5-Year Retirement Planning Dashboard

What separates a smooth retirement from a stressful one? Almost always, it’s whether the work got done in the five years before the date or crammed into the last six months. This dashboard is the tracker I wish every pre-retiree kept taped to the inside of a folder: one page, five columns, every move that compounds.

The whole idea is sequencing. Most of the decisions that save real money have to happen before income drops and before the rules change on you. A Roth conversion is cheap in a low-income year and expensive once an RMD is stacking your bracket. A relocation saves the most when you establish it cleanly, not retroactively. Run the moves in the wrong order and you pay for it for decades.

How the dashboard is laid out

Five columns, one per year, counting down. Year 5 is “still working, building.” Year 1 is “one foot out the door.” Down the left side run the categories you track across all five: income and savings, taxes, healthcare, Social Security, estate, and the soft stuff like what you’ll actually do all day. You fill a cell when a task is done and leave it blank when it’s pending. At a glance you see what’s slipping.

What to put in each year

Year 5 to 4 out. Max the accounts while your income still makes the deduction valuable. For 2026 that’s $24,500 into a 401(k), plus $8,000 if you’re 50 or older, or $11,250 if you’re 60 to 63. Build the cash reserve. Get a real spending baseline on paper, because every other number depends on it.

Year 3 out. Model your tax-efficient withdrawal order and start the Roth conversion math. This is the window where conversions are usually cheapest, before Social Security and RMDs crowd the brackets.

Year 2 out. Lock the healthcare bridge if you’re retiring before 65. Stress-test the date against a bad market in year one, because sequence-of-returns risk does its worst damage early.

Year 1 out. Decide the Social Security claiming age. Refresh beneficiaries and estate documents. Map the first 18 months of cash flow so the paycheck replacement is real, not theoretical.

Use it as a conversation, not a checklist

Print it, fill what’s done, and look hard at the blanks. The blanks in the early columns are the expensive ones, because those are the moves you can’t get back once the year passes. A conversion you skipped at 63 doesn’t wait for you at 73. By then the RMD is already doing the opposite of what you wanted.

Five columns. One page. The point isn’t the form. The point is that the costly decisions are the early ones, and a tracker is just a way to stop letting them slide.