I started learning Italian at 44 because I needed proof that my brain could still want something new

The first Italian word I learned was voglio. It means I want.

I sat at my desk in our apartment in Singapore with a secondhand textbook and a notebook I'd bought specifically for this purpose — not a recycled one, not the back pages of a business planner — and I wrote it out carefully. Voglio. I want.

And then I stared at it for a long time because I realized I couldn't remember the last time I'd used that phrase about anything that wasn't a business objective or a project deadline.

I was forty-four. I'd been running digital businesses for over a decade. My partner and I had built a life in Singapore that was — by every external measure — successful. Productive. Optimized.

And I was terrified.

Not of failure or financial ruin or professional irrelevance, though those fears had their own permanent seats at my table. I was terrified because I'd realized, somewhere in the fog of building companies and publishing content and constantly producing — that I 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 I opened that textbook

People assumed I started learning Italian because I wanted to travel. Or because I was optimizing my brain — and sure, I'd read those articles. Research published in Frontiers in Psychology shows that bilingual learning can strengthen executive function and improve cognitive flexibility. I filed that information away the way I file away all useful things — as justification for something I actually wanted to do for reasons I couldn't yet articulate.

The truth was simpler and uglier. I needed proof.

Proof that my brain could still reach toward something unfamiliar. Proof that I was still a person who could sit with difficulty — not the difficulty of scaling a business or managing teams or meeting content deadlines, which I'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.

I'd spent years building media companies. I knew how to create content. I 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 my work. My role. My identity — and somewhere around forty, I discovered something I've written about before: midlife doesn't strip away what you do. It strips away who you thought you were.

Italian was my attempt to find out who was left.

The wanting problem

I grew up in Australia. Middle-class family. Good people, practical people. We didn't really have the language of wanting in our 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 I 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 myself wasn't just impractical. It felt dangerous. A luxury I couldn't afford, not financially but psychologically. Because if I started wanting things — really wanting — I'd have to feel the gap between the life I was living and the life I might have chosen if I hadn't automatically equated my identity with my output.

So I stopped. Not all at once. Not dramatically. I just let wanting atrophy, the way a muscle does when you stop using it. I wanted things for the business. I wanted things from my relationships. I wanted to be a good partner, a reliable founder, a person who delivered. But wanting something purely for myself — something with no utility, no audience, no justification beyond pleasure? That circuit went dark sometime in my mid-thirties and I didn't notice until my 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. When I read that, I thought: of course. I write about this stuff. I publish 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 taught me

Italian conjugation is humbling. There's no way around that. You sit with a verb and you 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 surprised me: the difficulty wasn't the problem. The difficulty was the point.

For years, I'd oriented my life around competence. I got good at things quickly — building platforms, writing, understanding digital audiences — and then I stayed in those lanes because competence felt safe. Competence meant value. Competence meant I could justify my existence in a market that doesn't care about your feelings, only your output.

Sitting with Italian blew all of that apart. I was terrible at it. Embarrassingly, joyfully terrible. I mispronounced things. I forgot words I'd studied the day before. I 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 me. The world continued to turn while I sat at my desk in Sentosa Cove, butchering the subjunctive, and for the first time in years I felt something I hadn't expected to feel.

Relief.

The permission problem

Here's the part I think a lot of people in their forties — especially people who've built careers around creating, producing, and performing — don't talk about enough: we lose the ability to give ourselves permission.

Permission to be bad at something. Permission to pursue something with no outcome. Permission to want.

We talk about burnout. We talk about work-life balance. We talk about self-care. But those conversations tend to stay at the surface — take a vacation, meditate, do a digital detox. What they don't address is the deeper erosion: the slow, quiet death of personal desire that happens when you spend a decade or more pouring every ounce of wanting into professional achievement.

I co-founded Ideapod because I genuinely cared about ideas. I co-created The Vessel with Rudá Iandê because I believed in what we were building. I didn't become an entrepreneur out of greed or ego — I did it because I wanted to make something meaningful. But even the most meaningful work, over time, can consume the person doing it. And it consumed me. Not dramatically — I didn't collapse or have a breakdown. I just slowly became a person who only wanted things in service of outcomes.

Italian was the first thing in years that had no outcome. No launch date. No audience. No revenue model. Just me, a textbook, and the deeply uncomfortable realization that I'd forgotten how to do something purely because I wanted to.

What I've learned so far

I'm not fluent. I'm not even close. I can order food in Italian. I can have a very basic conversation. I can read simple articles if I have a dictionary open beside me. It's slow and awkward and sometimes frustrating.

But it's mine. That's the part that matters.

It's not content. It's not a brand exercise. It's not something I'm doing to build an audience or demonstrate expertise. It's something I chose, freely, for no reason other than I wanted to — and the act of choosing it, of protecting that space, of sitting with the discomfort of being a beginner at forty-four — has changed something in me that I'm still trying to understand.

I think a lot of us — especially those of us who've built our identities around work, around output, around being the person who delivers — reach a point where we've optimized ourselves right out of our own lives. We've become so good at performing competence that we've forgotten what it feels like to want something with no justification.

The hardest part of learning Italian wasn't the conjugation tables. It wasn't the grammar or the pronunciation or the vocabulary.

The hardest part was writing voglio in a notebook and realizing I'd spent years not saying it about anything that was just for me.

If you're reading this and you recognize yourself in any of it — if you've noticed that your wants have all become strategic, that your desires are all in service of something, that you can't remember the last time you chose to do something purely for pleasure — I'd encourage you to find your Italian. It doesn't have to be a language. It can be anything. Anything with no audience, no KPI, no justification required.

Just something that lets you practice saying I want again.