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One of the Hardest Things I had to Learn as an Agent

A car ride, a crisis of taste, and realizing your opinion isn't a fact
Jen Romolo  |  May 29, 2026

The last time I had a blog was my Xanga. I'm genuinely relieved that website is largely gone from the internet. Hopefully this one ages better.

I started doing real estate at 23, which is younger than most agents in Chicago. My aunt suggested I get my license and work with her while I saved money for law school. That was the original plan. Then I liked the job, turned out to be good at it, and every year I’d say “the next year I’m going back to school” until I finally admitted that I like my job, I’m good at it, and I’m lucky to feel that way.

Starting young meant I had a lot to learn. Some of it was the expected — contracts, negotiations, figuring out the Chicago market (what is an HVAC???). But one of the bigger lessons was something outside of that:

I had to learn (the hard way) that not everyone’s taste is the same as mine.

When I was 23, I had a lot of opinions (I still do 😊 ). I love/d vintage Chicago homes — the woodwork, the architecture, the details, the courtyard buildings, separate rooms with actual doors. I did not love the newer construction open floor plans. I thought they were boring, cookie cutter and ruining the character of the city.

My friends will tell you I have no filter and that’s partially true, but I think at this point in my life I have learned tact and other people in the world should probably learn how to discuss differences more easily. One car ride definitely put me in my place though and opened a different line of thinking.

I was driving my clients on a showing tour, and in between showings we were having a discussion. One of them and I had been bonding all day over old houses and Chicago architecture. I felt like I knew my audience, over-relaxed a bit, and we started riffing. He said open floor plans/newer construction all looked the same, that nobody was building anything with any soul anymore. I took it one step further and declared that this country was having a crisis of taste.

I caught the other person's face in the rearview mirror.

She loved open floor plans and these newer builds.

I wasn't trying to be rude. I genuinely thought I was stating a fact. Turns out I was just stating MY opinion, loudly, in a car, to someone who felt the opposite.

That was very mind opening for me and it was one of the first times I felt very challenged on what I liked and thought was true in a way that made me pause. It opened up a new pathway of thinking for me that aesthetics are subjective and personal and that my personal taste isn’t necessarily the right one. It’s my job as an agent to look out for my clients and think about functionality (what’s it going to be like to live there every day), resale (is there anything here that will give them trouble if they have to sell their home in a slower market) and quality of build (today in 2026 a lot of the new construction is really well done). It’s not my job to comment on someone’s personal style or how they want to live. Newer agents mix them up all the time, and I get it because I did too.

Taste is personal. Your clients have their own version and it's just as valid as yours. I've had clients walk away from homes I thought were incredible because they didn't want the maintenance or they didn’t like the fixtures/counters/details. I've had clients fall in love with homes  I personally wouldn't choose. They were right. It wasn't going to be my house.

Functionality and resale — that's where I'll speak up every time. Weird layout, no natural light, a location that's going to hurt them when it's time to sell, maintenance issues that are going to turn into a negotiation problem — those things matter and it's my job to flag them. That's what I’m there for.

My taste has actually changed. I get why people love open floor plans now. They're bright, they're social, they work for how a lot of people actually live. I've sold high-rises, new construction, ultra-modern spaces and genuinely found things to love in all of them. I was half way convinced to move to a sprawling open floor plan mid century condo the other day.

I still love a vintage Chicago home. A classic two-flat, a courtyard building, original woodwork — that hasn't changed. But I'm a better agent because I know that's my preference, not the standard (and not even something I’d always choose at this point in my life [as I sit here typing this from my 1905 home haha]).

When I talk to newer agents about showings, this is one of the first things I bring up. Your job is not to narrate your feelings about the aesthetics. Look at the stuff that's hard or expensive to fix — the layout, the light, the block, the bones. If you love something, say so, that energy is contagious. But if you don't love something, keep it. Nobody hired you to tell them their kitchen is ugly.

That car ride was a long time ago. I still have a lot of opinions. I've just gotten better about knowing which ones are worth hearing.

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