⛰️ Trail & Error: Antidote to Numbness

Welcome to Trail & Error—on building a resilient, meaningful life and career, especially if you’re stepping off the traditional path. Sometimes it’s coaching insights. Sometimes personal stories. Always honest, always a little unfinished.

This week’s topic: why running toward painful emotions might actually make you feel more alive.

Sound backwards? Read on 👇

You don’t need to feel good. You just need to feel.

I’ve been thinking about numbness.
How easy it is to slip into.
How sneaky it is—how it hides behind busyness, behind strength, behind being “fine.”

A coaching client this week told me about a funeral he went to. A college friend who’d died by suicide.

He admitted, almost in passing, that he was keeping distance from the sadness. Implying that it felt too heavy, that it was uncomfortable.

I get this a lot. There’s this idea—especially for men—that sadness should be managed, minimized, boxed up. That if you feel too much, you’ll fall apart. We often fear this will make us a worse partner or even worse father, because we’re supposed to be strong and stable for those around us.

But I’ve come to believe the opposite is true:
Feeling is the cure.

Not just good feelings—any feelings.

Sadness makes me feel alive. Getting uncomfortable while doing things like running in the rain, taking a cold shower, or getting knocked off my bike and scraping my knee… these things can be painful.

But if I feel pain, it means I’m still here.

I’m starting to think that the real burnout so many people feel isn’t from doing too much work.

It’s from feeling too little.

That’s part of what I meant the other day when I commented on Fair Play author, Eve Rodsky’s viral post about invisible labor and modern parenthood.

I wrote “Owning full tasks at home has become one of the most fulfilling parts of my life. It’s part of what I’ve started calling a ‘liberal arts life’—one that values presence, depth, and connection as much as achievement... It’s not a downgrade from ambition; it’s the foundation for a better kind of ambition.”

To my surprise, she replied:

I’m not sure about a TED talk, but this is a message I do want to keep repeating, and saying in bigger forums than my 1:1 coaching!

The big, full life we all crave, is not a checklist of career accomplishments and a bank account balance — it’s a full-body experience.

Our ambition, when we really think about it, absolutely includes having a vibrant emotional world.

Art, parenting, grief, movement—all of it—are pathways to feeling more. And feeling more (whether you’re feeling positive or negative emotions) all lead to an experience of a life that is more alive.

If your goal is happiness, a sense of flow, being able to be present in the moment - you probably don’t need a productivity hack or another $50k in income.

Next time, seek out an experience that makes you feel more alive.

That’s what a liberal arts life offers, at least to me.

💭 Your turn
What’s one small moment lately that reminded you you’re alive? I read every reply!

PS. Hello from Washington, DC where I’ve already gotten in a nice warm-up run for a 10k race this Sunday, while visiting my sister-in law and her family!