How AI Can Help You Plan Retirement Smarter in 2025

Retirement has always been a strange word for me. For some people it means freedom. For others it feels like the end of the story. But the truth is, retirement today doesn’t look anything like what our parents or grandparents went through. We are living longer, working longer, and paying more for just about everything. Most of us grew up thinking retirement was about money. Stack up enough savings and assets and you’ll be fine. That idea still matters, but I don’t think it’s the full picture anymore. When I talk to people in their 40s and 50s, money comes up, sure, but so do other things. They talk about their health. They talk about keeping their relationships alive. And more and more, they talk about finding a reason to get up in the morning once work is gone. That’s where AI is starting to creep in. I’ve had conversations with people using it to budget, to plan out their healthcare costs, even to map out where they might want to live in retirement. Others are more skeptical. I have a friend who laughs every time I bring it up because he thinks the whole thing is hype. Both reactions make sense. AI can be confusing and the first time most people try it, the results are usually terrible. This article is about pulling that conversation back to the middle. AI is not magic and it is not useless. It is a tool, and like any tool it only works when you set it up right. If you think about retirement as being built on three pillars - resources, relationships, and engagement - AI can help you get a clearer look at each of them. That is what this post is about, and it is also the first in a series where I want to show how AI connects to the bigger picture of aging.

Why Retirement Planning Needs a Smarter Approach

The old way of planning for retirement is pretty straight forward. Pick a number, figure out how much you’ll need, and hope nothing big changes. But if the last few years taught us anything, it is that change is constant. Jobs shift. Health costs rise. The basic cost of living can explode. Families look different than they did twenty years ago. Even the idea of “stopping work” is changing. AI doesn’t remove those uncertainties, but it does give us a way to work with them. Instead of one straight-line forecast, it can run hundreds of different “what if” scenarios. What if you retire a little earlier? What if healthcare costs jump faster than expected? What if you sell your house and downsize? These are the kinds of questions people used to pay planners thousands of dollars to model. Now AI can run them in minutes. Let’s ballpark some numbers around this for reference. Imagine you have $250,000 saved. At a 5 percent annual return, that produces about $1,040 per month before taxes. If your monthly living costs are $3,000, you can see right away there is a gap. Now imagine you doubled that savings to $500,000. The return would be closer to $2,080 per month. Still short of covering everything, but the picture changes when you add pensions, part-time income, or government benefits. Push that savings to $1,000,000 and the return is roughly $4,160 per month. That covers more, but it also shows how quickly the math can change depending on assumptions. AI can help you test dozens of these variations quickly. You can ask it to model conservative returns at 3 percent, or more aggressive at 6 percent, and compare them against your actual expenses. You can also build in things like healthcare shocks or lifestyle upgrades. Prompt Example: “Act as a retirement planning assistant. I have [savings amount]. Assume an annual return of [X%]. Show me the monthly income this produces and compare it to an estimated monthly cost of living of [Y]. Include scenarios at lower and higher return rates. Format the answer in a clear table.” But numbers are only part of the story. A smarter approach also means looking beyond the bank account. Who do you want around you in retirement? How do you keep those relationships strong when you’re not anchored by work anymore? And what will give you purpose when your calendar is wide open? That is why I see AI less as a calculator and more as a partner. It can crunch the data, sure, but it can also help you explore the softer parts of retirement, the social side, the health side, the meaning side. The trick is remembering that it is a co-pilot, not the pilot. The human questions are still yours to answer.

The Three Pillars of Retirement: Resources, Relationships, and Engagement

When I talk about retirement, I keep coming back to three things that matter most: resources, relationships, and engagement. You can think of them as the legs of a stool. Take one away and the whole thing tips over. Resources are the obvious one. This is the money, the housing, the healthcare, and the safety net you need to feel secure. AI can help here by making the numbers less overwhelming. Instead of vague spreadsheets, you can use AI-driven tools to forecast spending, model scenarios, or explore options like downsizing. This pillar will connect to a future post in the catalogue focused on financial tools and planning. Relationships are the part people don’t always plan for. Work gives you a built-in network of colleagues, conversations, and social contact. When you step away from that, the danger is isolation and stagnation. AI tools are starting to show up here too, from apps that remind you to check in with friends to translation tools that break down language barriers when you travel or connect with family abroad. This pillar will link to a post on maintaining and strengthening relationships in midlife and beyond. Engagement, or purpose, is the hardest to measure but maybe the most important. Retirement without purpose often feels empty. Every day can’t be a golf day. I know because I used to own a golf course. AI can play a role here as well, whether by matching you to volunteer opportunities, suggesting creative outlets, or even helping you start small side projects. It is not about replacing human meaning but about pointing you toward possibilities you may not have thought of. This pillar will link to a post on finding purpose and engagement in retirement. These three pillars — resources, relationships, and engagement — give you a more complete picture of what retirement can look like. AI adds a layer of support, helping you balance them in ways that feel less overwhelming. Each pillar will also form the backbone of linked posts in the site catalogue so readers can dive deeper into each topic.

The Role of Context Development

Preparing to use AI in any of these roles requires more than just downloading an app. It starts with context. A context planning document gathers information about the person using the AI — their history, goals, values, and expectations for the future. This becomes the framework that guides how the AI is used. Think of it as a bridge between who you are and what you want AI to help you achieve. Without it, you risk getting generic results that don’t reflect your reality. With it, you give the AI a much stronger foundation to work from, aligning outputs with your actual needs. I will be creating a context checklist that you can download for free. This checklist will show up in several of these posts, because it is central to using AI well. It is not about telling the AI what to do once, it is about building a reference that can keep your use of AI consistent over time. It combines your past experiences and your future expectations into one place, so that when you ask AI for help, the results are much closer to what you really need.

Conclusion and Next Steps

Retirement planning is no longer just about money in the bank. It is about balancing resources, relationships, and engagement in a way that gives you security and meaning. AI can help with all three pillars, but only when you use it with intention. Start small. Test tools that help you forecast expenses, strengthen relationships, or discover new ways to stay engaged. Keep the risks in mind, and remember that AI is a co-pilot, not the pilot. And don’t forget context. Before you dive in, build your context planning document. Use the free checklist I’ll be sharing to capture your goals, your values, and your expectations. That way, every time you bring AI into your planning, it will reflect more of who you are and where you want to go. If you are ready to take the first step, download the checklist and begin shaping your AI retirement strategy today. Your future self will thank you.