When I Learned to Listen

Pst…this essay is much better when read on our Substack 👇

I wasn’t always a good listener. 

A few years ago, after missing a promotion in a very embarrassing way and starting to work with an exec coach, I learned about playbacks. 

It’s when you repeat a few of someone’s words back to them verbatim. Yes, like a parrot. It invites them to share details they may have left out.

My coach gave me homework: do 5 playbacks in every meeting I had and take notes. Honestly, I thought it was beyond stupid. How would people not notice? 

But after a few weeks, I started to get it. People who were quiet started opening up about their problems. I realized how often I was jumping in with advice despite misunderstanding the problem at first. I developed an awareness and curiosity to find the hidden realness beneath the surface of the words spoken — and I had a simple tool to dig deeper. 

It had never occurred to me before that listening was a skill I could practice. 

I recently started a company, House 42, to teach people about relational fitness. 

Like physical fitness, this refers to the skills and practices we use to find, deepen, and maintain meaningful relationships with others. 

All around me, I see so many people focusing their attention on optimizing how they exercise, their nutrition, getting enough sleep, calculating the next career move, learning to grow their investments, but none of this matters if you aren’t paying attention to the quality of your relationships. 

You can have an amazing body, eat the perfect diet, get on that Forbes 30 under 30 list, have all the money in the world but if you don’t have friendships where you feel seen, romance where you feel safe, family where you feel loved, do you even care?

Why are we getting this backwards?

We live in a time where — due to globalization, tech, shifting social norms and just an unfortunate externality of the great many benefits of modernity — meaningful social connection doesn’t just happen automatically anymore the way it did for our parents and grandparents and countless generations before them. That sucks. But it’s not impossible to fix.

We have to take initiative. 

Most of us don’t realize that how we connect with people is a skill, like any other. That listening and asking questions and building trust and having hard conversations that matter, that these are all things we can learn and practice and get better at just like riding a bike. 

Most of us are fundamentally not paying enough attention to this. 

We assume we’ll figure it out. That once the other things in our life are in place, good relationships will take care of themselves. 

Or we’re frustrated but lack agency — it’s not clear what to do. 

For years, I struggled. 

To maintain romantic relationships.

To be real with my dad instead of pretending things were ok. 

With a quiet loneliness despite having lots of friends because I didn’t know how to look for or create the type of meaningful relationships I knew I wanted.

But it all started to change when I learned to listen. This simple, silly little thing called a playback. Something so small you could do it today with the next person you talk to and they probably wouldn’t notice. 

When I started, no one noticed. 

It took weeks before I noticed what was happening. At first, it was small shifts in conversations, pauses that felt richer, an openness from people who’d always been reserved. But once it clicked, it was like an invisible world opened up. Suddenly, colors I’d never noticed leapt into view, and I could see faint vibrations in every conversation— like sound waves, calling me into new threads, ideas, and possibilities. And I just kept thinking why did no one tell me about this sooner?

This morning I spoke with a friend who was looking for advice on her career. I thought it was about strategy for a negotiation. An older version of me would have only seen that. But I noticed something else, something subtle. I heard hints of pain, ego, maybe anger. I got curious about what was happening. I took a risk and asked. And I listened.

My friend noticed:

So that’s why I’m here. That’s why I’m writing this newsletter. That’s why I quit my job a few months ago and took a risk to see if I have something worth sharing with people. 

Because once I saw that my relational fitness was something I was overlooking and started to learn and to practice, so much of my life fundamentally changed. It’s still something I learn about and try to practice every day.

And the goal for this blog is to create a space for us to learn and practice together.

Thanks for reading :)