Choosing a Retirement Planning Firm in the Chicago Suburbs

Start with registration

Before anything subjective, there is a body of public record. FINRA BrokerCheck shows how long an individual has been registered, in what capacity, which firms they have been with, and whether there are any disclosure events. The SEC adviser search covers the advisory side. Both are free and take a few minutes.

Read what is there rather than only checking that something comes up. A long history in one place tells you something different from a series of short stops. A disclosure event is not automatically disqualifying, but it is a thing to ask about directly rather than discover later.

Do this first because it costs nothing and because everything after it is comparatively soft. Marketing is written to be persuasive. The registration record is not written to be anything.

Then compensation

Compensation is where the language gets slipperiest, so it is worth being concrete about what the terms actually mean.

A registered representative of a broker-dealer receives transaction-based compensation, meaning commissions, on the products they place. An investment adviser representative receives fees for advisory services, commonly calculated on assets advised. Many professionals are registered in both capacities and can offer both kinds of service, and in that case fee-based is the accurate description of the practice. Fee-only describes a practice compensated solely by client-paid fees with no transaction-based compensation at all.

None of those three is inherently better than the others, and treating one as a mark of virtue is a mistake. Each creates a different set of incentives, all of which are disclosed. A commission on a product creates an incentive to place that product. A fee on assets creates an incentive toward keeping assets under management rather than, say, paying down a mortgage. A flat fee creates an incentive toward efficiency. What matters is that you can see the arrangement clearly and weigh it.

So ask for it itemized by service line rather than summarized, and read the ADV Part 2A, which sets out advisory services, fees, and conflicts of interest in plain language. The test is whether you can state in one sentence how the firm makes money from each part of your plan.

Which standard applies

Fiduciary is used loosely in marketing, so it is worth separating the regulatory picture from the sales pitch. Different regimes govern different parts of a single relationship, and a professional can be entirely straightforward while operating under more than one of them.

A firm can carry a fiduciary duty on its advisory work and operate under a different standard on other service lines. Ask which of its services carry which duty, and ask for the answer in writing.

Four practice structures

Beyond registration and compensation, the practical question is who you will be working with. Practices across the Chicago suburbs generally fall into one of four shapes, and each has a genuine trade-off rather than a right answer.

• Founder-led practice. You work with the principal throughout. Continuity and accountability are high, and the constraint is capacity, so ask what happens when the principal is unavailable and what the succession arrangement is.
• Team practice. A lead advisor with associates handling day-to-day work. Depth of coverage is better and the risk is that you rarely speak to the person you hired, so ask which conversations involve the lead.
• Institutional platform. An advisor supported by a large firm's research and service infrastructure. Resources are extensive and the relationship is with an individual inside a larger system, so ask what happens if that individual moves.
• Project or hourly planner. Engaged for a defined piece of work, often without ongoing management. Cost is predictable and implementation stays with you, so ask precisely what is included.

Which fits depends on how complex your situation is, how much contact you want, and whether you intend to implement the plan yourself.

What credentials mean

The CFP® certification is administered by the CFP Board and requires education, examination, an experience requirement, and adherence to a code of ethics and standards of conduct, including a commitment to act as a fiduciary when providing financial advice. It is a meaningful signal about training and accountability. It is not a guarantee about any particular piece of advice, and it does not by itself tell you how a professional is compensated.

Other designations point at specific specializations. RICP® focuses on retirement income, RMA® on managing assets through the distribution phase, and a CPA brings tax expertise from a different direction. Any of them can be verified with the organization that issues it, and a designation that cannot be confirmed there is worth a direct question.

Be wary of comparing designation counts, which get quoted as percentages without much rigour. The useful version of the question is not how rare a credential is but whether the person holding it does this specific kind of work regularly.

The written plan

Of everything in this article, the written plan is the most useful single filter, because unlike philosophy or rapport it either exists or it does not.

A written retirement income plan should set out where each year's income comes from, in what order accounts are drawn down, how Social Security is being handled and why, what the plan assumes, and what would cause it to change. Ask to see the structure of one with the client details removed. A firm that produces them will have one to hand. A firm that describes its process in conversation but has nothing to show is telling you something.

Ask also what happens to the plan afterward. A document produced once and never revisited stops describing reality fairly quickly, since tax rules change annually and so do circumstances. A stated review cadence, and a clear trigger for an off-cycle review, is worth more than the initial document.

Why local matters here

Illinois has enough state-specific texture that familiarity is worth something. The state does not tax Social Security benefits, and distributions from IRAs, 401(k) plans, and most qualified pensions are excluded from Illinois income tax as well. That exclusion changes the sequencing arithmetic relative to states that tax retirement income.

Property tax runs the other way, and Cook County bills are among the higher ones nationally. For a retiree in a paid-off house it can be the largest fixed cost in the plan, and the available exemptions, including the senior exemption and the senior assessment freeze where income limits are met, are worth confirming rather than assuming.

Illinois also levies its own estate tax, with an exemption well below the federal one and not indexed for inflation. A long-held home in the south or southwest suburbs plus retirement accounts and life insurance can carry an estate past the state threshold while remaining clear of the federal one. Ask whether a prospective firm raises this without being prompted. It is a reasonable proxy for whether they work with Illinois households regularly.

Questions and red flags

These are the questions that tend to separate a practice from its marketing.

• Which of your services carry a fiduciary duty and which do not? Please put that in writing.
• How are you compensated on each service line, itemized rather than summarized?
• Will I receive a written income plan, and can I see the structure of one?
• Who will I actually be working with, and how often will we meet?
• How do you decide the order of withdrawals, and what changes it?
• How do you coordinate with my CPA and my estate attorney?
• What is your review cadence once the plan is delivered?

And the things worth slowing down for. A specific product recommended before a written plan exists, particularly one with a surrender period. A reluctance to put compensation or fiduciary status in writing. A withdrawal approach asserted with no modeling behind it. Language that implies upside without downside. Tax coordination treated as somebody else's problem. None of these is proof of anything alone, and each is a reason to ask one more question.

This practice is founder-led and based in Palos Heights, serving Chicago's south and southwest suburbs, and Richard Casolari has spent roughly fifty years in financial services. Clients work with him directly. The work coordinates retirement income planning, investment management with a documented buy and sell discipline, tax-aware withdrawal sequencing in coordination with your CPA, and protection planning through licensed affiliates, into one written plan. Fees, charges and expenses are detailed in the ADV Part 2A.