Am I the a**hole for walking away from someone I used to know – someone who clearly needed help – because I was too scared of what helping her might cost me?
I (50F) have worked in commercial real estate for almost twenty years. I know what it looks like when someone’s had the career, the wardrobe, the whole thing. I used to.
Her name is Diane Kowalski (52F). We worked at the same firm in Chicago for about four years in the late nineties. She made partner before I did. She was SHARP – the kind of woman who walked into a room and immediately became the most important person in it. I hadn’t thought about her in probably a decade.
I was eating lunch alone on a bench in Millennial Park last Tuesday. It was cold enough that I had my coat buttoned to my chin. There was a woman sitting at the far end of my bench, and she had three bags with her, and she was wearing a men’s fleece over what looked like a hotel bathrobe. And something made me look at her face.
My stomach dropped.
It was Diane.
I sat there for a full four minutes not saying anything. I watched her sort through one of the bags. Her hands were shaking, and not from cold – it was something else.
I almost left. I had a 1:30 meeting. I told myself she wouldn’t want to be recognized, that it would humiliate her, that I was doing her a kindness by pretending I didn’t know her.
Then she looked up.
She stared at me for a long second, and I watched her face go through four or five different things – recognition, something that looked like shame, and then this awful careful blankness, like she’d practiced it.
“Karen,” she said. Flat. Not a question.
“Diane.” My voice came out wrong. Too soft, like I was talking to someone sick.
She looked back down at her bag. “You can go.”
I didn’t go. I sat there and I asked her what happened, which I now understand was a TERRIBLE thing to do, and she told me – in pieces, in this quiet voice – some of it. Enough of it.
And that’s when I realized she wasn’t the one I needed to be thinking about.
Because as she talked, I kept doing the math – the years, the decisions she’d made versus the ones I’d made, where we’d diverged – and I wasn’t thinking about how to help her.
I was thinking about how close it was.
I was thinking about 2011, about the year I almost didn’t recover from, about the client I lost and the marriage that went sideways and the four months I barely got out of bed.
She stopped talking. She looked at me.
And she said, “You know what your problem always was, Karen?”
I went very still.
“You never could stand to look at something that scared you.”
She reached into her bag and pulled out a folded piece of paper, smoothed it against her knee, and held it out to me.
“I’ve been carrying this for two years,” she said. “Waiting for the right person.”
I took it. I unfolded it. I started to read.
What Was On The Paper
It was a list.
Handwritten, in Diane’s handwriting – which I recognized, which was insane, because I hadn’t seen it since the late nineties and it was still the same cramped left-handed print she used to leave on Post-its stuck to my office door. Urgent. Call Bill Ferris re: Lakeshore. And under that: You left your umbrella in the conference room again.
The list had eleven names on it.
Some were people I knew. Two of them I knew well. One of them I’d had lunch with three weeks ago, a woman named Pam Sloane who ran the acquisitions side of a mid-size developer out of Schaumburg. Another was a guy I’d worked a deal with in 2017, Greg Hatch, who’d left his firm under circumstances nobody discussed out loud.
Some names I didn’t recognize at all.
And at the bottom, in slightly different ink, like it had been added later, was a note. Two sentences. I read them twice.
I folded the paper back up.
“What is this?” I asked.
Diane was watching me the way she used to watch junior associates present their first deal analysis. Patient. Waiting for you to catch up.
“It’s people who know what happened to me,” she said. “What was done.”
I sat with that for a second.
“Done,” I said.
“Done.”
What She Told Me, Piece By Piece
I’m not going to lay out the whole thing here because some of it isn’t mine to lay out, and some of it I still don’t fully understand. But I’ll tell you what I got.
Diane made partner in 1999. She was thirty at the time, which was not nothing. She spent the next several years building a book of business that was, by any reasonable measure, extraordinary. She was the one who brought in the Devereux account, which anyone in Chicago commercial real estate from that era knows was a nine-figure relationship. She recruited two of the firm’s best people. She was, by her own account and by the account of basically everyone who worked with her, the reason that office hit its numbers for four consecutive years.
In 2004, there was a restructuring.
She was moved to a different role. Lateral, they called it. Same title, different portfolio. The Devereux account went to a guy named Mark Calloway, who had been at the firm for eighteen months and whose primary qualification, as far as Diane could tell, was that he played golf with the right people and didn’t make anyone in leadership feel like they were being outpaced.
She stayed. She shouldn’t have stayed, she said. But she stayed.
“I thought I could outlast it,” she said. “I thought if I just kept producing, eventually it would be obvious.”
She laughed. It wasn’t a funny laugh.
