Questions to Ask Yourself to Lead a Better Financial Life

If you read TwoCents, you are probably looking for advice on how to improve your financial life. You might want to be more responsible with your money, or learn how to invest better, or just get a daily reminder to take care of your money.

And while there are countless ways to get your finances in order, it all starts with exploring what’s important to you and your family: what are your priorities, what are your values? Once you do this, the steps you need to take will become clearer.

To better understand what’s important to you, here are 31 questions from Jonathan Clements, a former personal finance columnist for the Wall Street Journal and current editor of the Humble Dollar, about “getting the most of your spending happiness” with important goals:

  • If money weren’t an issue, what would you change in your life?
  • What worries you most financially?
  • What are the three smartest financial steps you’ve ever taken?
  • What are the three biggest financial mistakes you consider to be yours?
  • What financial assistance should be provided to the child?
  • When were you happiest in your life, what made that time happy, and what role, if any, did money play?
  • What is the minimum amount of money you need each month to keep your financial life afloat?
  • If you were out of work, how long could you cover the costs before you had to take drastic financial action?
  • What have you learned about money from your parents – and which of these beliefs have you adopted as your own?
  • Think of three people you know who are in excellent financial condition. What were the keys to their financial success?
  • It is important for you to drive a good car, and if so, why?
  • What moments during a typical week do you like the most and what do you dislike the most?
  • Is getting rich one of your most important goals in life?
  • Think about your weaknesses. Are they acceptable human handicaps or are they causing serious harm, including massive financial damage?
  • Who is financially dependent on you and how will they cope if you suffer an untimely death?
  • When can you get into debt?
  • Think about the main expenses of your life, such as buying a house, buying cars, renovations, expensive vacations, and college fees. Which ones are most likely to make you smile, and which ones are most likely to disappoint you?
  • What’s on your list of major expenses for the coming years?
  • Do you think a home is a good investment? Why?
  • What’s your net worth – the value of everything you own minus all debts?
  • Does your stock-to-bond ratio reflect your paycheck or lack thereof?
  • Imagine your perfect retirement day. How would you spend it – and would you be happy to do it every day for the rest of your life?
  • Are there children – your own or someone else’s – whom you would like to help financially and what kind of help would you like to provide?
  • In late 2008 – early 2009, did you buy shares, sell or sit idly by?
  • How much do you pay for the investment costs annually?
  • If you weren’t burdened with the knowledge of what you have, what you sold and how the markets are doing, would you own your current portfolio?
  • If you take your bonds and other interest-bearing investments and subtract all your debts, what is your net bond position?
  • Are you going to pay off all your debts before retirement?
  • If you died tomorrow, would you leave a legacy of disorder?
  • When was the last time you spoke candidly with someone about your finances?
  • If you were writing your own obituary, what achievements would you celebrate? What other achievements would you like to add in the coming years?

I took this question from the Humble Dollar newsletter , but Clements says he goes into detail about them in his new book, From Here to Financial Happiness .

Some of them may not apply to everyone, but almost all of them are good thought experiments: Do you think buying a home is a good investment for you and your family? What exactly are you trying to achieve in your only life, and what role does money play in this? Who are these people who depend on you and how much do you think you owe them?

Take time to be alone with yourself, with your spouse or other decision-makers in your life, to answer some, if not all, of the questions above. They will not only give you clarity, but they will also help pave the way to financial freedom, whatever that means to you.


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