For about twenty years I had a plan for the day my youngest left home. I was going to leave this small town and never look back.
It was not a fantasy exactly. It was closer to a promise. I had raised children in a place I did not choose so much as land in, and I had spent enough evenings looking at a map to know the shape of what came next. Somewhere else. Somewhere I picked on purpose. I have always been a wanderer, and wandering was the reward waiting at the end of the raising.
Then my oldest son planted roots here. Started a family here. And my grandson turned up, needing to be picked up from school on Fridays.
Nobody talked me out of anything. There was no conversation, no moment where I decided. It happened the way real reordering usually happens, which is quietly and slightly after the fact.
The quiet house I had been waiting to sell turned into a creative sanctuary. The town I was going to leave turned into the place where a two-year-old knows my kitchen. And a value I had held for decades, wandering, replanting, going where I please, got reorganized behind another one: family, and knowing my grandson on a Friday afternoon basis rather than an occasional one.
Reorganized. Not deleted. That distinction is where our discomfort lives.
I never thought I would choose to stay here. And yet here I am, happily, building the life I actually want.
Here is what I want to be careful about, because this is where advice usually goes wrong.
The leaving dream was a good dream. It was not avoidance, it was not a story I told to survive the hard years, and it was not something I needed to see through and outgrow. It was exciting and it was worthy, and if my life had gone slightly differently I think it would have been right.
It just stopped supporting the life I was actually building. Those are two different judgments, and we tend to collapse them. We ask whether a dream is good, when the useful question is whether it still fits.
Almost everything written about courage is about picking something up. Take the leap. Make the ask. Start the thing. Courage as acquisition.
But a lot of what stands between a person and the life they want is not something blocking the road. It is something already in their hands. The client roster that pays well and eats every Tuesday. Being the reliable one. The credential you are halfway through. A plan you made at thirty-four and have not opened since.
You cannot pick up the new thing while your hands are full. And the reason it takes courage is that the things you have to put down are almost never bad. Nobody needs courage to drop something obviously harmful. You need courage when the thing is genuinely good, and it still has to go.
You also have to survive the small embarrassment of it. I told people I was leaving. For years. There is a particular flavor of awkward in staying somewhere you announced you would not stay.
And then, because life enjoys this kind of thing, the moment I stopped defending the old plan I got a better version of it.
I will be in Italy for a month in October.
Not as a compromise, and not as a consolation prize for the life I did not pick. It turns out wandering and being firmly grounded can support each other rather beautifully, but only once you stop making them compete for the same job. As long as leaving was the plan, every trip was a rehearsal for it, and every reason to stay was an obstacle. Put the plan down and a month in Italy is just a month in Italy. It is better this way.
You are allowed to hold a dream for a long time. You are allowed to still find it exciting. Neither of those things means it is still doing you any good.
So here is the one I have been asking, and the one I would hand to you: is this long-held dream supporting the life I am creating now? Not the life I was creating when I first had it. This one. The current one, with its actual Fridays in it.
And if the answer is no, will you find the courage to put it down?
There is a free thinksheet for this: The Dream You Carry. Three pages for what you have been holding, the life you are actually building, and the space in between. And if you are still working out which thing to set down, there are usually only two kinds of stuck.
For years I named my practice after the thing I was most proud of surviving. This week I retired the word, and kept the hour.
Some stuck is a gap in what you know. Some stuck is a pattern in how you work. They feel identical from the inside, which is why we keep buying the wrong solution.
Every so often I write one of these before it is finished, and send it to whoever wants it.
No schedule, no pitch. An invitation, something worth passing along, or a question I have been asking myself that day.