Before the year gets away from you: five structural questions every retiree and pre-retiree should be able to answer heading into 2026. Not resolutions. Not goals. Not aspirations. Questions — the kind that have specific, verifiable answers that reveal whether your retirement structure is actually doing what you think it is. If you can answer all five clearly, you are heading into the year from a position of structural clarity. If you can’t, the gaps you find are worth more than any financial goal you could set.
1. What Does Your Income Floor Look Like?
Your income floor is the amount of dependable, market-independent income that will arrive each month regardless of what financial markets do. Social Security benefits, pension income, and contractually guaranteed income sources all count. Portfolio withdrawals do not — because they depend on selling assets, which means they depend on market conditions and timing.
Write the number down. Then write down your essential monthly expenses — housing, insurance, utilities, groceries, healthcare premiums, transportation. If your income floor meets or exceeds your essential expenses, the foundation of your retirement plan is doing its job. If there is a gap, you have a specific, solvable design question heading into the year.
2. When Was the Last Time You Reviewed Your Beneficiary Designations?
Beneficiary designations on retirement accounts, life insurance policies, and annuities control a significant portion of most estates — and they override everything your will says. If your designations were set at a previous employer, during a different marriage, or simply years ago without review, they may not reflect your current intentions. This is one of the highest-impact, lowest-effort items in retirement planning, and it is consistently neglected.
“A checklist is only useful if it leads to action. The goal of these five questions is not to check boxes — it is to identify where your retirement structure needs attention before circumstances force the issue.”
3. Do You Know Your 2024 MAGI — and What It Means for 2026 Medicare?
Your 2024 modified adjusted gross income determines your 2026 Medicare Part B and Part D premiums. If a financial event in 2024 — a Roth conversion, an asset sale, an unusually large RMD, a deferred compensation distribution — pushed your income above the IRMAA thresholds, your Medicare premiums this year are higher than the standard rate. Knowing this now allows you to plan 2025 income more deliberately to avoid compounding the issue into 2027.
4. Has Your Social Security Claiming Strategy Been Reviewed Recently?
Social Security is one of the most valuable assets in most retirement plans — government-backed, inflation-adjusted, and payable for life. It is also one of the most frequently under-optimized. The optimal claiming age depends on health, longevity expectations, spousal benefit coordination, and the interaction with other income sources and tax thresholds. If your claiming strategy was set more than two or three years ago, or was never formally evaluated at all, it is worth revisiting as the program’s projected trust fund timeline continues to narrow.
5. Is Your Growth Portfolio Positioned for Distribution, Not Accumulation?
The investment logic that builds wealth during working years is not the same logic that sustains it during retirement. Accumulation portfolios can tolerate volatility because contributions continue and time absorbs losses. Distribution portfolios cannot — because withdrawals are ongoing and early declines permanently impair the capital base. If your portfolio today looks essentially the same as it did in your late working years, without a deliberate shift toward income-layering, drawdown management, and sequence-of-returns risk mitigation, the structure may not be suited for the phase it is actually in.
Your 2026 Action Items
- Calculate your income floor and compare it to essential monthly expenses
- Pull and review beneficiary designations on every account
- Review your 2024 tax return for MAGI and identify any 2026 IRMAA exposure
- Schedule a Social Security review if your strategy hasn’t been formally evaluated
- Evaluate whether your portfolio structure reflects the distribution phase — not the accumulation phase
Five questions. Five specific, answerable items that tell you more about the state of your retirement plan than any resolution could. The year will get busy. The markets will do something unexpected. Legislative discussions will continue. None of that is within your control. Your structure is. Start there.
