What I’m Learning (Again) as a First-Time Buyer — 11 Years Later
field notes: from the other side of the deal
Back when I last bought a property, Netflix was still mailing DVDs.
My first sale was our first real estate purchase: a starter condo my husband & I bought together. I was new to real estate and even newer to being a client.
Now, after over a decade of guiding, advocating, troubleshooting, and celebrating for others, I’m back on the other side of the process.
Still learning — just differently.
(Read: more opinions & better spreadsheets.)
This is a different kind of field guide.
I’ll be updating it as we go.
The goal? Buy something by the end of 2026.
No rush. I want to be thoughtful, curious, and honest about the process.
If you’re reading this, maybe you’re on a similar journey. Welcome :)
1. You will get opinionated.
When you start your search, your flexibility feels like a badge of honor.
I’m easy. I could live anywhere. It’s just an investment.
No, you won’t. & no, it’s not.
You’ll spend a lot of time going to showings only to realize:
– This street doesn’t feel right.
– I hate this layout.
– Actually, I want a neighborhood with better parks. Something I didn’t think I’d care about, but now do.
So before reaching out to your Broker, spend time getting to know the neighborhoods. Ideally 6 - 12+ months out.
Walk around.
Grab groceries.
Commute there.
Then, talk to your Broker to see what they would add to the list.
When my husband & I started our haus hunt, I was convinced we belonged in Avondale. You couldn’t tell me otherwise.
Today? I’m a hopeful future Logan Square resident.🤞🏽
Knowing us, we’ll probably end up in a flat in Berlin.
Either way, our Zenlist search is locked in. Only one new property came on the market this week — and I’m already repeating the same thing I tell clients all the time: patience.
If you’re relocating to Chicago, just rent the first year — unless your gut really says otherwise.
2. Start with the money.
First step: file our taxes.
First call after our accountant: our lender.
We needed to know our buying power before either of us — especially my husband — started to daydream.
Normally, I’m the dreamer & he’s the spreadsheet.
But when it comes to real estate? We swap roles real quick.
I’m crunching numbers. He’s falling for fixer uppers.
Outside of my weekly cafe rituals & occasional boutique splurges, we keep a pretty tight monthly budget.
Travel, good food, and the people around the table matter more to us than square footage.
Once we figured out the monthly number that felt right, we started exploring what our budget could actually buy.
I’d send contenders to Joe (our lender) to gut-check how the monthly cost felt, not just what the price tag said.
I’m lucky to have a partner who trusts my lead in this process, especially as we balance lifestyle priorities with long-term goals.
He’s also the first to speak up when a number doesn’t feel right, which keeps us grounded in the kind of life we want to build, not just the home we want to buy.
3. Where we’ve been so far
February 2025
Scoped out the commute to a neighborhood we thought we were open to. Ruled it out.
April 2025
Got pre-approved. Learned how different property types affect monthly numbers.
(It’s one thing to know the math, another to feel it.)
One showing down: not the one.
Learned: I’m willing to trade the lakefront for more green space
Smart compromises are often tough.
May 2025
Stopped for bagels at Tilly’s next to Aberdeen East before an open house.
Didn’t love the house enough to go in but fell in love with the neighborhood.
Some streets feel like long-term fits, some like smart stepping stones — and now we know the difference.
A detour that helped define what we’re looking for (& introduced us to a bakery with a line down the block)
No new tours.
Current status (June 2025)
Heading out of town for a few weeks, but still keeping an eye on new inventory.
The team’s on standby for virtual tours or offers if the right one comes along.
Brokers always joke that clients find “the one” the second we leave town…
We’ll see.
To be continued…
What’s ahead: I’ll share more lessons as we go + summer breaks, fall resets, and whatever winter throws at us.
I’ve always said the right space is the key to living well.
& we’re giving ourselves the time to find it.
For now, we love where we are: near-daily walks to the grocery store & quiet mornings around Wrigley Field, feeling game day energy start to buzz.
But, we promised the dog a yard.
A tomato garden wouldn’t hurt, either.
Want to follow the journey? Part II Coming Soon
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