100 Questions To Ask Yourself About Your Financial Mindset

Recently, an old friend of mine came to me quite upset. She was drowning in debt, much like I was, and she told me she didn’t know where to even start. I told her that I would be glad to counsel her, but that I didn’t want to actually look at her financial numbers because she was very uncomfortable with that.

To begin the process, I started writing a list of questions that I wanted her to answer, and over time this list grew to one hundred questions. I sent them to her with the caveat that she answer them herself, but that she think about each one for a little bit to see what the question could reveal to her. The questions were grouped a bit when the topic was similar, and they also moved from more psychological questions to real money questions and back, in order to create contemplation of both aspects of personal finance management.

When I read through the questions myself and considered my own finances, even now as I have learned how to recover from my own financial errors, many of the questions really make me think about what I’m doing with my own money.

Without further ado, here are one hundred questions to ask yourself (or ask someone else) about your financial mindset.

How much of your debt did you pay off in the past month?
How much money did you save for the future in the past month?

How many name brand items did you buy at the grocery store the last time you visited?
Have you ever tried the generic alternative, just to make sure that it was significantly less quality?
Do you often avoid the large economy package of an item you use regularly because it looks too big in your cart?
Did you go shopping for food when you were hungry and thus bought unnecessary food?
Before you left for the store, did you make a shopping list and stick to it?

Does your credit card have a good bonus program or a particularly low rate?
Do you have an outstanding balance on your card that is generating finance charges that you could easily transfer to a new card?
Do you ever sign up for store credit cards just to get an initial bonus on a purchase?

Do you repeatedly get dinged with annual fees or minimum balance charges by your primary bank?
Does your savings account earn less than 4% on whatever you have in there?
Does your checking account earn less than 0.5% on whatever you have in there?

What was the last item you bought that you felt guilty about?
Are you still using that item?
Did the guilt of buying it outweigh the enjoyment of the item?
How much did it cost?

Do you carry your credit card with you every time you leave the house?
When was the last time you unexpectedly needed your card outside the house?

How much of your last paycheck did you put into retirement?
How much of that was matched by your employer?
How much free matching money did you fail to get because you’re not putting enough into retirement?

Are there any items that you replaced in your home in the last year when the original item was still functional?
Why did you replace them?
Was it worth the money?

Do you ever buy gifts for people to make it appear as though you have more money than you do?
Do you ever buy gifts for people in order to repair a relationship when a healthy phone call could actually clear the air?
Do you ever buy gifts for people “just because” when a nice handwritten letter would mean just as much?
Do you ever buy expensive gifts for people in order to “outdo” them?
Have you ever tried to make a gift for a person?

How many times in the last week did you eat or drink something and pay someone else for making it for you?
How much less would it have cost to make it yourself?

How many hours each day do you actually watch cable television, or any premium channels?
How much is your cable bill per month?

Do you ever use the internet to comparison shop before you buy an item?

Do you owe anyone in your family any money?
Has this changed your relationship with that person?
Was it really worth borrowing the money?

Do you fill up your gas tank only when it is empty, or always at the same place?
Do you pump your own gas?
Do you stop and fill it up whenever you see a particularly low rate?

Have you ever attended a paid event, not enjoyed yourself, then attended it again at a later date?

Have you ever had to hide a purchase from someone?
Was the item ever worth the feeling you had when you had to hide that purchase?

Do you drive to work every day?
Is there another worker that lives near you that you could ride with?
Is there public transportation near you that you could use?

How many times in the last month did you eat outside of someone’s home (including your own)?
Do you have a place at work where you can store a bit of food instead of going out to eat or ordering food?
Have you ever invited friends over to eat “pot luck” style instead of going out for a meal?

How many articles of clothing do you have that you’ve only worn once, or never at all?
How many articles of clothing do you have that you paid more for solely because of the label?

If you have a gym membership, how many times have you gone to the gym in the past month?
If you have a country club membership, how many times have you gone to the club in the last month?

Do you have a deep freezer?
Do you ever spend a day preparing a large number of meals in advance so you can cook them conveniently later?
Do you ever buy foods in bulk to store in your freezer?

Do you ever feel shock when you hear the price of the items you purchased at the register?
Do you ever feel guilt when you find a receipt?
Do you ever break up a receipt, item by item, to see exactly what you spent your money on?

Do you ever buy a new version of an item when a used one will suit your needs (book, DVD, car, clothing, etc.)?
Do you know where the nearest consignment shop is?

How many books are sitting on your shelves that you’ve never read?
How many magazines are sitting in your magazine rack that you’ve never read?
How many DVDs do you have that you’ve only watched once, or never watched at all?
How many CDs do you have that you’ve not listened to in a long time, or never listened to at all?

Do you have an extra bedroom that you could rent out?
Do you have a hobby that could earn you a few extra dollars, like cooking or writing or fixing computer problems?

Do you regularly have overage charges on your cell phone that add up to more than the cost of a better plan?
Do you ever use the operator to look up a phone number for you, and then have them connect you to that number?

Do you wait until the last minute to reserve your airline or train tickets?
Do you ever comparison shop for airline tickets?
Do you ever consider whether it would be cheaper to use different airports near you or near your destination?

Do you drink more than one or two drinks per day?
Do you drink more than one or two sodas per day?
Do you smoke more than one or two cigarettes per day?
Are you using any recreational drugs?

Do you pay more at certain stores just because of the name and atmosphere of the store?
Do you ever find the same exact item in another store later at a much lower price?

Is there anything in your closet that you haven’t touched in six months?
Are you familiar with using eBay?

When you make a nonessential purchase, do you count to ten and ask yourself if you really need or even want to buy that item?

Have you ever written out a complete monthly budget?
Have you ever stuck to it, or even tried seriously to stick to it?

When was the last time you got a traffic or a parking ticket?
Do you ever let your car idle while running a quick errand?
Do you have regular maintenance done on your car?
Do you keep your tires inflated?
Do you keep anything heavy in your car that’s not necessary?

How much was the finance charge on the last credit card bill you paid?
How much was the interest on the last loan bill you paid?

How many hours did you leave the lights on at your house in the last day or so?
When you bought light bulbs the last time, did you buy regular bulbs or CFLs?
How many hours did you leave the television on when no one was watching it, or the computer when no one was using it?
How much does the electric company charge you per kilowatt hour?

How new is your car?
How many miles per gallon does it get?
Are you leasing the car or are you paying on a car loan?
How much money would you have saved if you had kept your previous car for one more year and then had a larger car down payment?

Where did all of that money really go?

Trent Hamm
Trent Hamm
Founder of The Simple Dollar

Trent Hamm founded The Simple Dollar in 2006 after developing innovative financial strategies to get out of debt. Since then, he’s written three books (published by Simon & Schuster and Financial Times Press), contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.

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