🟪 I can overthink every purchase, even grabbing lunch while I’m out.
🇺🇸 Dacy Gillespie, 47, anti-diet and weight inclusive personal stylist and writer.
I write a lot about compulsive shopping, shopping addiction, and overconsumption on Money Feelings because it’s hurting our financial well-being, our mental health, and the environment. It’s also massively on the rise, and many of you have told me how much it resonates.
So when Dacy Gillespie interviewed me a few weeks ago for her newsletter unflattering, and asked:
Is clothing something people should plan to spend on?
I said no.
Because when we set aside a fixed amount for clothes, it might feel like we have to spend it + it reinforces shopping as a habit rather than an intentional choice + it disconnects us from our deeper motivations for spending.
For instance, if I always have a set amount for clothes, I’ll likely buy without stopping to ask:
Why am I shopping right now?
Am I soothing some discomfort?
Is it FOMO?
Am I just following the influencers?
Do I have decision fatigue? Etc.
I added a more personal reason, too: There are so many ways to have fun, and I want my fun money to be flexible. Clothes can be part of that, but they’re not the only option. I want my fun money to be open for whatever feels right each month, whether that’s clothes, an experience, or something else entirely. And I never want spending on clothes to take away my ability to live all the other experiences out there.
I still stand by this answer, but I was clearly thinking about people who struggle with compulsive shopping when I wrote it.
And Dacy’s personal perspective on this question reminded me that some people suffer from the opposite problem.
She said: “I never felt like I could spend ANY money on clothing until I had it budgeted, then I felt like I had permission!”
This is such an important piece of money psychology to highlight that many people experience. Some people feel guilty buying anything for themselves, like they have to earn every euro of joy. And while over-spending gets a lot of attention, under-spending can be just as emotionally loaded.
One thing we touched on in the interview: it’s often so hard for people with these two completely different spending patterns to understand each other.
To some, the idea that spending money could be enjoyable feels impossible.
To others, the idea that it could hurt feels just as foreign.
Meanwhile, the reasons behind both behaviors can actually be surprisingly similar. This is how I explained it in the interview:
“For example, past experiences and trauma can play a huge role. Someone who grew up in financial insecurity might overspend now as a way to soothe anxiety and feel in control like finally being able to buy whatever they want. Another person with the same background (it could even be a sibling for instance!) might take the opposite approach, becoming extremely frugal, fearing they’ll lose everything again, or hoarding money and struggling to spend, even on things they actually need.
Self-worth is another big factor. Some people shop to boost their confidence and feel validated, while others avoid spending on themselves because, deep down, they don’t feel they deserve it. Both overspending and underspending can stem from the same root experiences, they’re just expressed in completely different ways.”
That’s why I believe so deeply in telling personal money stories. They help us understand each other’s behaviors with more empathy and remind us that there’s rarely just one “right” way to do money.
So today, I’m excited to introduce an edition of the Money Feelings Questionnaire, the most detailed (and, as I’ve been told, “so much fun!!”) money psychology survey out there, where we’ll dive into Dacy’s money habits, psychology, and philosophies.
NAME: Dacy Gillespie
AGE: 47
FROM: I grew up in Mobile, Alabama, and moved around a lot. I currently live in St. Louis, Missouri.
ASTRO: Cancer
LOVES: My husband, my kids, restaurant meals, books, clothes, diet Dr. Pepper
MISSION(S): My mission is to help women stop wasting time, energy, and money on getting dressed because they’re trying to conform to a way of dressing or buying that doesn’t work for them, and actually, has actively been working to make them feel bad about themselves.
JOB(S)/PROJECT(S): I'm a personal stylist. I work one-on-one and with groups of women to help them figure out what their style is without the restraints of outdated fashion rules. I also write the "unflattering" Substack newsletter.
SURPRISE(S): I'm a former classical musician and I was in a scene of the movie Mr. Holland's Opus when I was in high school.
🟣 What is one positive thing about your money behavior? I'm very thoughtful about my purchases and aware of what I have and can spend. However, I can often take this too far and overthink every single little thing, even whether I should grab myself lunch while I'm out.
🟣 Which one of your money habits do you suspect annoys your partner/family/friends?My husband probably wouldn't mind if I was a little more relaxed about money. I'm usually the bad cop and the one who lets him know when we need to slow down our spending.
