bills, bills, bills #42

money advice, financial woes, and dishy purchase history from NFTG readers (volume II)

Bills, Bills, Bills is a monthly series of anonymous money diaries from theatre workers curated and edited by Jenna Clark Embrey.

The full archive is available here. We accept diarist submissions on a rolling basis.

editor’s note

It’s the most wonderful time of the year! (Just kidding, I hate the holidays, bah humbug.) This month, we’re running a second column of anonymous Bills, Bills, Bills reader responses. (The first one is here!) Once again, I’m blown away by the quality and quantity of responses from hundreds of readers and I’ve picked just a fraction of some of my favorite answers. In this edition, we dive into finance goals and woes, along with some money misconceptions (did anyone else think Grey Poupon was legitimately a luxury item as a child?) and guilty pleasures. Read on, and happy new year!

What was the most significant financial thing that happened to you in 2025?

• I had a baby! I was in the hospital for nine days and she was in the NICU for 24 days. Not only did we have hospital bills to pay but babies come with a lot of stuff that needed to be purchased.

• In 2025, my mom suddenly got very ill and I had to fly across the country to support her and my family. I took time off work and had to spend thousands of dollars on last minute flights and renting a car for two months. That being said, I was able to manage this because my past self prioritized saving an emergency fund with approximately six months of living expenses that I was able to tap into for exactly this reason: a true family emergency that required my undivided attention and commitment. If you are new to personal finance and saving money, I cannot recommend enough putting aside money every month to be used in a true emergency. You will not regret it.

• I got a full-time leadership job outside the theatre and started earning a six-figure salary. Life changing.

• I’m earning more for my time. It’s a mix of now having more experience as a designer, working consistently at larger regional theaters, a couple opera contracts, the new LORT USA 829 contract that went into effect this summer. (We now get paid a daily rate if we are beyond a certain number of days in residency.) I’m fortunate in that I have a rent-controlled apartment which allows me to take on work at a healthy pace. On paper my income isn’t high, however I have an incredible amount of agency and time.

• My union negotiations achieved a SIGNIFICANT increase in per diem that makes my steady out-of-town work less of a budget nail-biter.

• I relocated from Arkansas to NYC (and switching jobs/very different salaries and living expenses)

• I got a gigantic merit raise at my university this year that pushes my salary (after almost 20 years of teaching) close to six figures.

• My day job switched insurance carriers three times in 12 months. This was primarily due to an acquisition, but it meant my medical expenses wildly increased and fluctuated as providers flipped from in-network to out-of-network then back again and I paid three different co-pay amounts for the same medications. Overall, I paid about $8,000 more out-of-pocket compared to last year—and my costs are increasing in 2026. Never been more enraged or convinced that healthcare is a scam.

• I had a wedding! Definitely financially significant and we’re still a little bit feeling the impact from it.

• My investments (Roth IRA and Brokerage account) finally hit a combined $100,000 USD. I don’t have an employer 401k or 403b account, so I’ve been working hard to maximize and control my own retirement. I work a lot between several jobs, purposefully choosing cost-effective living situations and forgo “wants” to prioritize where I am saving 30-50% of my income in a given month.

What’s your strategy for holiday gift spending?

• I make little purchases throughout the year as I travel and keep a Christmas tab as part of my budget spreadsheet so I stay within range of the amount I set aside and remember what I purchased for whom. I’m the second eldest of eight—I have a birth and an adoptive family, so gift-giving is pricey. With my new budget I’ll be aiming for smaller gifts (food, snacks) and when appropriate, I’ll make jewelry or crafted items (if they seem gift-worthy).

• In October and November, I throw a couple hundred dollars in a sinking fund so the December spending doesn’t feel like it’s coming all at once.

• My family started doing white elephant-style gifts where everyone draws one name and gets that person a gift. (We’re a very practical family and aren’t really gift-givers by nature, so we’ve also normalized telling people what we want.) We spent about 75% of what we would have spent buying smaller gifts for everyone, everyone gets a gift they want, we all save money, we feel a bit less guilty about generating waste, and everyone’s less stressed about trying to buy the right gift for someone who doesn’t really like gifts to begin with.

• We don’t really do physical holiday gifts anymore. After my dad died at Christmas a few years ago, it’s just too hard and too sad. So what I have started doing as my gift to my mom and my sister is that I take us out for a really nice meal at a place with live music and we get all dressed up and just enjoy the time together. I buy small things for my little nephew, but I also spoil him with gifts throughout the year so it’s not that different from any other day .

