Downsizing and Home Transition Guidance for Families in Chicago
Helping families make thoughtful decisions about long-held homes—whether planning to downsize, age in place, or navigate what comes next.
The Kitchen Table Advisory helps families slow down, consider their options, and move forward with clarity.
A long-held home carries history, responsibility, and often uncertainty. Whether you are wondering if it’s time to downsize, adapt your home for the years ahead, or begin the process of letting go, the path forward is rarely simple. These decisions affect finances, family dynamics, and the future. They deserve thoughtful conversation, not pressure. The Kitchen Table Advisory offers a place to talk through the options, ask questions, and create a clear path forward.
There is no urgency here—just a seat at the table, thoughtful guidance, and a plan for what comes next.
The Kitchen Table Advisory Services
For many families, this work represents decades of belongings, meaningful financial decisions, and complex family conversations. Structured guidance can make the process far more manageable.
If you decide to continue working together, the consultation fee is applied toward a guided session package.
A starting point for families who want clarity before making decisions.
90-minute in-home or virtual consultation
Walkthrough of the home
Discussion of priorities
Three 4-hour on-site sessions
Guided Four Path Planning™ sessions
Comparative home market analysis
Vendor scheduling
One-week follow-up call
Five 4-hour on-site sessions
Guided Four Path Planning™ sessions
Comparative home market analysis
Vendor scheduling
One-week follow-up call
Who This Is For
The Kitchen Table Advisory is designed for families beginning to think about what comes next for a long-held home. Often the home has been in the family for decades. Belongings have accumulated over time, and the decisions ahead can feel both practical and deeply personal.
Families typically reach out when they are:
wondering whether it’s time to downsize
helping a parent think about the future
beginning to sort through a lifetime of belongings
preparing for an eventual transition but unsure where to begin
feeling overwhelmed by the number of decisions involved
The work is not about rushing decisions. It is about creating a thoughtful process so families can move forward with clarity and confidence.
About the Founder
The Kitchen Table Advisory was created to provide the kind of thoughtful guidance many families wish existed when facing decisions about a long-held home. Living in Chicago’s West Town neighborhood, the founder experienced firsthand how complicated it can be to sort through a home filled with decades of belongings and decisions about what comes next. What began as a personal challenge became a structured approach designed to help other families move through the same process with more clarity and less stress.
Sometimes the most important decisions about a home happen around a kitchen table.
The Kitchen Table Advisory Guides
For families working independently or located outside Chicago, these guides share several of the planning tools used during the Kitchen Table Consultation.
A Structured Framework for Informed Home Selling
Selling a home is more than just a transaction; it is a significant life decision that should be made with absolute clarity. Often, homeowners are presented with vast amounts of market data from different real estate agents, making it difficult to find the common thread or identify the most realistic path forward.
This CMA is a premium, 15-page advisory framework designed to help you plan with confidence. This document provides a side-by-side structure that allows you to transpose data from two independent real estate agents, giving you an "apples-to-apples" look at their conclusions and strategies.
How it Works:
Upon purchase, you will receive a secure link to download your digital PDF. You can then manually transpose the data provided by your prospective agents into this structured layout to reveal the most accurate market picture.
Note: If you prefer professional assistance with this process, you may book a Guided Session where The Kitchen Table Advisory will complete this analysis for you.
Three 4-hour on-site sessions
Guided Four Path Planning™ sessions
Comparative home market analysis
Vendor scheduling
One-week follow-up call
Five 4-hour on-site sessions
Guided Four Path Planning™ sessions
Comparative home market analysis
Vendor scheduling
One-week follow-up call
Questions Families Often Ask
Do we have to be ready to move to begin?
No. Many families begin simply because they want to understand their options.Will we be pressured to make decisions quickly?
No. The purpose of the advisory is to create clarity, not urgency.What if our family does not agree on what to do?
That is very common. The process helps families talk through options thoughtfully.What if we are unsure whether we need ongoing support?
That is exactly why many families begin with the consultation.