By 2009, she was gone. Not fired. Just… managed out. The kind of thing where your clients get quietly reassigned, your assistant gets moved to someone else, your office gets relocated to a floor where the lights flicker. You stop being invited to things. You stop mattering. And eventually you leave because staying has become a form of self-harm.
She landed at a smaller firm. Then a smaller one. Then she tried to go independent and it didn’t work. Then 2012 happened, and her mother got sick, and she spent two years as a caregiver, and by the time her mother died she didn’t have much runway left.
She told me this on a park bench in thirty-eight degree weather, in a hotel bathrobe, with three bags at her feet.
I kept my face very still.
The Part I Keep Coming Back To
Here’s the thing I didn’t say out loud, sitting there.
In 2001, Diane was asked to weigh in on a performance review for a junior associate. That junior associate was me. I didn’t know at the time what she said. I found out years later, secondhand, from someone who’d been in the room.
She’d gone to bat for me. Hard. There had been some question about whether I was on track, whether I was producing enough, whether I was a good cultural fit, which is always code for something. Diane had apparently been direct in a way that shifted the conversation. I don’t know exactly what she said. What I know is that I was still employed three months later, and that without that I’m not sure where I’d have ended up.
She never mentioned it to me. Not once. Not when it happened, not later.
I don’t know if she remembered. I don’t know if she’d done it for me specifically or just because she thought the process was unfair. I don’t know if it would have changed anything for her if I’d known sooner, if I’d been able to do something in return.
I sat on that bench and I thought about all the ways that one conversation she had in a conference room in 2001 had threaded through my whole life since then, and she had no idea, and I had never known to thank her.
My hands were cold. I’d stopped eating my lunch.
What I Did
I asked her if she had somewhere to be that night.
She gave me a look.
“Sorry,” I said. “That was a stupid question.”
“It wasn’t stupid. It was awkward.”
“Yeah.”
“There’s a shelter on Dearborn,” she said. “I’ve got a spot.”
I asked if I could give her my number. She looked at me for a long time.
“Why?” she asked.
And I didn’t have a clean answer. I didn’t have a plan. I didn’t have a solution to anything. I had a cell phone and a business card and a lot of feelings I hadn’t sorted out yet and a folded piece of paper with eleven names on it sitting in my coat pocket.
“Because I want to,” I said. “And because I think I owe you something, and I’m not sure yet what it is.”
She took the card.
She didn’t say thank you. She put it in one of the bags, the smallest one, which I noticed she kept close to her body the whole time. The one with the important things in it.
I stood up. I picked up my lunch, which I’d barely touched.
“The paper,” she said. “Those names. Some of them are still in positions to do damage. And there’s a journalist – she’s been working on something. She needs someone who still has standing in the industry to talk to her.”
I looked at the bench, at Diane, at the three bags and the hotel bathrobe and the left-handed cramped handwriting I’d recognized across twenty-five years.
“Send her my number,” I said.
I walked to my 1:30 meeting. I was four minutes late, which I’m never. My assistant, a sharp twenty-six-year-old named Trish, looked at my face when I walked in and didn’t ask anything, just handed me my folder and pointed me at the conference room.
I sat down with clients I’d known for a decade.
I thought about 2011 the whole time.
So. Am I?
I don’t know.
I didn’t walk away. That’s something. I sat on the bench, I listened, I gave her my number, I took the paper.
But I also know what I was doing for most of those twenty minutes. I was calculating. How much this could cost me. Whether the journalist was legit. Whether any of the names on that list could come back on me. Whether helping Diane Kowalski was a liability or an obligation or something I could do quietly enough that it didn’t touch my life too hard.
That’s the part I can’t get comfortable with. Not the fear itself. The fact that the fear was always about me.
She read that off me in about thirty seconds. She’d probably read it off me in 1998 too, which is maybe why she never told me she’d gone to bat for me. Maybe she knew I’d calculate what I owed her and pay the minimum.
I haven’t heard from her since Tuesday. I’ve looked at the paper maybe six times.
The journalist’s name is at the bottom, under the two sentences. I haven’t called yet.
I’m going to.
I’m pretty sure I’m going to.
—
If this one’s sitting with you, pass it on to someone who’d get it.
If you’re still pondering the complexities of difficult choices and unexpected encounters, you might find solace or further intrigue in these tales: discover what happened when My Brother Vanished for Eight Years. He Showed Up at Dad’s Funeral., delve into a moment of pure shock when The Principal Opened His Desk Drawer and I Stopped Being Able to Breathe, or unravel the mystery behind The Man on the Phone Went Silent When I Said Her Name.
