Prepared for Alan and Ruth Sutton

Your Retirement Roadmap

The three years before Medicare, and the thirty after

Prepared July 25, 2026. Account values as of July 17, 2026.

One

The big picture

Your savings tested against 400 different market histories. The dark line is the middle result; the shaded areas are the better and worse outcomes around it.

Current: middle result Half of all outcomes Nearly all outcomes With the rule Without the rule

Spending falls naturally with age, so the plan uses three stages. Each card shows two recommendations because the right number depends on one choice, explained in section three.

Change the assumptions and watch everything update

How to handle 2026 and 2027

Two

2026 to 2028: the years before Medicare

Three years with more decisions in them than the thirty that follow. Alan's Social Security still seven years away, health insurance at the most expensive age to buy it, and two income limits worth real money.

What "income" means here

Not what you spend. It is what the government counts: withdrawals from the IRA, the taxable part of Social Security, and investment income. Money from your trust barely counts, because it has already been taxed. That is why the order we draw from your accounts matters so much.

Through 2027, the insurance discount. Keep counted income under $84,600 and the government covers most of your premium. One dollar over and you lose all of it, so we aim well under the line rather than at it. The plan holds you under it in both 2026 and 2027, worth roughly $53,000 of premium across the two years.

From 2028, the Medicare surcharge. Medicare charges higher earners more, based on income from two years earlier. So 2026 sets your 2028 premiums, 2027 sets 2029. Crossing this line costs about $2,500 for one year, uncomfortable but not a cliff.

Your income each year against the limit that applies

From funding your spending From moving money to the Roth That year's limit

How we build the 2026 number

Your living trust has no built-up gain, so selling from it adds almost nothing to counted income. That is what leaves room to take about $63,700 out of the IRA this year at a rate near zero while still collecting the discount. It is the cheapest money you will ever move out of that account. There is no health account line for 2026, because your current plan does not qualify for one. That starts in 2027.

The health account, newly available to you

A rule change in January made every Bronze and Catastrophic marketplace plan work with a health savings account. Retirement does not disqualify you; only Medicare does, which is why the window shuts in 2028. Your current plan is not one of these, so 2026 is unavailable, but moving to Bronze at renewal opens 2027 and part of 2028. It helps three ways at once:

  1. What you put in is deductible, which lowers counted income and frees up room to take more from the IRA under the same limit.
  2. The money leaves the IRA for good and is never taxed again.
  3. From 2029 it pays your Medicare premiums directly, taking that cost off your savings.

Money in, money out

What it can pay for

Eligibility starts with your 2027 plan and ends when Medicare does: May 1, 2028 for Alan, October 1, 2028 for Ruth, prorated for the months each of you qualifies.

What health care costs you each year

Marketplace premium, your share Covered by the discount Part B and D, paid by the health account Part B and D, paid from savings Supplement Surcharge

Each bar is the full cost of cover, and the colours show who pays it. In 2026 and 2027 the pale band is the discount, and in 2027 it covers a Bronze plan almost entirely, which is why your own share falls to near nothing. The expensive year is 2028, when you buy part of a year of private cover and part of a year of Medicare at once. From 2029 the green band is Part B and D paid straight from the health account, so it never leaves your savings.

The choice in 2026 and 2027, priced out

Taking the discount in both years saves about $36,600 of tax and $29,800 of premium across the first five years. It costs about $51,000 more in lifetime tax, because income deferred now is taxed later, and it spends about $54,000 of the Roth in 2027. That is the right trade: the saving is certain, it lands in the years your savings are most vulnerable, and the conversion ladder rebuilds the Roth from 2028. Skipping the discount cuts lifetime tax the most, but only by taking extra out in the years that can least afford it.

What happens when

By December 2026age 63
Hold counted income under $84,600. About $63,700 from the IRA, the rest from the trust. We check the number before the last withdrawal of the year.
November 2026open enrollment
Move to a Bronze plan for 2027. Two things follow. The discount is worked out from a Silver benchmark, so applied to a cheaper Bronze plan it covers almost the whole premium. And Bronze plans now qualify for a health savings account. We price the real options before choosing.
2027age 64
The second discount year, and the cheapest year for cover in the whole plan. Income stays under the limit again, funded by the trust, a measured IRA withdrawal and about $54,000 from the Roth. Open and fund the health accounts.
November 2027the check that matters
Your margin under the limit is about $7,000, on top of the cushion already built in. We confirm the number before the last withdrawal of the year. Getting this wrong costs the entire discount, so it is the date on this page with the most money attached to it.
February 2028do not miss this
Alan's Medicare sign-up window opens. Nobody enrolls him automatically because he is not yet taking Social Security, and missing it adds a penalty to his premium for life.
May 2028Alan turns 65
Medicare starts, and a six-month supplement window opens that never reopens. During it you cannot be refused or charged more for your health. Your state gives no second chance. Health account contributions stop for Alan.
October 2028Ruth turns 65
The same two windows for Ruth. After this the expensive stretch is over.
Every Novemberfrom here on
We check the year's income against that year's limit before the books close.

