PLANNING MATTERS (January 30, 2018)
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 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. However, 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
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
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
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 are when we hold down full-time jobs and careers, rediscovering what
truly matters to us might take some work.