If I handed you a winning lottery ticket, would you cash it or throw it away? 

As real estate agents, that’s not a hypothetical question. Every one of us already holds a winning ticket in our hands: our real estate license. The difference is that this ticket doesn’t depend on luck; it depends on whether you recognize its value and choose to use it. 

Between the ages of 19 and 32, I was a hardworking real estate agent and investor. I earned between $200,000 and $300,000 a year. On paper, it looked like success. But underneath it, there was always a quiet anxiety that never left me. Because every Jan. 1, I started at zero. 

At age 32, everything changed. Not because of a six-figure commission, but because of a $500 check. That check came from my very first rental property. For the first time, money showed up whether I worked that month or not. It was small, but it was different. It was repeatable. 

That single check forced me to ask a bigger question: What happens if I stop working? 

Today, I own 300 properties, with 50 of them completely paid off. The passive income is significant, but that’s not the real story. The real story is what happens when you shift from earning income to building freedom. 

Agents are some of the hardest-working professionals in the industry. The challenge isn’t working harder — it’s working in a way that allows your past effort to keep paying you in the future. 

Early in my career, I cold-called six hours a day. I hustled. I closed deals. But every fall, I watched the same cycle repeat itself. Business slowed. The holidays arrived. January reset everything. And the question came roaring back: How do I do this all over again next year? 

That’s when I realized something most agents don’t want to admit — active income is fragile. No matter how skilled you are, no matter how productive your year is, if your income stops when you stop, you don’t own a business. You own a job. 

We are exceptional at building wealth for others. Buyers, sellers, investors — we guide them every day. Yet collectively, as an industry, we own far less real estate than we should. If we truly understand this business, why don’t we own more of the product ourselves? 

Your best client isn’t the next transaction. Your best clients are your family, your future and the version of you who doesn’t want to start over every January. 

Chicago is one of the most misunderstood markets in the country. It’s a market that isn’t landlord friendly, has high taxes, is difficult to do business in. Most investors fail to understand how to navigate the market, which leads to relatively less competition and high profit margins, which is why the Chicago market is extremely profitable. Chicago quietly continues to deliver strong returns and cash flow. 

Since 2011, it has remained one of the strongest rental markets in the nation. 

Every suburb is different. Every block has its own rules. Taxes vary. Municipal regulations change constantly. When a market is hard to navigate, knowledge becomes valuable, and no one knows these neighborhoods better than the agents who work them every day. 

Prices don’t move because of headlines. They move because of supply and demand, active listings versus pending contracts. Agents who understand absorption don’t guess; they guide.

Roughly 27% of all residential transactions in Chicago involve investors. If you’re not working with investors, you’re leaving opportunity on the table. More importantly, you’re missing the chance to become one yourself. 

Distressed properties like pre-foreclosures, tax delinquencies and probate sales are not abstract statistics. They represent real opportunity. Probate alone produces hundreds of potential listings every month, many tied to aging, paid-off homes. These are families who need guidance, and agents who understand this space can create both income and impact. 

The truth is simple: Most agents work hard. What separates those that work hard versus those that build wealth is the knowledge that their real estate license is not just a tool that helps others, but a vehicle that builds legacy and wealth for their own family. 

There are two types of people in real estate: those running on treadmills and those who own the treadmills others run on. Most agents are capable of becoming owners; they simply haven’t been encouraged to think that way. 

Owning four, five or six paid-off properties changes everything. It removes fear. It creates options. It allows your money to work while you sleep. The goal isn’t to flip endlessly or chase commissions; it’s to build a foundation that supports your life. 

Today, there are more financing options, more creative structures and more ways for agents to participate in ownership than ever before.

Many people at this stage of my life say they want to be like me. But I tell them, “Don’t be me. Be better. Start earlier. Invest in yourself and your family sooner. Use the knowledge that’s already in your hands.” 

Your real estate license is the greatest lottery ticket you’ll ever own. The only question is whether you’ll cash it.

Andrew Holmes is a nationally recognized real estate investor and educator who has helped thousands of aspiring investors build profitable portfolios and create long-term wealth through strategic investing and cashflow-focused systems.