From Chicago’s South Side to Bolingbrook: Why I Took the Leap of Faith

Growing up on the South Side of Chicago, city living was all I knew. Chicago was home, and I was comfortable with the lifestyle, the convenience, and the familiarity of my surroundings.
But as life changes, sometimes our priorities change too.
For me, that moment came when my son was preparing to enter high school.
As a single mother, I was balancing work, raising my son, and making decisions that I believed would be best for our family. One of my biggest concerns was something many parents probably don't think twice about: transportation to and from school.
I wanted my son to have access to school bus transportation rather than relying on public transportation, especially on days when my work schedule wouldn't allow me to be there.
It wasn't about wanting a bigger house or simply wanting to leave Chicago. It was about finding a community that could better support our everyday lives.
And that decision eventually led me to Bolingbrook, Illinois.
Leaving What Was Familiar
When you've lived in Chicago your entire life, moving to the suburbs can feel like a major adjustment.
I was accustomed to having everything nearby. I knew how to navigate the city, where to go, and what to expect.
One of my concerns about suburban living was convenience.
I assumed moving to the suburbs meant I would have to drive long distances to get to stores, restaurants, and other places I regularly visited.
But what surprised me most about Bolingbrook was just how accessible everything was.
The convenience I thought I might be giving up was still there. It just looked a little different.
And sometimes that's what happens when we step outside what we're accustomed to. We discover that things aren't necessarily better or worse. They're simply different.
It's About More Than Finding the Right House
After 18 years in real estate, one thing I've learned is that choosing where to live should involve much more than the house itself.
When I'm speaking with someone considering a move from Chicago to Bolingbrook or one of the surrounding suburbs, I encourage them to think about their everyday lifestyle.
How will your commute change? What conveniences are important to you? If you have children, how will their school schedules and transportation work? What type of community fits the life you're building?
These questions matter.
For me, school transportation was a deciding factor. For someone else, it might be proximity to work, more space, less maintenance, or simply wanting a different pace of life.
There's no single answer that works for everyone.
And that's why I believe the best real estate decisions begin with understanding what matters most to you.
Sometimes Change Requires a Leap of Faith
I often tell people that change can be scary, especially when you're leaving something familiar.
But just because something is familiar doesn't necessarily mean it's still the best fit for the season of life you're in.
Moving to Bolingbrook was a decision I made with my family's needs in mind.
And looking back, I'm grateful I was willing to take that step.
That doesn't mean suburban living is for everyone. Chicago is a wonderful city with so much to offer, and I will always appreciate my roots.
But sometimes the next chapter of your life requires you to consider possibilities you hadn't considered before.
Thinking About Moving From Chicago to the Suburbs?
If you're considering making the transition from city living to suburban life, my advice is to start with your lifestyle, not the house.
Spend time exploring communities. Consider your commute, daily routines, financial goals, and the things that are most important to you and your family.
And don't make assumptions about what suburban living will or won't offer.
Visit the communities you're considering. Get familiar with the neighborhoods. Ask questions. Understand what your everyday life might look like.
Most importantly, give yourself permission to consider something different.
As someone who made that transition personally and now helps others navigate real estate decisions professionally, I understand that moving is about much more than changing your address.
It's about making decisions that support the life you're building.
Sometimes taking the next step isn't about leaving something behind. It's about having the faith to move toward what's next.
If you're considering a move from Chicago to Bolingbrook or the surrounding suburbs, I'd welcome the opportunity to help you explore your options and create a plan that makes sense for you.
Sherri
IG: iamsherrijordan



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