Have you ever flown in a plane, a helicopter, or better yet a hot air balloon and looked down to notice that the whole world seems to divide itself into neat little squares?  And the funny thing is that we never notice those patterns from the ground.  It’s that view from several thousand feet that brings clarity and shows us the patterns of things.  Well, that’s what we’re going to do in this two-part article.

We’re going to catch a glimpse of your retirement design from the clouds to gain some perspective.  Then we will focus in on one of the six areas we’re about to mention.  Think of the next series of posts as hopping from one square to another, landing and exploring each one together.


The first area that we’ll check out is “Who”.  Who needs to be involved as you design your retirement?  Your spouse?  Your children?  Your doctor?  Your financial planner?  There are many possible players here, so let’s look at how to organize them.

As we work with people like you every day at Hillandale Communities, we suggest that folks think of these key people in three distinct groups – Daily People, Regular People, and Occasional People.  Because everyone’s world of family and friends is unique, we find that this organization makes it easy to prioritize just about any situation.

Daily People:  Daily people are those folks that interact with you on a daily basis.  These are ones who factor into every decision of any magnitude.  Some likely members of this group are your spouse/significant other, your children, your best friends, your neighbors, or your siblings.

Regular People:  Regular people are those folks that interact with you on a regular, but not necessarily a daily basis.  These are people with whom you have close enough relationships that they will be effected by the decisions you make.  Some likely members of this group are siblings, your pastor, priest, or rabbi, friends from the community (clubs, church, civic organizations etc.), neighbors, or your personal doctor.

Occasional People:  Occasional people are those folks that interact with you only occasionally.  You may see these people monthly or even less often.  Some likely members of this group are your financial advisor, your insurance agent, your accountant, your lawyer, or a medical specialist (cardiologist, oncologist, etc.)

The purpose of placing the people in your life into these categories is to decide the information that each one needs to know and/or provide to you.  It will also help you keep in perspective whose opinions and feelings matter most.  Sometimes the people who are most eager to weigh in on decisions like this may not be Daily or even Regular people, and it’s good to remember who the key players are.  This helps you keep everyone’s input in perspective and make sure that you handle the most important issues first, even if they’re not the loudest voices in the conversation.  Regardless, remember that your voice is the center of this discussion.


The second area to consider is “What”.  What do you enjoy about your life now?  What don’t you enjoy?  What would you change if you could?  What is different from who, but it still has it’s own three categories.  What do you want to keep about your lifestyle?  What do you want to let go of?  What are you going to do with the things you don’t want?  Let’s look at these one at a time.

What do you want to keep about your lifestyle? 

These are things that you can’t see yourself ever wanting to live without.  Maybe you don’t ever want to live apart from your spouse, so you are willing to live anywhere as long as you can remain together.  Perhaps you can’t imagine living without a pet or a car or the internet.  Whatever these things are for you, make a list of them and be honest with yourself.  This is your retirement and the whole point of this process is to have it your way.

What do you want to let go? 

These are things you deal with now that you would rather not have to deal with in retirement.  Maybe you don’t want to have to maintain your yard, your house, or your car.  Maybe it’s as specific as not wanting to ever shovel snow again.  Whatever it is, make this list and, again be honest.  We’re not making binding decisions at this point, we’re just getting all of the items on the table.

What are you going to do with the things you don’t want? 

This is nothing more than an exit strategy from your current life into your retirement life.  In this list, you’ll want to account for things like transitioning your job or, if you own a business, deciding how you will handle that in retirement.  Do you sell?  Will your kids take over?  What are the steps involved in that transition?  The other thing to consider here is what to do with the physical possessions you no longer want.  Determine how you’re going to pass on heirlooms, collections, and other material items.  How will you sell off property and possessions that your family and friends don’t want?  This list is likely to be more involved just because of the number of details you’ll need to include, but think of how much easier it will be to handle now, when you choose to, instead of later when you have to.


The third area we will discuss is “When”.  As we have discussed previously, timing is the key to preserving your choice.  If you want to “choose” the circumstances of your retirement, determining the timing of your actions is essential.  When will you make the final decision about moving from your home?  This doesn’t have to be a date.  It could be a situation such as, “When my spouse or I have to deal with X, we’ll make the decision about moving.”  Or, “When I can’t do X anymore, I’ll make the decision about moving.”  The details of your “When” are completely up to you.  The point of this article is simply to encourage you to think about it now.

The other “When” to consider here is the timing of the “What” and “Who” items that we’ve already listed.  For instance, do you want heirlooms to pass on to your children after you’re gone, or do you want to pass them on in person so that you can clearly convey the history and meaning that accompanies them?  When will you discuss your retirement plans with your Daily, Regular, and Occasional people?  When will you have a sufficient amount of money saved to make retirement decisions?  When will you know that it’s time to give up the things you don’t want anymore?  These are important questions to consider with regard to timing.

Well, that’s a taste of what our planning process will look going forward.  Next week, in part two, we’ll examine the Where, Why, and How of your retirement design.  I the meantime, if you have any questions, feel free to Contact Us at Hillandale Communities and we will be glad to tell you whatever you want to know.