Make Your Own Checklist for Semi-Retirement

Last evening, my husband and I were discussing a new employee of his who was struggling a bit with the process of the work.  I suggested that my husband make an outline, or checklist, for the kid to follow.   Perhaps having it written down is how he learns?  Or perhaps he just can’t “see” it when he hears it?

This works for planning too.   In flying, it’s “Plan the flight.  Fly the plan.”    Planning gives you an opportunity to examine the situation in advance, and make the necessary adjustments BEFORE you begin.

Starting is as simple as making a list of the variables that affect you.

Try taking these items and decide which of them would be relevant to what YOU need to live a semi-retired lifestyle.  Try putting them in an order that flows for you.  What has to happen first? Second?

Create YOUR checklist for Semi-Retirement.
What is your timeline?

(Is this something you can control or change?)

Debt  Minimization Plan
Physical location

(One or multiple?  Fluid?)


(Tiny house? Portable?  Multiple?)


(Public?  Vehicle? Scooter?  Combo?)

Present Job Skills Inventory
Needed Job Skills Inventory
Physical Limitations
Healthcare and Insurance
Income Sources in Place
Education or Certification Needed
Citizenship or Immigration Issues
Taxation Implications

(Start with how much you NEED.  Focus on how much you WANT.)

Job Stacking Options

(More than one “job” at a time for periods of time)

Equipment or Supplies Needed

(Sailboat?  RV?  High-end Camera? Laptop?)

Disposition of Unwanted/Unneeded/Unnecessary Belongings
“Ideal” day in your life
“Ideal” blocks of time off or time of year off
What is your “dream” job or work?

How can you get that job? What needs to happen?

What skills or training or experience can you get now that will make that happen?

Time off plans

(What do you want to do?  Where?)

Do you need or want a fall back plan?
Money handling and banking process

(Online?  International?)

Who are your cheerleaders or where can you find them?

(The ones who will support and encourage you.  Meetups?  HR?  Forums.)

This list isn’t all-inclusive, but it’s a great starting point.  Examine each point and see if it is a topic you will need to address.  If not, cross it off and move to the next one.  Start thinking (daydream!) about how you want your life to look.

How many things are on your checklist?  Are you closer than you thought you were to being able to make this happen?  Farther?

What do you need to do FIRST?  What CAN you do now?

Plan your semi-retired life.  LIVE your semi-retired plan.

Oh yeah.  MOST IMPORTANTLY….make it FUN.



Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.