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Insights

Retirement questions, answered plainly

Notes on the decisions that come up in the three years either side of a retirement date.

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Latest

For the decisions in front of you

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Medicare

Medicare Late Enrollment Penalties and IRMAA Appeals

Two of the three penalties last for life, and COBRA does not protect you from them. Plus the form that fixes a retirement-year surcharge.

· 8 min Read →
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Estate

The Illinois Estate Tax: What Retirees Should Know

A threshold that does not move, that a spouse cannot inherit, and that many estates cross without owing anything federally.

· 8 min Read →
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Social Security

Social Security Claiming Decisions for Married Couples

The higher earner's claiming age sets the survivor's income. Why couples usually need two claiming ages, not one.

· 9 min Read →
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Medicare

Medicare Supplement Planning Before You Retire

The plan letters are standardized. The window you get to choose one in is not, and it closes on a schedule.

· 8 min Read →
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Portfolio

How Investment Management Changes When You Retire

Same average return, different order, different outcome. Diversification does not address the order.

· 9 min Read →
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Taxes

Required Minimum Distributions: Timing and Tax Options

Your start age depends on the year you were born, and the first distribution has its own deadline.

· 8 min Read →
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Credentials

Find a CFP® in the Chicago Suburbs for a 30-Year Retirement

The mark tells you what someone studied. Practice type tells you whether they have run money through a thirty-year drawdown.

· 9 min Read →
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Practice Model

Retirement Advisor: Income, Medicare, and Investments

Three areas, three regulatory regimes, and no single license that covers all of them. What "all in one place" actually means.

· 8 min Read →
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Compensation

Fee-Based Financial Advisors in Chicago for Retirees

Fee-based and fee-only are one syllable apart. Item 5 of the Form ADV Part 2A settles which one you are dealing with.

· 9 min Read →
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Planning Horizon

Five Years From Retirement: What You Can Still Change

Contribution room, the conversion runway, the pension election, and the cash buffer each close on their own schedule.

· 8 min Read →
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Working Together

Working Directly With Your Advisor: What Continuity Means

What direct access to a principal actually covers, and the succession question a small practice should be able to answer.

· 8 min Read →
Due Diligence

How to Verify a Financial Advisor's Credentials

BrokerCheck, the SEC adviser database, designation directories, and Form ADV Part 2A. About twenty minutes, start to finish.

· 7 min Read →
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Retirement Income

Retirement Income Planning for Chicago Near-Retirees

What changes in the last two years before a retirement date, and how to tell whether a planner has actually done this work before.

· 9 min Read →
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Choosing an Advisor

Choosing a Retirement Planning Firm in the Chicago Suburbs

Registration, compensation, access, and what a firm will put in writing. The four things worth checking before you engage anyone.

· 9 min Read →
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Coordinated Planning

Coordinating Income, Medicare, and Investments

A withdrawal decision is also a Medicare decision two years later. Why these three stop being separate once you retire.

· 8 min Read →

The material on this page is for informational purposes only and is not individualized investment, tax, or legal advice, or a recommendation to buy or sell any security or insurance product. Consult your CPA or attorney before acting on anything described here.

Tax rules, Medicare premium tiers, and enrollment deadlines change and are indexed annually. Confirm current-year figures with a qualified professional.

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Have a question these do not answer?

Schedule a Retirement Readiness Review and we will work through it against your own numbers rather than the general case.

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Richard Casolari, CFP, in a navy suit and striped tie against a dark studio background

About the Author

Richard Casolari, CFP®

Founder, Advanced Financial Concepts · Palos Heights, Illinois

Richard Casolari is a CERTIFIED FINANCIAL PLANNER™ professional and the founder of a retirement income planning practice in Palos Heights, Illinois. He has spent roughly fifty years in financial services, working with pre-retirees and retirees across Chicago's south and southwest suburbs.

The work coordinates retirement income planning, investment management, tax-aware withdrawal sequencing in coordination with your CPA, Medicare enrollment and supplement timing, and protection planning through licensed affiliates, into a single coordinated approach that is reviewed on a schedule. Securities are offered through Cetera Wealth Services, LLC, member FINRA/SIPC. Advisory services are offered through Cetera Investment Advisers LLC, a registered investment adviser. The registration history behind that work is public on FINRA BrokerCheck, CRD #42779.

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