05/19/2026
โณ This is an updated version of the 12-month retirement countdown I posted about three months ago. A few items needed better wording.
Each number is one task, but some will overlap. Health coverage (month 11) may need to start earlier if you are retiring before 65. Estate documents and beneficiary designations can be addressed any time and should not wait until month 5. Social Security claiming strategy may need to begin well before month 4 if a spouse benefit, ex-spouse benefit, pension, or earnings test is involved.
Month 8 is withdrawal sequencing: which accounts you tap first, in what order, and at what tax rate. This decision affects your bracket, your Medicare premiums, and your Roth conversion opportunities for the next 20 years. It deserves more than a quick decision.
The practice budget at month 6 is the step most people skip and the one most people say they wish they had done. Spending one month on your projected retirement income reveals blind spots that spreadsheets miss.
Estate documents at month 5 are not just about a will. Beneficiary designations on retirement accounts override whatever your will says. If your ex-spouse is still listed on your 401(k), the money goes to them regardless of your current estate plan.
The final month is cash-flow setup. Activate withdrawals, set tax withholding rates, and confirm your cash buffer. That buffer should already be mostly in place before the final month. The last step is confirming where the first year of withdrawals will come from so you are not forced to sell investments at a bad time.
P.S. Every Friday I send a short email with the week's top post, my take on the best article I read, and what I'm writing about on the site. Link in the comments.\
*The content shared here is for educational and informational purposes only. It is not personalized investment, tax, legal, or financial advice. Consult a licensed professional before making decisions based on your specific situation.*