🟣 Are you more envious of:
(A) someone who is similar to you in most respects but is a bit wealthier (say 50% wealthier) or
(B) more envious of Bill Gates?Definitely A because I'm sickened by the hoarding of wealth by a few people.
🟣 Celebrate the wealth you already have by finishing this sentence: "I feel rich because..."I truly have everything I've ever wanted: a loving family, a home I love, work that fulfills me.
🟣 What's a purchase that brought you lasting joy?My house. We've owned it for almost 15 years. It took us a year of looking and seeing almost 100 houses before we found it, but I'm glad we held out.
🟣 Does your spending style resemble your parents, or did you rebel?It resembles my parents', although hopefully a little less strict. There were no extras when we were growing up and we heard "we can't afford it" a lot. I try to say yes to my kids here and there so they don't feel deprived.
🟣 When was the last time money stress had you wanting to scream into a pillow?Planning for our kitchen renovation this summer.
🟣 What are three core values that you want to influence your financial decisions?Mindfulness, safety, and joy.
🟣 Who handles the finances in your home?We've always handled things pretty equally, but I am starting to want to keep closer tabs on things.
🟣 What are you currently craving to buy that you know you don’t actually need?Our kitchen renovation. The money we'll be spending would result in more money later in life if we invested it instead of spending it and our kitchen is absolutely functional. However, I truly know that walking into the kitchen I've envisioned will bring me joy every morning.
🟣 What or who’s your vision of financial success?My vision of financial success is having enough money to live basically as we do now, but with a few more nice clothes, dinners and trips, enough saved to provide living expenses for us until the end of our lives, and the ability to help our kids with chunks of money along the way as my parents have.
🟣 What’s your go-to ‘quick fix’ when you’re feeling down? Is it buying something? Food? If so, what kind of food? Is it scrolling? Or is it something else entirely?Definitely food and scrolling. Either takeout of some kind or potato chips and Swedish fish.
🟣 What would be on your dopamine menu?*
*your own curated list of activities that give you a boost whenever you need it, which doesn’t involve scrolling and buying.You can find an example and more information here.
Breakfast: Going outside | Taking a walk | Having a second cup of coffee | Getting a hug from one of my children
Entree: Planning a trip | Working on a jigsaw puzzle | Taking myself out for lunch
Dessert: Watching thrifting videos on TikTok or Instagram | Doing the New York Times games
🟣 What's a positive money experience that shaped your financial beliefs?Not necessarily one specific experience, but since I've supported myself since I was 18, often having to get scrappy, I know that I can depend on myself whatever might come up.
🟣 The zombie apocalypse is upon us. Which possession do you save?The photo books I have printed every year.
🟣 At what age did you start having your own money? Did you receive pocket money, or did you earn it through work?I started working in a pizza shop at age 16.
🟣 If you could magically double your income but had to work twice as hard, would you do it?This is what it always comes down to for me. I have chosen not to work as much and therefore to make less.
🟣 What's your favourite tool for managing your finances?I just started using the app Copilot and I'm liking it so far.
💜 Thank you for sharing with us, Dacy.
And well done you for reading all the way through. Learning about other people’s personal money stories helps make money conversations a regular, comfortable part of your life. It’s not just a window into someone else’s world. It also holds up a mirror to your own. You might recognize parts of yourself, challenge long-held beliefs or feel less alone.
🎟️ New in the Paid Corner
Dacy is offering 20% off a subscription to her newsletter unflattering, as well as 20% off her personal styling services. I love her approach and what she stands for. Take a look!
I’ve also added a new Bingo Sheet exercise—an extract from the Money Feelings No-Buy Program. It’s designed to help you choose your “self-binding strategies”: simple rules you set ahead of time so you don’t have to make spending decisions in the heat of the moment. The Bingo Sheet is a powerful visual tool to help you stay motivated + it’s fun. Bingo!
As usual, all the details are here 👇
💡 You’ve seen a tool or service, anywhere in the world, our community would love? Share it with me and I’ll negotiate for us.If you enjoyed this piece, just let me know by clicking the heart 💜 below or the restack button (the recycle symbol that lets you share this session with your followers). I notice and appreciate every single one of them.
To join our next session, you can always sign up as a free subscriber, but a paid subscription gives you access to the No Buy Challenge, all the tools, a chance to unplug with off-screen exercises, and discounts on professional support. Plus! It helps keep the lights on here 🙏💜
See you in two weeks, or sooner on Notes.
Pauline 💜
Loved this! Learned a lot :)
Thank you so much for having me Pauline!!