UNLEASHING RETIREMENT’S POTENTIAL: DAILY PLANNING FOR OPTIMAL FLEXIBILITY 

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The period approaching retirement is fraught with many decisions, inflection points, and options. It can also be a period of confusion concerning how each day will be filled and how to schedule retirement activities. 

This blog will tackle Daily Calendars and clarify their function and best implementation practices for a daily retirement calendar. 

Research for this blog located zero results on the internet for daily calendars for use during retirement. An internet search returned paper calendars with cute quotes on the cover used to count down days until retirement.

Having a daily planner or a daily calendar should be a basic tool in every person’s retirement toolkit. Humans inherently want some daily structure, and having a calendar filled with activities gives form to that need for structure.

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Daily Planners in Retirement 

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There are three main ways to structure retirement planners. They will be listed here as Structured, Unstructured, and Hybrid Calendars.

Each of these three calendar types has unique benefits and drawbacks. The information provided should help to create the type of calendar that fits your retirement planning. The important thing to remember is that almost nothing is written in stone when referencing retirement. You can try one type of calendar and, if needed, try the second or third type until you find the one that works best for your individual needs.

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Structured Calendar 

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I am most familiar with the structured calendar setup, as most of my dental practice career was spent treating patients based on a daily schedule. With a structured calendar, patients were added to my calendar at specific intervals each day, and calendar days were filled months ahead of time. 

Using a structured calendar I could look ahead weeks to months and see exactly what days I would be working, what I would be doing, and what free time, if any, was available. 

One of the benefits of having a structured calendar is that there was no thought involved in each day’s schedule. Each day was planned, and I merely had to follow the pre-arranged schedule for that day. Having a structured calendar is a very efficient way to work through each day, as the schedule is known beforehand and can be implemented very efficiently.

Every person approaches retirement with fear and apprehension of the unknown. Facing a calendar of blank pages increases apprehension. Creating a structured calendar removes the fear and apprehension concerning how the 24 hours in each day will be filled. Apprehensive retirees can look at their calendars and be confident that they will have things to do for days, weeks, or months, depending on what level of scheduling they desire. Structured calendars also make it easy to schedule activities and events that you want to participate in regularly. 

For example, in my dental office, we had certain periods, reserved for certain types of procedures. We scheduled 2 to 4 hours each morning to do complex restorative cases. We scheduled smaller intermittent appointments for simpler procedures. At some point during the day, there would be time allotted to provide emergency treatment. Time slots were pre-arranged months ahead even though they may not be filled immediately. By using this approach, daily periods were set aside for things that were necessary, most productive, and most enjoyable. Once these time slots were reserved, it became a matter of filling those time slots with the proper scheduled treatment.

When creating a structured calendar in retirement, this same format can be applied. If, as a retiree, you want to increase your health status, you would want to set up time slots 3 to 5 times a week for physical activities for gym workouts. Time can be reserved for food prep and cooking, reading, spiritual pursuits, hobbies, or whatever activities are important during retirement. Like my dental practice, these timeslots can be filled days, weeks, or months in advance, depending on each person’s needs. 

It is also helpful to find a Calendar that is easily edited and can be color-coordinated. On my office calendar, each particular type of treatment was color coordinated. Color coordination made it very easy and efficient to visualize. Multiple online calendars can satisfy this requirement. Once activities and events are pre-scheduled and color-coordinated the coded colors simplify the viewing of the monthly calendar. One can view and quickly see all events, and all types of events scheduled for that month. Also, most online calendars allow the scheduling of recurring events which makes scheduling periodic events quick and easy.

Some operating systems such as Apple will automatically update desktop computers, iPads, laptops, and iPhones spontaneously when calendar events are changed. This makes it extremely easy to edit and change appointments, as my wife and I both use the same calendar. We can see each other’s events or edits spontaneously when they are recorded on the calendar. 

Once your calendar is populated and color coordinated a simple glance will show all events scheduled daily, weekly, or monthly. This can be very comforting to anyone concerned about how to fill their retirement calendar.

