Surepath Retirement Services · Licensed Nationwide

Your retirement income should be engineered, not improvised.

Most people reach retirement with a solid nest egg and no plan for turning it into reliable income. I help you build a paycheck you can't outlive — coordinated across Social Security, IRAs, annuities, and your investment accounts.

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Retirement Income Specialist
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Licensed in 49 States (Except New York)
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Fiduciary. Fee-Transparent.
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Real Conversations, Not Pitches
Planning Areas

Every dimension of a complete financial plan

Retirement isn't just an investment question. It's a tax question, an income question, a protection question, and a legacy question — all at once.

Building a paycheck you can't outlive

The biggest risk in retirement isn't a bad market year — it's running out of income before you run out of life. Income planning puts structure around your Social Security, IRA and 401(k) distributions, pensions, and any guaranteed income sources so your cash flow is predictable, year in and year out.

We coordinate every income stream into a sequenced strategy — so you're spending from the right accounts at the right time, minimizing taxes and maximizing how long your money lasts.

Talk through your income plan →
Why it matters

Most people know roughly how much they have saved. Very few know exactly how much monthly income that translates to — or how long it lasts if markets underperform. That gap between savings and income is what income planning is designed to close.

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Social Security Optimization

Timing your claim — and coordinating it with a spouse — can be worth tens of thousands over your lifetime. We model every scenario.

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Distribution Sequencing

Which account do you draw from first? The order matters for taxes and longevity. We build a withdrawal sequence tailored to your situation.

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Income Gap Analysis

We calculate exactly what your guaranteed sources cover — and how much your portfolio needs to fill in, and for how long.

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Guaranteed Income Options

Income annuities can create a predictable floor of income that never runs out. We explain when and whether they make sense for you.

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Pension Coordination

If you have a pension, we factor it into your broader income picture — including lump-sum vs. annuity tradeoffs.

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Ongoing Income Reviews

As markets shift and life changes, we revisit your income strategy to make sure the plan still holds.

Keeping more of what you've earned

Taxes in retirement are one of the most overlooked planning levers. Between RMDs, Social Security taxation, Medicare IRMAA surcharges, and the step-up in basis at death, every decision you make has a tax dimension. We make sure you're planning proactively — not just reacting at tax time.

The years between retirement and age 73 are often a golden window: income is lower, tax brackets are favorable, and there's time to strategically shift assets from taxable to tax-free accounts. We help you use that window before it closes.

Explore your tax planning options →
Why it matters

Two retirees with identical savings can end up with very different after-tax income depending on how they sequence distributions, when they convert, and how they structure their accounts. Tax planning is how you close that gap in your favor.

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Roth Conversion Strategy

Converting the right amount, in the right years, can dramatically reduce your lifetime tax bill and cut future RMDs.

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RMD Planning

We plan for required minimum distributions before they start — so they don't force you into a higher bracket at the worst time.

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Medicare IRMAA Management

Income above certain thresholds triggers Medicare surcharges. We monitor your income levels to help you avoid unnecessary premium increases.

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Bracket Management

Filling your current bracket efficiently — whether through conversions, harvesting, or charitable strategies — keeps future brackets lower.

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Asset Location

Placing the right investments in taxable, tax-deferred, and Roth accounts reduces the drag taxes put on your portfolio's growth.

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Charitable Giving Strategies

QCDs, donor-advised funds, and appreciated asset donations can satisfy giving goals while reducing your taxable income.

A portfolio built for income, not just growth

The investing mindset that built your wealth isn't the same one that protects and distributes it. In retirement, sequence of returns risk — the danger of a bad market in your early withdrawal years — matters more than average returns. Your portfolio needs to be structured for both sustainability and income.

We design investment allocations that match your income timeline, your risk tolerance, and your specific account structure — not a generic model based on your age.

Review your investment strategy →
Why it matters

A retiree who experiences a 30% market decline in year two of retirement faces a very different outcome than one who experiences it in year twelve — even if average returns are identical. Investment planning in retirement is fundamentally different from accumulation, and should be treated that way.

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Retirement Allocation Design

We build allocations designed for your drawdown phase — balancing growth, stability, and liquidity for your specific income needs.

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Sequence of Returns Management

Strategies like bucketing and dynamic withdrawal help protect your plan from a bad market at the wrong time.

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Portfolio Rebalancing

We monitor and rebalance your accounts regularly to keep your risk profile aligned with your plan as markets move.

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Fee & Cost Analysis

Investment costs compound just like returns — downward. We review what you're paying and whether you're getting value for it.

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Account Consolidation

Multiple old 401(k)s and IRAs are hard to manage and often costly. We help simplify without triggering unnecessary taxes.

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Risk Tolerance Assessment

Your stated risk tolerance and your actual behavior in a down market may differ. We build plans that hold up under both.

