Retirement planning comes down to answering six questions, in order: What will your life cost? What income will you already have? How big does your portfolio need to be? How should it be invested? How do you take money out without overpaying taxes? And what’s Plan B if something breaks? Get those six directionally right and you’ll be in a good place — even if every projection turns out to be a little off.
I’m Nick Stevens, a CFP® in Boston. I’ve spent 20 years helping people retire — 12 of them at Fidelity, and the last several running Evergreen Wealth Management, a flat-fee firm that works exclusively on what I call the retirement puzzle. This is the step-by-step version of what I actually do with clients, with real numbers. No “embark on your journey” fluff.
Step 1: What will retirement actually cost you?
Start with your spending, not a rule of thumb. The old advice says you’ll need “80% of your pre-retirement income,” but I’ve seen retirees who spend 110% of their old budget (travel, grandkids, a second home) and retirees who spend 60% (paid-off house, quieter life). Neither is wrong. The plan just has to match the life.
The practical way to do this: pull your last 12 months of actual spending, subtract what disappears at retirement (payroll taxes, retirement savings, maybe a mortgage), and add what appears (health insurance before Medicare at 65, more travel, hobbies). For most Massachusetts couples I work with, that lands somewhere between $70,000 and $150,000 per year — but the range is wide, and yours is the only number that matters.
Don’t aim for a precise figure. Aim for directionally right. A budget that’s honest within 10% beats a spreadsheet that’s precise and wrong.
Step 2: What income will you have before touching your portfolio?
For most retirees, the foundation is Social Security — often $40,000 to $75,000 per year for a couple, guaranteed for life and adjusted for inflation. When you claim it may be the single biggest lever in your plan. Claiming at 62 versus waiting until 70 can swing lifetime benefits by six figures, and the right answer depends on your health, your spouse’s benefit, and what you’d withdraw from in the meantime.
Add any pension, rental income, or part-time work. Whatever’s left between your spending number (Step 1) and this income is the gap your portfolio has to fill. One piece of good news for local readers: Massachusetts doesn’t tax Social Security benefits.
Step 3: How big does your portfolio need to be?
Take the annual gap from Step 2 and multiply by 25 as a starting point. A $60,000 gap suggests roughly $1.5 million. That’s a back-of-the-envelope version of sustainable-withdrawal math — useful for orientation, too crude to retire on. Taxes, market sequence, one-time goals, and longevity all bend the real number.
This is also where the classic benchmarks mislead people. I’ve written a full breakdown of whether $2 million is enough to retire — the honest answer is “it depends on your spending,” and the difference between a $90K lifestyle and a $130K lifestyle is the whole ballgame.
Step 4: How should you invest as retirement approaches?
Retirement investing has a different job than accumulation investing. The goal shifts from maximizing growth to balancing growth, income, and downside protection — because you’re about to start selling shares to eat, and a bad market in your first few retirement years does more damage than the same market ten years in (that’s sequence-of-returns risk).
We can’t control what the markets do, but we can control how much risk we take. In practice that means holding enough in bonds and cash — often 3 to 5 years of planned withdrawals — that you’re never forced to sell stocks into a down market, while keeping the rest invested for the 25-plus years the plan has to fund. Low-cost, diversified, tax-aware. Boring on purpose.
Step 5: How do you withdraw money tax-efficiently?
Most retirees pay more lifetime tax than they need to, because retirement money lives in three differently-taxed buckets:
| Bucket | Example accounts | How it’s taxed |
|---|---|---|
| Tax-deferred | 401(k), traditional IRA | Ordinary income when withdrawn; RMDs currently begin at age 73 |
| Tax-free | Roth IRA, Roth 401(k) | No tax on qualified withdrawals |
| Taxable | Brokerage | Capital gains rates; only gains are taxed |
The order and mix you draw from each bucket — and whether you convert some tax-deferred money to Roth during the low-income “gap years” between retiring and starting Social Security — can be worth $5,000 to $15,000 a year for many retirees. It also affects your Medicare premiums, since income above certain thresholds triggers IRMAA surcharges. I’ve covered the mechanics in detail in my guide to tax-efficient withdrawals in retirement.
Step 6: What could break the plan — and what’s Plan B?
Every plan I build is Plan A, and every Plan A comes with a Plan B. If markets are poor in the early years of retirement, Plan B might be starting Social Security a bit earlier, drawing on fixed income for two or three years, and avoiding selling stocks into a down market. The plan is built to flex.
The risks worth planning for explicitly: a long market downturn early in retirement, a long-term care event (a private room in a Massachusetts nursing facility runs well over $150,000 a year), the death of a spouse (which usually drops household income more than expenses), and — for estates over $2 million — the Massachusetts estate tax, which starts far below the federal threshold. You don’t need to fear these. You need a written answer for each.
When should you start, and do you need an advisor?
The best time to start is about 5 to 10 years before your target date — that’s when Roth conversion windows, Social Security strategy, and portfolio positioning still have room to work. But I’ve onboarded plenty of clients at 63 or already retired, and there’s always something worth fixing.
Can you do this yourself? Honestly — some people can, and I’ve told prospects exactly that. If you enjoy the work, stay disciplined in bad markets, and keep up with tax law, DIY is a legitimate path. I wrote an honest framework for the advisor-or-DIY decision if you’re weighing it.
If you do want help, understand how advisors charge, because it changes the math. The traditional model takes a percentage of your assets — commonly 1%, which on a $1.5M portfolio is $15,000 a year, every year, rising as you save more. A growing number of advisors instead charge a flat fee. At Evergreen it’s a flat monthly fee for both investment management and full financial planning — same price, same scope of work, whether you have $600K or $4M. I built it that way because the work of answering the questions above doesn’t triple just because someone’s portfolio did. You can see exactly how our fee structure works and compare it yourself.
Frequently asked questions
How much do I need to retire in Massachusetts?
For most couples, a portfolio between $1.2M and $2.5M plus Social Security supports a comfortable Massachusetts retirement — but the honest answer depends on your spending, your housing, and your health costs, not a universal number.
What’s the biggest retirement planning mistake?
Retiring without a written withdrawal plan. Most people spend decades optimizing saving and zero hours planning the order they’ll spend it in — and the spending order is where the tax money leaks out.
Is it too late to plan if I’m already retired?
No. Social Security timing may be settled, but withdrawal sequencing, Roth conversions, IRMAA management, and portfolio risk are all still on the table — often with meaningful dollars attached.
Retirement planning isn’t a product you buy once; it’s a set of decisions you get to make with the tradeoffs in plain view. If you’d like a second opinion on your own retirement puzzle — whether you’re five years out or five years in — I’d love to have a conversation. Here’s how to get started.