Is Being a Real Estate Agent Stressful?

The money gaps. That's the honest answer. I made $118,000 gross last year, which sounds great until you realize that $47,000 of it came in March and April. That's tax refund season, that's spring market, that's when half my buyers decide to move. From June through August I did OK. September through November I closed two deals. December I closed zero. January I closed one.

My mortgage payment doesn't care what month it is. My daughter's tuition at her dance studio doesn't care what month it is. My wife Heather works at a pediatric clinic, steady paycheck, and there have been months where her $62,000 salary was the only thing keeping us solvent. I'm embarrassed to say that because on paper I out-earn her by a lot. But "on paper" includes March and April, and November doesn't know about March and April.

When I was a bank teller I made $34,000 a year. Every two weeks, $1,307 after taxes, same number every time. I never worried about money then. Not because $34,000 was a lot but because I knew exactly what was coming. Now I make three times that and I worry about money constantly. My financial planner, a guy named Randall, he set up a system where I put 30% of every commission check into a separate account that auto-pays my bills. That helped. But the anxiety of a slow month, that physical thing in your chest when your phone doesn't ring for a week, Randall can't fix that with a savings account. That's just the job.

Deals dying. That's the stress I can't get used to. I had a buyer last fall, a woman named Paige. Single, first-time buyer, saved for four years to have a down payment. She found a house in Milwaukie she loved. A little Craftsman bungalow, 2-bed, listed at $395,000. We wrote the offer, got it accepted, and for about two weeks Paige was the happiest person I've ever worked with. She sent me photos of kitchen tile she was looking at. She asked me to measure the second bedroom so she could figure out if her desk would fit.

Then the appraisal came in at $371,000. Twenty-four thousand under the agreed price. Paige didn't have $24,000 to cover the gap. We asked the seller to come down. The seller's agent said no, they had backup offers. I watched Paige go from picking out kitchen tile to crying in a coffee shop on Hawthorne Boulevard in the space of 72 hours. She didn't blame me. She understood. But I drove home that night feeling like I'd failed her, even though I hadn't done anything wrong. The appraisal wasn't my call. The seller's decision wasn't my call. But I was the person who'd been there through all of it, and I was the person sitting across from her when the deal fell apart.

In my old job at the nonprofit, when a program didn't get funded, it was disappointing but abstract. Grant money is numbers on a screen. Paige's house was a life she'd pictured herself in. The gap between those two kinds of loss is enormous, and I feel it every time a deal goes sideways. It's been five years and it hasn't gotten easier. I've just gotten better at hiding it during the conversation and processing it in the car after.

The cycle length. People in residential think they know about slow periods. A residential agent might go three weeks without a closing. In commercial, I can go four months. My average deal last year took 14 months from first meeting to signed lease. Fourteen months of meetings, tours, proposals, LOIs, tenant improvement negotiations, and legal review before I see a dollar. Last year I closed six deals and my gross commission was $340,000. Sounds great. But there was a stretch from May through September where I didn't close anything. Five months. My overhead during that period, office rent in Oak Brook, my assistant Ramona's salary, insurance, car, was about $9,500 a month. That's $47,500 going out the door while nothing comes in.

My wife Eileen and I have been through enough cycles that we plan for it. We keep nine months of expenses in a money market account and we don't touch it unless I've gone three months without a closing. But the psychological weight of it never goes away. I'm 57 years old. I've been doing this for 22 years. I've made good money. And I still get a knot in my stomach when August comes and I haven't closed since April. Eileen says I get quiet. She's right. I get quiet because I'm doing the math in my head, which is: how many months of runway do we have if nothing closes? The answer is always "enough." But the question never stops asking itself.

A friend of mine, Doug, he was a commercial broker for 15 years. Good at it. Consistent performer. He left in 2019 to become a branch manager at a credit union. Took a $90,000 pay cut. I asked him why. He said, "Because I wanted to know on December 31st how much money I was going to make the next year." I understood that completely. I chose differently, but I understood it.

The phone. My phone is the source of all my income and all my anxiety and they are the same thing. I cannot turn it off because every missed call could be a lead, and every lead is potential income, and in real estate, if you don't answer, someone else will. My broker, a woman named Patrice, she told me during my first week: "The agent who answers the phone gets the client." She meant it as motivation. It functions as a leash.

