The Joke’s On Me
Little Career Moments I Can Laugh About Now (For The Most Part)
As we all know, yesterday was April Fools,’ and while I didn’t pull any jokes or pranks on anyone this year, I did laugh thinking about how many moments I’ve had since starting real estate years ago where—honestly—the joke was kind of on me. Not in a tragic way. Just in a “wow, okay. this is really happening” kind of way.
It’s funny to look back on these memories now, but at the time, I can assure you they felt very uncomfy and often soul-crushing. That said, they shaped me. I’ve come to now see these as experiences that quietly built my character, pushed me to grow, and gave me (much-needed) thicker skin.
So in honor of a day that’s all about not taking things too seriously, I thought I’d share a few early stories from when I was still figuring it all out as a new agent.
1. Stuck in a Vintage Elevator
This story is from early on, when I was still trying to master the art of mass-scheduling a long series of showing appointments with a buyer across the entire city. One of my best friends had sent me a referral—a buyer I didn’t know personally—and they were only in town for a short period so we had a packed schedule across multiple neighborhoods all day. Probably seven or eight condos back-to-back. I mapped everything out, travel timing was tight, but everything was locked in and confirmed. I had printed listing sheets, color-coded notes, snacks… I was ready.
One of the first showings was in this beautiful old building—historic, charming, classic Chicago. It was only a few stories tall, but it had one of those vintage elevators where you pull open a little metal gate to step inside. Definitely something you'd normally point out as a “cool detail.”
Until we got stuck in it.
And not just me and my client (of whom I barely knew)—but a resident of the building was with us in the vintage elevator, too. About ten seconds in the elevator jolted, made a weird little clicking sound, and then just completely stopped moving. The lights stayed on, but nothing else happened. The resident with us casually goes: “Damn, are you kidding me. Great. Yeah, this has been happening for over a week.”
I turned and looked at him—fully locked eyes—and was like, “Um, I’m sorry—what… what’s been happening for over a week?” And yes, I still can’t believe this happened, but we were indeed all stuck in an elevator together. For hours. Until this point, I truly thought this kind of thing only happened in movies. And now here I was, inside of what was essentially a four-by-four-foot metal closet, shoulder-to-shoulder with a stranger and a client I had just met. Our phones barely worked. It was grossly warm. The lighting was unsettling. We tried making conversation for the first forty minutes or so, but there are only so many small talk questions you can cycle through before everyone goes quiet and just starts dissociating.
Needless to say, we were in there for just under two hours before maintenance finally got us out. And while my client was unbelievably understanding, I don’t think either of us left that day with a great impression of the building.
I hated every second of this day.
I’ve never been back to that building. Not for a showing, not even to walk by. And I’m good with that.
2. My Very First Listing that Almost Broke Me
My very first experience on the listing side was a co-listing with my former team lead, Vince. It was a two-bedroom, two-bathroom condo in Edgewater. Really a prime location—super close to the lakefront, tucked into a cute pocket of the neighborhood. This condo was a top-floor unit in a well-managed building with good amenities, garage parking, and a private balcony. And because of all that, I really expected the listing process to be pretty straightforward.
It didn’t.
This seller had been renting out the place for a while, and the relationship with the tenants wasn’t exactly warm when it came time to sell. The unit had been somewhat neglected, so after talking with Vince and the seller, we all agreed that doing some renovations before listing would help increase their resale value significantly.
One catch: the seller didn’t live in the area. And to my surprise (feeling completely honored but also mildly terrified) Vince handed me the reins. And I mean like all the reins for getting the condo prepped and ready for sale. Vince trusted me to manage the entire job: coordinating with building management, lining up at least three quotes for each job, scheduling contractors, tracking progress, checking in on work, unlocking the unit for everyone—all of it. I’m so happy he had enough confidence in me to know what I was doing here, but oh boy—I was brand, braaand new. And while I was so grateful for how much Vince believed in me, I absolutely was just figuring it out as I went.
Sadly for me, the building manager? Horrible. Genuinely one of the most difficult people I’ve ever had to communicate with. Always delayed responses. One-word emails. Randomly unhelpful. But since I was the point of contact, there I was, reluctantly kissing this lady’s butt every day.
