Episode 138: Rental Markets: Checkers versus Chess: Which Game Are You Playing?
Summary
Every day is a difference in how you spend your time. Some people spend their time at their job, earning the wage that then gets reported on a pay check and depending on where you are, either gets reported on a W-2 in the US, a T-4 in Canada, or another instrument documenting how much money you’ve earned with your time spent. Limited moves and limited outcomes with a J-O-B. This is what many equate to playing checkers: limited moves and limited outcomes. Then there are chess players; chess has many pieces that have different moves, with over five million outcomes. In today’s episode, I explore the game of checkers versus chess, the players in those two games: tenants, landlords and developers, and then depending on which one you are, we talk about how each one would react in rental markets and other worldly events. I also offer options for growing and getting out of whatever game you are playing or role you are fielding. That and more!
Listen to the full episode :
This Week’s Blog Post:
What Kind of Player Are You?
Hi friends! I’m Dr. Jen, and in today’s episode of My Life as a Landlord, I’m diving into a concept I recently presented at a Toastmasters club: the idea that tenants, landlords, and developers are all playing one of two games—checkers or chess. This analogy is all about mindset, and how your current perspective shapes how you react to the real estate market. Are you just trying to survive? Or are you thinking strategically, planning moves several steps ahead? Let's break it down.
Defining the Players and the Games
I started by identifying the three players in the rental market: tenants, landlords, and developers. Then I defined the two games. Checkers is simple and reactive—limited moves and outcomes. Chess, on the other hand, involves complex strategies, foresight, and adaptability. A checker-playing tenant or landlord might be focused only on short-term survival, while a chess player is thinking about long-term gains and preparing for the unexpected.
Applying the Framework to Real-World Scenarios
Next, I laid out how these mindsets manifest in different roles. A checker-playing tenant may not have renter’s insurance and might panic at rent increases. A chess-playing tenant has a strategy—they might rent temporarily while saving to buy or choosing not to own for a reason. Similarly, checker landlords are reactive, often stressed, and handle everything themselves. Chess-playing landlords (like many of you listening) have systems, teams, and think long term. And when it comes to developers—there’s no such thing as a checker player. Developers must play chess, because creating new housing requires long-term planning and investment.
Real Estate Curveballs and How We React
Then I tested this framework against real-life curveballs—tariffs, natural disasters, inflation, even COVID-era supply chain disruptions. How each type of player reacts tells you everything. Checker players tend to panic or feel paralyzed. Chess players adapt, call their teams, file insurance claims, renegotiate timelines, and look for opportunities amid disruption. It’s all about perspective.
Tools to Help You Level Up
To wrap up, I offered tools to help each type of player level up. For checker tenants: start a side hustle or play the Cashflow board game. For checker landlords: read The E-Myth and start building systems. For chess players: define your goals using Think and Grow Rich. And for chess-playing developers: read Buy Back Your Time by Dan Martell to scale and delegate effectively. Because real estate isn’t just about buildings—it’s about playing the right game.
I recorded this episode on Maui, Hawaii. Why? Because real estate takes you places. Where do you want real estate to take you? Join me next week for Episode 139, where I join BID Academy to talk about the number one mistake real estate investors make—and how to avoid it. See you then!