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How to navigate retirement planning between AI and uncertainty

Retirement planning is more complicated than ever, according to expert financial advisors. New policy changes, like the to $24,500, and online resources from the federal government provide useful frameworks, but most people can’t afford to max out their 401(k), and many are experimenting with . New data from show that retirement conversations occur less frequently than conversations about , but when they do occur, they happen earlier in conversations and tend to run longer.

“Clients are coming in more informed, but also much more overwhelmed,” says Melissa Reaktenwalt, founder and lead advisor of . “There’s so much information available now via articles, podcasts, Reddit, YouTube — it’s literally neverending. Folks are consuming all of it before ever sitting down with an advisor, but information without context creates as much confusion as it does knowledge.”

What real retirement conversations actually look like today

Meanwhile, major risks are . Early retirement, long-term care costs, market volatility and policy shifts are all factors that can throw a wrench in retirement planning – and though more and more people are starting their retirement planning with AI, a lack of perspective and follow-through can create confusion. The report data also shows that nearly half of all meetings include at least one stated fear, with fear of outliving savings as one of the most impactful.

“People are more willing to talk openly about fear and shame around money,” says Reaktenwalt. “About the gap between where they thought they’d be and where they are now, and about not knowing what to do.”

These conversations are tied to real-life pressures. Clients are often in their late 50s, and cite health issues, caregiving, and major life transitions associated with aging. Yet retirement conversations also often lack urgency or follow-through. The data also shows that retirement conversations usually do not result in concrete decision-making on the client’s part — at least not initially.

What this means if you’re thinking about hiring a financial advisor

For consumers, there’s a hidden opportunity: Retirement planning doesn’t fail because of a lack of information, but because of inaction, confusion, or unclear guidance. Knowing how to approach an advisor, and what to ask for, can make the difference.

1. Don’t treat retirement as a standalone decision

In times of economic uncertainty, it’s often easier to focus on quick-wins, like taxes, short-term moves, or commodities. But retirement conversations should anchor investments, tax strategy, and long-term planning. As Reaktenwalt notes, many clients arrive with “information without context,” making it harder to connect individual decisions into a cohesive plan. That’s why retirement shouldn’t be treated as a standalone topic — it should anchor everything else.

2. Start earlier, and take action now

The best time to start retirement planning? “Earlier than most people think or assume,” says Reaktenwalt. Waiting to have conversations about retirement increases pressure and reduces flexibility. Even small steps compound over time — “The decisions you make in your 20s, 30s, and 40s all compound over time, for better or worse."

3. Don’t wait for a live event to get help

The data shows that one of the most common and impactful fears is running out of money. Naming it helps advisors build income strategies and risk management plans. Don’t wait for a triggering event to take this seriously. The best retirement plans are built before the pressure hits, not in response to it.

4. Ask for clear guidance on retirement income

Product recommendations like annuities are rarely discussed in client conversations — and when they are, fewer than half accept them.

“They have a complicated history. The negative reputation doesn’t disappear just because the product has evolved,” says Reaktenwalt. “The deeper issue is that most retirement income conversations focus on the product before the person.”

For clients, it’s important to seek clarity. Ask your advisor what problem the product is solving, how it fits into your plan, and what you should actually do next.

5. Create urgency, even if retirement feels far away

The data shows that retirement planning is always part of the conversation, but rarely the most urgent part. That makes it easy to push off. But the clients who benefit most are the ones who treat it as a priority early, not something to revisit later. The earlier you connect decisions to future income, the better outcomes tend to be. Though many people engage advisors reactively, more value comes from proactive planning.

Where DIY tools fit (and where they fall short)

isn’t a new conversation, with tools like ChatGPT increasingly becoming a starting point for financial and retirement planning. “These tools can be seriously useful for organizing your thinking and understanding concepts,” says Reaktenwalt. “For financial literacy, they’ve lowered the barrier for entry.”

But they can fall short in critical ways. “An AI tool can give you information, but it can’t actually do the planning,” she says. “It doesn’t recognize that your cash flow situation has changed, it cannot sit across from you and understand. Planning is an ongoing, living process, and it requires a human being who is paying attention.” Use AI to learn and ask better questions, but not to make final financial decisions.

From information to action

There’s no shortage of information and resources out there to help with retirement planning. What’s difficult is to turn that information into actionable decisions.

“People come in looking for a finish line,” Reaktenwalt explains, “ but the value of a plan is not the document. It’s building an ongoing, adaptive relationship with their own financial life.” The gap many are facing today comes down to follow-through. A good financial advisor helps close the gap, connecting long-term goals to real decisions and giving structure to what can otherwise feel uncertain or overwhelming.

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