Retirement Planning Questions, Answered
These are the questions we hear most from clients and prospective clients across Fond du Lac, Dodge, and Columbia Counties. If you don’t see your question here, just ask — we’re happy to talk through it.
CATEGORY 1 – Getting Started
For people who are just beginning to think seriously about retirement
1. How do I know if I’m on track to retire?
It comes down to three things: what you’ll need to spend in retirement, what income sources you’ll have, and whether the gap between them is covered by your savings. Most people have a rough sense of their account balances but have never actually run the projection. That’s usually the first thing we do — map out your real income picture and stress-test it against inflation, healthcare costs, and how long the money needs to last.
→ Run the numbers: Retirement Income Projector
⤓ Guide
2. When should I start working with a financial advisor?
There’s no single right time. The years leading up to retirement are when the decisions carry the most weight — there’s still room to increase savings, do Roth conversions in lower-income years, reposition risk, or change your timeline. If you’re already retired, the work shifts to withdrawal sequencing, tax management, and making the money last, which matters just as much. The honest answer is that it’s rarely too early and never too late.
⤓ Guide
3. How much do I need saved to retire comfortably?
There’s no universal number — it depends entirely on what you plan to spend. A common rule of thumb suggests you’ll need 70–80% of your pre-retirement income, but that varies widely. Someone with a paid-off house in Waupun and modest travel plans needs a very different number than someone planning extensive travel or supporting family. We build the number from your actual expenses, not a generic formula.
→ Run the numbers: How Long Will My Savings Last?
4. Should I pay off my mortgage or save more for retirement?
For most people the honest answer is both, in a particular order. Contribute at least enough to your workplace plan to capture the full employer match first — that is an immediate return no mortgage payoff can match. After that, it becomes a real comparison: your mortgage rate against what the money could reasonably earn invested, with taxes accounted for on both sides. A 3% mortgage and a 6.5% mortgage lead to genuinely different answers. But the math isn’t the whole decision. Walking into retirement without a mortgage payment lowers the income you need every year for the rest of your life, which means smaller withdrawals, which can keep you in a lower tax bracket and under the Medicare surcharge thresholds. That compounding effect is worth more than the interest rate comparison alone suggests. The one thing we’d caution against is emptying a retirement account to clear the balance in a single move — that withdrawal is taxable income, and it can cost more in one year than the mortgage would have cost over ten.
→ Compare the options: Mortgage Payoff Before Retirement
5. What’s the difference between a financial advisor and an insurance agent?
Insurance agents help you protect against risk — life, health, property. Financial advisors help you build and manage assets toward long-term goals. At SIA, we do both under one roof, which means your retirement plan and your protection coverage can be coordinated rather than managed by two firms that never talk to each other.
CATEGORY 2 – IRAS, Rollovers & Contributions
The mechanics of moving and contributing money
6. What is the 2026 contribution limit for Traditional and Roth IRAs?
$7,500 if you’re under age 50, and $8,600 if you’re age 50 or older (that includes the $1,100 catch-up contribution). You can’t contribute more than your total taxable compensation for the year, and the limit applies across all your IRA accounts combined — not per account.
7. What is the difference between a Roth IRA and a Traditional IRA?
The core difference is tax timing. A Traditional IRA gives you a tax deduction now but taxes your withdrawals in retirement. A Roth IRA taxes your money now, but all growth and qualified withdrawals come out completely tax-free. Which one makes more sense depends largely on whether you expect to be in a higher or lower tax bracket in retirement than you are today.
⤓ Guide
8. What is the “one-rollover-per-year” rule?
You’re only allowed one indirect IRA rollover per 12-month period. The good news: direct trustee-to-trustee transfers and Roth conversions do not count against this limit. This is one of the main reasons we recommend direct transfers whenever possible — they avoid the limit entirely and eliminate the risk of a missed deadline.
9. What is the 60-day rule?
If you take a distribution and handle the rollover yourself rather than doing a direct transfer, you have 60 days to deposit those funds into the new IRA. Miss the deadline and the entire amount becomes taxable income — plus a potential 10% penalty if you’re under 59½. Direct transfers avoid this risk completely, which is why we almost always recommend them.
