The first Italian word was voglio. It means I want.
Picture this: a forty-four-year-old man sitting at a desk in a Singapore apartment with a secondhand textbook and a notebook bought specifically for this purpose — not a recycled one, not the back pages of a business planner — writing it out carefully. Voglio. I want.
And then staring at it for a long time, realizing he couldn't remember the last time he'd used that phrase about anything that wasn't a business objective or a project deadline.
He was forty-four. He'd been running digital businesses for over a decade. He and his partner had built a life in Singapore that was — by every external measure — successful. Productive. Optimized.
And he was terrified.
Not of failure or financial ruin or professional irrelevance, though those fears had their own permanent seats at the table. He was terrified because he'd realized, somewhere in the fog of building companies and publishing content and constantly producing — that he didn't want anything. Not in the peaceful, Buddhist way. In the hollow way. The kind of not-wanting that comes from years of training yourself out of desire because desire got replaced by obligation, strategy, and the relentless forward motion of an entrepreneurial career.
The real reason that textbook got opened
People assumed the Italian was about travel. Or about optimizing the brain — and sure, the articles had been read. Research published in Frontiers in Psychology shows that bilingual learning can strengthen executive function and improve cognitive flexibility. That information got filed away the way all useful things get filed — as justification for something actually wanted for reasons not yet articulable.
The truth was simpler and uglier. He needed proof.
Proof that his brain could still reach toward something unfamiliar. Proof that he was still a person who could sit with difficulty — not the difficulty of scaling a business or managing teams or meeting content deadlines, which he'd had plenty of practice with — but the difficulty of choosing to be bad at something on purpose, with no audience and no KPI and no revenue model depending on the outcome.
He'd spent years building media companies. He knew how to create content. He knew how to analyze audience behavior and craft headlines and stand in front of a camera and make ideas about psychology and philosophy feel accessible. But all of that knowing was in service of something. It was his work. His role. His identity — and somewhere around forty, a discovery surfaced that he'd written about before: midlife doesn't strip away what you do. It strips away who you thought you were.
Italian was his attempt to find out who was left.
The wanting problem
He grew up in Australia. Middle-class family. Good people, practical people. There wasn't really a language of wanting in the house — not for impractical things, anyway. You could want a career. You could want stability. You could want to do well. But wanting something purely for the joy of it, something with no clear payoff? That felt indulgent. Suspicious, even.
That training doesn't leave you. It burrows in.
By the time he was deep into building businesses — working insane hours, moving to Singapore, pouring everything into Ideapod and the publications that grew around it — wanting things for himself wasn't just impractical. It felt dangerous. A luxury he couldn't afford, not financially but psychologically. Because if he started wanting things — really wanting — he'd have to feel the gap between the life he was living and the life he might have chosen if he hadn't automatically equated his identity with his output.
So it stopped. Not all at once. Not dramatically. Wanting just atrophied, the way a muscle does when you stop using it. He wanted things for the business. He wanted things from his relationships. He wanted to be a good partner, a reliable founder, a person who delivered. But wanting something purely for himself — something with no utility, no audience, no justification beyond pleasure? That circuit went dark sometime in his mid-thirties and he didn't notice until his forties.
Research by psychologists Kennon Sheldon and Tim Kasser found that pursuing goals aligned with intrinsic motivation — things chosen freely, for personal meaning rather than external pressure — is significantly more predictive of well-being than pursuing goals out of obligation or social expectation. Reading that, the reaction was: of course. He writes about this stuff. He publishes articles about this stuff. But knowing it intellectually and doing something about it are two entirely different acts.
What sitting with a conjugation table actually teaches
Italian conjugation is humbling. There's no way around that. You sit with a verb and realize it has six forms in the present tense alone, and then there's the past, and the subjunctive, and the conditional, and all of them have irregular exceptions that follow no obvious logic.
But here's what came as a surprise: the difficulty wasn't the problem. The difficulty was the point.
For years, he'd oriented his life around competence. He got good at things quickly — building platforms, writing, understanding digital audiences — and then stayed in those lanes because competence felt safe. Competence meant value. Competence meant he could justify his existence in a market that doesn't care about your feelings, only your output.
Sitting with Italian blew all of that apart. He was terrible at it. Embarrassingly, joyfully terrible. He mispronounced things. He forgot words he'd studied the day before. He conjugated verbs wrong in ways that would have made a seven-year-old Italian kid laugh.
And nothing happened. No one cared. No business metric shifted. No audience abandoned him. The world continued to turn.
