Making space to listen

I’ve been using AI daily since 2022, for coding and everything else at work. Aider was my first coding agent. I was fully onboard, drinking the Kool-Aid. For a while, that was a lucrative position to be in. I had consulting gigs helping companies figure out how to use AI with their teams and advising them on building and evaluating their AI products. There was a lot to learn, and I was putting it to use.

I spent the first half of this year building relentlessly on another project for myself. With the help of AI coding agents, I was as productive as ever. The project went nowhere.

Now I’ve committed to a new venture as my full-time work. I’ve deliberately avoided building for the past few months to give myself space to listen to people about their problems. Still nowhere close to product-market fit.

And I’m anxious about it. My feed is full of talk about one-person billion-dollar startups and tech firms laying off developers. Software engineering consulting gigs have dried up completely for me this year. Meanwhile, I’m listening and learning, with little visible output to show for it. I feel like I’m walking in the park while everybody is driving cars.

Does knowing that I’ve already tried driving fast make this easier? Apparently not. I’m more anxious than a few years ago about falling behind in my career and not "producing" enough. I think going slowly has been useful, but choosing it still feels uncomfortable.

What am I learning during all this listening? I started out wanting to help people have hard conversations. I assumed it was a communication skill problem. But through talking with therapists, midwives, and others, I’m realizing it’s more than that. Often, we just don’t quite know what’s really bothering us.

But giving myself months to listen doesn’t mean I’m actually listening well. In a recent discovery interview, I was talking with a mother about where she turned for support. She said, “Today, AI saved me.” My response was, “So you looking for personal therapy, basically,” and I moved on. I’d heard a similar response from another interviewee already, so I assumed I knew why she was using it. I hadn’t asked her to walk me through what had happened that day, what she’d asked the AI, or what happened afterward.

But she was not that other person. Maybe her response would have surprised me, and that was what I was supposed to learn. I’d made time for the conversation, then closed off part of it with an assumption. So much for giving space to listen.

I find the same thing in family relationships. We’ve known each other for decades. We build up habits and assumptions, and when someone says something, we presume we understand before asking what they mean or how they feel. I know how frustrating that is from the receiving end. I keep telling my wife that I don’t feel like she’s listening. Yet I can catch myself doing it too.

One of the more satisfying conversations recently happened during my mom’s visit from Canada. I have a strong presumption that she doesn’t listen. She still has me pulling my hair out. We’re polar opposites in our values and how we communicate. This time, I’ve been trying to really listen, particularly when she says something I disagree with. Instead of disagreeing upfront, I ask questions.

We were talking about how adults communicate with children. I want to be an adult who can listen to kids. My mantra is that I don’t know better than them. I don’t like adults expecting kids to just obey. My mom pushed back. To her, that was Western thinking, something for the new generation. She described how she treated her own mother: even when she thought my grandmother was wrong or nagging, she would acknowledge her and do what she said.

She was proud of that. My grandmother had gone through many hardships raising her as a single mother, and my mom didn’t want to add to her burdens by being "difficult." I was talking about mutual understanding between adults and children. She was talking about how she cared for a mother who had sacrificed for her.

I still wanted to make my point, so I asked whether the relationship she’d described with her mother was what she wanted to replicate with me and her grandchildren. I felt that clicked with her. For this particular matter, I learned that she’d made a deliberate choice based on a value I hadn’t considered.

And then there’s listening to myself. Giving myself idling time. Space for my random, irrelevant thoughts to wander. To stop fixating on doing and being productive.

For this, I have to give credit to Peace Is Every Step by Thich Nhat Hanh. Being aware and appreciative of the present. Making the best of what I have. I’m a glass-half-empty kind of person, so this is part of a bigger effort to be more optimistic and grateful, like my wife does so well.

Today, I picked up my daughter from school on my bike, and we had a spontaneous little date at a local park. I accepted that I was taking time out of my workday. The autumn foliage was gorgeous. We played with the leaves and made snow angels in them. I wasn’t thinking about getting my clothes messy. Usually, I’d assume I needed to get her home as quickly as possible and get back to work.

That thought flickered a couple times. But I was enjoying the moment, and I could see that my daughter was enjoying it too. So I let that thought be.