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Dear Friends,
To the new faces here this week, welcome. You showed up at a good time.
I had two conversations about money this summer, a few weeks apart, with two friends who are in roughly the same financial position.
They could not have gone more differently.
(Identifying details about both friends have been changed, and in places combined, to protect their privacy.)
The first friend moved to Mexico.
She had run the numbers more than once, and they kept coming out the same way. The life she actually wanted cost less than the life she was already paying for. Not marginally less. Enough less that the gap between the two figures was, in practical terms, years.
So she went.
She writes now. That was the part she never said out loud in all the years before she left, because saying it out loud would have obligated her to do something about it. For a long time she was a person who used to write. Now she is a person who writes in the morning, most mornings, before the day gets loud.
When I asked her how it was going, she did not mention the money at all. She said she feels like she belongs there. Like it was where she was supposed to have been the whole time.
I want to be careful with that, because it sounds like a tidy ending and it isn't one. She is a long way from people she loves. Her mother is getting older and the distance is not theoretical. Some weeks the belonging is something she has to keep choosing rather than something she simply found.
But she did not leave because she found a cheaper life. She left because she finally asked what the money was for, and the answer turned out to be something other than what the money was currently buying.
The second friend is still working, and he is building spreadsheets.
He is modeling what happens to his portfolio if the earning years he assumed he had turn out to be shorter than he planned. He is not being dramatic about it. He watches what is happening in his field, he runs the math on a career that ends sooner than he chose it to, and he stress-tests the number against a future whose shape he can see but whose timing he cannot.
When I asked him what he was actually after, he was more precise than I expected.
He wants to know. Not to hope, not to assume, but to know that if he is pushed out in three years instead of eight, what he has built holds. The house stays the house. The comfort stays the comfort. Nobody in his family has to be sat down and told that things are changing.
That is a real answer to enough for what. It might be the most honest one I heard all summer.
He also knows exactly what a spreadsheet can and cannot do. It gives you a range, not a promise. He runs it anyway, and I have stopped reading that as avoidance. It looks more like how a careful person sits with something that is not going to resolve.
Both of these people have enough. By any objective standard, both of them cleared that bar a while ago.
They are answering different questions.
Here is what I have been thinking about since.
In almost every other part of this transition, people eventually get to the design question. Where do I want to live. How do I want my days to feel. Who do I want around me. Those questions get asked out loud, sometimes for the first time in decades, and the asking is most of the work.
The money question rarely gets that treatment.
It stays on autopilot longer than anything else, for a reason that is hard to see from the inside. Accumulation looks like prudence. Nobody has ever been criticized for saving too much. There is no moment at which someone taps you on the shoulder and says that is enough now, you can stop.
So the number goes up by default. And default is exactly the right word, because a default is what runs when nobody makes a decision.
The thing about enough is that it is not a threshold you cross. It is a sentence you have to finish.
Enough for what.
That is the part most people skip. Most of the people I work with can tell you the number. Ask them what the number is for, and the answer gets vague fast. Security. Options. The kids. Not being a burden. All real, and none of them specific enough to act on.
My own answer, for whatever it is worth, is that I want to be generous while I am alive to see it. I would rather help someone at the moment the help matters than leave a larger figure behind that arrives after I am gone. That is a preference, not a verdict. It has real costs. It means carrying less margin than someone with a different answer would carry, and there are nights I am less sure about that trade than I sound right now.
And I should be honest about something else, because it would be easy to leave it out.
I run the same arithmetic my spreadsheet friend runs. I add a little more margin than I need. I have caught myself adjusting the number upward for reasons I could not defend if you asked me to write them down.
Knowing the question does not exempt you from the drift. It just means you notice it happening.
That is really what I am pointing at here. Not that my first friend got it right and my second friend has not yet. She has a life she chose and a cost she carries for choosing it. He has a real uncertainty and he is doing the most rational thing available to someone who cannot make it go away. Neither of them is the cautionary tale.
The thing worth watching is not either of their answers. It is the version of this where nobody asks at all, and the number climbs for thirty more years on nothing but momentum, and the life it was supposed to buy never gets specified.
So here is the small thing, and it is deliberately small.
Pick one thing you would do with money if you were certain you had enough. Not the whole redesign. One thing. Then do a small version of it in the next thirty days.
You find out what the number was for by spending a little of it on purpose.
Warmly,
Cara
Future Identity Strategist
Founder, Good Morning Freedom