Beyond a cranky manager, other weird and chaotic things started to happen.
For instance, we had brand-new engineered wood floors installed—and within a week, I showed up to find them warped and lifting in the center of one of the bedrooms. There was no visible water source nearby. It literally looked like it had come from underneath (which is hard to fathom how that’d happen). Vince sent me a number of this guy he calls the “Water Whisperer,” and after investigating this incident, we found out it was a building pipe leak. Not our fault—but the floors had to be redone. After just being redone. Yay.
Then, if that wasn’t already enough of a hiccup, not long after that, I walked in for an evening showing one day and found the balcony door completely shattered. Still in its frame, but spiderwebbed across the entire pane. We actually never figured out how it happened, and yes, the seller had to replace this. So fun.
At a certain point, the place, this listing, it all started to feel… haunted? I can’t really explain it. I was always there alone, usually late hours, walking really long echoey hallways. All I can say is that the vibes were really, really weird. The unit had weird luck (clearly). The whole building gave me the creeps.
This one ended up taking almost an entire year to finish all the renovations (with stupid delays from management) and finally sell. The building was only ten minutes from my place in the city at the time, but by the time we finally closed on this property, I never ever wanted to step foot in that neighborhood again.
Still, for my first listing, I do definitely look back now and only appreciate how much the experience really taught me. This condo threw me into the deep end—renovation planning, communication and overall team trust, weird property managers, unpredictable issues—but somehow I can say I did come out better for it. Even if slightly emotionally drained.
3. Trying to Fix a Toilet with 17 Tools & a Granola Bar
Another co-listing with Vince. This one was a two-bedroom, two-bath condo in Lakeview—maybe Roscoe Village? I honestly can’t remember. We actually went under contract relatively quickly on this one. After the buyer’s home inspection, they requested a handful of minor repairs be done prior to closing. Nothing major—mostly small things like light fixtures needing new bulbs and tightening up some hardware.
Vince was always big on trying to save our sellers unnecessary costs on silly, quick fixes, so we often just stepped in ourselves to handle them (instead of hiring a handyman). I always used to laugh because once he knew Alec (my boyfriend) was pretty handy, it became this unspoken thing where we both immediately assumed Alec would be the one to take care of things. To be fair, I got myself into this one—I had gotten very comfortable constantly saying, “Oh, Alec can do that,” without fully thinking it through or checking Alec’s availability.
In this case, I ended up going over to the condo myself. The issue at hand was the toilet in the primary ensuite bathroom. It had come loose and wasn’t properly secured to the floor anymore. I figured, no big deal. I’ll watch a YouTube video if needed.
So, I packed a bag full of like 17 random tools to try—convinced that surely one of them would do the trick. I also brought a granola bar, because your girl’s gotta have fuel for a tough job like this (pls sense my sarcasm). I get there—tools in hand—and within a few minutes I realize quickly I have zero idea what I’m doing. I’m crouched down on the bathroom floor, turning bolts, trying different angles, switching ends of the tools to try, Googling things mid-process—and absolutely nothing is working.
I think I may have assumed all I’d need to do was tighten something and call it a day. But it turns out what it actually needed was a new wax ring (or something. I think?) I don’t actually know 100% what the issue was or how it was fixed haha, but needless to say, whatever was needed was not in my bag of tools. After about an hour or so of trying and failing (and sweating), I gave up. I called Vince and explained that there was absolutely no fixing it—not by me, at least.
Since then, I’ve learned to stop volunteering Alec for things like plumbing jobs, because while he probably could’ve fixed the issue, free labor is never cool to automatically put on someone. So, point taken: just hire someone.
Your realtor can do a lot of things—but fixing your toilet is probably not going to be one of them.
4. Old, Shitty Blinds (the Unraveling of My Sanity)
This isn’t even a story, really—more of a recurring theme in my life as a realtor. And by “recurring,” I mean it has happened more times than I can count. Genuinely. I’m sure any former clients of mine reading this can also attest to this as well.
