12 Questions to Ask Yourself Before You “Un-Retire”

015When my colleague retired a couple of years ago, stuff I felt envious, find lamenting how lucky he was and wishing for the day when I could announce my own retirement. A few months later I saw him and asked how he was enjoying retirement. “I hate it, I never should have retired,” he said. He identified so strongly with his work that without it he felt lost. Unfortunately he’s in good company. According to Statistics Canada, 64% of retirees express some regrets within 1 to 3 years of retirement.

There are a number of reasons why boomers are regretting their decision to retire. The most prominent one is that few take time to consider and really plan for the lifestyle they hope to have. Many plan financially but give little thought to what their day to day will be like. In fact, research has shown that only 3% of people plan psychologically for retirement. The fact that boomers are living longer is also adding to the pressure to un-retire.

One way to avoid finding yourself retired and wishing you hadn’t is to do a bit more reflection and planning, much like you do with your financial plans. Start by asking yourself these questions to gain insight into what un-retirement might look like. 

  1. Work: Do I want to continue to work in some capacity?  If yes, what would that look like?
  2. Health: What activities will I continue or build into my daily routine to stay active and healthy?
  3. Financial: What adjustments will I have to make financially to fit my new lifestyle?
  4. Leisure: What leisure activities will be part of my un-retirement and how will they fit into my lifestyle plans? For example, how much travel do you plan on doing and what will it costs?
  5. Family: What plans do I have regarding my immediate and extended family?  How important is it that I live near my children and grandchildren?
  6. Friends: How do I plan to stay connected with my friends?  Are there common interests and projects we might pursue together now that we have time?
  7. Life Partner: Do I understand the interests my life partner has in retirement and how do they connect with the interests I have?  What individual interests or projects will we want to pursue?
  8. Community: What involvement do I want to have with my community? Is volunteering something I want to pursue? If yes, how much time do I want to spend and with which organizations?
  9. Knowledge: Is there something I’d like to learn more about, studies I’d like to pursue now that I’ll have more time? What opportunities exist locally or abroad?
  10. Environment:  Where do I want to live and what type of home do I want?
  11. Spiritually: Will my spiritual practice change when I retire? How?
  12. Sense of self:  How do I define my sense of self-worth and how will it change as a result of retirement? What activities will help me maintain a high level of optimism and self-esteem?

You may not have a complete answer for each question, but aim to get answers to  most of the questions before you retire, those that are important to you. With a little more planning, you’ll feel good about your decision and you’ll have lots to look forward to. A bit more planning will also help you create a bucket list of things that are important to you during this important chapter in your life. The hard work is done now and it’s time to enjoy all that you’ve worked so hard for. Celebrate your newfound freedom and live life to the fullest.


As a Coach and through her company, Dianne help individuals plan for retirement by actively discovering, designing and directing meaningful activities that address one of the most important transitions in their life.

Written by

Dianne Gaudet is a certified Coach who is passionate about helping her clients manage the dynamics of continual life transitions as they reach new heights of personal and professional success. Helping Boomers create rich and inspired lifestyle plans for the retirement life they want is one of her greatest joys. Dianne is the author of a new book, If There Are No Limits... A guide to living with passion, purpose and possibilities. She is also a motivational speaker, teacher and world traveller.