To Retire or Not to Retire... that is the question

Well, actually ... I retired back in '99 from the military after serving this great nation of ours for 20 years.   But, financially ...   no way was it enough so I took up  my second career.  I know guys that have made it work.  My buddy Ron H up retired at the same rank down in OK and he's living the dream.  Craig S retired at the 30 year mark and put his feet up.   But myself and most others, all pursued a second career.   I've never focused on the financials of my 'first retirement' but what I never took into account back them and cherish now, is the medical piece of it.   No matter what I do, my wife and I are covered.  That is a huge plus in today's world.

But the question really is...  do I pull the plug and go into 'full retirement?'  I've contemplated this question for several years.  If I did, my wife and I could travel unrestrained.   No need to stay 'plugged in' as I do now.  Stress levels lower on a daily/weekly basis.   Sleep in with no con calls.  No meetings.  No required travel.  So tempting.

But, I always come back to ... what changes?   My job is a virtual one.  As long as I have my cell phone and laptop with connectivity to the 'world,' I can travel to pretty much anywhere, anytime.  Cruise ships have full on connectivity today.  Most airlines have connectivity.  Most resorts, have connectivity.  And, my cell provider works natively in Mexico now, where I do most of my foreign travel to.  So, what is the upside of retiring?  I ask this question of myself .. many times.  Over and over.    In the big picture, there is no value.   But, the fact that I ask myself the question, has me digging deep inside for the answer.  Something must be calling deep inside for me to retire from the rat race.  For some reason I can't put my finger on it.. just yet

I used to 'love' what I do for a living.  Now, I just .. 'enjoy it'.   That's better than most.  I mean, most people go to work every day, doing a job that sometimes .. they hate.  Sometimes, they don't like.  Sometimes... because we all have to put food on the table.   I've been lucky enough to truly enjoy what I do for a living.  It was that way for me in the military.  It's been that way for me the last 21 years.  But, we change.  We evolve.    But.... what then?

Guess that's my biggest worry... if I pull the plug .. what .. next?  I mean I've got my hobbies.  But, my hobbies aren't necessarily 'our' hobbies.  As much as I love motorcycles and riding, my wife .. not so much. So, it's not as if we're going to throw legs over a bike and head down the road for weeks or months.   It's not as if we're going to head to the mountains and go hike for miles and miles.  It's not as if we're going to go off to the tropics, buy a condo or house and sit on the beach the rest of our lives.   So, if one retires.....   what then?   I've found in life, not matter what we do, where we go...   we get used to them.  Example: We've talked about moving to Hawaii, permanently.  But, after six months it wouldn't 'feel' any different. It'd just be "normal."   I know this. I've lived there.   I've lived in other exotic places.  After awhile.....  what you thought was 'incredible' .. is now.... just .. 'normal.'.  So, beware what you ask for and everything it all entails to achieve.

My dad retired at 56 up in MN.  He and mom moved down to Arkansas where they lived the dream. Dad still is 25 years later.  I look at my age and wonder.... should I go down that path?   Brother Dick just retired. He's contemplated it for the last couple of years and for several reasons, made the decision to pull the plug a few weeks ago.  No more 0200 mornings. No more 12 hour days.    My buddy Larry K retired a few years back in his fifties from the FD.  No more brutal BS dealing with an ungrateful public.  No more back breaking BS.  My IIRA Brother IndianDave just retired form the FD.  He too can move on from the crazy life that he enjoyed.  Seems like everyone I know is pulling the plug or .. planning it.

On track!

I find myself daily monitoring the 401k. The IRAs.  Other investments.   Looking over the budgets.   Working retirement models that show investment outlays and how long they'll last.  Good news is , all the numbers work out.  The budget works out.  All the numbers line up.  But yet.... I think ... do I really want to do this?   As I type this ... the answer is 'no.' .  The fact that I ask myself the question... .. even type this all out... ..  has me yearning deeeeep down to make sure I'm answering the right questions.  Do I really believe my own answers?

But ...  if I do pull the plug .. then ...what next?  Hmmmmmm