Retirement planning Enjoy retirement

5 conversations to have before you retire

Like other significant life changes (marriage, childbirth, relocation), there are things to do to prepare for retirement—and some meaningful conversations to have before the big day. The work you do ahead of your retirement can help make the transition and first few months of retirement easier. Perhaps unsurprisingly, open communication is beneficial.

Make sure to talk about these things before retiring

It’s helpful to speak with family members, friends and professionals who support you about your ideas and expectations before you retire. Getting on the same page can help prevent disappointment or even conflict. Here are some conversations to have.

Expectations for you and your partner

If your partner is retiring at the same time as you, have a conversation about your expectations for each other. Do you think you’ll spend time together daily? Do you want to do activities together? If they’re not retiring, discuss what you’re expecting regarding how the relationship and household responsibilities will change. As part of this, you may have a conversation about family responsibilities with aging relatives. Getting everything out in the open is helpful and can prevent resentment.

Time with grandkids

If you have grandchildren, spending time with them might be on your retirement to-do list. Consider how much time you’d like to spend and have a conversation with their parents. For example, are you or your grandkids’ parents expecting that you’ll provide regular childcare? If not, are you hoping for weekly family meals? Just like with your partner, it’s best to talk with family members about your ideas.

Financial readiness and spending

A conversation about finances with your partner and guidance from a financial planner might seem obvious. Get clear about how your cash flow will change and go over how your expenses will decrease – for example, you may spend less on fuel and clothing since you won’t be going to a workplace. Discuss your goals for retirement. Are you considering downsizing? Do you want to do certain activities or hobbies that have higher costs? Even if things are just possibilities at this point, it’s a good idea to be open about your thinking.

Work plans or ideas

Many people want to continue some type of paid work in retirement. They may consult or take contract work with their current employer. Some people start a whole new venture—a part-time job at a local business or organization or create a small business of their own. If you’re interested in contract work with your current employer, have a conversation with your supervisor before you retire. Make your interest is known and ask about potential opportunities. Otherwise, be sure to make your partner aware of your ideas for work in retirement, so there are no surprises!

Emotional preparedness

Retirement is a significant life transition, and it can bring up all kinds of emotions—excitement for sure, but also sadness and even dread. You might find yourself questioning your worth because you’ve gone from being so busy to having free time. And, because our society tells us retirement is supposed to be exciting, if you’re not feeling that way, you may wonder what’s wrong with you (spoiler alert: nothing is wrong with you. It’s common to have mixed emotions).

It can be helpful to have ongoing conversations about how you’re feeling—you can prepare for retirement emotionally! If your friends and loved ones know what’s going on for you, they can support you. Keep in mind that professionals in your community can help you through the transition. You could book some sessions with a social worker or other mental health professional to talk about any worries or feelings you have. Doing this proactively, before you are very concerned about your mental health, is always a good idea. Social work and psychology services are covered under RTOERO’s extended medical plan for retirees.


The conversations you’ll have as you prepare for retirement are an essential part of your planning. Financial planning often gets the retirement spotlight—but it’s one part of the planning process. For more information about retirement planning beyond finances, read our white paper Five ways to think about retirement planning… and money isn’t one of them.

Download the ultimate retirement planning resource bundle for Canadian education workers

We’ve packaged up our best retirement planning resources to
help you get retirement ready with confidence.

  • Retirement planning checklist
  • Template retirement letter
  • Your life by design ebook
  • Procrastinator’s guide to retirement
  • Esprit – our membership and insurance guide
  • Insurance comparison checklist
Estimated Retirement Year*
Email* (Please use your personal email address to make sure our emails get to you! We’ll never share your email with anyone else.)