Retirement
October 27th, 2026

Ask Yourself These 10 Retirement Questions

Retirement planning is a specialty of ours—the complexities of investing, tax, income, pensions, net growth, and drawdown. But effective retirement planning starts by setting all that aside.

If you were to put the financial dimension of it completely out of your mind, how would you think about retirement?

Below is a set of questions we recommend asking yourself about retirement, whether you’re two years out or 20, and whether you have a detailed plan in place or you’ve never considered it.

  1. If you didn’t have to work today, how would you want to spend the day?

  2. What hobbies or interests do you wish you had more time for?

  3. What is your current relationship to work (fulfilling, draining, challenging, etc.)?

  4. If money were not a consideration at all, would you retire right now?

  5. How do you want to change the world around you (helping loved ones, affecting your community, advancing your profession, etc.)?

Here are a few more questions to build on that first set:

  1. Would you enjoy participating in work of some kind in retirement?

  2. When you think of your retirement lifestyle, what aspects of it are age- or lifestage-dependent (athletic goals, family support, legacy building, etc.)

  3. Which is more important to you: building an estate or building your retirement life?

  4. How does your retirement vision line up with that of your spouse or immediate family?

  5. Right now, how does thinking about retirement make you feel (excited, galvanized, worried, etc.)?

Once we answer some of these questions with our clients, we can begin to turn our attention to the financial inputs—savings, investments, income sources, and tax considerations, for example.

Most importantly, however, these questions can start the conversations preretirees need to have about their life and wealth. Opening up to yourself, your spouse, your family, your business partners and, of course, your advisor, is just as important as making smart financial moves on the way to retirement.

Let me know if you would like to chat about these ideas, and feel free to pass them along to anyone you know who is thinking about the next chapter.


Jim Wilson, B.Comm., CFP®
Senior Wealth Advisor
jim.wilson@iaprivatewealth.ca | Tel. (289) 644-1476

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