10. What funds can I roll over into my employer’s 401(k) plan?
You can generally roll over funds from most pre-tax and Roth employer-sponsored retirement plans, as well as Traditional IRAs, into your current employer’s 401(k) — provided your specific plan allows it. Not every plan accepts incoming rollovers, so the first step is always checking your plan document or asking your HR department.
11. I have a 401(k) from an old employer. What should I do with it?
You generally have four options: leave it where it is, roll it into your current employer’s plan, roll it into an IRA, or cash it out (rarely a good idea — taxes plus penalties). The right answer depends on the investment options and fees in each plan, whether you want consolidated management, and your creditor protection needs. This is one of the most common things we help people sort out.
⤓ Guides: Employer Plan Options (PDF) · 401(k) Withdrawal Options (PDF)
12. Can I contribute to an IRA if I’m already in a 401(k) at work?
Yes. The IRA limit is entirely separate from your workplace plan limit. However, if you or your spouse is covered by a workplace plan, your ability to deduct Traditional IRA contributions phases out at certain income levels. Roth IRA contributions have their own separate income limits. We can walk through where you fall.
CATEGORY 3 – Retirement Income & Withdrawals
Turning savings into a paycheck
13. How do I turn my savings into reliable retirement income?
This is a genuinely different problem than building a portfolio, and most people haven’t had to solve it before. It typically involves layering income sources — Social Security, any pension, portfolio withdrawals, and sometimes annuity income — so that your essential expenses are covered by predictable sources and your discretionary spending comes from more flexible ones. The sequencing matters as much as the total.
→ Run the numbers: Retirement Income Projector
→ And then: How Long Will My Savings Last?
14. What is the 4% rule and does it still work?
The 4% rule suggests you can withdraw 4% of your portfolio in year one and adjust for inflation each year after, with a reasonable probability of the money lasting 30 years. It’s a useful starting reference point, but it was built on historical assumptions that may not hold. We treat it as a sanity check, not a plan — your actual sustainable withdrawal rate depends on your timeline, allocation, other income sources, and flexibility.
→ Test it yourself: How Long Will My Savings Last?
15. How much risk should I have in my portfolio as I approach retirement?
Less than you probably had in your 40s, but likely more than you’d guess. The bigger issue is usually the gap between how much risk you’re actually carrying and how much you’re comfortable with — most pre-retirees don’t know their real number. We use Nitrogen to score both and see whether they match. After a long stretch of strong markets, a lot of people are carrying significantly more risk than they realize.
16. What is sequence of returns risk?
It’s the risk that poor market returns early in retirement — when you’re first starting to withdraw — do permanent damage to your portfolio, even if average returns over your full retirement are fine. Two people with identical average returns can have very different outcomes based purely on the order those returns arrive. It’s one of the main reasons we look at income structure, not just total assets.
CATEGORY 4 – Taxes in Retirement
RMDs, Roth conversions, and tax-efficient withdrawals
17. What is a Required Minimum Distribution (RMD) and when do I have to start?
An RMD is the minimum amount the IRS requires you to withdraw each year from most tax-deferred accounts — Traditional IRAs, 401(k)s, 403(b)s. Because those accounts grew tax-deferred, RMDs are how the IRS eventually collects. Your starting age depends on your birth year: if you were born in 1959 or earlier, it’s age 73. If you were born in 1960 or later, it’s age 75.
First RMD deadline: April 1 of the year after you reach your RMD age. Every year after that: December 31.
Note: delaying your first RMD to April 1 means taking two RMDs in the same calendar year, which can push you into a higher bracket. Worth planning around.
→ Calculate yours: Required Minimum Distribution Calculator
⤓ Guide: RMDs (PDF)
18. Should I do a Roth conversion before I retire?
Often, yes — but timing matters enormously. The years between when you stop working and when RMDs begin are frequently the lowest-income years of your life, which makes them the best window for converting at a lower tax rate. The key is converting enough to fill up a lower bracket without spilling into a higher one, and watching for IRMAA thresholds that affect your Medicare premiums. We model this specifically for each client.
→ Model a conversion: Roth Conversion Advisor — married and single-filer versions
⤓ Guide: Roth Conversions (PDF)
19. What is IRMAA and why does it matter?
IRMAA (Income-Related Monthly Adjustment Amount) is a surcharge on your Medicare Part B and Part D premiums that kicks in above certain income thresholds. It’s based on your tax return from two years prior, and it operates on cliffs — going $1 over a threshold can cost you meaningfully more for a full year. This is a major consideration in Roth conversion planning once you’re near 63.
