Dear Jewish Fairy Godmother:

About six months ago, I got downsized from my advertising
job of ten years. While I’ve been looking for something real,
I’ve subsisted on unemployment and odd writing and editing
jobs. I’ve stayed in touch with my old co-workers because I
genuinely like some of them and also because if the
company does rehire I want to be at the top of everyone’s
list. My problem: My old buddies act like I’m still there in
terms of asking for favors I always did for them: Can you
please edit my son’s scholarship application. I need to write
to a noisy neighbor. Please help me with a cover letter for a
job app (sssshhhhhh). You get the idea. I want to help but
even coupla hundred dollars I’d make make each month
from their calls would make a difference. How can I politely
ask them for money?

Word Spinner

 
Dear Word Spinner:

Ask politely and consistently. Explain it is a cold and
expensive world outside the safety of a Monday-Friday job.
Say you’ve been supplementing your dwindling
unemployment with writing jobs and that you cannot agree
to help everyone who asks for free any longer. You can say,
If were just you asking I could do the favor. But I get calls
weekly from people I care about, each wanting an hour or
two of work. I’ve decided that for old friends, especially old
colleagues with whom I’d like to work again, I’m going to
have a special discounted rate that’s half/two-thirds (?) of
what I charge the strangers who’ve responded to my
marketing efforts. That means what you’re asking might cost
you $25-75. That’s probably small to you but in the
aggregate makes a big difference to me.

 
Some may recoil at the idea that you are monetizing a
friendship. But for most people, $25-75 is a bargain to avoid
writing a difficult letter or being responsible for something as
important as college essay. For those who act offended, say
you’re happy to help out when you have a steady income
again, but for now the freelance money is the difference
between paying your bills on time each month and sliding
down the rabbit hole of debt. Anyone who cannot
understand that logic is no one you should help out for free,
either now or later.