Published on August 17, 2025 9:07 AM GMT
I had a difficult conversation with my family recently. It left me questioning everything from my choices to my worth. Maybe I was overreacting, or finally seeing clearly.
The conflict arose when I tried to vocalise boundaries and assert my agency to make my own choices about relationships, including being honest about the current state of a relationship that isn't working. This honesty made my family uncomfortable. Rather than examining why the relationship had deteriorated or respecting my assessment of it, they questioned my qualifications to have an opinion at all.
The comment that cut deep was this, "You say you are a professor of relationships, what exactly do you teach if you aren't able to maintain your own?"
It was designed to shame me. To make me doubt the very expertise I've built over years of helping others navigate love, choice, and connection.
For a moment, it worked.
Soon after, I left. As I was driving back from my family home, through the maddening city traffic, their words kept echoing. My family said I wouldn’t understand their pain until twenty years from now when my own children grow up.
That thought made me reflect on my own parenting failures.
Just days earlier, I had shamed my daughter over something small. I acted like it was out of genuine concern, but in reality, it was my own frustration at not being able to control the situation. I told myself it was parenting, but I knew better. It was my inadequacy disguised as care.
So, I asked my daughter to come sit in front, next to me, as I halted at a signal. She had witnessed the whole conversation with my family, and was visibly disturbed by all the screaming. I wanted to make sure she was okay. I wanted her to not hate my family.
So I said, "The other day, mummy did something not nice too. I was wrong to say the things I did to you. I am sorry that I hurt you." My daughter unsure what I was talking about, said, "Oh I don't remember when you hurt me, mum".
In that moment, I had two options.
I could've gaslit her, and said "Oh well, forget about what I said then". Instead, I wondered what I would've needed if I were in her place. "I don't know if I hurt you, but I am disappointed with myself, not you. I acted from the wrong place, and for that, I'm sorry", I said.
That didn’t erase the mistake, but it broke the cycle. In that moment I realised that in families, we often mistake control for care, frustration for concern, and then weaponise experience or love to justify it.
We say we mean well, though we might, but we don't care enough to examine how our words land, to separate our discomfort from another's reality. We hurt others not necessarily because we want to, but because we don't care enough to do the harder work of understanding.
Relationships are two-sided. The Gale-Shapley algorithm, which has shaped much of my thinking as a matchmaker and relationship coach, works because it assumes all parties want to participate in finding a stable match.
Both sides have preferences, both sides engage in good faith. But family relationships often break this assumption. We're told that blood creates automatic stability, that love should be enough to overcome any dysfunction. That hurt is one-sided, only children can hurt parents, and it's never the other way.
It's concern. It's sacrifice. It's love. It's sanctimonious.
Stable relationships, whether romantic, professional, or familial, require something more than sentiment. They require mutual respect, genuine care for each other's wellbeing, and a willingness to do the work when things go wrong.
We can forgive each other but still recognise that we're not currently capable of the kind of relationship we need. We can understand each others' limitations while refusing to subject ourselves to behaviour that diminishes one another. We can choose to let go, and still love.
This connects to everything I think about regarding choice architecture, systems design, and how we build better decision-making frameworks. Whether we're talking about AI alignment, organisational culture, or family dynamics, the same principle applies. We can't optimise for outcomes without first being honest about the actual incentives and constraints in the system.
I wondered if I'm truly relationship-poor, could I possibly be a good teacher?
My experience with relationship-dysfunction is precisely what makes me more aware of unhealthy patterns, more capable of naming what's happening. Else, I'd be living my relationships, not analysing the hell out of them.
I can teach about healthy relationships precisely because I understand what the alternatives look like. I can help others navigate choice and connection because I've wrestled with these systems myself, failed at them sometimes, learnt from the failures.
In a society that is built on achievement and status, expertise gets weaponised against us the moment we show human struggles. Maybe this is why some of us don't become teachers, coaches or therapists, even if we could. But I don't think I've met a single doctor who studied medicine because everyone they knew was perfectly healthy.
So, the work continues. The inquiry deepens. How do we choose? How do we build trust? How do we create systems, whether in families, organisations, or AI, that honour human dignity and agency?
Sometimes the answer is choosing not to participate in systems that consistently diminish us, even when those systems are wrapped in the language of love. That's not giving up on relationship. That's designing for better ones.
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