Planning for a Long Life & Making Sure Your Wealth Plan Does, Too
When most people picture retirement, they picture the moment they stop working: that first morning without an alarm, the trip they've been putting off for years, or some version of finally having their time back. That moment is absolutely worth planning for and worth celebrating when it arrives.
But what some financial plans don't fully take into account is everything that comes after that moment. For most people retiring today, "everything after" could mean 25, 30, or more years of life - years that look and feel very different from each other, carry different costs, and require a different kind of thinking than the accumulation phase that came before. As a result, planning for retirement isn't one conversation - it's many, and they need to happen before you get there.
A Longer Life Means a Different Kind of Plan
Here's something that tends to land differently when you say it out loud: a 65-year-old today has roughly a one-in-four chance of living past 90 (Source: US Department of Health and Human Services). For couples, the odds that at least one person lives into their early 90s are even higher. Most of us already “know” that people are living longer, but we don't always translate that into what it means for the financial picture - which is that your money may need to work for three full decades after you stop earning.
And then there's inflation, which may seem insignificant when you're thinking about the next few years. But it becomes very real when you stretch the timeline out. At a modest rate of around 2.5% inflation, something that costs $100 today will cost close to $185 in 25 years. That math applies to groceries, utilities, healthcare, and every other bill you'll be paying in retirement. None of this is meant to be alarming - it's simply meant to be clarifying and to help ensure your plan has your today, tomorrow, and far into the future covered.
The good news is that planning for a long life doesn’t need to be complicated. It just requires thinking through a few things that many retirement conversations don't get to. Here's four areas we always recommend starting:
Retirement Has Different Phases, So Plan Accordingly
One of the most important things we do with our clients thinking about retirement is establish a different mental model for what those years actually look like. It isn't a single stretch of time with one set of needs. Instead, retirees typically move through phases that feel meaningfully different from each other, both financially and personally.
The early years of retirement tend to look a lot like an upgrade - more travel, more time with the people you love, room for the things that got squeezed out during the working years. Energy and health are usually at their best, and spending often reflects that.
Further along, priorities may shift in ways that are hard to predict in advance. The pace of your life changes and some things that mattered less start to matter more. For example, in the later years healthcare and long-term care move from things you know you should probably think about to things that need real answers.
The Conversation That Gets Put Off the Longest
If there's one topic we encounter more avoidance around than any other, it's long-term care. And we understand why - it requires imagining a version of yourself that needs significant help, which is an uncomfortable place to go. So people put it off, and then put it off again, and eventually it becomes something that gets dealt with reactively rather than thoughtfully.
Here’s an important statistic worth knowing: Someone turning 65 today has almost a 70% chance of needing some form of long-term care in their remaining years, whether that's help at home, assisted living, or memory care (Source: U.S. Administration for Community Living). And the cost of that care, which has been rising faster than general inflation for years, can have a devastating impact on a family's financial picture if nobody planned for it.
Example: A woman in her early 70s needs memory care. Her husband had always assumed they'd figure it out when the time came. What he didn't anticipate was the cost - upwards of $8,000 to $10,000 a month in many parts of the country - or how quickly it would draw down the portfolio he'd spent 30 years building. A long-term care policy taken out ten years earlier, when she was still healthy enough to qualify, would have covered most of it.
What makes this worth addressing sooner rather than later is that your options genuinely narrow over time. Long-term care coverage becomes harder to qualify for as your health changes, and the cost reflects that. There's no single right answer for every family. Some people do well with traditional long-term care insurance, others prefer hybrid products that combine life insurance with long-term care benefits, and for families with significant assets, a self-insuring approach can make sense. The point is to make the decision, with full information, before circumstances make the decision for you.
Being "Conservative" in Retirement Isn't Always the Safer Move
There's a widely held assumption that retirement is the time to move into safe, low-risk investments. But going too conservative too early introduces a different kind of risk that doesn't get talked about nearly enough: the possibility of outliving your money.
A portfolio sitting mostly in cash and short-term bonds at 65 may not generate the growth needed to sustain spending through your 80s and 90s, especially with inflation working against you the whole time. There's also something called sequence-of-returns risk - the idea that a bad stretch in the market early in retirement, when you're drawing down rather than accumulating, can do lasting damage that a similar downturn mid-career simply wouldn't cause. In retirement, the timing of when losses happen matters - not just the long-run average.
Getting this balance right - enough growth to outrun inflation over a long horizon, enough stability to weather the bad years without lasting damage - is an ongoing job, not a one-time decision you make the day you retire and never revisit.
The Part Nobody Puts in the Spreadsheet
Something we've observed over many years of working with people through the transition into retirement is this: The financial side of retirement almost always gets more preparation than the personal side - and that gap can catch people off guard in ways they genuinely didn't see coming.
Work, for all its demands, provides structure. It gives the day a shape, a sense of purpose, a reason to be somewhere. It connects you to colleagues, to problems worth solving, to a rhythm that's been part of your life for decades. And when it ends - even when that's exactly what you wanted and planned for - the transition can feel disorienting in ways that are hard to anticipate until you're actually in it. Some people thrive immediately. Others find themselves restless or lost a few months in.
This isn't a financial problem on its own. But we see it become one when it goes unacknowledged. Individuals and couples who navigate this transition most successfully tend to have thought about what their day-to-day life would look like alongside the money and often started those conversations earlier than you might expect. What does a meaningful week look like at 68? At 75? What role do you want to play in your family, your community, your own sense of purpose? Are there things you've always wanted to pursue that work never left room for? These aren't soft questions. They're the foundation of a retirement plan that actually holds up and they're worth talking through with someone who knows your full picture, not just your portfolio.
Our Advice: Start With Your Life, Not the Numbers
What we've found, working with families across many different life stages, is that the best plans for a long retirement don't begin with a spreadsheet. They begin with an honest conversation about what you actually want - and then the work of making sure the money is there to support it. If you haven't revisited your plan with longevity in mind, or you're not sure your current approach accounts for healthcare costs, the different phases of retirement, or what you want your legacy to look like, this is a good time to have that conversation.
Reach out to your Entrust Wealth Partners advisor, or call us at (860) 838-3730 to learn more and get started.
