My son was in tears. I gave him a pen.
Letter 149
Subject: My son was in tears. I gave him a pen.
Week 3 | Apr 2026
My son came to me this week in tears.
His teacher wanted him to participate in three things. A swimming competition. A cricket match. An art show. All around the same time.
He wanted to do all of them. He didn't want to disappoint her. And he'd got so tangled up trying to want the right things, for the right person, that he couldn't breathe.
I sat with him for a moment.
"I hear you," I said. "This is a tough spot."
Then: "Let's do one thing. Write down all the possibilities in front of you."
He wrote them down. Swimming. Cricket. Art.
"Good," I said. "Now. Are there any other possibilities? Ones we haven't thought of yet?"
He looked up at me.
That question had never occurred to him.
Here's the thing.
Most of us treat the options in front of us as the only options that exist. We didn't put them there. Someone handed them to us. A teacher. A parent. A market. An investor. A quiet expectation that's been sitting there for years.
And then we stand there, staring at those options, trying to choose between them. Overwhelmed. Stuck. Sometimes in tears.
We call it confusion. We call it a crossroads.
But a crossroads means roads exist. Someone built them. Someone decided where they go.
What if none of those roads are yours?
My son's list looked different on paper than it did inside his head.
Swimming. Cricket. Art.
We kept going. What if he did swimming and skipped cricket? What if he focused on the art show and had a proper conversation with his teacher about how he was feeling? What if that conversation was the actual thing that needed to happen?
What if the answer wasn't on the original list at all?
The overwhelm didn't come from having too many choices. It came from believing those three were the only ones.
The moment he picked up the pen, something shifted. His breathing changed. His face changed. The problem got smaller. The field got bigger.
Flannery O'Connor said: "I write because I don't know what I think until I read what I say."
That's it. That's the whole thing.
When something stays in your head, it fills all the available space. It loops. It contradicts. It grows. The moment you put it on paper, you have to choose words. And choosing words forces you to see what you actually mean.
Three things on a page look manageable. Ten things look like possibility.
I see this with founders all the time. They come in carrying the version of the problem they've been handed. By their board, their team, their industry, their own story about who they are. Arguing about options inside a box someone else built.
The question that changes everything is almost never "which of these should I choose?"
It's: are there any other possibilities we haven't thought of yet?
Nobody asks it.
Not because they're not smart enough. Because the options in front of them feel so real, so urgent, so expected, that questioning whether they're even the right options at all feels almost rude.
It's not rude. It's the real work.
Your crossroads might not be a crossroads at all. It might be an open field with three paths someone else laid down, and you standing there trying to decide between them like that's all there is.
Pick up a pen. Write down what's in front of you.
Then ask what my son asked himself this week, maybe for the first time:
Are there any other possibilities?
The answer, almost always, is yes.
, Adi
What's a choice you've been trying to make that might not even be the right question? Write back. I read every reply.
PS , This week's recipe: Adrak Chai (ginger tea, the kind that makes you think)
Because some conversations need something warm in your hands first.
What you need:
1 cup water · 1 cup milk · 2 tsp tea leaves · 1 inch fresh ginger, crushed · 2 cardamom pods, lightly crushed · sugar to taste
How:
Bring the water to a boil. Add the ginger and cardamom. Let it go for 2 minutes. Add the tea leaves. Then the milk. Let it come up slowly. Don't rush it. Once it rises, lower the flame and let it simmer for another minute.
Strain into a cup. Add sugar if you want.
Sit with it. Think. Write something down.