• My family went no-gifts-except-for-kids a few years back, and I’m supremely thankful for that. A good portion of my income comes from adjuncting, so I don’t get paid during my university’s six-week long winter break. My partner and I get each other gifts and give my nieces gifts, but we’d rather spend our money to take a trip together during my break instead.

• First of all, if you’re Jewish, you do not need to get eight nights of presents. And in the tradition I grew up in, those presents for Hanukkah were small trinkets (usually bigger gifts were given around Passover or Rosh HaShana). I’m also a big believer in gift cards. I don’t see them as impersonal; I see it as respectful of their time and likes.

• Books for the nieces and nephews, pictures for the grandparents, one big gift for the child, one big gift for ourselves.

• If someone says they don’t want you to get them gifts (I am one of those people), ask them if there is a charity or organization where you can make a donation in their name. Especially in a year like this where so many in Canada are suffering under our cost of living crisis and tariff war, or in the US with SNAP benefits being shuttered during the prolonged shutdown, and when folks are feeling like a recession is coming—why not spread the love elsewhere if you are solid and feeling comfortable, but your neighbor down the street isn’t?

• Holidays are tough for my budget, because I LOVE searching for the perfect gift and frankly, I have very expensive tastes. This year, I’m making an effort to actually stick to my budget, shop entirely locally, and focus on giving experiences/donations to charities for my immediate family, since none of them really need any more material possessions! (We all have a clutter problem.)

What are your financial goals for 2026?

• In 2026, I’m hoping to open another credit card (hopefully one for travel), budget frugally so I can contribute to my 401k at the maximum account that my company will match, and save enough that I feel comfortable treating myself to a solo vacation.

• Max out my Roth IRA, get my grad school savings fund up to $10K from $3K.

• My child from my first marriage turns 18 this year and her state-mandated child support will go away at some point next year, so my current husband and I will have to adjust our budget for that income loss.

• I want to delve further into investing and start setting up retirement funds. I am in my early/mid 20s, and my full-time job will start matching contributions now that I’m going to hit two years with the company, so it seems like as good of a time as any. I also want to start being smarter with my savings, rather than just setting aside some money in sinking funds at random intervals.

• I would like to save more money for what I assume is an impending apocalypse, both global and personal.

• I will be doing the same two side hustle jobs again, so my goal is to get my general savings up to around $50,000, which would be a year’s worth of living expenses if I live cheaply. The future of academia all feels VERY uncertain right now and I want to be ready in the event that my program closes or they eliminate my position. I don’t like living in a culture of fear, but being solid in my finances helps to ease the fear.

• Get rid of my student loan debt!

• Ideally, to be completely debt free. More realistically, to build my high-yield savings account to $7,000. I also really want to find more ways to find ethical alternatives to my shopping. I’ve been pretty good about cutting out places like Amazon and Target, but I’d love to do more with my money when I can.

• Marry my partner without going totally broke!

• For the first time in my life, I am seriously considering leaving the theater industry. My financial goal is to significantly increase my salary, and I am at a point where I need stability, benefits, parental leave, and a job that doesn’t cause me physical and emotional stress. I am exploring what options exist where my skills would be transferable.

• Essentially, be frugal enough that I don’t have to withdraw from my savings account to cover the four weddings I have to attend (one in Italy!)

• Maintain a budget and save enough to fund a self-production.

• To continue to increase the value of my time. Eventually I’d like to work at a rate of $100/hour and I’m slowly trying to push that as my goal. What that translates to is higher paying design gigs, a.k.a. breaking into commercial theater. I also have started working on branding and merchandising in the last year and plan to continue to grow that.

What’s something you spend money on that you try to avoid admitting to other people?

• Guitar lessons. I am not getting the type of gigs where this is a real benefit (not yet, I guess?) but I am loving learning something new from scratch. However, I feel like it’s a real indulgence at this point since I play other instruments well enough to be paid for it, and that’s definitely not the case with guitar.

• I hide nothing, but I do think people would be surprised exactly how many cheap foot massages I get. (All Seasons on West 8! A dream!)

• Before I tell you, I need you to know that I grew up keeping kosher (I’m now pescatarian and very veggie forward), I don’t drink alcohol, I don’t partake in substances, I don’t even drink coffee or sugary sodas (diet coke is nectar from the gods)—so what, dear reader, is my guilty pleasure? McDonald’s. I go maybe once a week and hide my receipts and wrappers like I’m a raccoon preparing for winter.

