Dear Jewish Fairy Godmother:
I started my current job 350 days ago. My wife and I just got an
opportunity to go on an amazing tandem bike trip that two friends
dropped out of at the last minute. My employer, an engineering firm
with values out of the Eisenhower administration, say I am not allowed
to take any vacation time until 365 days after my start date. I tried to
explain the circumstances, but I think the idea that I ride a tandem
bike is considered so wacko that he stopped listening to my very
reasoned arguments about making up the time in hours before I go,
working more hours afterwards, or even saying I wouldn’t take any
other time off until say Thanksgiving. I could sacrifice the trip, and I
don’t want to lose my job. But if this is how they run the place, maybe
I’d be better off freelancing again. BTW I have no projects with
deadlines; in fact we’re a little slow.
Tethered

 
Dear Tethered:
Quitting for a trip seems like a radical response to what sounds like
petty and restrictive personnel policies. You must be good at what you
do to have landed a job 350 days ago. And possibly you’d find another
or better one if you looked now, or even make it as a freelancer again.
But if you’re willing to risk such extreme options, why not go with one
that may be bad financially in the short run but keeps you employed
long enough to look for your next job while still working for Mr. Old
Fashioned.

 
Write your boss a memo and say you’re taking the time off as leave
without pay. Document that you have no current deadlines and are
fully up to speed and on schedule with your projects. Say you
understand you will not be eligible to take any more time off until
_____ [insert your understanding of his personnel math, knowing that
he’s likely to reinterpret this not in your favor]. Go and have a great
time. Come back and work really hard, being appreciative through
gritted teeth and a forced smile for his “understanding and                                      cooperation.” Then rewrite your resume, including “Confidential
search: Please do not contact current employer.” Look for a new job
that matches your own values re project mix, culture, and
compensation.