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When Do You Stop Chasing

April 17, 2011   •   By Master Hobbit

Posted under: Finances, Lifestyle


When Do You Stop Chasing

Midlife men: I don’t know if this blog entry will be characterized as whining or simply the mumblings of one confused midlife male.  As always, I invite you to go with me as I talk out loud here and hopefully WE will arrive at a mutually satisfactory place by the end of this.


Let me start by saying that I am a somewhat driven person, achievement oriented.  Some might say overly so.  I have to admit that at times I would agree with those who say the latter.  I’m in that place these days. 


Hang with me a moment.  In addition to my regular job as an academic, you know, classes, committees, research, and the like, I started a new center in the university in the past year or so that’s focused in an area outside my primary expertise.  It’s heavy lifting, like most anything started from scratch.  I did get some release time from teaching to do this.  Oh, then there is the little matter of a book I am co-authoring with some former colleagues this year.


Then on the personal level, I recently started and manage this website for which I also write most of the content.  Another one or two are in process as of this writing.


Then there is the decision to manage more directly my investment portfolio, which is to say I opened two or three brokerage accounts which allow me to invest in different kinds of assets.  I’ve subscribed to and study daily a number of investment newsletters in order to do this.


I also am looking to establish a second residence outside the U.S., so have been researching options and looking to take specific actions within the next couple of years.


I used to work diligently at pursuing a life partner – I think they’re called women, but I stopped doing that a year or so ago.  Quite frankly, aside from not finding any with which there was mutual interest, I concluded that I didn’t have the time it took to invest in this aspect of life anyhow. 


Actually, someone told me that the minute and a half per week I had available was probably not enough to really be very successful in a relationship with a woman.  I was stunned by such a claim, but the few times I did invest the minute and a half in a woman I found some evidence to support this view.  These creatures come pre-loaded with expectations!


Look, I’ve not laid out this list of ‘what’s Kermit doing’ in order to boast, or to seek pity.  Further, the things I am doing are things I’ve either always wanted to do and/or enjoy doing.  AND, I’ve chosen most of them because a priority for me is to grow wealth in multiple ways and at a faster rate than ‘normal.’  I feel like I’m way behind where I need to be financially in order to live a more independent lifestyle (namely, one that doesn’t require a place-based job in order to hold it together).


The struggle I find myself in is determining when the pursuit of these worthwhile things actually replaces living the life I seek?  For the most part, I pursue these things in the hope of living a certain kind of life in the future.  Yet, there is a point where always preparing turns out to BE your life!


There has been many a man who was so busy in his ‘business’ or whatever his pursuits that he failed to live life as it was unfolding before him day-by-day, and then dies never having ‘smelled the roses.’  I describe this as falling face forward in your cereal some morning.  And I’m thinking few guys have this interruption entered into their appointment calendar.


As midlife men, we are living in those years where we are faced with making transitions from the accumulation-emphasis to the letting-it-flow emphasis.  I sense that I am fairly good at the discipline and focus required to accumulate.  Work one more year, save another $10,000, $50,000, or $100,000, buy one more asset, do this, or do that.


I may very well accumulate a respectable some of wealth, but risk not being able to explore the very life for which the wealth was accumulated.


It seems to boil down to the age-old question as to what is this life about, really… ultimately?  And am I living that life today, and not simply preparing to live it tomorrow. 


For some of us, it is very difficult to do both.  But doing both is probably a more sensible route.

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About the Author: Master Hobbit

Master Hobbit is the creator of 4060men. After a marriage of over 30 years ended in divorce, he journeyed for over 5 years as a single midlife man. He remarried in 2012. He is also the owner of the blog platform,, and a blog platform review site,

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