Learn. Speak. Belong.

I once coached a Dominican sales squad that sold cloud storage to small Colombian clinics. They opened every call with the literal translation of their English opener—“¿Tiene un minuto para hablar de la nube?”—and wondered why most lines went dead in four seconds. In Medellín, la nube means “bad weather,” not AWS. Prospects pictured thunderstorms, […]

The Night the Motoconcho Driver Became My Mirror One humid evening in Santo Domingo, I hopped on a motoconcho after a long day of remote work. I greeted the driver with what I thought was flawless Caribbean Spanish: “Hermano, llévame a la Zona, por favor.” He smiled but replied, “¿Eh? ¿A la ‘Sona’?”—copying my slightly […]

Stepping off the plane from Medellín last August, my six-year-old son Nico immediately spotted his Dominican friend Dariel in the arrival hall. The two boys—one fresh from Colombian kindergarten, the other from Santo Domingo’s first grade—collapsed into a giggle-filled bear hug, speaking a rapid cocktail of “¡ven acá, bro!” and “let’s play tag!” Their makeshift […]

A late-night scramble in Santo Domingo Two summers ago my partner and I scored last-minute tickets to a Juan Luis Guerra concert. Euphoric—until we realized no trusted family member was free to watch our two-year-old, Emma. We opened WhatsApp and frantically typed “¿Conoces a una niñera disponible esta noche?” to every neighbor on the block. […]

A Bus, a Baby, and a Language Time Machine One humid morning in Santo Domingo I jumped on a guagua—our battered local bus—only to spot a Peruvian backpacker giggling at the name printed on the windshield.“In Lima, guagua is a baby,” he said, showing me a WhatsApp sticker of a bread roll shaped like an […]

I still laugh at the memory of showing up to my first Dominican baby shower with a six-pack of diapers tucked under my arm like contraband. I’d assumed we’d play “guess the belly size,” hand over gifts, and go home before sunset. Instead, a live merengue trio blasted “Felicitaciones, Mamá” while abuelo led a toast […]

The Moment “Cool” Fractured into Three One Friday night at a rooftop bar in Medellín I found myself juggling three beers, three currencies, and three different words for “awesome.” A Dominican buddy raised his glass and shouted, “¡Eso está chévere, manín!” A paisa friend responded, “Sí, parce, está bacán.” Meanwhile, a backpacker from Madrid grinned […]

I first tasted the power of Mexican mini-suffixes on a scorching afternoon in Cartagena. A backpacker from Oaxaca spotted my Dominican flag patch and asked, “¿Quieres un tequilita para el calorcito, compita?” I caught tequila and heat, but the rapid-fire “-ita/-cito” duet melted into the Caribbean humidity. Minutes later a Colombian vendor chimed in, “Esperen […]

The day my “bilingual ninja” fell flat Five years ago I translated my English LinkedIn summary word-for-word into Spanish: “Soy un ninja del marketing, bilingüe y apasionado.” Within a week, three Dominican contacts messaged politely: “James, ‘ninja’ suena raro.” A Colombian recruiter ghosted after viewing my profile for exactly seven seconds (yes, I checked). I’d […]

La mañana que volé desde Santo Domingo a Bogotá con un carry-on lleno de mamajuana bottles, I slammed it onto the overhead bin—and one leaked. Sweet, spiced rum dripped onto a crisply suited Colombian exec beneath me. My autopilot English blurted, “So sorry!” He looked puzzled, more by my language switch than the sticky blazer. […]

I cut my sales teeth on the sun-baked streets of Santo Domingo, hustling a SaaS platform that nobody could pronounce. We were bootstrapped, hungry, and convinced that if we just dialed faster we would sell more. One Tuesday I cranked out seventy calls using an English script awkwardly translated by Google: “Hola, este es James […]