My friend sent me a video message this week that absolutely broke my heart. She’s a fellow business owner who runs a property management company in another state. We met at a conference last year and instantly clicked. It was almost eerie how similar we were—same company size, same systems, same goals, and so many shared experiences. On one hand, we’re basically the same person. On the other, total opposites. But I’ve grown to deeply value our connection. Most of our conversations revolve around property management—because, well, that’s our world.
In her video, you could tell she was emotionally spent. What should have been a quiet dinner break had become the tipping point in an already overwhelming day.
Her day had started at 5:00am—nonstop meetings, fires to put out, a two-hour drive to meet with a mastermind group, and she was completely spent. On her way home, she decided to stop at a restaurant on a golf course to treat herself to her first meal of the day… at 8:00pm. I was actually on the phone with her when she pulled in. She sounded excited for a little reset—a nice dinner and a cocktail to unwind.
Instead, she waited 12 minutes just to be greeted. Then another 10 for her drink. She ordered a steak… only for the manager to come out 50 minutes later to tell her they were out. No apology. No warmth. Just cold and dismissive. Eventually, she ordered something else, and while the food was good, the experience was awful. She felt ignored the entire time.
After almost two hours, they finally brought her the check. While they comped the food, her two drinks were $16 each, plus a 20% “service charge”—bringing her total to $45. And yes, she still felt obligated to leave a tip. So much for a “quick, relaxing dinner.” She still had a 90-minute drive ahead of her.
But here’s the thing—that night at the restaurant wasn’t what caused the breakdown. It was just the last straw. The real weight? It was everything she’s been carrying from her business. The stress. The pressure. The feeling of being pulled in a thousand directions while trying to build something good in a challenging industry.
So what does it really look like to run a property management company? What are 95% of business owners quietly carrying, while the other 5% seem to have figured out how to stay afloat—or even thrive?
Here’s a closer look at what a few truths I’ve come to know about running a small property management company, and what a typical day looks like now.
Table of Contents
It’s Extremely Lonely
I remember the overwhelming feeling of loneliness when I first started doing property management.
Before I added it as a service, I was basically a solo act. I wasn’t trying to grow a real estate team or build something big—I was just trying to find my own way. Honestly, I never had intentions beyond doing my own thing. But two years in, my clients—who were buying investment properties—started asking for help managing them. The demand was strong, and I decided to say yes.
The first 100 doors came easy. I managed them on my own while still flipping houses and helping clients buy and sell. But when it came time to hire my first employee, I had a moment of panic:
“Oh shit. Can I afford this?”
Then came the mountain of doubt: Can I lead someone? Am I ready for this?
I had managed people before, but nothing compares to the weight of being responsible for someone else’s livelihood.
As expected, I made a ton of mistakes with that first hire. I was too eager. Too lenient. Unorganized. Overly generous. (Y’all—I gave her my car and bought myself a new one because hers broke down and she didn’t have transportation.) I even paid for her to get her real estate license and let her take the courses during work hours. Shortly after she got licensed… she disappeared. Never saw her again.
So who made the mistake here?
Back then, I blamed her. But now I know—it was me.
The next few hires went pretty much the same way. Each one took advantage, disrespected me, and exited dramatically—whether I ended it or they did. I kept going through this cycle while also navigating COVID and the many market shifts of the last seven years. During all of this, my personal life was just as turbulent: I was in an on-again, off-again relationship that led to an engagement, a breakup, three moves, a new love, and—most recently—another engagement.
Before I started this business, my life looked completely different. I had a solid group of friends from work and past jobs. I went out often—dancing the night away any night Cutters was open (IYKYK). I traveled for fun, stayed up too late, and didn’t stress much. I made great money, was working on my master’s degree, and life felt full.
After starting my business, everything changed. It was a full 180.
