Sept. 14, 2026

Episode 144: We’re All on the Same Sideline: Loneliness, Connection, and Being a Witness

Episode 144: We’re All on the Same Sideline: Loneliness, Connection, and Being a Witness

Are we actually lonelier than we used to be?

In Episode 144, Kasey and Brian wade into loneliness: why so many people feel disconnected even when they are surrounded by people, why independence may not be the strength we’ve made it out to be, and how technology can give us more ways to connect while leaving our relationships increasingly shallow.

Kasey argues that we’ve been sold three promises that haven’t quite delivered: work hard and you’ll have what you need, independence will make you strong, and technology will bring us closer together. Brian describes the “monster” we’ve created: a world so efficient that we can meet almost every need without actually needing another person.

But this isn’t an episode about diagnosing the problem and walking away.

They talk about asking people for help, giving others opportunities to be useful, finding people who will celebrate with you, turning whatever work you do into service, and intentionally becoming a witness to the people around you.

See people. Notice them. Celebrate them. Let them help you. Let yourself be known.

We may not have the perfect answer to loneliness. Maybe we don’t need one.

Maybe we just need to remember that we’re all standing on the same sideline.

Loneliness is everywhere, but admitting that you’re lonely can feel different than admitting you’re stressed, anxious, or struggling. Kasey and Brian explore what has changed about the way we live, work, communicate, and depend on one another, and why genuine connection requires more than simply being around people.

  • Why loneliness can exist even when we are surrounded by people
  • The three “failed promises” of work, rugged individualism, and technology
  • What Frankenstein can teach us about the monster of isolation we’ve created
  • Why efficiency isn’t always a human good
  • The difference between being alone and being lonely
  • How social media creates wide but shallow streams of connection
  • Why comparison and constantly editing ourselves can make real connection harder
  • The importance of asking other people for help, even when we could figure it out ourselves
  • Why allowing people to be useful to one another builds relationships
  • “Will you think out loud with me?” as an invitation to connection
  • How asking parents, colleagues, and friends for help can put us on the same team
  • Why belonging requires intentionality
  • Finding people you can call when you need help and when you have something worth celebrating
  • Turning any job into a service job
  • The importance of being a witness to someone else’s work, joy, struggle, and success
  • Why waiting for the perfect solution can become an excuse to do nothing
  • Choosing the process of connection even when we can’t control the outcome
  • The reminder that we are all experiencing the human condition together


We spend a lot of time looking for a big solution to loneliness because loneliness feels like a big problem.

Maybe the response is smaller.

Ask for help.

Let somebody help you.

Celebrate someone.

Call somebody with good news.

Notice what another person is doing and tell them specifically what you saw.

Be useful to one another.

Be a witness.

Connection doesn’t happen accidentally. We have to keep choosing it.

Show NotesIn this episode:A few moments along the way:The Big Idea