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

When Ian retired a few years ago, I found myself 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 full retirement. There are several reasons why 2 out of every 3 retirees regret their decision.

  • Few people take time to plan for the lifestyle they hope to have in retirement. According to the Transamerica Center for Retirement Studies, only 14% of Boomers actually plan for the lifestyle they want, while most plan financially to some extent.
  • Boomers are living longer which may lure them into thinking that there is no rush to plan. The pressure mounts when they find themselves unexpectedly out of work and retired with little to no time to plan a smooth transition. We all want to retire on our own terms but it doesn’t always work out that way.
  • Boomers define what retirement means for them differently than their parents did. With more choices than ever before, unlimited possibilities and fewer role models to guide them, it’s easy to see why many feel lost or uncertain about what retirement will look like.
  • Many want to continue to work beyond age 60 or 65, but they often face age barriers from companies who haven’t quite caught up to the benefits of mature workers.

One way to avoid finding yourself retired and wishing you hadn’t is to look at this transition as “un-retirement” – a combination of work, volunteerism and leisure – rather than the traditional view of retirement. This new perspective examines all the possibilities available to you so you can continue to contribute, on your own terms. One way to ensure that your retirement lifestyle is the one you really want to pursue is to take time to ask yourself these questions.

  1. Work: Do I want to continue to work in some capacity? What will that look like? For how long?
  2. Health: What activities will I build into my daily routine to stay active and healthy?
  3. Financial: What adjustments will I have to make financially to fit my new retirement lifestyle?
  4. Leisure: What leisure activities do I want to pursue (e.g. hobbies, travel)
  5. Family: How important is it that I live near my children and grandchildren?
  6. Friends: Are there common interests and leisure activities we might pursue together?
  7. Life Partner: What interests do my life partner and I have? Which ones are different?
  8. Community: How involved do I want to be in my community? How much time will I give?
  9. Knowledge: Is there something I’d like to learn more about (e.g. genealogy, philosophy)?
  10. Environment: Where do I want to live and what type of home do I want or need?
  11. Spiritually: Will my spiritual practice evolve in retirement? How?
  12. Sense of self: What activities will help me maintain a high level of optimism and self-esteem?

These questions are designed to get you thinking about and gain insights into what your unique un-retirement might look like. The full answers may only come in retirement. That’s OK. The aim is to help you identify the hopes and dreams you have for your retirement. Take time now to do a little more lifestyle planning will help you feel good about your decision to retire and give you lots to look forward to. The hard work of career building is done now. It’s time to enjoy all that you’ve worked so hard to achieve.

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I help Boomers clarify what’s important in retirement. As you begin one of the most important life transitions you’ll make in your lifetime, I will help you create an inspired lifestyle plan so you can thrive and create your own unique legacy. No regrets.