Making sure the right people get what you intend

Estate planning isn't just for the wealthy — it's for anyone who wants to decide what happens to their money, their property, and their loved ones when they're no longer able to. Without a plan, those decisions get made by default rules you didn't write.

We work alongside estate planning attorneys to make sure your financial accounts, beneficiary designations, and legal documents are all aligned — so nothing falls through the cracks.

Start the estate planning conversation →
Why it matters

A beneficiary form on an old 401(k) overrides your will. An unreviewed trust can fail to account for new tax laws. Estate planning is as much about maintenance as it is about creating documents — and it's easy to let it slide for years without realizing how much has changed.

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Beneficiary Review

We audit every account to make sure your beneficiary designations reflect your current wishes — and don't conflict with your will.

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Trust Coordination

We work with your estate attorney to make sure accounts are properly titled and trusts are funded correctly.

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Spousal & Survivor Planning

We model income scenarios for a surviving spouse — Social Security, account access, RMDs — so nothing is left uncertain.

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Legacy & Gifting Strategies

Annual gifting, 529 contributions, and charitable vehicles can move wealth efficiently while reducing estate exposure.

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Inherited IRA Guidance

The SECURE Act changed the rules for inherited IRAs significantly. We help beneficiaries understand their options and obligations.

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Attorney Referral Network

We don't draft legal documents — but we can connect you with estate planning attorneys we trust and collaborate with them on your plan.

Protecting the plan you've worked to build

Insurance isn't the most exciting topic in financial planning — but it's often the most consequential. A single long-term care event, an unexpected death, or a serious health crisis can unravel decades of savings in a matter of years. Protection planning puts a floor under your financial plan.

We evaluate your current coverage, identify gaps, and help you make informed decisions about life insurance, health coverage, and long-term care — without overselling or overcomplicating.

Review your protection coverage →
Why it matters

The average long-term care stay costs over $100,000 per year. Most people assume Medicare covers it — it doesn't, beyond very limited short-term circumstances. Having a plan for this risk before you need it is one of the most protective things you can do for your retirement income strategy.

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Life Insurance Review

Is your current coverage still the right amount and type? We review existing policies and assess whether they still serve their intended purpose.

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Health Insurance Planning

For clients retiring before 65, bridging to Medicare is critical. We help you evaluate marketplace, COBRA, and retiree coverage options.

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Long-Term Care Planning

We walk through your options — traditional LTC policies, hybrid life/LTC products, and self-insuring strategies — so you can make an informed choice.

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Medicare Planning

Original Medicare, Advantage plans, Medigap, and Part D all interact in complicated ways. We help you navigate enrollment and coverage decisions.

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Spousal Protection

Life insurance and survivor benefit elections can protect a spouse's income if one partner dies earlier than expected. We model the tradeoffs clearly.

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Coverage Gap Analysis

We look at your full picture — what you have, what you'd need, and what it would cost you out-of-pocket without adequate protection.

Planning Tools

Run the numbers yourself

These calculators are a starting point — real planning takes more context. But they'll give you a useful first look.

Retirement Income Estimator

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Enter your numbers and click Calculate

Roth Conversion Estimator

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Enter your numbers and click Calculate

Social Security Breakeven

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Enter your numbers and click Calculate

Safe Withdrawal Rate

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Enter your numbers and click Calculate
Tax Strategy

The Roth Conversion window — and why it matters for you

For many people within 10 years of retirement, there's a limited window to move money from taxable accounts to tax-free ones. Most people miss it entirely.

A Roth conversion means moving money from a Traditional IRA or 401(k) — where it will be taxed when you withdraw it — into a Roth IRA, where it grows tax-free and you'll never owe taxes on it again. You pay the tax now, on your terms, rather than later when rates and account balances may be higher.

The strategy is especially powerful in the years between retirement and age 73 — when many people are in a lower income bracket than they were during their working years, and before Required Minimum Distributions (RMDs) begin forcing withdrawals at potentially higher tax rates.

Done correctly, a Roth conversion strategy can reduce your lifetime tax burden, lower future RMDs, protect a surviving spouse, and leave a more tax-efficient legacy for your heirs. Done at the wrong time or in the wrong amount, it can push you into a higher bracket, trigger Medicare surcharges, or create unnecessary tax liability.

Roth conversions tend to make sense when:

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You've recently retired and your taxable income has dropped — creating room to convert at a lower rate

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You have a large Traditional IRA balance that will generate significant RMDs starting at age 73

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You believe tax rates are likely to be higher in the future than they are today

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You want to leave a tax-free inheritance to your children or grandchildren

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Your current income puts you below the top of your tax bracket, leaving room to convert without jumping tiers

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You want to protect a surviving spouse from high tax rates on inherited IRA distributions

Talk Through Your Roth Strategy →
The Core Tradeoff

You pay taxes now at known rates, so you never pay them again on that money — not on the growth, not on the withdrawals, not when it passes to your heirs.

