Stay Classy, Contractor: A Survival Guide

Every office is a community, and most are weird little communities. Here are a few things I have learned to sort out the strangeness and up the niceties in the contractor lifecycle.


office is a community, and most are weird little communities. Having
hired contractors over the past ten years and now working as one, here
are a few things I have learned to sort out the strangeness and up the
niceties in the contractor lifecycle.

Insist upon introductions.
you are Alice in Wonderland, for just like that marvelous book, you
will meet all sorts of characters who think you are quite odd. Many of
them will perpetually be in a terrible hurry somewhere, but you do need
to tell each person you meet your role, the length of your contract,
what teams you are working with, and some relevant piece of your
background experience. Stationing yourself near the printer is
particularly helpful when trying to meet everyone.

bonus Alice tips: Avoid eating cakes in their entirety (or really
anything lying around in the break room), and do not mention your cat.


Bring one piece of memorabilia in for validation.
of us in Contractor World have worked for at least one company in a
long-term capacity. Doubtless, you received some silly swag from a
company retreat, party, or from an industry event. I have a large
glamour shot of a ferret with former colleagues’ signatures that works
well for this purpose. The reason to bring old office swag in? Something
to point at if (when) someone mistakes you for an intern. Introductions
mitigate the risk of this happening, but accept the compliment on your
youthful vitality, point to the ferret image, and say, “I’m a
contractor, actually. I’m hoping this office cherishes ferrets as much
as my last office did.”

Defeat the Mean Girls.
for every style guide and documentation available to understand the
office etiquette, even and especially from groups you may only be
working with indirectly. Know the guides better than staff do. Often as a
contractor you are marooned in a desk where you cannot know the email
chains that encircle your reputation if you misstepped. Make sure to
resolve any confusion face to face, always including HR, and take pains
to thank your manager for helping you understand the office culture.

Serve up your opinion, but start through private channels.
of the main things you’ll miss as a contractor is that feeling of
responsibility to a team, that ownership of some part of a project.
Being copied on team emails can be deliciously tempting: a moment to
step in and share your great insight! This usually backfires. Try
emailing the project lead instead of replying to all and offer your
opinion in a way that doesn’t reflect badly or undercut anyone else’s
domain expertise. (e.g. “When I worked for ___, we solved this by _____
and it worked really well.”) Be prepared for your vote to be ignored and
your email unanswered.


Don’t take the fish.
one startup, about an hour before the weekly company meeting that the
founders had introduced me at the week before, I was asked to leave.
With a forced smile and assurances that “Google has police escort
contractors out before meetings,” my supervisor followed me back to the
workspace island I was working from and then watched as I walked to the

the news right before a meeting makes your exit a walk of shame, so
muster up a few casual “Rachel, I should have that document finished in
about an hour,” remarks on your way out, then work from remote during
the private, recurring meeting. Make sure to submit your receipts from
the coffee shop, and vow to ask about team meeting attendance first
thing at the next job. Rejoice that you are excluded from some big, long
meetings in this role.

Speak softly and carry a voided check.
at smaller companies there is unbelievable lag time about payroll. Be
prompt in returning your W-9, contract agreement, and anything else that
needs your signature. HR will be pleased that you share their devout
belief that their forms are important. Use an invoicing service that
allows you to see if a client has looked at an invoice and makes it easy
to send gentle reminders. If at all possible, lawyer up enough to have
someone who can call and inquire firmly about unpaid invoices.


Leave a forwarding address.
after your email access is cut off, many unsolved issues on projects
are attributed to you. Make sure to write your own goodbye email copying
as many officemates as appropriate and address the email from your
internal account to an external account; attach a document detailing
your work. Do write a note to yourself on the overall experience and
keep a record of the names of those you worked with so you can recognize
them in future contexts. Try to assist the company by finding someone
to replace you as the contract ends.

Above all, remember that ‘permalancing’ is not a word.

Taylor works with companies as a digital storyteller and content
strategist. She drinks raw milk, blogs at, and tweets from


About the author

Founder of, a geolocative mobile application launched in September 2010 to help friends hide and find real gifts for each other. Editor and founder of Saucy Magazine, a new food + story quarterly publication