The Best, And Worst, Questions You Can Ask Yourself If You Ever Want To Be Financially Free


There’s an old saying that goes like this: “You can have anything you want in life if you’ll simply ask the right questions.” Indeed, Voltaire said “Judge a man by his questions rather than by his answers.” Which begs a question (sorry for the pun). Do you know how to ask good questions of yourself? Really good questions?

That may seem like a strange question, but many people don’t. For some, the questions that they ask themselves tend to be superficial and not deep. Passing and not engaged. Or they often stop asking questions right before the answers become interesting!

As part of today’s essay, I focus on asking yourself better questions financially. If your wealth isn’t growing at the pace you desire, it could be that you are not asking yourself the right questions and therefore not getting the feedback you need to make better decisions.

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Psychologists tell us that there’s a distinct pattern we follow when we make purchases that are either expensive and/or questionable as to whether we really need to make them.

First, we decide that we are going to make the purchase. Yippee!

But what we do next is the more interesting part…

The next thing we do is craft a story to justify the purchase. Now, this isn’t any old story. No. It’s an emotion-filled narrative with rock-solid explanations, iron-clad excuses for why we HAVE to make the purchase. The primary reason we do this is to defend. To defend the purchase to a spouse, a friend…or even to ourselves. You see, we create the story to fend-off future shame.

“It has the faster processor and I do use my tablet a lot, so I should buy that new model.”

“It claims to help me hit the golf ball an additional 50 yards and I’ve really been working hard to improve my game so it makes sense that I should buy that new club.”

“It has a really good built-in camera and I’ve been dissatisfied with the way my camera has taken pictures lately, so I should buy that new phone.”

“If I wait to purchase a new car, my old car could break down and leave me stranded on the side of the freeway where a pack of wolves could eat me. I don’t want to be eaten by a pack of wolves, so I should buy the new car.”

We have met the enemy and it is us

Take a moment and think back to the last time you picked up a coffee on your way to work. Were you asking yourself if you could afford this purchase? Of course not. Sure, dropping a couple bucks on a fancy coffee may not be the best use of that money, but you already know subconsciously that buying it won’t break your budget.

Now think back for a minute and look at a larger purchase that did give you pause. It could have been that $150 dollar dinner out, a new plasma TV, or even a new car. Did you think about whether or not you could afford it? Did you make justifications as to why even though it wasn’t in your budget you could still make it work? Did you tell yourself a story as to how you can afford it?

Asking yourself if you can afford it, is actually a bad question to ask yourself financially. Depending on the person, being able to afford it could mean that it doesn’t completely zero-out or overdraw their checking account or that it doesn’t max out their credit card. Neither of those are necessarily good “affordability” answers.

Affordability is also relative. Assume both a 20-year old and a 55-year old are able to “afford” the payments on a new car. But what if the 55-year old only has $75,000 in their retirement account and they are 10 years away from retirement? The 55-year old obviously can’t afford it.

In Spanish the phrase “I can afford it” becomes “me lo puedo permitir”, which means “I can permit myself.” Now, that’s more intellectually honest than “I can afford it” because it implies that you are seeking approval from yourself, which is what’s really happening. But, let’s take it a step further.

Another (perhaps more common way) to say the same thing in Spanish is “darse el lujo” which literary means “give in to the luxury of.” Giving in. That’s exactly what is happening. Now we’re really talking the truth. And we know what they say about the truth – it can hurt!

Stop being a story teller

But for those seeking financial freedom, you have to be a lover of the truth, no matter how inconvenient it may be. As Shakespeare said, “To thine own self be true.” Roughly translated for today’s essay that means this – don’t tell yourself stories.

So, how can we eliminate the story-telling that comes with buying expensive or potentially unnecessary purchases? We can start by asking better questions. Here are some more useful questions than “Can I afford it?”:

1. What else could I do with this money that could grow my wealth?

2. How much would these dollars be worth in the future if I invested them, rather than spent them today?

But there are two questions that are even better than those to ask yourself. Instead of asking “Can I afford it”, ask this question instead: “Do I *want* to afford it?” The answer to that question will inevitably lead to the next better question – “Is it worth it?”

Is what your about to spend money on worth spending another year in a job you hate?

Is what your about to spend money on worth delaying your retirement another five years?

Is what your about to spend money on worth giving up your freedom for?

The next time you catch yourself creating a story about a upcoming purchase, take a moment to pause and reflect. Spending money has an opportunity cost. For every dollar that we spend today, we are not doing something (potentially better) with that money. Also, money has a time value. It decays. A dollar today is worth more than a dollar tomorrow. Once you spend it, you no longer have the compounding power of that dollar in the future to earn you more dollars.

Ask yourself, “Is it worth it?” Better questions mean better answers.

Be free. Nothing else is worth it.

Financial Freedom Monty Campbell

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Ready for more tips on how to achieve the free life? Check-out these articles from the blog archives below:

Would You Reject Free Income? These People Did, Because They Knew It Would Make Them Miserable.

Overcoming Financial Myopia: How To Think Long Term, In A Short Term Obsessed World

Is Premature Eye Drying Syndrome Keeping You From Achieving Success, Especially When Your Close?

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  • Hazel Collins

    Asking questions like these is a great way of figuring out if you’re working on the right things at the right time.

    • https://www.montycampbell.com/ Monty Campbell

      That’s right. It focuses the mind on what’s important.

  • mzashley

    Asking great questions is very important to find answers that are really meaningful. Breaking down the generic “what do you want most out of life?” into more concrete and specific questions is very helpful to face issues that matters in your life. So thank you.

    • https://www.montycampbell.com/ Monty Campbell

      Good points.

  • Ena

    I really prefer the written to the video blogs – and thanks for this one – since I can chew over the ideas and read and reflect on them at my own pace… Thanks!

    • https://www.montycampbell.com/ Monty Campbell

      Thanks. Glad you liked it.

  • JuminRhee

    I love your emails and articles. They make me be honest with myself.

    • https://www.montycampbell.com/ Monty Campbell

      Love that comment. Glad it resonated with you.

  • kay

    Very thought provoking post. And I have enjoyed reading the articles so far… equally thought provoking

    • https://www.montycampbell.com/ Monty Campbell

      Thank you very much.

  • Daniel Vincent

    Your post hit the nail on the head. Thanks for the reminder and instilling the motivation to get back to work on the stuff that matters.

    • https://www.montycampbell.com/ Monty Campbell

      Awesome!