• Too many Legos…

• At the beginning of this calendar year, my partner and I decided to hire a cleaning service. It’s expensive, but it’s worth it for our relationship.

• A GLP-1 subscription.

• How much my Pilates classes cost, especially in light of the fact that I could do Youtube Pilates in my house for free. You don’t understand, the group environment and the presence of the instructor is what actually makes me follow through! I need the threat of public judgement!

• Shoes. I love shoes. I have so many, and yet never enough. But I always buy them on sale! I also have tiny feet, so I’m usually able to buy some things in kids’ sizes. You would be shocked at how much that saves me.

• Melanzana hoodies! I love them so much, and it takes so long to get an appointment that when I get one, I have to seize the day! But I try not to tell people how much they cost. (They’re locally and sustainably made! Does that make it better?) And smoked mozzarella cheese. It really makes for a great vegetarian sandwich.

• I don’t hide it very well but Olipops and expensive protein powders. I’ve cut Olipop down a lot and my protein powders had lead in them, so maybe that will change?

• Dunkin’ iced coffee, more often than I should.

• I’ve spent like $100 this year on coins in a dumb phone game called Two Dots that I play while listening to podcasts.

• I will always have expensive shampoo now. I can’t go back.

What’s your dumbest purchase—the one you still regret years later?

• Bike rollers/trainer for indoors. Cost me like $200 and I fell off it once.

• I bought a planner that I ended up hating and never really using effectively. The next year, I went searching for my new planner and I bought the same planner in a different color because I didn’t pay enough attention...

• I got caught once jumping the subway turnstile and was fined. Not that I had a choice in paying, but I felt extremely mediocre afterwards.

• I regret how much I’ve spent on food delivery apps since COVID. I made a real effort to cut back this year and my spending is down significantly.

• A giant body pillow with an ochre linen pillow case from Parachute. It looked beautiful. ‘Twas not functional with a husband and dog in the bed. It lived on the floor for over a year before I managed to find someone to take it off my hands.

• Does a boyfriend count? JK, but also not really. I lost so much money.

• My massive TV that I never use. I watch everything on my iPad in bed while my TV lives in my living room. My apartment is far too tiny to entertain more than one/two people, so it truly never gets used. Why did I do this?

• I spent like a lot of money on a webcam when I was in high school because I thought I was going to be a BookTuber.

• My first car. I didn’t need it. I lived in a major city with public transit. Spent way too much on the car, the repairs, insurance—only to get into a car crash one year later that totaled the car.

What’s the biggest financial mistake you’ve made that you want to warn others about?

• Not having the password to my husband’s student loan account. He’s terrible with numbers and let so much interest accrue without even realizing. (For context, I’m the one that pays all the other bills each month.)

• Asking for an external ultrasound and then agreeing to an internal ultrasound without asking first if I would be charged twice.

• A stupid skirt with suspenders. It’s not big, but why did I think I could or would wear it? I don’t know.

• A cheap washing machine. It broke within a year. We should’ve done more research and bought a nice one the first time around.

• Not saving early enough for retirement.

• Two expensive unreturnable jumpsuits from a niche British brand, purchased sight unseen, NEITHER of which remotely fit, so bizarrely sized that even tailoring didn’t help.

• Not planning for taxes on non-taxed income. I was just out of college and barely scraping by, so putting myself on even thinner margins likely would have failed, but still, I wish I’d thought about it during my year as a stipend fellow. Even if you don’t have it then, it can help you plan to get it before April.

• I love a Kickstarter project and in the middle of the pandemic, I bought a standing desk that hasn’t been fulfilled by the creator.

• When I finally paid off my loans and got a relatively healthy savings account (well into my 30s), I stopped paying as much attention to how much I spent on eating out or on that random candle or just had too many “treat yourself” moments. I used to use cash for everything because I was a waitress for so long and with that life I always knew how much I was spending. The tap and pay life is dangerous! Now that I’m scrimping to pay for childcare (among other things related to having a baby), I wish I didn’t make so many dumb “treat yourself” purchases when I didn’t have to worry about every nickel and dime. There’s a line between enjoying feeling more financially stable and spending money on too many things you just don’t need/don’t bring you joy.

• This isn’t a super big mistake, but I didn’t realize that you can pick the day your credit card bill was due. Mine was due on the third of the month because that’s what it was when I opened my account, and since this was so close to when rent was due it was hard to pay off in full each month. After I moved it to the 16th to be in line with my mid-month paycheck things became much more manageable.

