13 Awkward (But Necessary) Money Conversations I Had This Year

By | Friday, December 11, 2015


  1. Talking to my healthcare providers about how much they’d charge me without insurance. When I left my full-time job and got rid of my benefits, I had to go around to every doctor or dentist I saw and ask if I could come see them without insurance (because my interim insurance wouldn’t cover them). My primary care physician said no, which was expected, but the specialist I see actually lowered her hourly rate so I could still make appointments with her without insurance.

  2. Talking to my roommate about splitting costs. My roommate and I are really consistent about discussing housing costs (utilities, toilet paper, the excessive amounts of candles we buy for shared spaces), and making sure that the other person understands why we’re charging them $30 on Venmo. When it comes to shared costs, I’ve always preferred up-front communication because it eliminates confusion, and no one is left pointing fingers at the end of the month when we’re trying to work out the electric bill. 

  3. Talking to my alma mater about money when they call asking for donations. I donated last year but, this year, I chose to donate to a local cancer resource center instead. I appreciate everything my school has done for me, and I might donate again down the road, but it’s not in the budget right now. I’m two years out of school and getting incessant calls for money — when I’m only just exiting entry-level territory — is frustrating. I said no, but I still managed to feel awkward and guilty about it. 

  4. Deciding how much my roommate and I were willing to pay for an apartment. If you don’t get your price range out in the open, before you start searching, I think it can be a recipe for trouble. It’s uncomfortable to sit down and decide on a price range, but the sooner you do, the more agony you save yourself. I was never in a position where I was saying no to an apartment my roommate loved because we both felt strongly about sticking to our price range. 

  5. Coordinating special occasions with my friends. As Chelsea pointed out this week, determining who does and who doesn’t want to pay for a nice dinner out is a stressful part of friendship. Personally, I rarely miss the opportunity to have a nice meal with friends. However, I’m also able to politely decline the invitation if splitting a pricey check will be too hard on my budget. This year, for New Year’s Eve, my good friends are going to a fancy bar with an expensive cover. I, of course, want to spend time with them, and I could spend the money, but there are other parties to go to that are free, and that don’t involve me standing in a crowded bar holding a watered-down glass of champagne. I ended up being honest, and saying I’d rather not pay the cover, and they were very gracious about it. 

  6. Asking for a raise. This year, for the very first time, I had to ask one of my clients for an improved contract, because I honestly felt like my work merited better compensation. However, trying to verbalize that and stand by it is incredibly hard for me. But I successfully asked and, after negotiating, got a better rate than the one I had initially. I put that conversation off for so long, but when I finally addressed it, it wasn’t nearly as bad as I thought it would be.

  7. Asking how much I’ll be paid for a piece. There is a lot of debate about how to ask for money, and when, but I’d say the well-favored route is to ask about payment up-front. While I am all for asking up-front, I have often completed the assignment before asking about payment. It leaves me fairly vulnerable because I’ve already handed in the leverage I have. Making compensation demands is a huge challenge for me, but I’ve finally started learning when to ask, how much to ask for, and when I’m happy to write pieces for free.  

  8. Telling my old landlord that I had to move out because my rent was too expensive. I was making the right choice, but it still isn’t fun to admit to your landlord that the building is too expensive for you.

  9. Talking about money in my exit interview. When I left my full-time job, they asked whether I would be making more or less money at my next position. I was stuck, because the honest answer was, “I have no clue if I’m going to make more or less money.” I don’t even remember what I said because I’ve blocked the rest of that conversation from my memory.

  10. Talking to my boyfriend about debt. I don’t live with my boyfriend, nor are we ready to sit down and ~plan our future~, but we still like to openly talk about financial challenges we might face, and how we would deal with them. Because he is in grad school, and I am fortunate enough to not have loans, we openly talk about how to handle debt productively. Even though this is a touchy subject to breach, it makes me a lot more comfortable in my relationship knowing that we can handle these types of conversations.

  11. Deciding with my boyfriend whether we can afford to go on vacation. We’ve been invited on two big trips this year. The first was to Europe, and the second was a ski trip in Montana. Because we each have to come up with our share of the money, we had to discuss whether we both had the money and felt comfortable spending it. It can be uncomfortable when one of you wants to go, and the other thinks it will be too tight, but we were able to come to a mutual agreement both times, and even found a cheaper “consolation prize” vacation to go on instead of either trip.

  12. Talking to other people in my industry about how much they make. When I worked an entry-level advertising job, it took my favorite coworker and me six months to finally discuss how much we were making. Similarly, I talk to others writers about per-article rates, and it is incredibly helpful. Starting a money conversation with someone in your industry almost feels wrong, as if we can only do it in FBI-like whispers, at least three miles from our workplace. It shouldn’t feel that way. 

  13. Talking to an Obamacare representative about how much I was going to have to pay for health insurance. When I first had to enroll, I went into the office and waited in line so I could have an in-person conversation. It’s unsettling to sit in a tiny, graying room and reveal your exact income, but the more accurate I was, the more they were able to help me figure out what I had to pay.
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