Retirement Preparation Protocol

Pre-Retiree Readiness Checklist:
5 Questions Before You Retire

Retire with confidence. Download the free checklist — five questions that determine whether retirement goes the way you planned.

If you would rather talk through your situation first, the 30-minute call is below.

Who This Is For

This checklist is designed for pre-retirees who are within 5 to 10 years of retirement, have been saving consistently, and want a structured way to assess whether what they have built is actually enough — and what to do if the answer is not yet yes.

It was written for Minnesotans and Floridians specifically. Several sections — Social Security timing, the ACA subsidy calculation, snowbird tax planning, and the Medicare gap — reference the planning realities of both states. If you split time between the two, the checklist addresses that directly.

If you are already retired, the withdrawal rate and sequence-of-returns sections still apply. But the checklist is built around decisions that are still on the table — which means its primary value is in the decade before the finish line, when the moves you make are still reversible.

Question 1 — How much can I actually spend without running out?

Most retirement calculators give you a number. What they do not give you is a plan for how the sequence of your returns — not the average, but the order — can quietly cut a decade off a portfolio that looked fine on paper. The checklist walks through the difference between a withdrawal rate and a spending plan, and why the first five years of retirement carry more weight than most people expect.

Question 2 — What if the market drops right before I retire?

Sequence-of-returns risk is the thing that makes a good average return feel terrible if you retire at the wrong time. If the market falls sharply in the years just before or just after you stop working, the same portfolio that would have sustained 30 years of withdrawals might sustain 20 instead — and a recovery does not undo the damage the way most people assume it does. The checklist covers five structural moves that reduce this exposure before the window closes.

Question 3 — When should I take Social Security?

The break-even calculation is real and it matters. But it is not the whole answer. Spousal benefit strategy, Roth conversion timing, and how Social Security interacts with your taxable withdrawal plan all affect the right claiming age — and the right answer for someone in good health with a younger spouse looks nothing like the right answer for someone with a pension and a high RMD exposure coming at 73. The checklist gives you the framework for your situation, not a universal rule.

Question 4 — How do I handle health insurance before Medicare?

The Medicare gap — ages 55 to 65, or wherever you retire to age 65 — is the most common planning blind spot we see. The ACA marketplace is the answer for most people, but the income cliff is real: a single planning decision around Roth conversions or capital gains can shift your subsidy by thousands of dollars in a year. The checklist maps the four main bridge options and the decisions that affect the cost of each one.

Question 5 — Should I consolidate my accounts before I retire?

Most pre-retirees arrive with four or five accounts across three or four former employers, a couple of IRAs, and a brokerage account they opened in 2003. Consolidation is usually the right move — but the order matters for tax efficiency, the rollover rules matter more than most people realize, and there are specific situations where keeping accounts separate is the correct call. The checklist walks through when to consolidate, what to ask before you move anything, and what a clean account structure actually makes possible in retirement.

If You Would Rather Talk Than Read

Some people prefer a checklist. Others are past the reading phase and want a real conversation.

The 30-minute call is not a presentation. There is no slide deck and no product pitch. It is a conversation about where you are and what you are trying to figure out — and at the end of it, you will have a clear sense of whether there is anything here worth continuing. If there is not a fit, John will tell you. If there is a better match somewhere else, he will say so.

My advisor says I am on track. Why would I need a checklist?

"On track" usually means your savings rate and projected balance look right against a retirement date. What it often does not mean is that anyone has walked through how you will actually draw down those assets — in what order, from which accounts, in which market conditions, with what Social Security timing, and with what plan if the first two years of retirement happen to look like 2008 instead of 2019. The checklist is about the spending side. Most retirement planning focuses on the accumulation side. They are different problems.

I have been saving for 30 years. Am I really at risk of running out?

The risk is not usually about the total amount saved. It is about sequence. A portfolio that would sustain 28 years of withdrawals at an average 7% return can sustain significantly fewer years if the first three years happen to return negative 20% — even if the long-run average ends up the same. Most calculators show you the average. They do not show you the distribution of outcomes. The checklist addresses this directly.

Social Security feels straightforward — take it later, get more. Is there actually a decision to make?

The break-even math is real, but it is only part of the picture. If you delay Social Security to 70 while drawing down a taxable IRA to cover expenses, you may be paying a higher marginal tax rate on those withdrawals than you would have if you had sequenced it differently. The Roth conversion window between retirement and age 73 — when RMDs start — is one of the most valuable planning opportunities most pre-retirees do not know they have. Social Security timing is a piece of that larger sequencing decision, not a standalone choice.

Healthcare before Medicare is just COBRA, right?

COBRA is one option, and for a short gap it is sometimes the right one. But COBRA premiums are the full cost of the coverage — employer contribution included — which can run $700 to $1,400 a month for a single person depending on the plan. The ACA marketplace may be significantly cheaper if your income in early retirement falls in the right range. The catch is that the subsidy cliff is steep: if your income comes in even slightly over the threshold — from a Roth conversion, a capital gain, or a small amount of part-time income — you can lose thousands of dollars in annual subsidy. That is a plannable outcome if you know it is coming.

My 401(k) is still with my old employer from eight years ago. Does that actually matter?

It depends on what is in it and what the plan charges. Some old 401(k) plans have institutional-class funds with expense ratios that are hard to match in an IRA. Others are expensive, limited in options, and sitting in whatever allocation you set in 2016. The consolidation decision is not "always roll it over" — it is a comparison of costs, options, creditor protection rules, and RMD timing. The checklist walks through the questions to ask before you move anything.

I am 57 and plan to retire at 62. Is five years enough time to prepare?

Five years is a meaningful window — enough time to make intentional decisions about Roth conversions, Social Security strategy, account consolidation, and healthcare coverage. It is also the sequence-of-returns risk window: the five years before retirement are when a market downturn causes the most damage to a retirement portfolio, because you have not yet had time to recover before withdrawals begin. Working through the checklist now means you understand what structural moves are available and when they need to happen.