What No One Tells You About Life
After Work (and Why Your Old Playbook Won’t Save You)
Your
post-employment days are likely to be much longer than you might think.
EXPERT OPINION BY HOWARD
TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH
INVESTORS @HOWARDTULLMAN1
Apr 7,
2026
One of the great quotes
from the writer and podcaster Gretchen Rubin is that “the days are long, but
the years are short.” Every day may seem like a dreary Sisyphean struggle, but
then one day you wake up and you’re carrying a cardboard box of your belongings
out of the building and on your way to whatever’s next. Whether you want to
admit it or not, for millions of us, retirement—whether voluntary or
otherwise—is much closer than we imagine and now’s the time to start thinking
about it.
I’m not talking about
anything relating to financial matters, buying cheap life insurance, or whether
it’s wise to have a will. You can see ads for those concerns everywhere you
look. I’m talking about making some plans and decisions about how you’re going
to spend your post-employment days which—in somewhat of a mixed blessing
way—are likely to be much longer than you might think.
For better or worse,
we’re living much longer these days, although the quality of life in those
bonus “golden” years is an entirely different question. This longevity is
largely because we’re paying much more attention to our diets, we’re exercising
more regularly, the meds and medical treatments available to keep us alive are
far more powerful and effective, and only the morons are still smoking and/or
drinking too much.
Having lived through
this transitional process several times and talked with dozens of others who
are similarly situated, I have a few ideas and suggestions, warnings and words
of encouragement, and other observations which I hope will be of value to you
as you start to give some serious thought to an increasingly uncertain and
challenging future.
First of all, try to
avoid squandering your savings, severance and social security payments (such as
they may soon be) on a startup or in buying a quaint neighborhood business that
you’ve always liked and frequented. You may think you’re ready to roll up your
sleeves, do whatever it takes, and jump back into the game, but the game has
changed radically in many ways and you’re most likely not up to the task. And
if my list of perils isn’t persuasive enough, try filling out a loan
application or a new credit card app and putting the words “unemployed” or
“retired” on the form. The word “retired” on a loan app is like a bright red
stop sign for lenders—even at your own bank—and the pitiful excuses they give
you are even more depressing.
Second, don’t try to
teach anyone younger than 35 anything. It doesn’t matter whether it’s a bunch
of high school kids who really don’t care, college students who simply can’t be
bothered, or MBAs in grad school who think they already know everything. You
probably don’t have the patience to deal with their lack of patience, the thick
skin to deal with their arrogance, or the disposition to put up with their
indifference and laziness. Worse yet, if you try to instill a little rigor or
discipline, it’s like walking on eggshells among a bunch of snowflakes. It
turns out too often that you’re the nasty ogre who just doesn’t get it.
Teaching exec education courses is a slightly safer path, but even there no one
is really interested in paying a ton of money to hear you rehash your old war
stories.
Third, don’t expect or
try to replace your prior earnings. That’s a pipe dream. It’s an employers’
market and there are dozens of over-qualified and out-of-work candidates
chasing the same slots and opportunities. Sadly, it’s often a race to the
bottom in terms of salary or other compensation and it rarely includes health
insurance or other fringe benefits. It takes an especially strong stomach to
settle for something which you regard as beneath your abilities and experience
and it’s even more painful when you end up reporting to supervisors and
managers who may be younger than your own grown kids.
Fourth, most of
your technical skills are going to be regarded as
anchors to the past rather than valuable tools. Look for jobs that take
advantage of your negotiating experience, social skills, and storytelling
ability. These may be the most satisfying positions anyway because you won’t be
spending your days in a race trying to catch up with constant technological
changes and dealing with patronizing nerds who are half your age.
Fifth, get comfortable
with answering the omnipresent question: what are you doing now? Men and
women who have worked hard and successfully for decades have a great deal of
difficulty answering this inquiry without being embarrassed in one way or another.
If you’ve retired after 40 or 50 years, be proud of that and understand that
it’s perfectly fine to say either that you’re doing “nothing” or that you’re
“looking” for what’s next. You’ve earned a break and some time off and there’s
nothing to be ashamed of or any obligation on your part to be rushing around
trying to get back in the saddle.
And finally, remember
that it’s a great time to get back in touch with your kids, grandkids, and old
friends you haven’t seen lately. You never know how much time you have
left and no one’s kids ever said, “we wish he’d spent more time at the office.”
