How I Think Through Complex Problems And Make Decisions In Business And Real Estate

One of the questions I get asked the most is how I make decisions. People want to know how I look at a deal, how I evaluate a business, how I navigate problems, and how I continue moving forward even when the circumstances are complicated or unclear. The truth is, decision-making is one of the most important skills an entrepreneur can develop. Good decisions compound. Bad decisions multiply. Slow decisions kill momentum. And indecision is often worse than any mistake.

I’m Dr Connor Robertson, and over the years I’ve learned that thinking clearly is the ultimate competitive advantage. You don’t need to be the smartest person in the room. You just need to see the situation accurately, remove the noise, and choose the path that moves you forward instead of sideways. In this article, I want to walk through how I think about decision-making and how I break down both simple and complex problems in business and real estate.

The first principle I rely on is reducing emotional noise. Emotions confuse logic. They distort risk. They amplify fear. They exaggerate optimism. Whenever I’m faced with a decision, whether it’s buying a property, hiring a team member, walking away from a partnership, or choosing a strategic direction, I start by removing the emotional charge. I ask myself what the facts are. Not the feelings. Not the assumptions. Just the facts I can verify. A decision is almost always hiding in the facts.

From there, I break the problem into smaller pieces. Most big problems aren’t really big; they’re just bundles of small problems. People get overwhelmed because they look at the entire situation at once. When you isolate the parts, everything becomes easier to analyze. If I’m evaluating a real estate deal, I break it down into income, expenses, management complexity, capital needs, risk scenarios, and long-term positioning. If I’m analyzing a business, I separate operations, customer flow, pricing, margins, systems, leadership, and scalability. The moment you break apart the components, the direction becomes clearer.

Another part of my decision-making process is thinking in probabilities instead of absolutes. Most people ask “Will this work?” That’s the wrong question. The real question is, “What is the probability this works, and what is the upside if it does?” When you think in probabilities, you make better bets. You stop expecting certainty and start looking for advantage. You don’t need every decision to be perfect. You just need the upside to outweigh the downside over enough repetitions. That’s how you build a high-performing career.

I also rely heavily on sequencing. Good ideas fail all the time because they’re executed in the wrong order. Sequence is everything. It determines whether a plan works or collapses. Before I move forward with anything, I ask: “What is the correct sequence?” Without the right sequence, even the best strategy is fragile. With the right sequence, even a simple strategy becomes powerful. Sequencing is one of the most underrated skills in entrepreneurship.

Another part of my approach involves evaluating friction. Every decision has friction points, places where the plan slows, breaks, or becomes inefficient. When I’m analyzing a path, I identify where the friction will be and whether it’s worth dealing with. Some opportunities look great on paper but fall apart in practice because the friction is too high. Others look messy but work extremely well once the friction is removed. Understanding friction helps you make decisions based on effort versus reward, not just vision versus hope.

Clarity also comes from understanding opportunity cost. Every decision you say yes to requires a no somewhere else. Most people don’t think about what they’re giving up when they agree to something. I do. I ask myself, “If I choose this path, what path am I closing? What time am I giving up? What freedom am I sacrificing?” When you calculate opportunity cost, your decisions become sharper and more aligned with your long-term direction.

I’ve also learned to make decisions faster. Speed matters. Most people spend too much time gathering information they don’t need. I gather the critical information, analyze it quickly, and decide. The longer you wait, the more momentum you lose, and the more doubt creeps in. Fast decisions are not reckless, they’re structured. Slow decisions often signal fear disguised as diligence. I’d rather move fast and adjust than move slow and stagnate.

Another part of thinking through complex problems is zooming out. When tension builds or pressure rises, most people zoom in too tightly. They start focusing on the smallest detail and lose sight of the bigger picture. I force myself to zoom out, look at the entire timeline, and place the decision in context. When you zoom out, clarity returns. Small problems become insignificant. Big problems become solvable. The long-term direction becomes obvious again.

The final piece of my decision-making framework is bias awareness. Everyone has biases. Experience creates bias. Trauma creates bias. Success creates bias. Fear creates bias. If you don’t acknowledge your biases, they make your decisions for you. I constantly question my own assumptions. I ask myself whether I’m projecting past experiences onto current opportunities. The more you understand your biases, the clearer your thinking becomes.

My decision-making framework has evolved and will continue evolving, but the core principles remain the same: remove emotion, isolate the components, think in probabilities, value sequence, evaluate friction, consider opportunity cost, move fast, zoom out, and stay aware of biases. This framework helps me analyze real estate deals, business acquisitions, partnerships, operations, and personal goals with clarity that compounds over time.

I’m not perfect. I’ve made bad decisions. I’ve made slow decisions. I’ve made decisions based on emotion instead of logic. But the more I follow this framework, the better my outcomes become. Decision-making isn’t something you master once; it’s something you refine for life. The better you get at it, the more your life evolves into something aligned, intentional, and built with purpose.