Jennifer Romolini
Updated Jul 14, 2015 @ 12:19 pm

Work can be weird and awkward, first jobs especially. There’s so much to navigate—from performance stress and boss pressures to co-worker relationships, office-fridge etiquette, and just the feeling of ‘Am I doing this right?’ ‘What does it all mean?’ Which is why, today, we’re introducing a new advice column, Ask a Boss (Who Is Not Your Boss), written by HelloGiggles editor-in-chief Jennifer Romolini. Have a burning workplace or career question? Email Please Include a your first name or nickname and where you are from. Questions may be edited for length and clarity.

Dear Jenn,

I’m interning at a place I really, really love. The work is inspiring —I’m not just making copies, but actually doing some writing, which is my ultimate career goal. The people I work for are super supportive, always letting me sit in on brainstorming meetings and encouraging me to share my opinions. I feel like this is a work environment I could really grow and thrive in. The only problem: I’m not getting paid.

The internship was for school credit, but since I recently finished school, I didn’t need the credit. Although I agreed to the terms of the job initially, I’m working two other jobs just to make a living and I feel really overstretched and exhausted.
I really want to ask the internship job for money. I’ve heard from friends that legally they have to pay me, but I really like this company and the people who work there and I don’t want to spoil that relationship.

Do you think I should ask for some compensation and if so, what’s the best way to go about it without coming off as rude?

Exhausted in New York

Dear Exhausted,

OK, so first thing’s first. You should be paid. Not just because in New York it’s mostly illegal when a for-profit company doesn’t pay its interns (you can see all the rules about interns at this .gov page) and because recently there’s been a huge, justified hullabaloo (including some high-profile lawsuits and articles with titles like “Interns, Victimized Again“) to put an end to exploiting interns and the free labor they provide, but also and most importantly because you are a valuable human in the world and your time has value and that value has a price. So you need to ask for money.

But… before we get all burn-it-down/BBHMM on this problem, let’s strategize the best way to play this. Imagine every job you’ll ever have as a kind of math problem, which, if I understood math in any concrete way, I think would go something like this: What you are using them for (money, experience, career satisfaction) – What you give up/take on in order to do the job (time, in some cases, your soul) = the basic professional happiness or crushing unhappiness you feel about work.

Using that logic, it sounds like you like this place quite a bit and your job satisfaction equation is actually pretty good. It also sounds like you are gaining valuable experience that will set you up for a next position or at least more writing work. If we were to put the whole money thing aside, you’re in an ideal entry-level situation—generous co-workers, access to the inner-workings of an institution you respect, actual writing, which is huge and so many steps up from getting coffee. So here’s what I’d do next: Ask for a meeting with your supervisor. In that meeting, explain very politely that you love working there but your situation has changed and you’re trying to find a paid position and you’d love that position to be there. (You’ll notice I’m side-stepping the paid-internship angle. While I think all internships should be paid, I don’t think fighting for internship money is in your best interest at this point, you should be fighting for entry-level $$$). See what the person says. Maybe they will say, “Hooray! We were feeling the same! You can start full-time next Monday!”

But if they don’t (and only after they don’t, don’t begin negotiating until you know what they’re bringing to the table) offer a few alternatives: Could I get paid for my writing? Are there tasks beyond what I’m doing that could be paid on a part-time basis? Try to to make it work with what they can offer, if they can offer something. If they claim they have no funds/no positions/everything is dry and cold there and the money river has long stopped running—then it’s probably time to go. But I’d plan this exit carefully and not immediately. Ask yourself: What would be useful to learn at this company before I leave? Are there systems/programs/strategies you don’t know, but should? Is there a meaty/attention-getting story you’d like to pitch that you think they’d take? Is there an editor whose brain you want to eat/ask a lot of questions? You’re in a position of access and you should use it before you go.

In the meantime, start thinking about your dream next job, where it is and what it would look like. Start looking at job postings, kicking the tires around your professional network and grab coffee with as many connections as you can. These early stages of a career can nerve-wracking, but exciting too. Good luck!