The Discipline of Letting Go

The older I get, the more I believe that wisdom isn’t just about adding; it’s about subtracting. It’s about letting go.

Letting go of things that once seemed so important. Things you spent years pursuing. And that’s the irony: when you stop clinging to things, life often gets richer, deeper. Because the life you envisioned isn’t always the life you actually want. It’s humbling to admit you no longer want it.

There’s a quiet grief in that realization. You mourn the energy you spent. The identity you wrapped around it. But there’s freedom there too. A lightness. As if you’ve been dragging something heavy for so long you forgot what it felt like to walk without it.

Nobody really teaches you discernment of letting go. Nobody tells you that sometimes the smartest thing you can do is just walk away.

Letting go feels counterintuitive. It feels like failure. But is it? Life seems to have seasons. Spring and summer are for growth. Fall and winter are for pruning. What if winter is actually the most instructive season—not the end of something, but the beginning of something new? A reset. A necessary pause. After all, we need winter to get to spring.

As William Bridges points out in his timeless book Transitions, every transition starts with an ending. You must first let go of an old, before a genuine new beginning is possible. Resisting endings keeps you stuck and makes the whole transition longer and more painful.

Winter is nature’s way of cutting back what’s no longer needed, preparing for the growth that is surely coming. The tricky part is that growth and decay can look and feel identical. Both are uncomfortable. Both are uncertain. You have to risk one to experience the other.

As my friend, John P. Weiss recently wrote, “each of us carries an unseen garden. Seasons pass within it. Some corners are bright and newly planted. Others lie fallow, holding what once bloomed. We walk through it quietly. Sometimes we kneel and touch what remains. Sometimes we clear a small space and begin again.”

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Pruning is rarely dramatic. It’s quiet. It happens in the margins — not in the things you start doing, but in the things you stop doing. No one applauds what you release. There’s no ribbon-cutting ceremony. But your life feels simpler. Less heavy.

Endings involve disengagement from people and places, dismantling old structures, disconnecting from who you used to be, and feeling disenchanted with what once made sense. Processing this grief is healthy, not a sign of weakness.

And maybe the measure of a life well-lived isn’t how tightly you held on — but how gracefully you let go.

Here are a couple of quick examples of things you can prune away, if you need a nudge:

In our 20s, we want everyone to like us. In our 30s, we realize not everyone does. (I’m not everyone’s cup of tea.) By our 40s, we stop caring. By our 50s, we wonder why we ever did. Maturity is, in part, the slow erosion of needing applause. Letting go of approval is one of the earliest — and most liberating — forms of growth.

(Example: Scrolling social media first thing every morning to see who noticed you.)

Eventually, you realize being right isn’t as important as being kind. Most conflicts are smaller than they feel. And most victories cost more than they’re worth. Letting go of the need to win — in arguments, careers, or relationships — signals emotional security. (

Example: Asking someone, “Help me understand how you got there,” instead of arguing the counterpoint.)

You stop keeping score. Someone else’s timeline stops being your measuring stick. The day you stop comparing your journey to someone else’s is the day you finally start living your own. Comparison shrinks your life to someone else’s outline.

(Example: A six-figure job that requires 70-hour weeks and constant travel to afford things you don’t really care about anymore.)

I saw a tweet recently that said, “Remember when we used to laugh at the old people who took a nap, ate dinner at 5:30, drank one glass of wine, and went to bed at 9 p.m. to read a good book? Yeah, I’m not laughing anymore.”

When you’re young, stillness feels like death. Later, you realize it’s life. Rest isn’t laziness. Quiet isn’t emptiness. Presence — not productivity — is the real success. Busy is often just a socially acceptable form of avoidance.

(Example: Taking a Saturday afternoon nap instead of tackling another project.)

At some point, you realize you’re not obligated to keep being who you were. You’re allowed to outgrow old narratives — “That’s just who I am” or “I’ve always done it this way.” Letting go of that story might be the hardest pruning of all. Because it requires admitting you’ve changed. And that’s not weakness. That’s growth.

(Example: “That’s just how I am,” which quietly becomes the most limiting statement of all.)

Maybe the art of aging well is learning what to carry and what to set down. Not everything deserves unending loyalty. Some things just weren’t meant for you long term. They were stepping stones. They were the scaffolding, not the structure.

If you find yourself in a season of pruning right now, don’t rush it or fight it. Trust that the quiet work being done beneath the surface is preparing you for whatever comes next.

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