Suddenly, I didn’t have time for anyone—not because I didn’t want to, but because I had to work. Constantly. It never stopped. I was doing 80+ personal real estate transactions a year, launching a PM division from scratch that quickly grew to 100+ doors, and flipping multiple properties at once. Free time? Sleep? Those were luxuries I couldn’t afford. And when I did get a chance to step away, I couldn’t fully unplug—someone always needed something. Clients didn’t care that it was 8pm on a Friday. I always answered. I made myself available 24/7.
And eventually, people stopped inviting me out. Or maybe I stopped saying yes so often they just gave up. Either way, I was suddenly out of the loop. No one really understood what I was building, and I was no longer relatable. Even my ex-fiancé constantly commented that I was always on my phone or stressed about work. He didn’t get it—and I didn’t understand that he didn’t get it.
So, we broke up.
And then I had no one.
I’m not super close with my family. I didn’t have a business partner. My friends were gone. I was newly single.
So… I got a dog.
You Doubt Yourself A Lot
I’m just going to come out and say it: when you start a property management company, you have no idea what you’re doing. None of us do. When I stumbled into this industry, my personal motto became “fake it till you make it.” And to be honest, some days… it still is.
The truth is, wisdom doesn’t come from reading books or following someone else’s blueprint. It comes from doing. From falling on your face and getting back up. From learning the hard way—over and over again.
I remember one moment, early on, when I truly didn’t think I could keep going. It was right when COVID hit. At the time, my primary business was real estate sales—and almost overnight, that business came to a halt. I had about 120 doors under management and a small team of employees. Within weeks, I had to let them all go.
All my cash was tied up in investments that completely froze when the world shut down. I got to a point where I had $1,000 left in my bank account. I was literally one click away from applying for a job delivering pizzas at Domino’s—because at that moment, that seemed like the only thing still open and operating with contactless delivery. I was out of options, running on fumes, and nearly out of hope.
But I did the only thing I knew how to do: I took it one day at a time. I shifted all my focus to property management and grinded it out. By some miracle—and the grace of God—I made it through. I eventually sold those investments when the market bounced back and was able to rebuild from the ground up.
The truth is, I’ve doubted myself every other day for the first five years. And even now, those thoughts still creep in. “You can’t do this.” “You’re in over your head.” But I take a breath, push them aside, and keep going.
To anyone out there who’s been brave enough to face yourself in this business—who’s kept going when everything in you said to quit—you deserve every ounce of credit. Because this path isn’t easy. It’s gritty and thankless and full of hard-earned lessons.
And as for me? I’m still learning. Still growing. Maybe halfway to the wisdom I know I’ll need. But I’m here. I’m showing up. And sometimes, that’s enough.
You Evolve and Adapt Quickly
Seven years into real estate and five years into property management may not sound like a long time in the industry—but to me, it feels like twenty. That’s because the pace of growth has forced me to evolve at a speed I never anticipated. In the beginning, I was energized and excited. I poured everything I had into the business. But by year three, burnout was creeping in. I was working nonstop—literally waking up and rushing to the office by 7 a.m., working straight through until 2 a.m., barely remembering to eat.
What made it harder was the revolving door of employees. My business was growing quickly, but I couldn’t keep staff. I had no real boundaries, no clear expectations—just a desperate need for help. I was happy to have a warm body, but I quickly learned that hiring without intention is worse than being short-staffed. Every time someone left, I was left cleaning up a mess: broken promises, missed tasks, things swept under the rug. It was exhausting. But it also taught me something important—if I wanted real relief, I had to build a real team. And to do that, I had to become a real leader.
One of the most defining moments of that leadership journey was the day I had to let my sister go. She had worked for me for nearly three years. During that time, we experienced some of the highest highs and lowest lows. Working with family is incredibly hard—at least it was for me. She stood by me through some of my most difficult seasons and gave everything she had to the business. But as the company grew, the line between work and personal life blurred, and eventually, we lost our connection as sisters. The arguments became more frequent, and the emotional toll became too heavy to ignore. I realized that if I wanted to protect the relationship that mattered most, I had to make the hard decision to end the working relationship.
