
Most people approaching retirement are focused on one question above all others: do I have enough saved?
It's a reasonable place to start. But it's only the beginning of what a complete retirement plan needs to address. In our experience working with pre-retirees across the country, the people who retire with the most confidence aren't necessarily the ones with the largest balances. They're the ones who have worked through five specific questions — and have clear, written answers to all of them.
Most people can answer the first. Very few have worked through the rest.
This seems straightforward, but most people have never converted their savings balance into a monthly income figure.
A $1 million portfolio sounds substantial. But translated into monthly income over a 25 or 30-year retirement, after accounting for inflation, taxes, and market variability, it generates far less than most people assume.
The starting point for any retirement plan is a specific monthly income target — not a savings number. What does your lifestyle actually cost? What will it cost in five years when healthcare expenses rise? What does a fulfilling retirement look like for you in practical, monthly terms?
Until you have that number, everything else in your retirement plan is built on uncertain ground.
This is the question most retirement plans don't answer directly — and it's one of the most consequential.
The risk of poor market performance in the early years of retirement is significant and well-documented. It's called sequence of returns risk, and it means that two people with identical savings and identical long-run returns can have dramatically different retirement outcomes depending on when a major market decline occurs.
If your retirement income plan relies primarily on drawing from an invested portfolio, a major downturn in the first two to three years can permanently reduce your income capacity — even if the market recovers fully afterward.
A complete retirement plan has an explicit answer to this question. It doesn't leave the answer as "we'd reduce spending" or "we'd wait it out."
Healthcare is consistently the most underestimated expense in retirement planning.
If you retire before 65, you'll need to bridge the gap to Medicare eligibility. Private health insurance for a couple in their early 60s can cost $2,000 to $3,000 per month — a figure that rarely appears in retirement projections.
After Medicare begins, costs don't disappear. Premiums, supplemental coverage, dental, vision, hearing, and out-of-pocket costs add up to a significant annual figure that rises with inflation. For higher earners, income-related Medicare premium surcharges (IRMAA) can add hundreds of dollars per month — and these are directly tied to how you structure your retirement income.
A solid retirement plan treats healthcare as its own line item, with a specific funding strategy — not a footnote.
The income gap is the distance between what arrives in your bank account automatically each month — Social Security, a pension if you have one — and what you actually need to maintain your lifestyle.
For most people, this gap is larger than expected. And it has to be funded from somewhere.
There's a meaningful difference between filling that gap by drawing reactively from savings and filling it with a deliberately constructed income strategy — one that includes reliable, predictable income sources that don't depend entirely on market performance.
If you don't know your income gap number, you don't yet have a complete retirement income plan. This is one of the first calculations we do in every consultation.
Longevity planning is the question most retirement plans address least thoroughly — and it's arguably the most important.
The average American who reaches 65 today has a 50% chance of living past 85. For a married couple, there's a 75% chance that at least one spouse lives past 90.
A retirement that begins at 62 and runs to 92 is a 30-year financial plan. That changes everything: the size of the income floor you need, how aggressively you can draw down savings in the early years, the importance of inflation protection, and the role of healthcare planning.
Most retirement projections run to 85. That's not a plan for longevity — it's a projection that ignores one of the most significant risks a retiree faces.
Each of these questions points to the same underlying truth: a retirement plan is not a savings target. It's an income plan — one that needs to work reliably, in any market environment, for as long as you live.
The good news is that once you have clear answers to all five, the path forward becomes significantly clearer. You know what you need, you know where the gaps are, and you know what decisions to prioritise.
That's exactly what we work through in a complimentary retirement planning consultation.
If you're within ten years of retirement and haven't worked through all five of these questions with an advisor, that's the conversation to start now.
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