The RMD Problem

Starting at age 73, the IRS requires withdrawals from Traditional IRAs whether you need the money or not. Large RMDs can push you into a higher tax bracket, increase Medicare premiums, and make up to 85% of your Social Security taxable. Conversions now reduce that forced income later.

The SECURE Act Impact

Under current law, most non-spouse beneficiaries must fully distribute an inherited IRA within 10 years — potentially at their peak earning years. A Roth IRA passed to heirs is still tax-free under the same rules, making it a far more efficient legacy asset.

How Much to Convert

There's no single right answer. Converting too much pushes you into a higher bracket or triggers Medicare IRMAA surcharges. Converting too little leaves opportunity on the table. The goal is to fill your current bracket efficiently — year by year — over the window you have.

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Use the Roth Conversion calculator in the Tools section above to get a quick estimate of your potential conversion impact — then let's talk through whether the timing and amount makes sense for your specific situation.

How It Works

Planning that starts with listening

A retirement plan that doesn't fit your life isn't a plan — it's a document. Here's how we work together.

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A Conversation, Not a Sales Call

We start by talking about your life — what retirement looks like to you, what you're worried about, what you've already figured out. No pitch, no pressure.

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A Clear Picture of Where You Stand

We map your current accounts, income sources, and projected needs against your retirement timeline — so we both understand the gap before we talk about filling it.

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A Strategy That's Built for You

Not a product recommendation — a coordinated income plan. We put the right assets in the right places to give you predictable income, tax efficiency, and flexibility.

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Ongoing Partnership

We review your plan regularly and adjust when life or markets require it. You'll always know where your plan stands and why.

Most of my clients didn't need a radical change — they needed someone to coordinate what they already had in a way that made sense.
— Derek, Surepath Retirement Services
About

Meet the advisor behind the plan

Derek Dressler - Retirement Consultant
Derek Dressler
Retirement Consultant
B.S. Economics — ISU Licensed in 49 States 10+ Years Experience Retirement Specialist
10+ Years Experience
49 States Licensed
100s Families Served

Derek Dressler is a seasoned financial services professional with over a decade of experience in retirement planning, income planning, tax mitigation, asset protection, and legacy planning. Throughout his career, he has helped hundreds of families build confidence in their financial future through a proven, comprehensive retirement planning process.

Derek specializes in translating complex financial strategies into clear, actionable plans — built around each family's unique goals, timeline, and income needs. His clients don't just get a product recommendation; they get a coordinated plan that covers every dimension of retirement, from Social Security optimization and Roth conversions to long-term care and estate coordination.

A consistent top producer among leading financial firms nationwide, Derek has earned recognition for his expertise, client-centered approach, and commitment to putting people's outcomes ahead of transactions. He operates two offices in the southwest suburbs of Chicago and is licensed to serve clients in 49 states — bringing the same disciplined, personalized approach to families across the country.

Born and raised in central Illinois, Derek earned a Bachelor's Degree in Economics from Illinois State University. Outside the office, he is deeply invested in family and community — spending time with his four sons and two grandchildren, volunteering at his church, and cheering on local sports teams. An avid traveler with a love of the ocean, Derek brings the same curiosity and sense of adventure to his work that he brings to exploring new destinations.

"Most of my clients didn't need a radical change — they needed someone to coordinate what they already had in a way that made sense. That's what I do."

Common Questions

Things people ask before we talk

That reputation comes from the wrong products sold the wrong way. Income annuities — not variable or indexed annuities — can be straightforward, low-cost tools for guaranteeing a base of income you can't outlive. The key is using them for the right purpose, in the right amount. We'll always show you the full cost structure before recommending anything.
That's exactly why we have the first conversation. Many people are in a stronger position than they realize once we coordinate Social Security, account distributions, and any pension income. Others need a plan for maximizing what they have. Either way, knowing is better than guessing.
Absolutely — and I'd encourage it. Major financial decisions go better when both partners understand the plan and have had a chance to ask their own questions. I'm happy to schedule a meeting that works for both of you, at whatever pace feels comfortable.
I'm transparent about compensation from the start. Depending on the services and products involved, I may earn a commission, charge a planning fee, or both. I'll explain exactly how I'm compensated before we do any business together — no surprises.
For many people in the years between retirement and age 73 (when RMDs begin), there's a window where converting a portion of your IRA to Roth makes a lot of sense. The right answer depends on your current and future tax brackets, your timeline, and your legacy goals. The calculator above gives you a rough idea — a conversation fills in the rest.
Then our first conversation will feel low-stakes — because it is. I'll explain everything in plain language, won't assume any prior knowledge, and won't push you toward anything before we've both had a chance to make sure it's a good fit. Many of my clients came to me having managed everything themselves for years. That's a strength, not a gap.
Let's Talk

A 30-minute call costs you nothing. A bad retirement plan costs a lot more.

Tell me a little about where you are and what you're working toward. I'll reach out within one business day.

🔒 I only use your contact info to follow up. Nothing else.