Rich Dad, Poor Dad was a game-changer in my life. It totally opened my eyes to how money actually works. ~ Coach Holdren
My Lightbulb Moment About Money
Let me take you back to the moment everything changed for me financially. I was in my mid-30s, about 12 years into my military career, grinding hard and doing everything I thought was “right”—working long hours, chasing qualifications, and climbing the ladder like it was the championship bracket. Then I got the call no one ever wants: my grandmother had passed away. To get home for the funeral, I had to take a series of military hops—Europe to the East Coast, then the East Coast to the West Coast.
Somewhere on those long, uncomfortable flights, with too many hours to think and not much to do, I bought a book to pass the time: Rich Dad, Poor Dad written by Robert Kiyosaki. I didn’t know it then, but opening that book was like flipping on the stadium lights in the middle of a night practice. It didn’t just give me new ideas—it completely reshaped how I understood money. That was my “a-ha” moment when I realized the game of money has rules, and most of us hardworking folks were never taught how to play. Financial literacy isn’t optional. It’s the scouting report you need before you take the field.
The Two Coaches Who Taught Kiyosaki About Money
Kiyosaki tells the story of two father figures: his “Poor Dad” and his “Rich Dad”, who had completely different philosophies about money. Poor Dad followed the traditional playbook: go to school, get a stable job, work until retirement. Rich Dad saw money as a tool and understood how to make it work for him through cash flow, smart investing, and building assets. That contrast hit me like a coaching correction you don’t want to hear but absolutely need. I realized that earning a high income doesn’t create wealth. Understanding how money works does. It was like discovering the real formation behind the winning team instead of just chasing the ball around.
Understanding What Truly Counts as an Asset
One of the first concepts that opened my eyes was Kiyosaki’s definition of an asset: anything that puts money in your pocket. Not someday, not in theory—right now. Rental properties, dividend-paying stocks, small businesses, intellectual property—these are star players who keep scoring whether you’re on the field or not. No coach wants a team full of players who only show up when they feel like it; in the same way, your financial life needs performers that don’t rely on your constant effort.
Rethinking Liabilities and Hidden Money Drains
Next came the definition of a liability: anything that takes money out of your pocket. This simple definition reshaped how I viewed most of the purchases I had made over the past several years. Many of us grew up believing our home, car, and lifestyle upgrades were assets. But month after month, they drain cash like a defense that can’t stop a breakaway. When I looked at my own finances through that lens, I realized I had assembled a roster full of underperformers eating up all my playing time and energy.
How the Rich Actually Buy Their Luxuries
Then came the game-changing insight: the rich buy assets first, let those assets produce income, and then use that income to buy their luxuries. They don’t use their paychecks to buy toys, cars, or lifestyle creep; they let their assets fund the extras. It’s the difference between a disciplined team following a proven strategy and a pickup squad making it up as they go. Once I adopted that mindset, everything changed. My money finally had purpose and direction.
Why Cash Flow Is the Real Scoreboard
The heartbeat of Rich Dad, Poor Dad is understanding cash flow. Kiyosaki teaches you to always know which way your money is moving. Is it flowing toward you or away from you? Most people earn money and immediately spend it on liabilities, staying trapped in the “Rat Race”—like a soccer team that controls the ball beautifully but never actually scores. The wealthy direct their money into assets first. Those assets generate more income, and eventually that income covers their entire lifestyle. Once I saw this clearly, I realized I wasn’t playing the money game wrong—I just wasn’t playing the right game.
CASHFLOW: The Game That Brings the Lessons to Life
After the book shifted my mindset, Kiyosaki’s board game CASHFLOW shifted my behavior. The game mirrors real financial life: income, expenses, opportunities, surprises, investments—the whole field. Your mission is to escape the Rat Race by building enough passive income to cover your expenses. Every turn, the game forces you to update your financial statement, so you see the impact of each decision instantly. It’s hands-on financial training, like running scrimmages that teach real strategy instead of just chalkboard theory. And the more you play, the more naturally you start thinking like an investor.
Practicing Financial Strategy Like a Team Sport
Playing CASHFLOW with friends or family feels like a friendly training camp. You get to practice the mindset, the math, and the decision-making in a safe environment. Just like in soccer, reps matter. Nobody becomes great from one practice, and nobody becomes financially free from one paycheck. Improvement comes from consistent reps, reflection, and a willingness to adjust the playbook.
Coach Holdren’s Final Thought
Rich Dad, Poor Dad gave me the mindset, and CASHFLOW gave me the practice. Together they gave me clarity, confidence, and eventually freedom. If you’ve ever felt like you’re working hard but not getting ahead, or like you’re running laps while others sprint forward financially, these tools can absolutely change the direction of your life. They changed mine. And if you’re ready to take the next step in mastering your financial life, dive into my Core Financial Habits blog series—where I break down the four essential habits that create lasting financial freedom. Here is a link to the first post in this series: Developing the Core Financial Habits – Introduction.
How the S.E.M. Calculator Helps You Estimate Your Financial Freedom Timeline
After learning these principles, the natural question becomes: How long will it take me to reach financial freedom? That’s exactly why I built the S.E.M. Calculator. This tool shows you how long it will take to reach either Financial Freedom (your investments cover your expenses) or Financial Independence (your investments cover your entire income), based solely on your savings rate and a few adjustable assumptions like inflation, growth rate, and the safe withdrawal rate. You enter your numbers, and the calculator projects year-by-year how your portfolio grows and how close you are to escaping the Rat Race.