Three

Living on savings until 70, and the rule that protects it

Ruth's benefit covers about $12,680 a year. Everything else, until Alan claims at 70, comes out of your savings. The share you draw starts modestly at 5.4 percent, then climbs through the bridge and peaks above 8 percent just before his benefit arrives. That is the stretch where market returns matter most, and what makes it workable is agreeing in advance what happens if they disappoint.

How much of your savings you spend each year

Your rate 4 percent, the usual rule of thumb

The rule, step by step

Once a year, at your review, we compare what you actually have to what this plan expected you to have by then. One of three things follows.

  1. You are more than 15 percent below. Spending comes down 8 percent for the next twelve months. On today's figure that is about $13,900 a year, or $1,160 a month. Nothing else about the plan changes: same investments, same accounts, same withdrawal order. What changes is only how much leaves the portfolio.
  2. You climb back to within 5 percent of plan. One step of the cut comes back off, automatically. You do not have to ask and we do not wait for a full recovery.
  3. You are more than 25 percent above. Spending goes up 5 percent. The rule is allowed to work in your favor, and in a good decade it will.

Cuts stop after 20 percent, increases after 15 percent. So across every future in this plan, your spending stays between roughly $139,200 and $200,100 in today's money.

The work we have not done yet

We can tell you the rule takes $1,160 a month off your spending. We cannot yet tell you which $1,160, because we do not have a breakdown of what you actually spend. Everything in this plan is estimated from the money leaving your accounts, which tells us the total and nothing about the shape.

That gap has to close before the rule means anything. What we need to do together, and soon, is take your real spending apart and sort it into three buckets: what is fixed and untouchable, what is comfortable but flexible, and what is genuinely discretionary. Then we agree the order things come off in, write it down, and both sign up to it.

Agreed in advance, applied without exception. When the rule fires, we do not reopen the conversation, we work the list. That is the whole reason for deciding it now, on a calm afternoon, rather than in the middle of a falling market when every line item suddenly feels essential. A rule with a negotiation attached is not a rule, and the odds in this plan quietly assume you have one.

What "15 percent below plan" actually means in dollars

These are the numbers we check against at each review, using your December 31 balances. Nothing is judged in the moment or in the middle of a bad month.

A worked example

You start 2026 with about $3.23 million. Over the year roughly $175,000 leaves the portfolio to cover spending and tax, and markets fall 20 percent. You end the year near $2.45 million, against a plan expectation of about $3.31 million. That is 26 percent below, so the rule fires: 2027 spending is set at about $164,000 instead of $178,350. If 2027 recovers, the cut comes off. If it does not, another step follows.

How often this actually happens

This is worth being blunt about, because "if markets go against you" makes it sound rare and it is not. A single poor year early on is enough to put you 15 percent behind, and across a 35-year projection with a draw that reaches 8 percent, ordinary market variation gets you there sooner or later. Across all the futures in this plan:

Futures where the rule fires at least once74%
Typical number of adjustments over your lifetime3 times
Typical low point for spending, in today's money$135,500
Futures that reach the full 20 percent reduction65%

Read that honestly and it changes how you should hear the recommendation. This is not a plan that occasionally needs a nudge. It is a plan that expects to be adjusted, probably more than once, and in most futures it works its way down to the floor at some point. That is the deal you are being offered, and it is a reasonable one, but only if you go in knowing it.

So what do you get for accepting that?

The alternative is simple: set spending at about $147,000 now, permanently, and never be asked to adjust again. That lands you in much the same place on the odds, 82% with the rule at today's spending against your 80 percent target without it. The difference is where the spending sits over time.

Total spending over the plan, with the rule
Total spending over the plan, at a fixed lower figure
Difference in your favor

Both figures are in today's dollars, over the whole projection, in the middle outcome. Without the rule your odds fall to 49% at your current spending, which is why the fixed alternative has to start lower.

So the trade is this. Start higher, spend meaningfully more through your sixties and seventies while you are most able to enjoy it, and accept being asked to step down when markets disappoint, possibly to a little under the fixed figure in your late eighties. Or start lower, spend less in the years you are most active, and never have the conversation. Neither is wrong. It is a question of which you would rather live with, and it is the one decision on this plan we cannot make for you.

The condition

Everything above assumes the step down actually happens when it triggers. A rule that gets talked out of in the moment is worse than no rule, because you will have spent the extra money in the good years without taking the medicine in the bad ones. If you would not follow it, tell us now and we will build the plan at the lower fixed figure instead.

