Eight Items to Consider If You Want to Semi-Retire

The most important piece of advice to building a semi-retired life is to embrace flexibility.  Try something, and if it doesn’t work, try something else.  This article covers several variables for you to consider.

Here are some of the questions and conversations you will need to have with yourself, your families, and/or anyone else impacted by your decision to modify your work lifestyle. Don’t worry about ordering these yet – just ponder each of them.

Where do you want to live?

Where you are?  Somewhere else? Nowhere in particular?  Part of the year one place and the rest elsewhere?  Do you want to expatriate part of the year or at all?

What is your “enough?”

This is a critical one.   What constitutes enough of anything in your life?  Do you need opulent living quarters, or are you happy in a tent or camper?  Do you want to have no-deductible health insurance with extensive access to care?    Do you still have a mortgage?  Do you want to take one on if you don’t?   What do you like to eat – is it expensive?   Medications you need?   Types of insurance besides health – auto, hazard, life?

When do you like to “work?”

Are you an early bird or nocturnal?  Do you like putting in a long day, or more short ones?  Office?  Outside?  With others? Alone?   How about time of year?  Do you prefer a summer environment or a winter one?   Do you want a structured schedule?

What about healthcare?

Yeah, you knew this topic was coming.  How healthy are you?  Could you get healthier? How risk averse are you?  How much healthcare do you consume now?   If you currently have employer provided health insurance, do you have any idea what the cost of insurance is these days?   (There will be entire posts devoted to this topic, FYI.)

What do you want to do with your time off?

Travel?  Visit family?  Contemplate your navel?   Do you have an agenda?  (You don’t have to.  “Sleep” is a perfectly acceptable answer)

What kind of work can you or WILL you do?

One big question is going to be whether or not you do work that makes you stressed or unhappy in order to have the time off you want.   Would you like to do two or three different jobs a year, each for 2 – 4 months?   Are you a planner setting things up in advance, or do you want to finish one job or season then decide what to do next?

When do you want your time off?

For example, I do not want mine in the summer.   Ideally I would be “off” from about Nov 15 until March 1st.     But I am flexible on that.  Two six week gaps would work for me too.  Maybe.

What skills and or experience do you already have that you can use in this new life?

Certifications, practical experience, great attitude, quick-study? Don’t overlook little things like being able to touch type, read out loud, translate, teach.

Don’t start out trying to order these in importance.   At this point we are doing what can be called “Blue Sky Planning.”  If there were no other obstacles, nothing to keep you from creating the semi-retired life you want…what would it look like?

The sky is the limit.



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