I didn’t plan to get back into poker.

It happened almost accidentally, the way many things do when you’re tired, curious, and already halfway committed. I was in New York for FarCon, and the poker game was the last side event on the calendar. I hadn’t played seriously in years, but I’d already paid the twenty-dollar entry fee, and at the end of a long week, that felt like reason enough to show up. Besides, I have a deep aversion to flaking. It’s one of my pet peeves.

That night, I arrived fully expecting to be the fish at the table. I was exhausted, oversocialized, and quietly hoping for an early exit. That intention disappeared the moment I started stacking a few big winning hands. Beginner’s luck, I assume. Soon, I was one of the loudest players in the room, talking shit to the men sat beside me. “You’re like a cockroach!” I exclaimed, after one player came back from busting out for the third time. “In a good way,” I quickly added. At some point, I even DoorDashed a couple of bottles of whisky for the table.

I left with a three-hundred-dollar profit and a very good mood.

Despite the euphoria, I don’t remember a single card from that night. I rarely do. What I remember instead is the feeling of being watched. Not in a threatening way, and not even an unkind one; just the persistent awareness of being the only woman at the table. At one point, when we had to draw cards to decide who would leave to start a new game, I joked to the dealer, “Surely you wouldn’t do this to the only woman here?”

It was a joke, mostly. But it also wasn’t.

I’ve learned how to both embrace and recoil from what that presence tends to invite: curiosity, assumptions, and the quiet, unspoken question of whether I belong.

That night kicked off a run I didn’t expect. After tentatively playing my first casino game at Caesar’s Palace in Vegas, I picked up a player’s card and somehow became a regular at Hard Rock Casino Hollywood, right up until I moved. I played at the Hippodrome Casino in London and snuck in another successful round at the Venetian back in Vegas. I even entered my first ever tournament and outlasted more than eighty of the hundred players. It was free to enter, with a Rolex for the winner at stake, but I was still the last woman standing.

Eventually, a poker table was delivered to my new place in New York, assembled with more determination and sheepishness than I care to admit. Somewhere along the way, poker stopped being a novelty and became a ritual.

When my friend and longtime poker player Sean recommended The Biggest Bluff by Maria Konnikova, I learned a few things I was unsurprised to discover. Only about three percent of poker players are women. And while poker is, on its surface, simply a game, it offered something else entirely. It was a way to enter rooms where the rules were explicit, the stakes visible, and the outcome determined by a combination of skill, chance, and nerve.

For the entirety of my career, I’ve worked in male-dominated industries. I started in traditional finance, moved into combat sports, and eventually found my way into tech and crypto. These are spaces where women are still outnumbered, still scrutinized, and still expected to prove that they are not tourists. By the time I reached my mid-thirties, I had grown accustomed to the unspoken evaluation that seems to follow women into these rooms: how we speak, how we dress, how confidently we occupy space.

Poker felt like a continuation of that pattern. Another room. Another table. Another set of rules that everyone else seemed to inherit without question.

I remember speaking at my first crypto conference in Los Angeles in 2022. I was walking through the exhibition hall when a man stopped me to ask whether I knew what NFTs were. When I told him I was speaking on a panel later that day, he looked genuinely startled. Not embarrassed. Just surprised, as though he had misread the room.

That moment lodged itself deeper than I expected. Not because it was egregious, but because it was so ordinary. It was a reminder that credibility, when it comes from women, is often provisional. Granted, but only after inspection.

In the years since moving to the US, I’ve thought a lot about what it means to be a woman in business, a woman in tech, and now, somewhat unexpectedly, a woman who plays poker. There are nights when I post photos from games and notice the same visual pattern: one woman, eight men. I think I know how it reads. I also know how little control I have over that reading.

What has changed more recently, and what I still struggle to articulate, is how being single seems to amplify all of this.

In my mid-thirties, unattached, and moving through professional and social spaces that skew heavily male, I’ve become newly aware of an additional layer of scrutiny. Conversations that feel harmless in one context suddenly feel risky in another. Talking about my weekend, my dating life, even my hobbies can start to feel like a liability, as though sharing too much might quietly erode the seriousness I’ve worked to build.

No one has ever told me outright that this is inappropriate. A close friend suggested that this tension might be self-imposed, shaped in part by my Singaporean upbringing. In a society so marked by convention, living life off the beaten path can be awe-inspiring to some but incomprehensible to most.

