Jason is a self-employed entrepreneur. David
took early retirement five years ago, at age
44, when his technology company was
acquired. The two had been college friends.
They had drifted into careers and families far apart
but later moved by chance to the same suburban
Boston town. Each had worked hard and made a lot
of money—enough to wonder what money and
success are really about and to question the meaning
of each in their lives.
They went to a discussion group for men with
similar questions and were urged to express their
goals, conflicts, values and questions around money
and careers as honestly as possible. Jason and
David decided to continue in that spirit by writing
Below are excerpts from their correspondence,
edited to disguise their identities and published here
with their permission. The men ask questions rather
than pose answers. We share their words to throw
a fresh light on questions that many of us ask ourselves
privately—and in the hope that their spirit of
frank inquiry and reflection will be an example to
... On money, I want to earn 30 percent more than l did last year (that is, about
$300K) with about the same time commitment. I want to take one week more vacation
each year for the next 10. Alternatively, I want to have a new way of looking at
life that makes a different income OK. In truth, I don’t like the thought of doing
the same work for the same money
for the next 10 years. That feels like a
trap and a defeat.
But the problem is, I know in
advance I’ll resist all the suggestions
you make for how to break into some
new mode. I want to be free, creative,
bold, energetic—but my first response
is to keep on doing what I’m doing
and find reasons why anything else is
a bad idea.
Like the idea that I could stop working.
How does that make me feel? Several
things. One is disdain for myself
for giving up. I have to face it: my selfworth
is tied very closely to my earnings.
I’m afraid I won’t find anything
else to give meaning to my life. Or I
worry I won’t have enough money. My
wife thinks I’m too money-oriented.
She thinks my retirement goal of
$1.5M net worth is too high. Right
now, it’s $1.1M. Part of me wants to
keep plugging till I hit that number,
but then I look around at age 49 and
realize, I do want to do greater things
than I have so far, as measured by
impact on the world, personal growth
and satisfaction. I want to do different
work than I am doing now. I want my
wife and me to have some common
understanding about the focus of our
lives after our children are grown. So
even though I’m stubborn about
change, I want you to keep being
tough on getting me to a better place.
I am grateful for where I am, but I still
have lots of fire to want to be the best
I can be, not just good.
Is it $300K per year that you want? Perhaps thinking less about the money and more
about what you really want could take you to a better place. I see money as a proxy. It
can’t directly get me what I want most. I’m thinking back about gadgets and cars—the
length of time they ‘thrilled’ me was remarkably short.
... I know what you mean about fearing you won’t find something else in life that
gives you meaning. Since I left, it’s only been the support of my wife and family that’s led
me to feel that my “non-work self”’ is important and loved.
... It sounds crazy, but my top question is whether I’m retired. Our net is over $1.5M
(plus insurance), and we’ve adjusted our lifestyle to make that work. But I’m not at peace
with that being enough, given my life expectancy of 90, kids in college, my Dad, who will
likely run out of money, and a son-in-law who is unable to work (and grandkids in that
family). Then there are my parents-in-law; we’re not even sure of their financial ‘legs’.
Also: what’s my financial responsibility to all that [extended] family? Money spent to
help them could cause me to run out of cash late in life. Plus there’s a chance my wife
could outlive me by 10 years, and I have first-line responsibility there.
So, despite what I said above, I feel I should go back to work. When I retired, I quit with
no real idea about the future other than a deep and desperate need to get the heck out. I
don’t regret it. I remember all too well those anxious talks when [my wife] would say my
job was going to kill me! Whatever “goals” I had when I quit I have already exceeded just
by getting back in touch with my family.
But it’s never so easy, right? I have this worry thing about money and am thinking I
should start over somewhere. I do get some joy from work. On the other hand, I’ve felt like
that before, and I know it can get old quick. Then there’s the emotional pull of having one’s
self-worth tied to job and pay. It took me a long time to get over (and I still haven’t completely)
missing the respect I got as a chief operating officer. Fact is, people treat you as
your job. Most people cannot fathom how I would ever give up that role and the status and
money that went with it.
I have to remind myself that most of the senior managers at the company had problems
at home, which I saw as a consequence of mental and physical time away from their families —a frightening array of problems with kids, wives, affairs, divorce, drinking and more.
I honestly can’t remember one person who worked at that level and had balance.
Oh yes, balance. I’m just not sure how to get over this question about having
“enough” to retire. One way is just to have so much money that it’s a no-brainer. Another
is to trust fate. Not my style to do that. But I want to try. I will say again that I’m blessed
with my wife, probably the only person who could put up with what I’ve been describing.
A lot is in flux, but she is my rock.
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