“I wish I’d done this years ago.” It’s a sentence I hear more than any other from retirees I work with — and the surprising part is, it’s rarely about money. Over the past 12 years of helping Canadians approach or enter retirement, I’ve noticed a clear pattern: the biggest retirement regrets are about life, not finances.
Even with a fully funded RRSP or a solid pension, retirees often feel they missed out on the moments that truly matter — spending time with loved ones, enjoying meaningful experiences, staying socially connected, or having a clear purpose. The good news? Most of these retirement regrets are completely preventable with thoughtful planning.
In this post, we’ll break down the five most common retirement regrets and provide practical steps to ensure your retirement is fulfilling, purposeful, and free from unnecessary regrets.
The 5 Retirement Regrets Money Alone Can’t Fix
1. Not Retiring Earlier When You Could Have
Many retirees delay retirement to hit a financial milestone, only to realize later they’ve traded time for money. Extra working years often cost health, energy, and opportunities to enjoy life.
Example: David worked two additional years to reach his RRSP goal. By the time he retired, his wife’s health had declined, and their dream trip was no longer possible.
Tip: Know your numbers and retire when you’re financially ready. Time cannot be bought back.
2. Not Planning the Social Aspect of Retirement
Work provides social connections, and leaving it can create isolation if you haven’t planned ahead. Retirees like Susan often feel disconnected even with financial security.
Tip: Build your social network before retiring. Volunteer, join clubs, reconnect with friends, and find hobbies that involve others to prevent loneliness in retirement.
3. Not Spending on Meaningful Experiences
Fear of running out of money often stops retirees from investing in travel, hobbies, or family adventures. Missing these moments leads to lasting regret.
Example: Linda delayed a Disney trip with her grandchildren. By the time she finally went, her oldest grandchild was no longer interested.
Tip: Use your early retirement years — when energy and health are at their peak — to enjoy meaningful experiences.
4. Not Having a Clear Purpose or Routine
Retirement is a new chapter, not just an endless vacation. Without goals or engaging activities, retirees can feel lost and unfulfilled.
Example: Robert retired at 62 but felt purposeless, missing the sense of accomplishment work had given him.
Tip: Identify hobbies, volunteer opportunities, or projects that energize you. Create a routine and purpose before retiring.
5. Not Helping Loved Ones Earlier When It Mattered
Delaying support for family or friends can result in regret, even if money is eventually passed down. Helping loved ones when it truly matters creates a lasting impact.
Example: One client delayed assisting his children financially. While the inheritance eventually went to them, it didn’t have the same meaningful impact as helping when they really needed it.
Tip: Plan how to balance your retirement security with helping loved ones when it counts most.
Final Thoughts
Financial security alone cannot prevent retirement regrets. A fulfilling retirement requires planning for time, purpose, relationships, and experiences.
Ask yourself:
- Am I ready to retire when I can?
- Have I planned for social connections outside work?
- Am I prioritizing meaningful experiences?
- Do I have a clear purpose and routine?
- Can I support my loved ones when it truly matters?
By addressing these areas now, you can avoid the regrets many retirees face and enjoy a retirement full of freedom, connection, and fulfillment.
Plan your retirement with confidence. Explore our Retirement Toolkit for checklists, calculators, and step-by-step guidance. Use our Atlas system to align your financial plan with your life goals and ensure your retirement is everything you’ve dreamed of.
For more practical tips, real-life stories, and strategies you can implement today, visit the Trans Canada Wealth Management YouTube channel and subscribe for regular retirement insights.