Four

Moving money to the tax-free side

Roughly $3 million sits in the IRA and none of it has been taxed. That bill gets paid by you, by whichever of you is left, or by your children at their own rates. The only question is when, and at what rate.

So each year we move a slice into the Roth and pay the tax deliberately, sized to fit inside the 22 percent bracket. It is never taxed at a higher rate than the one we are avoiding later, and once it is in the Roth it grows and comes out tax free.

How much we move each year

Nothing moves in 2026 or 2027, when income is already being managed for the discount.

The third row counts the IRA at 76 cents on the dollar, because the tax owed on it is real even if unpaid. On that basis this is worth about to you.

One trade we make on purpose

In some years a slice pushes income over the Medicare surcharge line and adds a couple of thousand dollars two years later. Worth it: a one-year surcharge in the thousands buys a permanent rate cut on six figures.

Five

If one of you is on your own

Alan holds the large IRA and the larger benefit, so his dying first changes the most.

Modeled as Alan dying at 73, the survivor spending 80 percent of the joint figure and keeping the larger benefit.

Income does not halve but the tax brackets do, and the Medicare surcharge line drops from $218,000 to $109,000. The same money and lifestyle produce a much bigger tax bill, so the risk is the rate, not running out. That is why Alan waits until 70, locking in the largest possible benefit for Ruth for life, and why moving money to the Roth now matters: of the survivor's tax disappears if it happens while you are both here.

Money you may not know you are owed

Ruth draws her own $12,680 today. When Alan claims at 70 she becomes entitled to a top-up of roughly $6,500 a year for life, paid automatically once he files. It is worth about by the end, and it is easy to overlook because nothing prompts you to claim it.

Six

The two things that actually break plans

Not average returns. These two. Both are carried in every number here rather than left out.

A period of care

The first chart has a shaded band around age 88 and the lines dip through it. This is why.

What we assumed

How long3 years
Starting at age88
Cost, in today's money$100,000 a year
Rising each year by4 percent
Which by then is$266,584 a year
Normal household spending during those yearsdown 25 percent

Where the figures come from. The 2025 national cost of care survey. Your state runs well below the national average: a semi-private nursing home room is about $84,315 a year, assisted living $73,800, memory care $92,400, against a national private-room median of $129,575. We used $100,000 for a private room close to home. Normal spending drops a quarter during those years because a facility already covers food and housing.

Why 4 percent and not 2.5. Care has not tracked general prices. We use 4 percent for care and 5 percent for insurance premiums because they behave differently. It is the most consequential number in this section: the picture improves noticeably at 3 percent and worsens at 5. Using general inflation for premiums too would flatter your odds by about .

What those years look like

Ordinary years shown for comparison. Look at the last column: you go from taking 4.6% of your savings in a normal year to 17.3% in the third year of care.

Why the chart dips, in one sentence. For three years your spending roughly doubles while your savings stay the same size, so the share you have to take out each year more than triples, and the money taken out in those years is no longer there to grow back afterwards. The line never fully returns to where it was heading.

The care bill is not the whole cost

Care itself comes to $832,167 across the three years. But the household needs $1,892,899 in total over that stretch, and about $246,680 of that is extra tax, created purely because a sum that large has to come out of a pre-tax IRA in a single year and lands in the highest brackets you will ever touch. Roughly $34,000 of higher Medicare premiums follows two years behind it. Your savings fall about $818,000 across the period.

So a care bill near $832,000 costs closer to $1.1 million. That gap is the best argument for everything in section four: the smaller the pre-tax IRA is by 88, the cheaper a bad year becomes.

How much it depends on what actually happens

Duration matters far more than timing: starting at 82 rather than 88 barely moves the result, lasting five years rather than three moves it a lot. Carrying the assumption at all costs about of your odds.

What we are doing about it. Not buying a policy today. The Roth is the reserve, which is exactly why the conversion ladder matters: it is quietly building the account we would draw on. We look at insurance again at 70, while price and health still work in your favor.

A bad first few years

Selling investments to live on while markets are down is the hardest thing to recover from, because those shares are gone and never participate in the rebound. It is worst in the years before Alan claims, when your savings are carrying almost all of your spending.

Two answers, both already in the plan: keep the next 18 to 24 months of spending in cash and short bonds so no withdrawal is ever forced at a low, and use the spending rule in section three, which exists for precisely this.

