Ready for a Regret-free Retirement? Test Yourself with 11 Questions!

As a certified professional retirement coach, I understand that today’s Baby Boomers face a different reality than previous generations did when preparing for retirement. This list of 11 questions could help you assess your readiness for creating a regret-free retirement. While these questions do not address all that you should consider before retiring, they could provide a starting point

1. Do you have enough passive income to meet your needs plus emergency funds?

As the Social Security Administration projects that one in four Boomers over 65 will live to be at least ninety, are you prepared financially for a long retirement?  Passive income could include pensions, social security, rental property, royalties from creative works, dividends, or other streams of revenue. Of course, any of these sources could be less stable than we may want to believe.

2. If you want to make additional money or work part-time, have you considered how to make this desire a reality?

Because we’re likely to live a lot longer than previous generations, a growing number of Boomers plan to work at least part-time during retirement. The reality is 65% of Boomers report they have experienced age discrimination. Still, some Boomers are able to scale back their hours and keep working for their current employers. Others have found free-lancing or working for themselves best meets their needs.

3. Have you given yourself sufficient time to prepare for the nonfinancial aspects of retirement?

Retirement is one of the biggest transitions we’ll make in life. Part of our life will end when we leave our jobs. A new beginning awaits us. Yet if we don’t sufficiently plan, we could end up with a lot of regrets. Research suggests we give ourselves about two years to plan for the nonfinancial aspects of retirement before leaving our jobs.

4. How strongly do you feel your work role or position is a central part of your identity?

One of the biggest struggles many new retirees have is trying to figure out who they really are after they no longer have a specific work role or title. Dr. Who? Who are you becoming?

5. Are you confident that you can develop enough structure in your life so that you feel like you can make the most of potentially decades of retirement?

Having a job generally provides enough structure to give us feelings of accomplishment and helps us keep focused. When you retire, how will you structure each day, week, and month? A lack of structure is one area that can be very difficult for some new retirees.

6. Have you developed interests or hobbies that you will pursue in retirement?

Just like saving for and planning a trip around the world, it is wise to make sure you have some idea of the activities you want to pursue and the things you plan to do once you are free to do them.

7. Do you have at least the beginnings of a social network beyond work?

We may believe that we’ll still see the same ‘friends’ from work after we retire, but that’s not usually the reality for most. Loneliness is a significant issue for some retirees. Having a social network also helps keep us engaged and often healthier. If you are an extrovert, finding new friends might be easier than if you are not so outgoing. Volunteering or belonging to an organization or religious group is one way to connect with new people.

8. Are you currently doing a good job of managing your overall health?

Eating a healthy diet, getting regular exercise, managing stress, getting sufficient sleep, and getting routine check-ups are more important than ever as we age. Studies show that these behaviors may lead to longer, more satisfying lives and are also good for our brains. However, if you currently are not managing your health, don’t expect to become a fitness guru after you retire.

9. What are your plans that involve keeping mentally stimulated?

Do you enjoy reading, taking classes, interacting with people, or learning something new as a self-directed learner? Studies suggest that a lack of mental stimulation after retiring can contribute to some cognitive decline.

10. If you’re in a relationship, have you each shared what your vision of retirement looks like?

Retirement not only affects our lives, but it affects the lives of those who are closest to us (including family members). It is vital that we talk to the important people in our lives about our goals and our vision for our retirement. Have you had ‘the talk’ about retirement with those closest to you

11. Are you able to identify some of your core values, and do you know some possible ways you might act on those values in retirement to give your life new meaning?

Having a sense of purpose or meaning tends to become increasingly more important as we age. For some, this quest for meaning or a ‘life vision’ can become an all-consuming task. Identifying our purpose or that personal mission that gets us going in the morning usually starts by unearthing our core values. What values are so important that we are willing to sacrifice, to prioritize, and sometimes even take a stand for them? Examples of core values could include faith, family, service, social justice, friendship, making the world a better place for future generations, etc. Because many of us sacrifice part of who we really are when we hold down full-time jobs and careers, rediscovering what really matters to us might take some work.

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I am an associate professor of communication in Southern Oregon. I'm also an ancient spirit who has learned how to create positive changes in my own life and use unexpected changes to become more of the person I believe I am meant to be. My vision is to help empower others by sharing how to dream big and develop measurable action steps to achieve those dreams.

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