What’s the wildest money misconception you believed as a child?

• I thought in order to get new nickels you had to melt down old pennies, to get new dimes you had to melt down old nickels and so on and so forth. I have no idea how this manifested in my mind but it made the most sense to me at the time!

• That children are cheap. I guess I figured I was small, so I couldn’t possibly cost that much.

• I believed if I worked hard enough, I would make enough money to afford to buy a house in my hometown.

• I remember in high school looking up AEA minimums for Broadway contracts and fully believing I’d easily be able to pay back a $250,000 loan for a BFA in musical theatre. Adorably presumptuous, endlessly embarrassing.

• Paying for convenience. My parents see that as a waste of money and it took me a while to shake that off and realize that my time is very valuable and sometimes it’s worth the convenience of saving time.

• That I would share a bank account with my husband and it would be easy and no big deal.

• I thought that I would only need $35,000 to live comfortably. My parents made $55,000 and had 5 kids, so I figured $35,000 would be just fine. Turns out inflation is real, and they lived in a very different part of the country.

• That a house was just something everyone bought. HAHAHAHAHA. Hilarious.

• That most people only worked one job or, sometimes, if you were poorer, you had to work two jobs. I could never have imagined the weird tangle of part time, freelancing, and gig work that I have gotten myself into as an adult and what that means for complications in taxes, insurance, applying for benefits, and juggling your gig work with your “steady” part-time job that pays like dirt but gives you an income before your next show starts.

• That losing my lunchbox wasn’t a big deal. (They are so expensive!)

What financial topic do you wish you understood better?

• Picking an investment portfolio. (Editor’s Note: FORTY-FIVE PEOPLE submitted this exact response. You are not alone!)

• Insurance. Why so many kinds? Which ones are important? How will the policies actually work? (For instance, I have instrument insurance...but I am not sure exactly what its deal is.)

• Taxes. I feel like there are people who know how to really play the system and get the most out of it and I’m just over here scanning my little receipts for Planned Parenthood donations hoping it makes some difference in my annual bill.

• Saving for retirement, specifically with a Roth IRA. It feels simple at face value but since opening one I feel like I’m in a labyrinth.

• How to not be audited and then how to prep for that audit when you can’t find all your receipts from two years ago... and making income from the stock market.

What’s something in your financial life that you celebrated this year, or something you did with your money that made you proud?

• I am in a place to purchase theater tickets and that feels like a good way to spend my money. I’m proud to be able to buy a ticket at a theater I want to support. But no shame to the times if trying to get discounts and comps!

• I set up recurring donations on a card that has a minimum monthly transaction limit. These small donations are almost the only thing I use this card for and gain points on, and I feel proud that I am doing something good with my money every month.

• I opened a high-yield savings to set aside tax money and let it grow interest! If I need it next year, I’ve got it, and if not, it’ll grow more money!

• My partner and I had a lengthy conversation this year where we decided we were not going to pursue having children of our own. Foster parenting: yes, adopting and/or surrogacy (we are but heathen homosexuals) was a no. And I have to say, it really frees up something in your soul about how you view your money. We are fortunate where I have so many friends with children and a host of nephews and nieces. There are plenty of children in my life where I get to be a parent figure for, children I get to spoil, and children who I am an active part of their lives. I just get to be the (hopefully someday) rich, fun, gay uncle who takes them to Disneyland.

• On track to max out my Roth IRA for the first time!

• I reached my savings goal of $40,000 for a future down payment. Mortgage rates are insane right now and I want a bit more career stability, so I’m not going to seriously pursue buying an apartment for a few years, but I’m so proud of myself.

• While I have a lot of mistakes to fix and need to build a lot more stability, I stopped deluding myself and turning a blind eye to my finances and made the decision to prioritize my financial well-being in the coming year. I have a ways to go, but that first step is always important to celebrate.

• It was really nice to be able to afford a nice vacation with my family this year and know that was something we will continue to be able to do moving forward, knock on wood.

• Bought my girlfriend a couple pieces of jewelry in the ~$100 range.

• I’m really proud of myself for saving enough for three months of rent. There was a very short period of time earlier this year when I was unemployed, and it was the first time I really understood the importance of an emergency fund. I ended up getting a job very quickly, but I’m proud of myself for being able to fund my rent if I needed to!

• I got my first LORT SM contract this year so I made the most money a week that I’ve ever made.