Questions to ask yourself when planning for retirement

There has been many articles in our newspapers saying that a significant portion of Canadians is woefully prepared for their retirement. Some studies show that future retirees can expect a significant drop in their lifestyle at retirement.

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The amount of money that one needs in retirement varies from person to person depending on their specific situations. Although everyone seems to focus on the dollar amount needed for retirement, it’s more important to understand how someone wants to spend their time in retirement.

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Here are six simple questions to ask yourself prior to retirement to help plan better for those golden years.

1. Will you work during your retirement?

The days of retiring and never going back to some form of work are over. We are living much longer now than in the past and in order to finance a retirement that might last 30-40 years some form of income-producing work might be in order. Not just getting a paycheque, it is also important for our physical and mental well-being. Staying relevant and staying in contact with people are essential components in retirement. You want to be in a position at retirement to say that you can walk away from the job you are at but go on to do something completely different. Maybe you stay on as a consultant? Many options are available.

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2. How will you go about keeping healthy?

What do you do now to keep yourself fit and healthy? Are these activities that you can continue to do in retirement? How are your eating habits? Do changes need to be made in order to eat healthier? We are designed to move so we must in retirement age. Recently a woman ran a marathon at the age of 92 I believe. The oldest woman to ever do so. Times have changed from our Grandparent’ retirement. We are more active than ever before. Keeping yourself healthy and fit will prolong the enjoyment in your retirement.

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3. Where will you live?

My clients that are closing in on retirement look to where their children are living to help guide their decisions on where they, in turn, will live. Are you moving to a place that is more expensive or less expensive? Downsizing, does it work in major centers? Condo vs homeownership? Warm climate? In another Country for part of the year? How does that affect your benefits?

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4. How does your family fit into your retirement plans?

My parents, for example, are in their late 70s and live in a smaller city. They have been retired for over 20 years and have no interest in leaving their town because of the grandchildren. “Not until the grandkids are grown,” says my Mom. They will stay put until the grandchildren are well on their way. Retirees have the opportunity to spend time with grandkids that they didn’t have time for when they were working.

5. What plans have you made for changes in your day to day lives?

What contingencies have you made if your health changes? Or the health of your partner or spouse? What will you do and where will the money come from to pay for extra care and costs? We are living longer than ever before and we are living longer with illness so these are real issues that can de-rail a plan quickly. Have a discussion on how you go about funding for changes in health.

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6. How do you feel about retirement?

Probably the simplest question to ask. How do you feel about retiring? My view of my retirement plan has completely changed over the past 25 years. My plan says I can retire at 60 but as I look around and see what retirement is I think I might just work for a few more years beyond that. I love my job, I will have income coming in to pad my retirement accounts. The fact that I could live into my 90s perhaps makes me wonder how I could fill 30 years of retirement. Everyone is different. I have some clients who say they will never retire and I have others that can’t wait. Everything in between as well.

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It is never too early to start the process of thinking and planning for retirement. Here are some questions to ask yourself before you crunch the numbers to determine how much you need.


  1. Rosemary Wells

    The questions are good but perhaps they should be asked in the context of ten year increments….as in between the ages of 65 and 75; 75 – 85 and 85 – 95…. Each period requires separate reflection in order to plan appropriately. For example, many retirees travel to various parts of the world between 65 and 75 but slow down travel after this point. This means more money for travel will be required in that decade. Similarly, where will one live between 85 and 95? In their own current home? A condo? With children?

  2. Marie Lang

    Have to agree with Rosemary. These questions are very general and the way you frame retirement seem to apply to any period after 50. More like transitioning into the “golden years” instead of a full stop retirement from generations ago. Still a great resource for people starting to plan for retirement or approaching middle age.

  3. Joey Sapien

    Great Post! You touch on a lot of important topics to consider while planning for retirement. For me, unless I’m not healthy, I plan on continuing work. Perhaps start a new business venture. I also plan on going for nice long bike rides to stay fit. Perhaps join a community of active, over 50 like-minded individuals. For family, we plan on visiting lots and helping out with the grand kids. Overall, I feel pretty good about retirement.

  4. Sheryl Smolkin

    Great piece Scott. Check out my blog which was inspired by yours.

    “Questions I asked myself when planning for retirement (

  5. Alexa Green

    The key is to start early. Too many kids are being weighed down by student loan debt, I fear that the next generation may be in a worse position than we are!

    Planning for retirement is especially for hard for people without certain incomes. Photographers are just an example, but there are plenty of freelancers who don’t even want to think about retirement.

    How do you think student loan debt will play into retirement for the future generations?

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