That is what makes this so hard to name. The pressure is ambient rather than explicit. A sense that being open, whether about who I am seeing, where I went, or how I spend my time, might invite the wrong kind of attention. The kind that flattens complexity and replaces intellect with intrigue.

I often wonder if this would feel different if I had a partner. Or children. If I were married, anchored, visibly accounted for. On one hand, I doubt I would even let myself into these rooms, out of an abundance of caution and respect for a significant other. On the other, I suspect I could show up to the same spaces, with the same hobbies, and be viewed entirely differently. Stable. Serious. Safe.

Instead, there is something about being single and highly visible in male-dominated spaces that seems to unsettle people. Or perhaps it unsettles the stories they tell themselves. The attention that follows can be off-putting, like the man at the Hard Rock who hollered across the room asking if he could buy me a drink. More often, it is simply misplaced. Attention focused on my presence rather than my ideas, my availability rather than my capability.

Poker, oddly enough, has helped me see this more clearly.

At the table, everyone is playing with incomplete information. Judgments are made based on what is visible: posture, timing, confidence. Bluffing is part of the game, but so is restraint. You learn quickly that revealing too much, too early, can cost you. Not because you are wrong, but because others will use whatever you offer to construct their own narrative.

I have started to recognize how often women are placed in a similar position off the table. Expected to perform competence without appearing threatening. To be personable without being misread. To take up space, but not too much of it. The tension is familiar enough that it has already been named and popularized, most memorably in Barbie, which articulated what many women already understood long before it reached a screenplay.

What I wrestle with most is not the imbalance itself. It is the way it quietly shapes behavior. How it teaches women to self-edit. To hold back stories that might humanize them, because it is never quite clear whether humanity will be read as depth or as distraction.

I will continue to choose rooms where I am in the minority. Poker tables. Conference halls. Industries that have not yet figured out how to make space without suspicion. I am not sure whether this is defiance or habit, or simply where my interests have led me.

What I hope for, plainly, is a day when my legitimacy is no longer conditional. When my intellect no longer needs guarding, my complexity no longer needs rationing, and my personal life no longer needs to be strategically obscured.

At the poker table, at least, the rules are honest. You play the hand you are dealt. You read the room. You decide when to show and when to fold.

I am still learning how to do that everywhere else.

I didn’t plan to get back into poker.

It happened almost accidentally, the way many things do when you’re tired, curious, and already halfway committed. I was in New York for FarCon, and the poker game was the last side event on the calendar. I hadn’t played seriously in years, but I’d already paid the twenty-dollar entry fee, and at the end of a long week, that felt like reason enough to show up. Besides, I have a deep aversion to flaking. It’s one of my pet peeves.

That night, I arrived fully expecting to be the fish at the table. I was exhausted, oversocialized, and quietly hoping for an early exit. That intention disappeared the moment I started stacking a few big winning hands. Beginner’s luck, I assume. Soon, I was one of the loudest players in the room, talking shit to the men sat beside me. “You’re like a cockroach!” I exclaimed, after one player came back from busting out for the third time. “In a good way,” I quickly added. At some point, I even DoorDashed a couple of bottles of whisky for the table.

I left with a three-hundred-dollar profit and a very good mood.

Despite the euphoria, I don’t remember a single card from that night. I rarely do. What I remember instead is the feeling of being watched. Not in a threatening way, and not even an unkind one; just the persistent awareness of being the only woman at the table. At one point, when we had to draw cards to decide who would leave to start a new game, I joked to the dealer, “Surely you wouldn’t do this to the only woman here?”

It was a joke, mostly. But it also wasn’t.

I’ve learned how to both embrace and recoil from what that presence tends to invite: curiosity, assumptions, and the quiet, unspoken question of whether I belong.

That night kicked off a run I didn’t expect. After tentatively playing my first casino game at Caesar’s Palace in Vegas, I picked up a player’s card and somehow became a regular at Hard Rock Casino Hollywood, right up until I moved. I played at the Hippodrome Casino in London and snuck in another successful round at the Venetian back in Vegas. I even entered my first ever tournament and outlasted more than eighty of the hundred players. It was free to enter, with a Rolex for the winner at stake, but I was still the last woman standing.

Eventually, a poker table was delivered to my new place in New York, assembled with more determination and sheepishness than I care to admit. Somewhere along the way, poker stopped being a novelty and became a ritual.

