The last few weeks of the year feel busy. And somewhere in the middle of all of it, quiet deadlines pass.
Benefits that expired unused. Contribution room that wasn’t filled. A tax receipt that needed to be in by December 31. A subscription that renewed automatically. A flexible spending account that reset to zero.
None of it dramatic. All of it avoidable. Work through this checklist once before the year ends. Use AI to help with the parts you’re not sure about. Arrive in January with nothing left on the table.
How to use this
Read through each section. For anything you’re unsure about, paste the relevant section into AI and ask:
Health and workplace benefits
These are the ones with the hardest deadlines. Many reset on January 1 and cannot be carried forward.
Health spending account — Do you have one? If yes, how much is left? Unused balances in many plans are forfeited at year end. Eligible expenses typically include prescription glasses, dental work, physiotherapy, massage, prescription medications, and medical devices.
Dental coverage — Have you used your annual dental benefit? Most plans reset in January. If you’ve been putting off a checkup or cleaning, book now.
Vision coverage — Have you used your vision benefit this year? Eye exams and contributions toward glasses or contacts are often annual and go unused.
Paramedical coverage — Physiotherapy, massage therapy, chiropractic care, psychology, and other paramedical services are included in many employer plans. Check how many sessions remain and book before the year ends.
Employee assistance program — Free counselling sessions, legal consultations, and financial advice are often included. These typically don’t carry forward.
Wellness and lifestyle reimbursements — Some plans reimburse gym memberships, fitness equipment, mental health apps, or wellness programs. Check whether yours does and whether there’s an unclaimed amount.
Savings and investments
TFSA — Tax-Free Savings Account (Canada) — December is a good time to check how much room you have, consider whether you’re using it effectively, and plan contributions for the new year.
RRSP — Registered Retirement Savings Plan (Canada) — The RRSP deadline is typically the first sixty days of the following year. December is the right time to check how much contribution room you have and decide how much you want to contribute.
401(k) — United States — Contributions must be made by December 31. Check whether you’re maximising contributions and getting the full employer match.
Pension and workplace plans — Check your contribution level and confirm the employer match is fully used.
Tax planning
These are the ones most people think about in April — when it’s too late.
Charitable donations — Donations made by December 31 count for this year.
Medical expenses — Gather receipts for prescriptions, dental work, glasses, devices, therapy, and travel for treatment.
Childcare expenses — Ensure receipts or statements are ready.
Home office expenses — If you work from home, check eligibility and make sure records are in order.
Insurance
These often renew quietly. Check whether your home insurance still reflects your situation, whether your car insurance renewal is coming up, and whether any life or disability coverage needs updating after changes this year.
Subscriptions and recurring expenses
Review your bank and credit card statements for the year. Ask: do I use this? Is it worth renewing? Cancel anything unused before it renews automatically.
Things most people forget
Update your address everywhere it matters. Check that beneficiary designations on accounts and insurance policies are still correct. Make sure important documents are organised and accessible. Check that passwords and shared account access are up to date.
Important note
This checklist highlights what to review. For specifics, confirm with HR, your provider, or a professional. AI helps you understand what to check — official sources confirm the details.
The fifteen minutes most people skip
You don’t have to do everything. But fifteen minutes on this list — with AI helping where needed — can save real money. Start with one section. Then the next. That’s enough.
What to read next
→ End of Year Checklist — 5 Minute Version
→ How to Make the Most of Your Health Benefits
→ How to Use AI to Understand Financial Products — RRSPs, TFSAs and Beyond
→ Or visit the Decision Hub for all decision-prep guides in one place