In late 2005, our first company got acquired. We had only one investor who owned 25% of the company, and all of our employees’ options vested on acquisition. That meant everyone, even a few people who’d already left, was suddenly about to come into money.

Not I-can-retire money. But it was still a meaningful chunk of change. On top of that, the acquiring company was offering dollar-denominated RSUs.

After two near-deaths, two pay cuts, and delayed salaries more than once over the previous five years, this should have felt like pure relief. But I learned something then that has stayed with me since.

There are happy outcomes. And then there is the path people take to arrive at happiness.

Almost everyone on our team went through the same four emotional steps.

First. “Yay. We’re going to get money.”
Second. “Wait. I have to pay taxes on this?”
Third. “How much more is there? RSUs. Perks. What else?”
Fourth. “Never mind all that. What’s my role going to be now?”

What surprised me wasn’t that people went through these steps. It was how differently they moved through them. Some crossed this terrain in an afternoon. Others took days. A few took weeks.

Which meant that for the better part of a month, I found myself having the same conversation nearly fifty times.

One line from Stumbling on Happiness¹ helped me make sense of what I was seeing years later:

Each person on our team was dealing with the same objective outcome. Same acquisition. Same vesting event. Same headline.

But their minds were busy doing something else. Filling in what this outcome meant for them. Projecting how it would feel. Rewriting their future in real time.

What slowed some people down was not a lack of information. We explained vesting. We explained taxes. We explained timelines.

What slowed them down was something quieter. Their internal story had not caught up yet. Gilbert’s argument is simple and unsettling.

We are far better at explaining our feelings after the fact than predicting them ahead of time. Our minds rush to complete the story of a happy ending, even when the emotional work is still unfinished.

That gap is where a lot of confusion, anxiety, and misalignment lives. Especially in moments we label as “wins.”

In the last issue, we looked at why some ideas persuade before they are proven. How people often feel their way to a decision and then use logic to explain it.

This is the same pattern, just stretched over time.

The story people tell themselves about an outcome begins forming immediately. Logic arrives later. Self-awareness later still.

As storytellers, leaders, and communicators, we often make the mistake of speaking to the end state too quickly. We talk as if everyone has already arrived emotionally, when many are still mid-journey.

Map the emotional lag.

The next time you tell a story about a success or a future outcome, pause before the conclusion and ask:

Then adjust your story accordingly. Not by adding more explanation. By meeting people where they are in the story they are already telling themselves.

That is often where persuasion and understanding really begin.