“Why y’all playing checkers on a chess set?” D’Angelo – “The Wire”

Would you like to feel less stressed about money?

Would you like to have less doubt about whether you’re making the right moves with your money?

If “yes,” you need to heed D’Angelo’s advice.

Granted, he was using the checkers-chess metaphor to explain the hierarchy of selling drugs on the streets of Baltimore in this HBO critically-acclaimed drama (and one my favorite shows). But his point about playing the wrong game is especially fitting when it comes to making smart, strategic moves with your money – on your street.

Far too often, like Bodie and Wallace, people think they’re playing one money game when in fact they are playing another. As an example, consider these questions as you think about the most recent money decision you made:

  • Did you give it much thought?
  • Was it reactive?
  • Was it impulsive (and you hoped for the best)?
  • Did you think about how this move might affect subsequent moves?
  • Did it feel like you were putting out (yet) another financial fire?

Perhaps your money decision was truly simple and answering the above questions “no; yes; yes; no; and yes,” respectively, was appropriate.

Yet, what I notice is that most people answer in the same fashion when it comes to the larger, more complex decisions, too. You know, the ones that have a greater impact on your money game overall and your current reality along with the future you’re planting seeds for.

In other words, they were playing checkers when they should have been playing chess!

What about you; which board game best reflects your approach to money?

True checkers aficionados take issue with the checkers-chess metaphor, believing the former requires just as much strategy as the latter. That’s never been my experience.

What I’ve found is…

-> Chess is usually played at a slower pace. Largely because it values “thinking” time as much as “doing” time.

-> With chess, strategic thinking comes into play not just because you think about the impact of your current moves on subsequent moves ahead. But also because you consider those moves in the context of what your opponent might do. I liken it to being both a defensive and offensive driver.

Don’t be more intentional about how you play a board game than how you manage your money and make your financial decisions.

-> Chess is multi-dimensional, but it has a singular goal: Capture the king!

Want to greatly improve your money game? Approach it as if you were playing chess – be slow, strategic, and focused.

Sure, you probably don’t have just one financial goal. It’s more like you have multiple goals competing for your attention, time and resources. This fact shouldn’t overshadow that you do actually have one singular goal, and that is: to have a financial strategy and plan that reflects what goals take priority right now.

Do you have a singular goal in the form of a plan? Or, are you winging it and hoping it all works out.

By the way, a plan doesn’t need to be fancy. You simply need to have benchmarks and metrics you’re tracking? And, track them!

If you were to audit your calendar for the last month, how much time did you spend thinking about and thinking through your next money move…and the one after that…and the one after that?

Do you give yourself permission to invest the time to be contemplative about the money moves you’re making today and how that may affect what you do in a month…in a year? Or, do you leap from decision to decision without much reflection and forecasting?

Simply pausing for 10-minutes to an hour before you make a move can work wonders in terms of the results you experience and the opportunities or options you discover.

Do you practice scenario planning in the event any of what you forecast (or hope for) falls through?

Thinking about what could go wrong doesn’t mean you aren’t practicing “abundant-thinking.” It means you’re being calculating.

D’Angelo said it best, don’t play checkers on a chess set.

This mindset is critical if you want to have less stress and less doubt about money.

It’s also helpful when it comes to managing your money fears and/or what triggers your fear.

Especially when you consider the ways in which your fears may be holding you back and keeping you from growing and thriving in the ways you most want.

Maybe you can’t focus? Maybe you are so entrenched in being busy that taking the time to plan feels like not only one more thing to do, but a misuse of your time? Or, maybe you can’t see beyond survival mode so apathy has set in.

What most people don’t get about their money game – whether that’s handling your money fears, or doing what it takes to have less stress about money and less doubt about whether you’re making the right money moves is this: Don’t play checkers when you should be playing chess.

What I want is for you to make smart, strategic moves with your money. For that, you need to a) know which game you’re playing, and b) be sure you’re playing the right one.


p.s. I answered a few questions from Stacey Tisdale, of Black Enterprise Magazine, about what impact a Hillary Rodham Clinton or Donald J. Trump presidency would have on the stock market. Check it out here:
“(DNC) How Clinton or Trump Would Affect The Stock Market”
(The post is NOT political, but it is about the election and investing.)

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