Dear Jewish Fairy Godmother

I’ve had the same job for fifteen years. The boss is very eccentric and
values me for my calm ability to manage any crisis. His extended
family has had many of them! I’ve gotten paid for everything from
arranging bail for his nephew, moving his mother to assisted living as
well as normal things helping the company get a bid out the door. He’s
the owner and president so there’s no distinction between “work” work
and any other responsibilities he asks me to undertake. My ability to
solve strange problems has gone way up, as has my ability to talk to
strangers. (I’d been very shy before this job.) But my computer skills
and knowledge of software have declined in a scary way. I am
competent at what I know how to do, but when I look at what current
job openings are asking for I feel old, intimidated, and out of my
league. Now he’s going to sell the company and I am afraid the new
owners will put me out on the street. Friends who worked here and
saw the handwriting on the wall had accounting skills and got new jobs
pretty quickly. I am in my fifties, which doesn’t help in this economy.
Any ideas on what to do?

Out of Date

 
Dear Out of Date:

First things first. Even though you hear a loud clock ticking, you still
have a job. You&'re wise to prepare but being fatalistic won’t help your
mood or impress prospective employers. The new owners may keep
you on longer than you think. If you have a lot of corporate history
between your ears they may look for easy things for you to do with
your hand to keep access to you, at least during the transition. Worst
comes to worst you will get unemployment if the new owners lay you
off. But the time to mobilize is now.

 
But you’re wise to prepare. Go to the websites of prospective future
employers, especially larger organizations like local government,
colleges, doctor/lawyer office, hospitals, and insurers. See what job
titles they hire for that are similar to your skills and look very carefully
at the computer qualifications. Then put yourself on a tutorial regimen
during down time and personal time. Look also at the supplemental
questions most employers ask these days, even of administrative
employees. Everyone likes having staff who are calm and reliable,
strengths you should not sell short in interviews. PS Don’t be surprised
if the old boss calls for help later. Charge him double what he used to
pay you.