Personal Finance

50 money questions to ask yourself

“How are you going to find out about things if you don’t ask questions?” – L. M. Montgomery (Anne of Green Gables)

As a new year approaches, many people are reflecting on the year that’s almost complete and are setting goals for the upcoming one. I’m an avid goal setter and I find that going through the process of evaluating where I am, and deciding on where I want to go over the next 12 months, helps create a sense of calm in an often chaotic existence. Money and finances are often at the heart of the goals people set and so, for this week’s post, I thought it might be useful to share a series of money questions I use when evaluating my own financial situation and when helping others evaluate theirs.

Related article: Setting Financial Goals

A lot of the questions have yes/no answers. As a general rule of thumb, any question you answer “no” to is an area that you could attach a goal or a “to do” item to. For example: if you answer no to the question, “do I have a spending plan?” then you might want to ask yourself if having a spending plan would help you financially. If it would, then it makes sense to challenge yourself to create one. The idea of the activity is to help you get in touch with your finances, give you a sense of where you stand financially and show you where you might want to focus your attention if you’re looking to make changes.

Income and outgoings:

  1. What do I earn per month?
  2. What do I spend per month?
  3. Do I have a spending plan?
  4. Is it written down?
  5. Do I follow it?
  6. Do I have a plan for extra income and incidental expenses?

Non-mortgage debt

  1. How much do I owe?
  2. Who do I owe?
  3. What interest rate do I pay on my debts?
  4. Do I have a plan to pay off my debts?
  5. Is it written down?
  6. Do I follow it?
  7. What date will I be debt free?
  8. If I die, how will my debts be paid?

Mortgage debt

  1. Do I have a mortgage? (If no, go to question 23)
  2. What’s my current mortgage balance?
  3. What interest rate am I paying?
  4. Is it fixed or variable?
  5. When is the renewal date?
  6. How many years are left until it’s paid off?
  7. Is it insured?


  1. How much do I save per month?
  2. Where do I save? (Savings account, RRSP, TFSA etc.)
  3. Who are my beneficiaries on each savings account?
  4. Is my saving automated?
  5. What is my savings rate? (amount saved per year divided by your gross income)
  6. Am I saving at least 10% of my salary towards retirement?
  7. If I missed three paycheques, would I have enough in (non-retirement) savings to get by?

Protecting assets

  1. Do I have a will?
  2. Do I have a Power of Attorney?
  3. Do I have Personal Directives?
  4. If I answered ‘no’ to Q. 20, 21 or 22 – why?
  5. If I answered ‘yes’ to Q. 20, 21 or 22 – when was it last updated/reviewed?
  6. Do I have life insurance?
  7. If yes: how much? Is it enough?
  8. If no: Do I need it?
  9. Do I have Critical Illness insurance?
  10. If yes: how much? Is it enough?
  11. If no: Do I need it?
  12. Do I have disability insurance?
  13. If yes: how much? Is it enough?
  14. If no: Do I need it?

General questions

  1. On a scale of 1 (terrible) – 10 (excellent), how would I rank my current financial situation?
  2. Hasmy financial situation improved over the past 12 months?
  3. If yes: how?
  4. If no: why not?
  5. What financial changes wouldI like to see 12 months from now?
  6. What doI need to do in order to create those changes?
  7. What’s the first step in making that happen?
  8. When willI take it?

While there are obviously more money questions that can be asked, this list is intended to be a starting point, a simple way to give you a sense of how much you have, where you want to go and where you might be vulnerable. Going through the questions helps you see where you are knowledgeable about your financial situation and where you’re not, which in turn gives you an idea of where you might want to focus your energy when it comes to making changes. Managing money and building wealth isn’t rocket science; a lot of the time it comes down to developing a few key habits and then doing them consistently. Hopefully the 50 questions above will help you identify a few areas that you can focus on over the next 12 months which will help you improve your personal situation and get you closer to your goals.

If you have suggestions for other questions that could be added to the list, I’d love to hear them!


  1. Florence C. Johnson

    that is ok if I am perfect woman, in perfect world, with perfect habits, otherwise I am what I am, over spender, over borrower, but I manage somehow. If you ask me how, I don’t know

  2. Tim

    I believe that questions 32 and 33 are referring to the wrong questions. Am I wrong?

  3. Max Ji

    Good list. Under Protecting Assets, how about long-term care insurance?

  4. Jess @ Best Credit Cards Canada

    Your “Protecting Assets” questions hit home for me because this is a spot where my husband and I are really behind. We totally understand the value and need but keep putting it off: we’ll sort it out once we’re married, once we have a baby, once the second baby arrives….I also think it will be a hard decision to choose legal guardians for our children. We have 2 excellent choices and we don’t know how we’ll choose!

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