→ Check your thresholds: Medicare IRMAA Surcharge Calculator
⤓ Guide: Medicare & IRMAA (PDF)
20. What do I do about health insurance if I retire before 65?
This is the expense people underestimate most, and it’s the reason a lot of retirements get delayed a year or two. Until Medicare starts at 65, you generally have three options: COBRA from your former employer, which is usually the most expensive and runs out; coverage through a spouse’s plan, if that’s available to you; or a marketplace plan under the ACA, which is where most early retirees end up. The part worth understanding is that ACA premium tax credits are based on your income — and once you’ve stopped working, your income is largely something you control. Two people with identical savings can pay very different premiums depending on how they draw money. That creates a real tension: the years before Medicare are also the best window for Roth conversions, and a conversion that saves you tax later can cost you subsidy dollars now. We look at both sides together rather than one at a time. SIA also has ACA and individual health specialists in this office, so the coverage question and the income question get answered by people who talk to each other.
→ Estimate the cost: ACA Healthcare Bridge Calculator
- What is a Qualified Charitable Distribution (QCD)?
A QCD lets you donate directly from your IRA to a qualified charity once you’re 70½ or older. The distribution counts toward your RMD but is excluded from your taxable income entirely — which is often better than taking the distribution and claiming a charitable deduction, especially if you take the standard deduction. For clients who give regularly, this is one of the most underused strategies out there.
- In what order should I withdraw from my accounts in retirement?
The conventional sequence is taxable accounts first, then tax-deferred, then Roth last — but that’s a starting point, not a rule. The better approach often involves blending withdrawals across account types to manage your tax bracket year by year, especially before RMDs begin. Getting this right can meaningfully reduce your lifetime tax bill.
→ See where your income lands: Federal Tax Bracket Visualizer
⤓ Guide: Withdrawal Sequencing (PDF)
CATEGORY 5 – Social Security
Timing and strategy
- When should I claim Social Security?
It’s one of the most consequential decisions most people make, and there’s no single right answer. Claiming at 62 gives you a permanently reduced benefit; waiting until 70 gives you roughly 8% more per year of delay. The right choice depends on your health, your spouse’s benefit and age, whether you’re still working, if you’re eligible for a deceased spouse’s Social Security benefit, and what other income you have available to bridge the gap. We model the scenarios so you can see the numbers.
→ Compare claiming ages: Social Security Claiming Optimizer
⤓ Guide: Claiming Social Security (PDF)
24. Will my Social Security be taxed?
Possibly — it depends on your provisional income, which is your other income plus half your Social Security benefit. Depending on where you land relative to the IRS thresholds, anywhere from 0% to 85% of your benefit may be taxable. This is one reason withdrawal sequencing matters so much: pulling from the wrong account in the wrong year can inadvertently make more of your Social Security taxable.
→ See the interaction: Capital Gains Tax Calculator
25. Can I claim spousal benefits and switch to my own later?
Under current rules, no. Deemed filing means that when you file, Social Security calculates both your own benefit and any spousal benefit and pays you accordingly — you don’t get to pick one and save the other for later. The restricted application strategy that allowed this was eliminated for anyone born after January 1, 1954.
CATEGORY 6 – Annuities
Guaranteed income and how the different types work
26. What are the different types of annuities?
Annuities split along two lines, and the differences matter far more than the label does. The first is timing: an immediate annuity starts paying you income right away, while a deferred annuity grows first and pays out later. The second is how the money grows. A fixed annuity credits a set interest rate for a defined term, with no market exposure. A fixed-indexed annuity credits interest tied to a market index, with a floor that protects you in a down year and a cap that limits what you earn in a good one. A variable annuity invests directly in market subaccounts, so the value rises and falls with no floor underneath it. Each type carries its own fee structure, surrender schedule, and trade-offs. None is better than the others in the abstract — what matters is which problem you’re trying to solve.
