Thinking About a Move? Start Here.

by Laurie Field

What should you think through before buying or selling a home?

Before you list your home or start searching for your next one, the most valuable thing you can do is get clear on three things: your timing, your equity, and your real next step. Most people start with the visible parts of moving, browsing listings, guessing at a sale price, picturing a new neighborhood. But the decisions that actually determine whether a move makes sense happen before any of that. This post walks through the questions worth asking yourself first.

By Laurie Field, Real Estate Advisor | Engel & Völkers Chicago North Shore | June 2026

When most people start thinking about moving, they jump straight to the visible parts of the process.

They look at homes online. They wonder what their current home might sell for. They start picturing a different neighborhood, a different layout, a different life.

Those are all real parts of the conversation. But they're not where the conversation should start.

Before you list or start your search, the most useful thing you can do is sit down with three questions: what's your timing, what's your equity, and what does your next step actually need to look like.

Here's how to work through each one.

Start With Timing

Timing isn't just about the season or what the market is doing. It's also personal, and that part is often skipped.

Ask yourself:

Is there a specific date driving this, a job change, a school year, a family situation?
Do you need to sell before you buy, or could you manage owning two homes briefly if the right property came along?
How much flexibility do you actually have if things move faster or slower than expected?

Your answers here shape everything downstream. Someone with a hard deadline needs a different approach than someone who's simply watching for the right opportunity to appear.

There's also a "why" underneath the timing. Are you looking for more space? Less to maintain? A shorter commute? A home that fits how you actually live now, not how you lived when you bought it?

The clearer you are on your why, the easier it becomes to make a decision instead of reacting to whatever comes up first.

A practical note on timing: if your current mortgage rate is well below today's rates, that's a real factor, not just a feeling. It doesn't mean you shouldn't move. It means the math on your next purchase needs to account for it honestly, both the new payment and what your current equity can offset.

Know Your Equity, Not Your Estimate

If you own your home, equity is usually the single biggest lever in your move. It determines your down payment, your flexibility, and in some cases whether moving makes financial sense at all right now.

But there's a difference between your equity and an online estimate.

Automated valuations are built from public data and broad algorithms. They don't know about your kitchen renovation, your finished basement, or the fact that the house two doors down sold for less because it backed up to a busy street. They also don't account for what selling actually costs: commissions, transfer taxes, attorney fees, and any prep work your home might need.

If you've owned your home for several years, especially five or more, there's a good chance your real equity position is stronger than a quick online number suggests. Appreciation alone can move that number significantly, even without major updates.

The only way to know your real number is to have someone look at your specific home, in its current condition, against what's actually selling near you right now. That number, not the online estimate, is what tells you what your next step can realistically look like.

I walk clients through this before we talk about anything else. It's usually the single most clarifying conversation in the entire process.

Get Clear on Your Real Next Step

This is where most people start, and where they should actually finish.

Once you know your timing and your real equity, the question becomes: what does your next home actually need to do for you?

Not what looks good in photos. What needs to feel different.

What's frustrating about your current home that you want to solve?
What are your actual must-haves, versus things that would just be nice?
Are you prioritizing less maintenance, more space, a different layout, or simply a change of scenery?
If you're downsizing, have you run the real numbers? A smaller home doesn't always mean a smaller monthly cost. HOA fees and assessments can offset some of what you'd expect to save.
If you're moving up, have you looked at what the new mortgage payment looks like at the price point you're considering, not just whether the down payment works?

Knowing the answers before you start touring homes makes the whole search faster and less exhausting. You stop getting pulled in by places that look great online but don't actually solve what you need solved.

You don't have to have all of this figured out before reaching out.

Some of the most useful conversations I have are with people who are months away from doing anything. They're not ready to list. They're not sure if selling makes sense yet. They just want to understand their equity, their options, and what a realistic next step could look like.

That conversation doesn't commit you to anything. It just gives you something most people are missing when they start: an actual picture of what's possible.

Frequently Asked Questions

How do I know if now is the right time to sell my home?

The right time depends on both market conditions and your personal situation, and you need a clear read on both. Start with your timeline and flexibility, then layer in your real equity position. If those line up with what you're hoping to do next, it's worth exploring further. If they don't yet, that's useful to know too, since it tells you what needs to change before it makes sense.

What's the difference between an online home value estimate and my actual equity?

An online estimate is generated from public data and broad algorithms. It doesn't account for your home's condition, updates, or how it compares to what's actually selling in your immediate area right now. Your real equity is your likely sale price minus your remaining mortgage balance and the costs of selling, including commission, transfer taxes, attorney fees, and any prep work. That number can be meaningfully different from an online estimate in either direction.

Should I sell my home before I start looking for my next one?

It depends on your equity, your comfort with potentially owning two homes briefly, and how competitive the market is for what you're buying. Some people sell first and rent short-term while they search. Others buy first using a bridge loan or HELOC against their current equity. There's no single right answer. The right approach depends on your specific numbers and risk tolerance.

I'm not ready to move yet. Is it too early to talk to someone?

It's not too early at all. Some of the most useful conversations happen well before someone is ready to list or buy. Understanding your equity and your options early gives you time to plan, rather than scrambling to figure things out once you've already decided to move.

What should I actually figure out before I start touring homes?

Get clear on your timing, your real equity, and what your next home needs to solve for you, not just what looks appealing. Knowing these three things before you start touring makes the search faster, because you'll be able to tell quickly whether a property actually fits what you need versus just looking good in photos.

Your Next Step

Thinking about a move doesn't mean you need to rush into anything. It means getting clear on your timing, your real equity, and what your next step actually needs to look like.

If you're working through any of this, even if you're not sure you're ready, I'm happy to walk through it with you. No pressure, just a conversation about what's possible.

Reach out and let's talk.

HELPING YOU MOVE FORWARD®

About Laurie Field

Laurie Field is a Real Estate Advisor with Engel & Völkers Chicago North Shore, serving buyers and sellers across Highland Park, Deerfield, Northbrook, Glenview, Glencoe, Winnetka, Wilmette, and Lake Forest, as well as Chicago. With over 10 years of experience and more than 110 career transactions, Laurie specializes in move-up sellers, first-time buyers, and downsizers navigating the timing, equity, and planning questions that come before any listing or search. A lifelong North Shore resident and University of Michigan graduate, she brings a direct, strategy-first approach to every conversation.