When my friend and longtime poker player Sean recommended The Biggest Bluff by Maria Konnikova, I learned a few things I was unsurprised to discover. Only about three percent of poker players are women. And while poker is, on its surface, simply a game, it offered something else entirely. It was a way to enter rooms where the rules were explicit, the stakes visible, and the outcome determined by a combination of skill, chance, and nerve.

For the entirety of my career, I’ve worked in male-dominated industries. I started in traditional finance, moved into combat sports, and eventually found my way into tech and crypto. These are spaces where women are still outnumbered, still scrutinized, and still expected to prove that they are not tourists. By the time I reached my mid-thirties, I had grown accustomed to the unspoken evaluation that seems to follow women into these rooms: how we speak, how we dress, how confidently we occupy space.

Poker felt like a continuation of that pattern. Another room. Another table. Another set of rules that everyone else seemed to inherit without question.

I remember speaking at my first crypto conference in Los Angeles in 2022. I was walking through the exhibition hall when a man stopped me to ask whether I knew what NFTs were. When I told him I was speaking on a panel later that day, he looked genuinely startled. Not embarrassed. Just surprised, as though he had misread the room.

That moment lodged itself deeper than I expected. Not because it was egregious, but because it was so ordinary. It was a reminder that credibility, when it comes from women, is often provisional. Granted, but only after inspection.

In the years since moving to the US, I’ve thought a lot about what it means to be a woman in business, a woman in tech, and now, somewhat unexpectedly, a woman who plays poker. There are nights when I post photos from games and notice the same visual pattern: one woman, eight men. I think I know how it reads. I also know how little control I have over that reading.

What has changed more recently, and what I still struggle to articulate, is how being single seems to amplify all of this.

In my mid-thirties, unattached, and moving through professional and social spaces that skew heavily male, I’ve become newly aware of an additional layer of scrutiny. Conversations that feel harmless in one context suddenly feel risky in another. Talking about my weekend, my dating life, even my hobbies can start to feel like a liability, as though sharing too much might quietly erode the seriousness I’ve worked to build.

No one has ever told me outright that this is inappropriate. A close friend suggested that this tension might be self-imposed, shaped in part by my Singaporean upbringing. In a society so marked by convention, living life off the beaten path can be awe-inspiring to some but incomprehensible to most.

That is what makes this so hard to name. The pressure is ambient rather than explicit. A sense that being open, whether about who I am seeing, where I went, or how I spend my time, might invite the wrong kind of attention. The kind that flattens complexity and replaces intellect with intrigue.

I often wonder if this would feel different if I had a partner. Or children. If I were married, anchored, visibly accounted for. On one hand, I doubt I would even let myself into these rooms, out of an abundance of caution and respect for a significant other. On the other, I suspect I could show up to the same spaces, with the same hobbies, and be viewed entirely differently. Stable. Serious. Safe.

Instead, there is something about being single and highly visible in male-dominated spaces that seems to unsettle people. Or perhaps it unsettles the stories they tell themselves. The attention that follows can be off-putting, like the man at the Hard Rock who hollered across the room asking if he could buy me a drink. More often, it is simply misplaced. Attention focused on my presence rather than my ideas, my availability rather than my capability.

Poker, oddly enough, has helped me see this more clearly.

At the table, everyone is playing with incomplete information. Judgments are made based on what is visible: posture, timing, confidence. Bluffing is part of the game, but so is restraint. You learn quickly that revealing too much, too early, can cost you. Not because you are wrong, but because others will use whatever you offer to construct their own narrative.

I have started to recognize how often women are placed in a similar position off the table. Expected to perform competence without appearing threatening. To be personable without being misread. To take up space, but not too much of it. The tension is familiar enough that it has already been named and popularized, most memorably in Barbie, which articulated what many women already understood long before it reached a screenplay.

What I wrestle with most is not the imbalance itself. It is the way it quietly shapes behavior. How it teaches women to self-edit. To hold back stories that might humanize them, because it is never quite clear whether humanity will be read as depth or as distraction.

I will continue to choose rooms where I am in the minority. Poker tables. Conference halls. Industries that have not yet figured out how to make space without suspicion. I am not sure whether this is defiance or habit, or simply where my interests have led me.

What I hope for, plainly, is a day when my legitimacy is no longer conditional. When my intellect no longer needs guarding, my complexity no longer needs rationing, and my personal life no longer needs to be strategically obscured.

At the poker table, at least, the rules are honest. You play the hand you are dealt. You read the room. You decide when to show and when to fold.

I am still learning how to do that everywhere else.