vantage point as a sommelier, AI has completely transformed the way in which wine nerds study, evaluate, and recommend wines. Whether in the board room or the tasting room, I am observing a daily grappling with how we navigate an unknown future. In these settings, curiosity is the salve. Nobody can fully predict the future of how AI will change our lives and businesses. Instead, we must approach today’s moment with open-ended wonder, mixed with deep-seated instincts born from years of expertise.

An Invitation to Engage... or Why On Earth Am I Writing This

As I’m retraining the vines of my mind to grow in new directions, I’m also rewiring how I choose to engage. This substack is an example of my practice in action. Kat of years past would be quick to delineate the end game of this space, to get clear on what she’s seeking to accomplish and how long it’ll take to achieve. But, the reality is that I can’t possibly know my end game here. What I do know is that I crave more space to reflect and connect on the topics I’m curious about - marketing, wine, technology, AI, mindfulness, and all the mess in the middle. My hope is to root this space in what matters to me, and perhaps along the way, uncork an idea or an inspiration for others, too.