⤓ Guides: Annuity Basics (PDF) · 1035 Exchanges (PDF)
27. What is a fixed annuity and is it right for me?
A fixed annuity guarantees a set interest rate for a defined period — no market exposure. They work best for money you won’t need to touch during the term, when you want guaranteed growth or a predictable income floor for essential expenses. They’re not right for everyone, and the headline rate isn’t the whole story — carrier strength, surrender period, and withdrawal provisions all matter. We compare options across the A-rated carriers we work with rather than pushing a single product, and we post current rates on our fixed annuity rates page so you can see where the market actually is before we ever talk.
→ Current rates: Fixed Annuity Rates page
28. Should I consider an income annuity?
It comes down to whether there’s a gap between your guaranteed income and your essential expenses. Add up Social Security and any pension, then compare that to what it actually costs to run your household each month. If those sources already cover the basics, you may not need one at all. If there’s a shortfall, an income annuity is one way to close it with a payment that arrives every month for life, regardless of what markets do. The trade-off is real: you’re generally exchanging a lump sum for that income stream, which means giving up access to the principal and the growth it might have produced. That’s why we tend to look at covering the gap rather than annuitizing everything. It makes the most sense for people without a pension, people worried about outliving their money, or anyone who wants a floor under their essential expenses so a bad market year doesn’t affect whether the bills get paid.
CATEGORY 7 – Life Insurance & Long-Term Care
Coverage, how much, and planning for care later on
29. What is the difference between term and whole life insurance?
Term life provides temporary coverage for a specific period — typically 10 to 30 years — with a death benefit only. Whole life provides lifelong coverage and includes a cash value component that builds over time. Term is significantly cheaper upfront; whole life costs considerably more but functions as a permanent asset. Which fits depends on what you’re actually trying to protect against and for how long.
30. How much life insurance do I need?
Rules of thumb like ten times your income are a starting point, not an answer. The real number comes from adding up what your family would actually need — replacing your income for as long as they’d depend on it, paying off the mortgage and other debts, covering final expenses, and funding education if that’s part of the picture — and then subtracting what’s already in place: existing policies, group coverage through work, savings, and Social Security survivor benefits. The gap between those two numbers is your actual need. It also changes over time. The coverage that made sense with young children and a new mortgage is often more than you need once the house is paid off and the kids are grown. We run this calculation with clients regularly, and the calculator on our site walks through the same steps if you’d like to see the math yourself first.
→ Work out your number: How Much Life Insurance Do I Need?
31. Do I still need life insurance in retirement?
Sometimes, sometimes not. If your mortgage is paid off and your spouse is fully provided for by your retirement assets and Social Security survivor benefits, the need may have passed. But life insurance can still play a role in estate planning, covering final expenses, replacing pension income that stops at death, or leaving a legacy. It’s worth reviewing rather than assuming either way.
32. Should I plan for long-term care, and how?
Most people will need some form of long-term care eventually, and it is the largest uninsured risk sitting in most retirement plans. The part that surprises almost everyone is that Medicare does not cover extended custodial care — the help with bathing, dressing, and daily living that makes up the bulk of what long-term care actually is. Medicaid does cover it, but only after you have spent down most of your assets. That leaves three realistic approaches: self-funding by earmarking part of your portfolio, traditional long-term care insurance, or a hybrid life insurance policy with a long-term care rider, which pays a death benefit if you never end up needing the care. Which one fits depends on your asset level, your health, and how much of the risk you are willing to carry yourself. Timing matters more here than in most planning decisions — premiums climb steeply with age and a single health event can make you uninsurable, so this is a conversation for your fifties or early sixties rather than after something happens.
⤓ Guide: Long-Term Care Planning (PDF)
CATEGORY 8 – Working With Us
Process, fees, and what to expect
33. How do you get paid?
Depending on the type of account and service, we’re compensated through advisory fees, commissions, hourly fees, or a combination of these. We’ll walk you through exactly how compensation works for your specific situation before you commit to anything — and it’s outlined in our Form CRS, which you can review any time.
34. What happens in the first meeting, and is there a cost?
There’s no cost and no obligation. The first conversation is about understanding where you stand and whether we’re a good fit for each other. We’ll talk through what you have, what you’re hoping for, and what questions are on your mind. It usually takes about an hour — by phone, video, or in person at our office in Waupun. Most people leave with at least one thing they didn’t know before.
35. Do you have an account minimum?
No. We do not set a minimum account size, and we would rather have the conversation than turn someone away over a number. Some of the people we work with are repositioning a seven-figure rollover. Others are five years out with a 401(k), a pension, and a question about whether the math actually works. What matters more than the balance is whether the planning is genuinely useful to you, and that is something an hour will tell both of us at no cost.
