Thrown in the Deep End and Swam
There’s a certain point in Chicago when everything shifts.
You feel it before you even see it.
The air changes. The trees start to come back to life. You catch a little more green out your window. And suddenly, the city starts moving again.
Leases end.
“For Sale” signs go up on every corner.
There isn’t a first of the month without a moving truck parked on someone’s street.
People make decisions in the spring.
They leave what no longer fits.
They step into something new.
And every year, it brings me back to my first deal.
It wasn’t a small one.
It was 4407–4415 Greenview. Forty-four units.
No warm-up. No smaller stepping stone. Just a moment where I had to decide if I was going to figure it out… or fall behind.
At the time, it didn’t feel exciting. It felt overwhelming. Like I had been thrown in the deep end without knowing exactly how I was going to swim.
But I wasn’t alone in it.
My mentor, Terry Folks, had a very specific way of guiding me through that deal, one I didn’t fully understand at the time, but think about often now.
She didn’t take over.
She didn’t make every decision for me.
She helped me see what mattered.
She pointed out what I wasn’t seeing yet.
And then she gave me the space to move.
There was a calm confidence in the way she approached everything. An underlying belief that it was all going to work out.
And eventually, I started to believe that too.
Somewhere in that process, something shifted.
Not just in how I handled that deal, but in how I understood what this work really is.
Real estate, at its core, is about transition.
It’s about stepping into something new before you feel completely ready.
Making decisions without having every answer.
Trusting that what’s ahead will make sense… even if it isn't fully yet.
Spring just makes that more visible.
The market moves faster.
The energy feels higher.
Everything starts to feel a little more urgent.
But underneath it all, it’s the same thing I experienced in that first deal:
Uncertainty. Movement. Change.
What I didn’t realize then, but understand deeply now, is how much that experience shaped the way I guide my clients today.
Because I remember what it feels like.
To step into something unfamiliar.
To make decisions that matter.
To not feel completely certain, but to move forward anyway.
And I remember what made the difference.
It wasn’t having all the answers.
It was having someone beside me who knew how to guide me through it.
Now, every spring, when the city starts moving again, I see that moment play out over and over.
Different clients. Different homes. Different circumstances.
But the same underlying feeling, standing at the edge of something new.
And my role in that has never felt more clear.
Not to push.
Not to rush.
Not to overwhelm.
But to guide.
To help people see what matters.
To bring clarity when things feel noisy.
To know when to step in, and when to give space.
The same way Terry did for me.