Last Tuesday, I was at dinner with my boyfriend Caleb. It was his birthday. We were at a restaurant on South Congress, one of those places where you wait 45 minutes for a table. Our food had just arrived. My phone rang. It was a lead from Zillow, a woman who wanted to see a house the next morning. I excused myself, took the call in the parking lot, booked the showing, and came back to dinner. Caleb didn't say anything but the look on his face said everything. I've taken calls during his sister's baby shower, during a movie, during a hike. He's never asked me to stop because he knows I can't. Or I feel like I can't, which might be the same thing.

When I was doing event planning, I worked crazy hours too. But the events were on a calendar. I could see them coming. I knew that the two weeks before the corporate gala would be insane and then I'd have a normal week. In real estate, the "event" is constant. There's no build-up and wind-down. There's just on. I've started leaving my phone in another room when I sleep because I was checking it in the middle of the night. Not because anyone was calling. Just because the habit of being available had become a compulsion. Caleb noticed that before I did. He said, "You picked up your phone at 2 AM and there were no notifications." He was right. I was just checking to see if the world still needed me. It didn't. But what if it had?

Needing to be liked. That's my stress. It's not what people expect when you've been doing this for 14 years. You'd think you get past it. I haven't. My business runs on relationships. Eighty percent of my deals come from referrals. Past clients telling their friends, their coworkers, their family. If someone I worked with has a bad experience, they don't just not refer me. They tell three people not to use me. One bad Zillow review can cost me $30,000 in lost referrals over a year. I did the math with my CPA, a woman named Tanya, and we estimated that each five-star review is worth about $4,800 in downstream business. Each one-star review costs roughly double that.

So I perform. I am warm, patient, available, enthusiastic, and attentive with every single client, regardless of how I'm actually feeling. I had a client last year who changed her mind about the paint color she wanted in a negotiation credit, after we'd already agreed to the amount, and I spent an hour on the phone helping her recalculate whether the $2,200 credit would cover the new color at the square footage of her living room. That is not my job. But if I'd said "that's not my job," she wouldn't have referred her sister to me two months later. The sister bought a $520,000 house in Kirkwood. That referral was worth $7,800 to me. So the paint color conversation was worth $7,800. Except I didn't know that at the time. I was just being nice because the alternative is losing people.

My wife Shanice works in corporate HR. She tells me that I'm a people pleaser. She's not wrong. But in most jobs, being a people pleaser is a personality trait. In real estate, it's a business model. I can't separate who I am from what works. That's the part that stresses me out. I genuinely don't know anymore whether I'm being kind because I'm a kind person or because being kind is worth $4,800 per interaction.

The weight. I don't mean workload. I mean the emotional weight of being the person standing next to someone while they make the biggest financial decision of their life, and knowing that if something goes wrong, they'll remember you. Not the lender. Not the inspector. Not the title company. You.

Last year I had a couple, Terri and Dustin, who bought a house in Richfield. $285,000. Nice little rambler. They did the inspection, everything looked fine. They moved in. Three weeks later, the basement flooded. The sump pump failed. The inspector had tested it and it worked during the inspection, but it was 11 years old and it died three weeks later. The repair plus water damage remediation cost them $8,400. Terri called me. Not the inspector. Not the home warranty company. Me. She was crying. She said, "You told us this house was good." I did tell them that. Because the inspection report said it was. But Terri didn't call the inspector. She called me. Because I was the one she trusted.

In social work, I carried emotional weight all the time. I was a case manager for families in crisis. Abuse situations, custody cases, housing insecurity. That weight was different, it was about systemic injustice and human suffering. Real estate weight is about money and trust. It sounds lighter. It's not, exactly. It's just a different frequency. When Terri called me crying about her basement, I felt the same thing I used to feel when a family's housing voucher got denied. The helplessness of being the point of contact for a problem you didn't cause and can't fix. In social work, I had a supervisor and a team to process that with. In real estate, I hung up the phone and sat in my kitchen for 20 minutes staring at the wall before my husband Malcolm asked if I was OK.

I helped Terri file the home warranty claim. I called the inspector and asked about the sump pump. I did everything I could. The warranty covered $3,200 of the $8,400. Terri still sends me a Christmas card every year. She's forgiven me, I think. But I drive past that house sometimes and I think about the sump pump. Seven years of closings and I can tell you the address of every deal where something went wrong after. There aren't many. But I remember all of them.