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Unstructured Calendar 

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An unstructured calendar is the polar opposite of a structured calendar. This type of calendar is not best for those apprehensive or concerned about filling each day on their retirement calendar. This type of calendar allows for the greatest degree of flexibility. 

For example, a person decides to eat out with friends on Friday. Once the decision is made, that event is added to the calendar.  The same person decides to take a trip in a month. Again, once the decision is made the event is added to the calendar. No activities or events are pre-arranged or pre-scheduled.

When I initially transferred my practice to another practitioner, this unstructured calendar was what I used for the period after the practice transfer. Because I had operated within a highly structured calendar for multiple years, my primary desire was to experience a highly unstructured calendar for a time. This was very desirable for me initially, as each day was a clean slate to schedule as I pleased. I used this type of calendar for approximately six weeks after my practice transfer, and then eventually moved to a……….

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Hybrid Calendar 

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During the first few weeks following the transfer of my dental practice, I wanted my time in the calendar to be unstructured. But, I soon realized that having an unstructured calendar, even though more flexible, creates scheduling problems. Not knowing ahead of time when certain activities and events occurred created scheduling conflicts that were difficult or impossible to resolve. 

For example, scheduling a meal with friends on Friday, then later finding out that your spouse has other plans for that evening that make your event unworkable. Or, scheduling a trip to occur two months in the future and finding out later that you forgot about your best friend’s wedding scheduled for the same period! Even worse- make a tennis date and then find out you previously scheduled with your wife to repaint the bathroom! All of the above are real problems that can occur when a Calendar is unstructured.

Creating a hybrid calendar with a combination of both structured and unstructured time solves many of the above-stated scheduling conflicts. Hybrid Calendars represent a blending or melding of both structured and unstructured calendars.

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This is my strategy for formulating a Hybrid Calendar
The first task to be accomplished is to schedule important recurring events (Most calendar applications automatically populate calendars with annual holidays.)


Events such as such as birthdays, and annual trips or events can easily be entered as recurring events. These events will be designated with a specific color. 


Since I still work on a limited basis, I would next enter all the work periods scheduled for the whole year. These are then designated with a different specific color. 


Next, I add seasonal events such as Mardi Gras (which is a multi-week event that changes dates each year), hunting seasons (which are also adjusted each year), concert series, music festivals, etc. These are annual events whose dates differ each year. These events are also given a special color. 


The next additions are planned and potential trips. These can be overnight, weekend, single-week, or multi-week trips. Delaying the addition of pleasure trips to this point makes it much easier to spot potential conflicts with work, holidays, seasonal events, special events that you may want to attend, or unalterable events that can’t be rescheduled.

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At this point, I normally stop adding scheduled events to minimize the potential of a tightly structured calendar.                  Someone who’s not comfortable with this level of scheduled events can further reduce the number or designation of events to be scheduled ahead of time.                                            For someone who feels that a calendar at this level of scheduling can be further populated, periodic gym workouts, exercise schedules, hobby classes, or any unfixed activities can be added. I choose to not add these types of activities to my calendar because I prefer to shift these activities around from daily to weekly depending on availability.

Using this Hybrid Calendar strategy maintains a certain level of structure while still allowing maximum flexibility to add activities on a space-available basis.
I’ve used this hybrid style of Calendar for almost 10 years and find that it is adaptable to almost any situation I’ve experienced this in the last 10 years. The maximum flexibility of this system allows for schedule changes and avoids most scheduling conflicts.

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Final Thoughts

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  • Since there is no available content online about event scheduling during retirement, I have detailed my Hybrid Calendar strategy. This hybrid strategy is what I have personally used for the past 10 years and have found that it provides maximum flexibility.
  • Different types of Retirement Calendar strategies are available, and each person can choose which one best suits their needs.
  • Hybrid Calendars represent a blending or melding of Structured and Unstructured Calendar strategies.
  • Hybrid Calendars with all events scheduled and color coordinated provide an easy and simple way to view activities on a daily, weekly, or Monthly basis.

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