Please, I am begging you— if your home still has the kind of blinds or shades that were installed 15–20 years ago, and you know they don’t function anymore... please just take them down before showings. Or, at the very least, tell your listing agent they don’t work so we can pass that information along to buyers and their agents.
Because here’s the thing. As a buyer’s agent, I love getting a full feel for a space—including the views and how the natural light moves through the unit. So what do I do when we walk into a listing? I go to open the blinds. I want to show the sunlight. I want to show the view. I want to show that this is a bright, happy home.
And then, with one gentle tug: an entire set of blinds falls off the window.
Every time this happens, I am so unbelievably embarrassed. It’s loud. I feel guilty. Panicked. I’m trying to reassure my client while also preparing a full damage control script in my head for the listing agent. And even though it’s never actually been my fault, I still find myself apologizing like I broke someone’s family heirloom. I’ve offered to pay for replacement blinds pretty much every time. No one’s ever taken me up on it, thankfully, but that doesn’t stop the deeply unsettling moment when you’re just standing there with a pile of broken plastic in your hands.
So I’ve now reached a point where I simply do my best to not open any blinds at showings. I’ll lift them up carefully to peek at the view or show my clients, but I don’t care how beautiful the view is or how perfect the lighting could be— I live in fear of window treatments now. You win.
5. Dripping Wet Man Opens the Door
This should’ve been such a simple showing. It was the last stop on a full afternoon of tours, and both my buyer and I were feeling good—we had seen a couple strong contenders, and this final listing was one that we were both excited to check out. The listing agent hadn’t planned to be there, but they confirmed everything was set up for us to access via lockbox.
Great. Fine—I’m certainly used to lockboxes. It’s all good.
We get to the property, I grab the keys from the lockbox, and…what happens? Oh, the key to the unit doesn’t work. I try it again. And again. It’s the only key in the box that goes to the unit. I try turning it slightly harder, slightly softer, jiggling it—nothing. Just a fully non-working key.
So now I’m standing there awkwardly, texting the agent, calling them, calling their office, emailing—nothing. Crickets.
While I’m in the middle of trying everything, I hear music coming from inside. Like, loud music. And the sound of running water— a shower. So now I’m standing outside this unit with my client, fully aware someone is definitely home, definitely showering, and definitely unaware that we’re outside with a scheduled showing.
At this point, we had nothing else left on our schedule and we weren’t in a rush, so we decided to wait it out. I figured once the shower stopped, they’d hear us knocking and let us in.
I knocked gently(ish) at first, but chose to knock louder and louder in effort to try and get this person’s attention. The music, however, started getting louder. It was like the volume increased in direct response to my knocking, so now I was like: “Oh, okay, this mother f’er hears me… And he is ignoring me.” I’m now super annoyed and the gentle knocking is long gone.Twenty minutes later, the door finally opens and there he is: a twenty-something year old male standing in a towel, soaking wet, clearly confused and equally annoyed, just staring at me like I was the problem.
I explained that we had a confirmed showing, showed him the time and address on my phone, and he just goes, “Okay,” and then steps outside and gestures for us to go in while he waits in the hall.
We did a fast, very awkward tour.
And I still don’t know if he was ever told about our showing or not—or if he was told and just didn’t care.
Either way: if you’re a homeowner thinking about selling— please, please, please make sure your agent is someone who will actually show up in person for all showings! Or at the very least, sends a colleague who covers for them. Especially when tenants are involved… Especially when annoying, fresh-out-of-college tenants are involved.
And I Think That’s All For Now
Since writing this I’ve thought of like ten additional stories I could share. Bottom line is that real estate as a career really has a way of keeping you on your toes—even when you're just trying to show a home or open a window. Somewhere in the mess of trying moments, late-night frantic calls, dripping wet strangers, and broken blinds, you start to get better at it. Or at least less surprised.
Hopefully you enjoyed reading about these very humbling early moments of my career—just in case you needed a reminder that behind every agent is someone quietly spiraling in an elevator somewhere.
Thanks for reading. I’ll be back with more “joke’s on me” moments eventually. There’s always something happening.