That moment changed everything for me. If I could be strong enough to make that call—I knew I could set boundaries with anyone moving forward, family or not. That clarity became the foundation of my growth. I adopted EOS for structure, started attending industry conferences, and leaned into mentorship and learning. I wasn’t afraid to admit I needed help.
Because when you truly care about your business, investing in yourself is non-negotiable. Growth never stops. And in the early years especially, you’ll have to evolve and adapt faster than you think you’re capable of. But trust me—you are.
Your Brain is Overstimulated and Overworked
What many people don’t realize is just how mentally challenging this business can be. Sure, there’s the physical toll—staring at a screen for far too many hours a day—but the real weight comes from managing the emotions of everyone around you: owners, residents, vendors, team members, even family and friends who start to feel ignored or neglected. By the end of the day, you’re often left with nothing in the tank. All you want to do is collapse into bed so you can wake up and do it all over again.
There are days when it feels almost too painful to keep going—when the mental exhaustion completely takes over. And to make it even harder, I’ve struggled with migraines since I was a teenager. Not headaches—migraines. There’s a big difference. A headache is inconvenient. A migraine is debilitating. It can stop you in your tracks. But in this business, there’s no pause button. Whether I’m suffering or not, the work has to go on.
Over time, I’ve learned a powerful lesson: the work will still be there tomorrow. Do what you can today, and give yourself permission to let the rest wait. It’s the only way to preserve your sanity and stay motivated. Things do eventually get better—but there will be moments when you ask yourself, is this even worth it?
The answer is yes. You just have to keep going until you reach the other side.
What A Typical Day Looks Like Now
I know this post might make running a property management business sound terrible. And honestly, there are terrible moments—sometimes even entire seasons or years. But here’s the truth: it gets better.
When you’re intentional about your growth—both inside the business and personally—things start to shift. You build systems that make your operations more efficient. You develop a strong team. You find your niche. And slowly but surely, things start to feel lighter. Eventually, they become not just manageable, but good.
So, what does my typical day look like now?
I usually wake up around 7 a.m. I’m not a morning person, so yes—I snooze my alarm until the last possible minute. My morning routine is simple but grounding: a quick shower, tidying up the house (because I never have the energy to do it at night), mellow music in the background, and a quiet cup of coffee before the day starts. Then I head to the office and greet my amazing team—I genuinely look forward to seeing them every day. I make my morning rounds, grab a second coffee, and settle into my office to answer emails before meetings begin.
Meetings usually start at 9 a.m., and I’m involved in most of them since I sit in multiple leadership roles. We run on EOS, so my weekly meetings include L10s for Leadership, Operations, and Sales. I recently stepped out of the Admin Meetings—because my admin manager is now fully trained and absolutely crushing it. I also attend our Leasing, Maintenance, and Project meetings, host monthly team check-ins, quarterly one-on-ones, and quarterly & annual off-sites for goal setting. Supporting my team and removing obstacles is the heart of my role now.
Sometimes, I’m the one grabbing lunch or coffee for the crew—especially from CJ’s, our favorite local coffee shop. It might seem small, but if you’re a leader, trust me: asking “CJ’s, anyone?” and delivering someone’s favorite latte can turn their whole day around. It’s the little things that make a big impact.
The rest of my day? It’s a mixed bag. I might be handling a house fire (yes—really, more on that another time), resolving a resident dispute, attending court (though we’ve only had one eviction in the past two years), meeting with partners or clients, refining processes, or working on my Rocks (our 90-day EOS priorities). And when I can steal a quiet moment, I’m dreaming up the next big idea that will move us one step closer to our vision.
Right now, I’m genuinely happy with the balance I’ve found. I have an incredible team that handles the daily grind so I can focus on leading—and I feel incredibly grateful for that.
The truth is, no two days are ever the same. Different seasons require different things from you as a leader. But what I know for sure is this: because of the hard work I’ve put in, I’m finally starting to experience the payoff. And I can’t wait to see what the next few years bring.
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