Opening Day for the Cubs: Chicago-style Baseball Analogies that Ring True in Personal Finance

As the Chicago Cubs step up to bat at Wrigley Field, fans throughout the Windy City are eagerly anticipating another exciting season of baseball. In the spirit of the game, let's explore how Chicago's favorite pastime can teach us valuable lessons about managing our money like the pros.

Baseball is a game of strategy, patience, and discipline – qualities also crucial for effective financial management. So, grab a hot dog, and let's delve into some key insights we can glean from the game of baseball.

1. Embrace the Cubs' Resilience

The Cubs' historic 2016 World Series win, ending a 108-year championship drought, is an inspiring example of resilience. In personal finance, you'll face setbacks and challenges, but it's essential to stay persistent and focused on your long-term goals. Learn from the Cubs and embrace the spirit of perseverance in your financial endeavors.

2. Don't Swing at Every Pitch

When you're at the plate, you need to be patient. You don't swing at every single pitch that comes your way. You wait for the right one - the one that's in your sweet spot, the one that you know you can knock out of the park. The same goes for personal finance. You don't have to jump on every investment opportunity that comes your way. It is best to be selective, wait for the right moment, and go for the investment that matches your goals and risk tolerance. Don't let FOMO drive you to make impulsive decisions that could jeopardize your long-term financial objectives.

3. Stick to Your Circle of Competence

Now, I don't know about you, but I'm not going to be playing center field anytime soon. Baseball players have different positions and roles on the team, and they all have different strengths and weaknesses. The same is true for personal finance: stick to what you know. As investors, we all have different areas of knowledge and expertise, so avoid investing in companies or industries you don't understand, regardless of their popularity or potential high returns. Focus on investments you know well and that match your expertise and goals. If you need help, don't be afraid to ask for help from someone who knows the game better than you do – consult a fee-only financial advisor.

4. Buy and Hold Quality Investments with the Patience of a Seasoned Cubs Fan

The secret to success in both baseball and personal finance is playing the long game. Don't be in a rush to sell off your investments as soon as they turn a quick profit. Hold on to your investments, let them grow, and watch your wealth multiply over time. One of the biggest mistakes that unseasoned investors make is trying to time the market. Don’t go buying and selling based on short-term trends and news. Your priority should always be on the long-term prospects of a company. Remember, Chicago Cubs fans are no strangers to patience, having waited over a century for a World Series win. Market trends may be unpredictable, but staying the course with a well-diversified portfolio can lead to more consistent results over time.

5. Adopt a Data-Driven Approach Like Theo Epstein

When Theo Epstein took over as President of Baseball Operations for the Cubs, he used a data-driven approach to build a winning team. Adopt a similar mindset in your personal finance by working with a fee-only financial advisor who can provide you with data-driven insights and recommendations. Utilizing their expertise and experience, they can help you make informed decisions and optimize your financial performance, much like how Epstein transformed the Cubs into a championship team.

6. Know When to Take Risks Like Lou Piniella

In baseball, sometimes risks are necessary to win the game – such as attempting a daring double steal or making a high-stakes pitching change. Lou Piniella, who managed the Chicago Cubs from 2007 to 2010, was known for his fiery personality and bold strategic moves. Piniella's aggressive style led the Cubs to back-to-back division titles in 2007 and 2008.

Similarly, in personal finance calculated risks can lead to big rewards. However, be strategic: you don't want to take on excessive risk and lose everything but playing it too safe might result in missed gains. Consider your risk tolerance and investment goals when deciding how much risk to assume. Also, your money mentality should change in retirement. A fee-only financial advisor can expertly guide you in creating a well-balanced investment portfolio that aligns with your risk tolerance and objectives, allowing you to make fearless, informed moves that contribute to your long-term financial success.

7. Learn from Your Mistakes

Nobody's perfect, and even the greatest baseball players occasionally strike out. But you know what sets them apart from the rest? They learn from their mistakes, and they don't make the same ones twice. The same applies to personal finance. If you make a mistake, don't dwell on it. Reflect on what went wrong and why, and use that information to adjust your strategy and boost your chances of future success. A few strikeouts shouldn't deter you from hitting it out of the park.

8. Adjust Your Game Plan Like Joe Maddon

Former Cubs manager Joe Maddon was known for his adaptability and innovative tactics. In personal finance, be prepared to adjust your game plan when circumstances change. Regularly review and update your financial goals and strategies with your financial advisor to ensure you stay on track for success.

9. Celebrate Small Victories

Cubs fans cherish every win, knowing the journey to the top is filled with highs and lows. In personal finance, celebrate small victories like paying off debt or reaching a savings milestone. These accomplishments can help maintain motivation and make the path to financial success more enjoyable.


Though baseball and personal finance may seem worlds apart, they share some important similarities. By taking a page from the baseball playbook and applying these lessons to your investment strategy, you can improve your chances of hitting a financial home run and successfully achieving your goals. For additional guidance, reach out to a fee-only financial advisor. That’s what coaches are there for!