You've been saving for decades. Your calendar is full of mental retirement dates — "maybe 63," then "okay, 65," then "let's see how the market does." Now you're genuinely wondering: could I actually do this? The answer isn't a single number in your brokerage account. It's the answer to seven questions that, together, give you a real picture of whether you're ready.
Before you schedule that meeting with HR, work through each of these honestly. Some will confirm what you already suspect. Others may surprise you. All of them matter. If you want a broader framework to think through, our guide to questions to ask before retirement covers additional territory worth reviewing alongside this checklist.
Question 1: Will My Savings Last 30 Years?
The foundational question. A common rule of thumb is the 4% rule — you can withdraw 4% of your portfolio in year one and adjust for inflation each year after, with a high probability your money lasts 30 years. If you have $1 million saved, that's roughly $40,000 a year. If you need $70,000 to live comfortably, you need closer to $1.75 million.
But the 4% rule has critics, especially given today's longer lifespans and market uncertainty. Many financial planners now recommend a 3% to 3.5% withdrawal rate for people retiring in their early 60s, who could easily spend 35 years in retirement. The key question isn't just how much you have — it's how much you need, and whether your savings can sustain that level of spending for the rest of your life.
Question 2: What Will My Monthly Income Look Like?
Retirement income rarely comes from a single source. Before you retire, map out every income stream you'll have and when each one starts. This is what a complete picture often looks like:
- Social Security — your benefit amount and your planned claiming age
- Pension or annuity income — if you're lucky enough to have one
- Portfolio withdrawals — from your 401(k), IRA, or taxable accounts
- Part-time work — even modest consulting income changes the math significantly
- Rental income or other passive sources
If there's a gap between what you'll need and what you'll have in the first few years — say, before Social Security kicks in — you need a plan to bridge it. For a deeper look at structuring these income sources, see our guide to securing your retirement income.
Question 3: How Will You Handle Healthcare Before Medicare?
This is the question that derails more early retirement plans than any other. Medicare eligibility begins at 65. If you retire at 62 or 63, you could face two to three years of purchasing your own health insurance — and it's expensive. A healthy couple in their early 60s can easily pay $1,500 to $2,000 per month in premiums on the ACA marketplace, depending on income and location.
Know your options before you retire: COBRA (typically limited to 18 months and usually costly), ACA marketplace plans, coverage through a working spouse's employer, or part-time work that includes benefits. Don't let this be an afterthought. Healthcare costs are the single biggest wildcard in early retirement planning.
Question 4: Have You Decided When to Claim Social Security?
Claiming Social Security at 62 versus 67 versus 70 results in dramatically different monthly payments — sometimes a difference of 70% or more between the earliest and latest claiming age. The decision affects your finances for the rest of your life, and your spouse's finances too.
If you're in good health and have other income to draw on, delaying your claim — even a year or two — can pay off significantly over a long retirement. If you're in poor health or need income immediately, claiming earlier may make sense. There's no universally right answer, but there is a right answer for your specific situation. Our comprehensive guide to when to take Social Security walks through the breakeven analysis and key factors in detail.
Question 5: Have You Stress-Tested Your Plan?
A retirement plan that only works in a bull market isn't really a plan — it's a hope. Before you retire, run your numbers through a few difficult scenarios:
- What if markets drop 30% in your first two years of retirement?
- What if inflation averages 4% instead of 2.5% for the next decade?
- What if you live to 95 instead of 85?
- What if one spouse needs long-term care that costs $100,000 per year?
These aren't meant to scare you — they're meant to surface vulnerabilities before you're in the middle of them. If your plan survives these stress tests, you can retire with real confidence. If it doesn't, you have time to adjust: work an extra year, reduce planned spending, or shift your asset allocation.
Question 6: Do You Know What Retirement Will Cost You?
Many people overestimate how much they'll spend in retirement — but some underestimate it dramatically. Research shows that spending in retirement typically follows a "smile" pattern: higher in the early active years, lower in the quieter middle years, then rising again in late retirement as healthcare costs climb.
Build a realistic retirement budget that accounts for travel and leisure in your 60s, a possible reduction in spending in your 70s, and potential long-term care costs in your 80s. Don't forget inflation: $80,000 per year today will cost the equivalent of about $130,000 in 20 years if inflation runs at 2.5%. The numbers aren't meant to discourage you — they're meant to make your plan durable.
Question 7: Are You Emotionally Ready?
Financial readiness gets most of the attention, but emotional readiness is just as important — and often harder to assess. Retirement is a major identity shift. Work provides structure, purpose, social connection, and a sense of accomplishment. When it ends abruptly, many retirees are surprised by how lost they feel, even if their finances are solid.
Before you retire, ask yourself: What will my days look like? Who will I spend time with? What am I moving toward, not just away from? Having even a rough answer to these questions — a volunteer role, a project, a community — makes the transition dramatically smoother. Retirement is most satisfying when it's a beginning, not just an exit.
The Bottom Line
Retirement readiness isn't a single threshold you cross — it's a picture that emerges when the financial, logistical, and personal pieces align. If you've worked through these seven questions and feel confident in your answers, you may be closer than you think. If a few of them revealed gaps, you've just saved yourself from a very stressful surprise. Either way, you're asking the right questions at exactly the right time.
Written by: Seeking Retirement