Hello Reader,

By the first week of October, the village has gone quiet in a way it will stay until spring. The rental cars thin out. You can finally get a reservation or even walk in at your favorite restaurant. The light arrives lower and departs sooner, and the sea, which is warmer now than it was in June, belongs to the few of us who knew to wait for it.

This is the month I notice people deciding things. Not out loud. I notice it in the hour the emails arrive, which is later at night than in July.

Something to do with the year running out.

Most of the women who write to me in October are not in trouble. Their work is good. The people they love are cared for. There is no crisis to point at, no failure, nothing that would explain to a colleague why they are awake at eleven at night reading a letter from a woman in Portugal.

The absence of catastrophe is exactly what keeps them where they are.

The belief underneath goes something like this. I am allowed to want a different life once something has gone wrong enough to justify it. Until then, wanting it is ingratitude and selfish.

I held that one for years, which is why I recognize it quickly in someone else.

For a long stretch of my life I drove two hours each way into Washington to meet clients. When people asked how I was, I said I was tired. Tired was acceptable. Tired was a season, and seasons pass. What I did not say, because I had not yet found the words for it, was that the work had stopped meaning very much to me, yet I was still giving it the better part of my life.

Nothing went wrong. Clients still hired me. My business didn't collapse, and my health held.

What finally moved me was an ordinary Tuesday, stopped on the Beltway, doing the arithmetic on how many hours I had spent inside that car. It came to something close to a year of waking life. I remember the number arriving and the odd calm that came with it.

That arithmetic had been available to me the entire time. I had simply never let myself do it, because doing it would have obliged me to answer for it.

So here is what I have come to think about the crisis you may be waiting for, quietly, without ever putting it that way.

It is not permission. It is a bill.

It arrives whether you were ready or not; it charges you at a rate you didn't agree to, and what it delivers is information you already had. The diagnosis, the redundancy, the marriage that ends. People describe these as wake-up calls. Mostly they are invoices for a knowing that was postponed.

The first time my wake-up call came, it was in an emergency room, dressed in a paper dress while a doctor in white shot medicine into my butt. Oh, yes, I have had several wake-up calls in my life, and chances are you have, too.

You can have the information earlier. It costs considerably less. It is also much harder to reach for, because nothing is forcing your hand and no one will applaud you for it.

A woman who came to me in the middle of a hard year wrote to me afterward. "I arrived broken and feeling alone. Ten days later, I am transformed. I can't explain what happened, but my life began again."

I have thought about her last four words for a long time. Not that her life improved. That it began again, which is a thing she did herself, and which she had been able to do for some time but had not.

Today's Threshold Question

What would have to go wrong before you would let yourself reach for something you long for? And why is that the price of admission?

I am not asking that rhetorically. Write it down somewhere you can see it. The answer is usually more specific than people expect, and once it is on paper it stops looking like a reason and starts looking like a rule somebody handed you a long time ago, which you have been keeping ever since out of habit.

With care,

P.S. I keep a small number of private retreats here in the Algarve, and a few advisory conversations each quarter. November and January, then spring.

Write Your Healing Story

Join us for Write Your Healing Story on Saturday, November 7, 2026 in Carvoeiro. A one-day memoir writing retreat in the Algarve. This one-day retreat is an invitation to step away from your daily life and into a quieter space—where you can begin to listen more closely to your own story. For anyone writing a memoir or Those who want to explore a deeper relationship with themselves through storytelling.

A Reminder: Essays, notes, and poems from the Algarve coast of Portugal on my Blog, Between Root and Sky. ​READ THE MOST RECENT POST​

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