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My Favorite Questions

Jonathan Clements  |  September 15, 2018

YOU’RE UNLIKELY to get the right answers—unless you ask the right questions.

That’s especially true when it comes to managing money. We have answers thrust in our faces all the time, as marketers and salespeople exhort us to buy this mutual fund, that car, this stock, that home and this insurance policy.

But are these really what we want or need? It’s hard to know unless we ask the right questions. There’s ample evidence that many folks end up with financial products they don’t need and spend money in ways that bring little or no happiness. It isn’t that we can’t figure out the answers—but to do so, we need to eschew snap decisions and instead take the time to ponder key questions, so we build the financial life we truly want.

That’s the goal of my new book, From Here to Financial Happiness, which was published last week by John Wiley & Sons. The book takes readers on a 77-day journey that helps them figure out where they stand, what they want and what steps they ought to take.

I view all this as a conversation, with questions posed by me and plenty of room in the book for readers to write down their answers. Want to make sure you squeeze maximum happiness from your spending, buy the right portfolio, pursue the goals you really care about and avoid major money mistakes? Consider these 31 questions—all of which are drawn from my new book:

  1. If money were no object, what would you change about your life?
  2. What are your top financial worries?
  3. What are the three smartest financial moves you’ve ever made?
  4. What do you consider your three biggest financial mistakes?
  5. How much financial help should you give a child?
  6. When in your life were you happiest, what made it a happy time—and what role, if any, did money play?
  7. What’s the minimum amount of money you need each month to keep your financial life afloat?
  8. If you were out of work, how long could you cover expenses before having to take drastic financial steps?
  9. What did you learn about money from your parents—and which of these beliefs have you adopted as your own?
  10. Think of three people you know who are in great financial shape. What have been the keys to their financial success?
  11. Is it important to you to drive a nice car and, if so, why?
  12. In the typical week, which moments do you enjoy the most—and which do you dislike the most?
  13. Is getting rich one of your overriding life goals?
  14. Think about your weaknesses. Are they acceptable human failings—or are they inflicting major damage, including major financial damage?
  15. Who depends on you financially—and how would they cope if you suffered an untimely demise?
  16. When is it okay to go into debt?
  17. Think about your life’s major expenditures, like buying homes, purchasing cars, remodeling projects, expensive vacations and paying for college. Which are most likely to make you smile and which ones disappointed you?
  18. What’s on your wish list for major expenditures in the years ahead?
  19. Do you believe a home is a good investment? Why?
  20. What’s your net worth—the value of everything you own, minus all debt?
  21. Does your stock-bond mix reflect your paycheck or lack thereof?
  22. Imagine your perfect retirement day. How would you spend it—and would you be happy doing these things every day for the rest of your life?
  23. Are there children—either your own or somebody else’s—whom you’d like to help financially, and what sort of assistance would you like to provide?
  24. In late 2008 and early 2009, did you buy stocks, sell or sit tight?
  25. How much do you pay in investment costs each year?
  26. If you weren’t burdened by the knowledge of what you hold, what you sold and how markets have fared, would you own your current portfolio?
  27. If you take your bonds and other interest-paying investments, and subtract all your debts, what’s your net bond position?
  28. Are you on track to have all debt paid off by retirement?
  29. If you died tomorrow, would you bequeath a mess?
  30. When was the last time you talked honestly about your finances with somebody?
  31. If you were writing your own obituary, what accomplishments would you include? In the years ahead, what further accomplishments would you like to add?

Special Offer

For the next seven days, the hardcover edition of From Here to Financial Happiness will be available from Amazon for $22.46—a 25% discount from full price. Meanwhile, the Kindle edition costs just $11.99. If you click through to Amazon using these links and buy the book, this site earns a modest referral fee. You can also purchase the book from Barnes & Noble and elsewhere.

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Follow Jonathan on Twitter @ClementsMoney and on Facebook. His most recent articles include Striking a ChordTell Us a Story, Bad News and No Place Like Home.

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