A client I have worked with for a while called me a few months ago, not to set up a review, just to talk. He is in his late fifties, has spent his career in marketing, and has watched the ground shift under his industry in a way that would have been hard to believe even three years ago. The tools he built his career around, the strategic instincts, the creative judgment, the relationships with agencies and vendors, are being replicated or replaced by platforms that cost a fraction of what a seasoned marketing professional does. He is still employed. His company still values him, at least for now. But he told me the uncertainty was starting to wear on him in a way he had not expected.
"I keep wondering," he said, "whether I should just go ahead and pull the trigger. Or at least start thinking about what comes next. Because I am not sure this goes on the way it has been going."
That makes sense. That question, or some version of it, has come up more in my practice over the past year than in any other period I can remember. And what strikes me about it is that the people asking it are often not asking what they think they are asking. The surface question is about timing. The real question is about whether the plan they have been building is actually designed for the world they are living in right now.
Two Camps, and Then a Third
There are two kinds of people raising this question with me, and they look similar from the outside but are in very different situations underneath.
The first group is being pushed. They are in industries where AI disruption is no longer a conversation about the future, it is a daily reality. Marketing is a good example of this, and an honest one. A discipline that used to require teams of writers, strategists, designers, and media buyers can now be partially run by platforms that do not take vacations or ask for raises. The people who built their careers in that world are not being asked to leave, at least not yet. But they are watching what is happening around them, and they are reading the signals correctly. What they are really asking me is not whether they should retire. They are asking whether their plan is strong enough to handle it if the decision gets made for them before they are ready.
The second group is being pulled. Their jobs are fine. Their performance reviews are fine. But they have watched the economy move fast enough in the last two years that the old script, grind until 65, collect Social Security, then figure out what retirement looks like, feels less like a plan and more like inertia. The general uncertainty that AI has introduced into the workforce is making people who have built real financial security willing to question assumptions they used to take for granted. Why wait until the traditional finish line if the math already works?
Both of those people deserve a serious answer. But there is a third kind of person I am starting to see more of, and I think it deserves its own category.
The Pivot Question
That client I mentioned is actually in this third group, and his situation reflects a pattern I have seen with enough clients that it is worth describing on its own. He does not want to stop working. He is not ready for retirement in any traditional sense, and when we got further into the conversation, it became clear that full retirement was not really what he was after. What he was asking was something closer to: what if I step off this treadmill and do something completely different? Not retire. Pivot. Maybe move into something with less intensity, less pressure, lower compensation, but work he could see himself doing into his mid-sixties or beyond because it actually suited him rather than demanding everything from him.
That is a different planning question than retirement, and in some ways it is a harder one to model.
When someone wants to fully retire, the math is relatively straightforward. You have assets. You have a withdrawal rate. You have a projected Social Security benefit. You work through the scenarios until the numbers either hold or they do not. A career pivot to lower income is more complicated. You are layering a period of reduced earnings onto your existing savings trajectory. That affects your accumulation. It affects your tax situation. It affects your benefit projections and potentially your sequence-of-returns exposure, all at the same time.
The priority now is understanding what the next chapter actually looks like financially, and whether the plan as it is currently built has room for it.
In a case like his, the work involves modeling what a meaningful income reduction would look like over a five to ten year runway, what that does to the retirement income picture on the other side, and whether the flexibility being sought is actually available given how assets are currently structured. The answer is rarely a simple yes or no. But having modeled it out, a client in that position has something he did not have before: a framework for making the decision clearly rather than reactively.
The Risk Nobody Is Talking About
If you have spent your career in a sector being disrupted by AI, your portfolio may be carrying the same exposure that your career already is.
Here is the broader thing I want to say to anyone in a field where AI disruption is a live conversation.
Most people in that situation have not stress-tested their plan against the world as it actually is right now. They built their retirement projections around an income that felt stable, a timeline that felt certain, and a portfolio that may be carrying more risk than they realize in a specific and often overlooked way.
This shows up most often with people who have accumulated company stock, stock options, or significant equity compensation. The value of those positions is tied to how the market is pricing your employer's future. In an environment where AI is redrawing competitive advantages across entire industries, that pricing can shift faster than many people expect. I am not suggesting panic. I am suggesting that a concentrated equity position in a single employer, in an AI-affected sector, within the last five to ten years of a working career, is worth a deliberate and current review with a real plan attached to it.
Beyond that, there are structural questions that matter a lot in a pivot scenario specifically. How liquid is the plan if income drops? What does the healthcare bridge look like if employer-sponsored coverage disappears before 65? What does sequence-of-returns risk look like if the runway to retirement extends rather than shortens? These are not abstract questions. They are live planning questions for a lot of the people I work with, and the time to answer them is before the transition, not in the middle of one.
The Decision Worth Making Deliberately
What I told my client, ultimately, is that the question he was asking was the right question. He just needed to ask it inside a real plan rather than in the abstract. The option he was exploring, a slower gear, a longer runway, work that fit differently, was not out of reach. But it required understanding what the numbers actually looked like before making a move, not after.
AI is not going to stop reshaping the way people work. In my experience, the clients who handle that uncertainty well are not necessarily the ones with the most money. They are the ones who took the uncertainty seriously enough to look honestly at their plan before the disruption arrived at their door. That is the work worth doing now, while there is still time to make deliberate choices rather than reactive ones.
If that question is live for you, in any form, I will get back to you with a game plan. It is worth having the conversation.