Your Chicago next chapter is closer than you think, and it probably looks nothing like what you imagined five years ago. Life has a way of shifting priorities. The home that felt perfect at 45 might feel like too much at 60. The neighborhood you loved for its school district might not be what you need now. So before you make any decisions, it helps to understand what you actually want from this next stage. Take this quiz and find out what your next chapter style really is. Whether you are brand new to the idea or have been thinking about your Chicago next chapter for a while, your answers will point you in the right direction.
Answer each question honestly. There are no wrong answers. At the end, add up your letters and find your result.
Question 1: When you picture your ideal morning five years from now, what does it look like?
A. Coffee on the porch of a smaller, easier-to-manage home with a garden I can actually keep up with. B. Walking to a cafe in a walkable neighborhood, running into neighbors I know by name. C. Waking up in a completely different city, state, or even country, fully untethered. D. Honestly, I just want mornings that feel less stressful than they do right now.
Question 2: What does your current home feel like most days?
A. Like it’s asking more of me than I have to give: maintenance, space, upkeep. B. Like it’s in the wrong place. I want to be closer to people, activity, and life. C. Like a starting point. I have always wanted to live somewhere completely different. D. Like home, but I know something needs to change. I just have not figured out what yet.
Question 3: When you think about the next move, what feels most important?
A. Simplifying. Less stuff, less space, less to manage. More time for what matters. B. Community. Being around people, having walkable amenities, feeling connected. C. Freedom. No ties, no obligations, just the ability to go wherever life takes me. D. Security. Knowing my finances are solid and my next step is the right one.
Question 4: How do you feel about your current neighborhood?
A. I have outgrown it. My needs have changed, and it no longer fits my life. B. I like it, but I wish it had more going on. More restaurants, more people, more energy. C. It feels too settled. Part of me wants something completely new and different. D. I actually love it. If I move, staying nearby would feel right.
Question 5: What would make you feel most confident about making a move?
A. A clear financial picture and a straightforward plan with no surprises. B. Knowing exactly which neighborhood fits my lifestyle and getting there efficiently. C. Permission to be bold. Knowing it is okay to do something unexpected at this stage. D. A trusted guide who will walk me through every step without pressure or judgment.
Question 6: When you imagine the home you move into next, what does it look like?
A. Smaller, smarter, easier. Everything I need and nothing I do not. B. Part of a community, close to everything, with neighbors I will actually know. C. Somewhere I never expected to be. A fresh start in every sense. D. Similar to what I have now, but better suited to who I am becoming.
Now Add Up Your Letters
Count how many A, B, C, and D answers you chose. Your highest letter is your Next Chapter Style. If two letters tie, read both; you might be a blend.
Mostly A: The Simplifier
You are ready to shed the weight of too much space and too much maintenance. Rightsizing is not a compromise for you; it is a relief. You want a home that works for your life as it is now, not as it was twenty years ago. Your next chapter is about reclaiming your time and your energy. Furthermore, you probably already know deep down that the right move will feel like exhaling. The question is not whether to simplify. It is how to do it well.
Mostly B: The Community Seeker
Location matters more to you than square footage. You want to walk to things, know your neighbors, and feel like part of something. A 55+ community, a vibrant urban neighborhood, or a smaller town with a strong sense of identity could all fit your style. Equally important to you is feeling connected, not just housed. Your next chapter is about belonging somewhere that energizes you rather than isolating you.
Mostly C: The Bold Mover
You are not afraid of a fresh start. In fact, you are drawn to it. Whether that means relocating to another state, exploring a completely different lifestyle, or making a move that surprises everyone, including yourself, you are ready. Notably, bold movers often feel the most stuck right before they make their best decision. Your next chapter is out there. You just need the right support to take the leap.
Mostly D: The Thoughtful Planner
You are not in a rush, and that is a strength. You want to understand every angle before you move. Financial clarity, neighborhood research, and a trusted guide matter enormously to you. Moreover, thoughtful planners often make the smoothest transitions because they ask the right questions early. Your next chapter will come together methodically, and it will be exactly right because of it.
Whichever style resonates, one thing is true for all four: your Chicago next chapter deserves a plan that is built around who you are now, not who you were when you first moved in. That is exactly what I help homeowners over 50 figure out, one conversation at a time. Because your Chicago next chapter should be built around who you are now!
My goal is simple. I want to make sure you feel informed, empowered, and supported at every stage of this process. That is why I put together a free resource library packed with guides covering everything from downsizing and aging in place to senior living options and financial planning. And if you would like to understand more about what an SRES® does and why it matters for homeowners over 50, the Homeowners 50+ page is a good place to start.
If you’re starting to think about what comes next, you don’t have to figure it out on your own. Sometimes it helps just to talk things through.
You can always take the next step at your own pace, with no pressure and no expectations. I’m always happy to help you get a clearer picture of your options.
Michelle Williams is a REALTOR® and SRES® serving Chicago and the South Suburbs, helping homeowners 50+ make confident decisions about their next move.