Seven

Year by year

Eight

What happens next

  • Price the Bronze options and switch for 2027. Us, at open enrollment in November. The highest-value action on this list: it should take your 2027 premium to near nothing and it opens the health accounts.
  • Send Ruth's Social Security statement. You, when convenient. It sets the size of her top-up.
  • Get us twelve months of bank and card statements. You, and now the priority. Either send them to us and we will run them through Helmsted, our planning system, or simply drop them into your client portal and it will pick them up from there. Either way it categorizes every transaction and gives us the shape of your spending, rather than the single total we estimated from your withdrawals. Flag any large one-off items as you go, a roof or a big trip, so they are not read as normal spending.
  • Review what comes back, together. Together, next meeting, once the statements are through. The system does the sorting; deciding what is fixed, what is flexible and what is genuinely discretionary is a conversation. This is the session that turns the spending rule from an idea into something that will work.
  • Agree the reduction list, in order, in writing. Together, straight after. What comes off first, second and third if the rule fires, agreed while nothing is wrong and applied without exception when something is. Nothing else on this list is worth as much.
  • Set the 2026 IRA withdrawal to the income budget. Us, in December.
  • Correct the tax withholding. Us, next withdrawal. The current split takes out more than your state now charges.
  • Diary both November income checks. Us, 2026 and 2027. Roughly $7,000 of margin under the limit each year, and crossing it costs the whole discount.
  • Diary the Medicare and supplement windows. Us, now. February and May 2028 for Alan, July and October 2028 for Ruth.
  • Check the contingent beneficiaries, not just the primary. Together, next meeting. The primary is each other and that part is simple. What goes stale is the line underneath: who receives the accounts if you go together, or if the survivor never gets round to updating it. Left blank or pointing at your estate, it costs the children the ten-year window, cuts it to five, and drags the whole thing through probate. We also want the wording that carries a share down to a grandchild rather than sideways to the other sibling, and we want to be sure no trust is sitting there as IRA beneficiary without a reason. Designations override your will and your living trust, so this is the one piece of your estate plan that is not covered by the documents you already have. The new health accounts need beneficiaries set the day they open.
  • Decide whether you want the spending rule at all. Together, next meeting. If the answer is no, we rebuild the plan at the lower fixed figure and you never have the conversation again. Both are respectable answers; drifting between them is not.
The detail behind the numbers

Accounts, July 2026. IRA $2,983,326 (Alan $2,850,752, Ruth $132,574). Trust $159,064, a living trust with no material built-up gain. Roth $89,851. Health accounts start at zero.

Spending. Estimated from your withdrawals over the past two and a half years, after tax withheld and health premiums. Recurring large items left in; the one-off 2025 gift removed and treated as pre-funding five years of giving. Steps to 85 percent at 75 and 75 percent at 85.

Care. Three years from age 88 at $100,000 a year in today's money, rising 4 percent, with normal household spending reduced 25 percent during those years. Based on 2025 cost of care survey medians for your state, where a semi-private nursing home room is about $84,315 a year and assisted living about $73,800, against a national private-room median of $129,575.

Markets. 400 simulations at the average return shown with 12 percent year-to-year variation. Inflation 2.5 percent, health costs 5 percent.

Health care. Your state's 2026 marketplace medians, age-rated for a couple at 63: benchmark Silver about $33,500 a year, lowest-cost Bronze about $25,600. The discount equals the benchmark premium less your required share, taken as about 10 percent of income under the rules that returned for 2026, and it applies to whichever plan you buy. Silver for 2026, Bronze from 2027. Health savings account contributions run from 2027 to the month each of you reaches Medicare. Out-of-pocket medical costs are not a separate line; they sit inside the living expense figure, which came from your actual withdrawals. Medicare from 2028 at published 2026 rates: Part B $202.90 a month, Part D $34.50, supplement $158, plus the surcharge where income two years earlier crossed the line, with the line rising 2.5 percent a year.

Tax. 2026 federal brackets and the $32,200 joint standard deduction, both indexed; the extra deduction at 65 and the temporary $6,000 senior deduction each through 2028, phasing out above $150,000; 85 percent of Social Security taxable; dividends and long-term gains at their lower rates. Your state at the 4.5 percent top rate effective for 2026, $10,000 of retirement income excluded each, Social Security untaxed. Required IRA withdrawals begin at 75.

Social Security. Alan deferred to 70 at $61,068, per his statement dated July 21, 2026. Ruth drawing $12,680; her full retirement amount is estimated from that pending her statement. Neither of you has earned income now or plans to.

Still moving. The 2027 discount rules are unsettled. The enhanced version lapsed January 1, 2026 and the $84,600 cliff returned, which this plan assumes. A three-year extension passed the House in January and the Senate compromise stalled. If a version passes that caps premiums as a share of income instead of cutting them off at a cliff, the whole exercise of managing income to a line disappears: you would keep the discount without constraining withdrawals, and 2026 and 2027 would be rebuilt around filling low tax brackets instead. That would be a better outcome than the one modelled here, not a worse one.

These are estimates, not predictions. Every figure moves with the assumptions above.