Retirement planning Insurance

Retiring in June: Month-by-month retirement planning

Many people who work in education choose to retire in June. It’s a natural endpoint. If you plan to retire next June, this article is for you. We’ve broken down the tasks covered in our blog post about everything you need to think of to retire in Canada into a month-by-month schedule. Even if you’re not retiring in June, this post can still be helpful! Just change the months based on your own plans.

Did you know: RTOERO is for anyone who has worked or works in any role in education, including private schools and post-secondary? Your RTOERO membership gets you access to our group insurance for retirement, plus many other benefits. You have options when it comes to retirement insurance, and our nationwide plan is one to consider.

Month-by-month retirement planning for education workers

September – 9 months before retirement

Take a few deep breaths; the school year has just begun. Set an intention for the year. You know things will get busy at times, and there are always uncertainties. Keep your well-being a priority, and let’s plan to end your career positively.


October – 8 months before retirement

One month down! And autumn is upon us. Enjoy the feeling of fall sunlight on your skin. Take a moment to daydream about this time next year when you’re retired. Might you enjoy some more daytime walks? A late morning coffee?


  • Learn about how to sustain your finances in retirement
  • If you have a financial planner, set a meeting to talk through anything you need to do this year as you prepare, including when you want to start your CPP, how you can pay down any remaining debt and add to your emergency fund over the next year
  • Contact your HR department to ask for a retirement planning information package and any forms you may need. These may also be easily available on your staff website.

November – 7 months before retirement

The days are getting cooler, so it’s a great time to spend a few weekend hours working on your retirement plan.

  • Identify your income sources and expenses and make a budget. Here are two government tools that can help:
    • The budget planner from the Financial Consumer Agency of Canada is a great tool to generate a budget based on your specific life stage and goals
  • Contact your pension provider to discuss your situation. Things to discuss may include: what happens if you marry/separate while on pension, survivor benefits, the timeline and process for applying for your pension, what happens if you work while retired.
  • Update your pension information – register for online tools and name your survivor. Use the online calculator to check potential retirement dates.
  • Add ‘apply for pension’ to the excel checklist you saved in your retirement planning folder. Add the date based on what your pension provider said.
  • Explore your retirement insurance options and decide on your insurance. Our comparison checklist can help. You can look at our retirement insurance plans here.

December – 6 months before retirement

That’s a wrap on the calendar year. Last month we did a lot of financial planning. This is a natural point to plan to implement small changes to help you prepare emotionally for retirement.


January – 5 months before retirement

Welcome to the new year. It might be cold outside, but let’s keep the energy going as we wrap up your last year of work. Use this month to consider your retirement lifestyle.

  • Think about activities you’d like to try – our members often share retirement is an ideal time to try things you’ve always wanted to do or to get back to activities you used to enjoy but haven’t had time to do. Need help coming up with ideas? Here’s a list of 50 activities for retirement.
  • Go to your retirement planning folder and review the Your life by design ebook. It can help you get clear on your goals for retirement.

February – 4 months before retirement

This month is all about making your retirement official!


  • Notify your supervisor of your retirement plans.
  • Write and submit your letter of retirement. Use the template you saved in your retirement planning folder in September. Or, get some tips and download the template here.
  • If you’re interested in contract or supply work in retirement, discuss opportunities and the process with your supervisor. Check with your pension provider to learn if your post-retirement employment plans will have any impact on your pension.
  • Check the expiry date on your passport and provincial health plan card.
  • Let your colleagues know you’re retiring. Be prepared to share with any groups and committees you’re part of.

March – 3 months before retirement

Next time maple syrup season rolls around, you’ll be retired! Take some time during this sweet season to gain peace of mind for your future.


  • Review your life insurance. Consider whether you have enough life insurance to meet your family’s needs should something happen to you. RTOERO members have access to preferred universal and term life insurance rates through Johnson Insurance, our insurance partner since 1985.
  • While working on your income taxes, investigate tax credits for retirees. See our post How to make tax time more manageable in retirement for considerations and tips.
  • Consider if you want to attend the Retirement Planning Workshop again. It’s always free, and you can join as many times as you wish.
  • If you have specific questions, contact RTOERO to book a person call or virtual meeting – [email protected] or 1-800-361-9888.

April – 2 months before retirement

It’ll be here before you know it. This month’s big task is to take care of your insurance.


  • Apply for retirement health insurance. We always recommend applying one to three months before your retirement date. You have until 60 days after your current group insurance plan ends to sign up with automatic approval. Usually, that’s 60 days after your retirement date. When you sign up now, your coverage will kick in the day following the termination of your current plan, so there will be no gaps in your coverage.

It then takes less than 20 minutes to complete the RTOERO insurance form. Here’s what you’ll need:

  1. Your RTOERO membership.
  2. Your health card number and the health card number for your spouse and any dependents, if applicable
  3. Current insurance information
  4. A cheque for reference for bank deductions or your SIN if you’re an Ontario Teachers’ Pension Plan (OTPP) member and want to deduct premiums from your pension
  • Review your will. Retirement is a natural point to revisit your will and ensure you’ve identified a power of attorney for personal care and property. Read six qualities of a solid estate plan for advice.

May – 1 month before retirement

It’s probably hard to believe it’s May already. There aren’t many tasks left. You’ve done so much by tackling the tasks in monthly blocks.


  • Write your retirement speech. Here are some tips to help you!
  • Update the email subscriptions you want to keep, so they go to a personal email address.
  • If you’ve decided to start CPP/QPP, apply for it. If you’re 65, you can also apply to begin Old Age Security (OAS). OAS is a government-provided pension, intended to supplement income after age 65. There’s an option to defer CPP/QPP and OAS if you wish.
  • Contact your car insurance provider. You may be eligible for a reduction in your auto insurance costs since you won’t be commuting to work anymore.

June – retirement month

It’s here. The last month of work. You deserve all the accolades you receive! Congratulations.


  • Now that everything is in order, you can enjoy your last month of work!
  • Remind yourself that however you feel about retirement, you’re not alone. It’s natural to have mixed emotions. It’s also natural to be excited or even nervous. There’s no one right way to feel at this time!

After retirement


  • Purge your closet! You might find your wardrobe needs change when you’re not going to work every day. If you have professional clothing, it could be beneficial to someone else. Look for somewhere to donate clothing you don’t need anymore.
  • Connect with your local RTOERO district and other retiree groups

It’s no secret that breaking things into smaller chunks makes a big job, like planning for retirement, feel manageable. We hope this month-by-month retirement planning calendar is helpful to you. Be sure to download the retirement planning bundle to easily access the practical tools we’ve listed above.