- What happens to my accounts if something happens to my advisor?
You are not tied to one person. SIA has multiple licensed advisors, and your accounts, your plan, and the history behind both are held at the firm rather than by an individual. If someone is out — on vacation or unexpectedly — another advisor here can pull up your situation and pick up the conversation without you starting over. That is a large part of why we work on plans together rather than in separate corners. The firm has been locally owned and operated in Waupun since 1925 and has handled its own transitions before, so continuity is something we plan for rather than sort out after the fact.
CATEGORY 9 – Family, Legacy & Life Events
Planning for the people who depend on you
37. We just got married. What should we be doing financially?
Start with beneficiary designations on retirement accounts and life insurance, because those override your will. A former partner or a parent listed as a named beneficiary years ago will inherit regardless of what any other document says, and this is the single most common thing newly married couples leave undone. From there it is a practical list: deciding what to combine and what to keep separate, coordinating employer benefits so you are not paying twice for overlapping coverage, comparing health plans at the next open enrollment, and reviewing your tax withholding, since filing jointly often changes what you owe. If either of you brought debt or property into the marriage, being explicit now about how you will handle it prevents a harder conversation later. Most of this is an afternoon of work that saves years of confusion.
⤓ Guide: Newlywed Financial Checklist (PDF)
38. What’s the best way to start investing for my kids or grandkids?
There’s no single best account — it depends on what the money is for and who should control it. A 529 plan is the go-to if the goal is education, with tax-free growth and even a path to roll leftover funds into a Roth IRA. A custodial UTMA/UGMA account offers no restrictions on how the money’s used, but the child gains full control at 18–21 and it can affect financial aid. If your child or grandchild has earned income, a custodial Roth IRA lets even small contributions compound tax-free for decades. Families with young children may also want to look at the new Trump Account, which includes a one-time $1,000 federal deposit for kids born 2025–2028. Most families end up using a combination, matched to their goals and timeline — that’s usually the first task we sort out together.
⤓ Guide: Investing for Kids (PDF)
39. What are the first financial steps to take after losing a spouse?
Not a lot has to be decided in the first month — the early weeks are about paperwork and keeping bills current, rather than about the big decisions. Order certified death certificates, locate the will and any insurance policies, and don’t rush to close joint accounts. Over the following month or two, you’ll file life insurance and Social Security survivor claims and notify pension or annuity carriers, keeping a log of every call. Big, hard-to-undo choices — selling the house, investing a large payout, gifting to family — are almost always fine to wait a year on so that you can focus on creating stable ground. One thing worth planning ahead for: your tax filing status typically shifts within a year or two, and that “widow’s penalty” is where a little advance planning can save real money. We regularly help clients through this exact process, and you don’t have to sort it out alone.
⤓ Guide: Losing a Spouse Checklist (PDF)
40. Do I need a trust, or is a will enough?
For most people, a will and up-to-date beneficiary designations do the job — a trust earns its cost in specific situations, not by default. It’s worth considering if you own real estate in more than one state, have a beneficiary with special needs, have minor or young heirs, want distributions staged out rather than paid as a lump sum, or you’re blending a family and want more control over who gets what. Wisconsin also allows transfer-on-death deeds for real estate and has no state estate or inheritance tax, which covers the single most common reason people look into a trust in the first place. If a trust does make sense, the real work is funding it — retitling your home, brokerage accounts, and business interests into the trust’s name, since an unfunded trust accomplishes nothing. Retirement accounts and life insurance are the exception; those pass by beneficiary designation and usually shouldn’t be retitled into a trust. We can walk through whether a will, a trust, or both fit your situation.
⤓ Guides: Trusts: Do You Need One? (PDF) · Estate Planning Basics (PDF)
Don’t see your question here? Every situation is different, and the questions that matter most are usually the ones specific to your circumstances. Give us a call or schedule a conversation — no cost, no obligation.
Call us: (920) 324-4324 | 999 West Main Street, Waupun, WI 53963
Last reviewed: August 2026. The information on this page is general in nature and should not be considered tax or legal advice. Contribution limits, tax thresholds, and retirement account rules change periodically. Consult your tax professional regarding your specific situation.