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changing the cultural conversation, imposter syndrome, and the numbers

changing the cultural conversation, imposter syndrome, and the numbers

on two years on substack

Dacy Gillespie's avatar
Dacy Gillespie
May 16, 2025
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changing the cultural conversation, imposter syndrome, and the numbers
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Today is the two year anniversary of starting this Substack. Part of me is wondering why it’s necessary to write a post commemorating this date. But like we do at the new year, I appreciate moments to stop and take stock, and maybe even acknowledge some successes, which I’d never otherwise do.

It also seems like a good time to remind you (and me) why I’m here. My mission is audacious, no less than wanting to change cultural thinking around getting dressed. I want us to reject fashion rules that make us uncomfortable or hinder our progress in the work we want to do. I want us to question why we should wear something someone else is telling us we should wear or why we should buy something someone is telling us we should buy. I want us to know that the shape and/or size of our bodies has nothing to do with what we have to wear or whether we can have personal style. I want us to be able to show up wherever we go knowing that even if we’re dressed differently than others, we’re wearing what feels authentic to us and therefore feel confident. Everything I share or write about here (and elsewhere) is part of spreading this idea.

unflattering
you deserve clothes that fit
After sharing my personal experience with spending on clothes and before we get into the experts’ advice next week, I thought I’d share a bit about how I advise my clients to think about money and clothes…
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4 months ago · 124 likes · 7 comments · Dacy Gillespie

When I first started this Substack two years ago, I never expected that it would become such a big part of my life or my job. When I used to send email newsletters through the email marketing platform Active Campaign, I would spend a few hours a week writing a newsletter and send it off. I might have had a few email responses to respond to, but that was it. I expected that to be the same on Substack, but I spend more time per post (this post took me 6+ hours to write), often post twice a week, spend hours reading and commenting on others’ newsletters, share and engage in Notes, respond to comments on my posts, and participate in the chat. The time spent on Substack is ⅓ to ½ of the amount I spend working each week, with the remainder of the time spent working with one-on-one clients, my group program, social media content, email, and administration.

Get 20% off for 1 year

I’m sharing some of my most popular posts from the last year throughout this post. To get access to the archives, subscribe now for 20% off the current price ($3.33/month) before the price goes up ($6/month) this weekend!

unflattering
four external messages to reject
Even though I’ve always loved fashion, for a long time I never thought of it as something I had any control over. It was always something that was externally dictated to me. There were things that were trendy or “right” to wear, and some external source told me what those were. If Tim Gunn said every woman should have a tailored white button down shirt in their closet, I bought a white button down shirt. If a magazine article told me that I should wear a specific color because of my coloring, I’d wear it…
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5 months ago · 167 likes · 43 comments · Dacy Gillespie

Over the past year, I’ve struggled with some of the same issues I mentioned in last year’s reflection post. I’m not sure I’ll ever not have imposter syndrome about my writing. Just a few weeks ago I was in tears because I felt like I had no plan and didn’t know what I was doing. Last year, I was happy to take things as they came, but this year, I’ve felt a tension between planning content ahead and feeling organized (and professional?) and also wanting to write about things that come up in the moment.

New in the past year

A huge help for me in all things Substack has been the mastermind group that I organized in January. I’ve been a solopreneur since 2013. Except for very brief periods of time, I’ve worked completely alone and done everything myself. When I’ve needed a sounding board, I’ve turned to my husband or my friends for advice. Pre-pandemic, I had an in-person group that I met with weekly and this year, I decided that I needed to have that specifically for Substack. Our group (made up of

Sally Ekus
,
Emmy Singer (she/her)
,
Laura Fenton
,
Jen Baxter ✒️
,
Hillary Dixler Canavan
,
Eleanor
,
Kara
,
Lisa Sibbett
, and
Ryan Rose Weaver (she/hers)
) meets weekly and we usually have a nerdy topic for discussion, such as how to write a good welcome email, how to involve the community in chat, and how we plan out our content calendars. In between meetings, we have a discussion thread where we can ask each other opinions on how to handle trolls or whether Substack has an algorithm and what it is (anyone know? 🤣). If you are interested in starting your own group, it can be as easy as asking on Notes if people are interested and setting a meeting time!

you can see why I might want some graphic design help as mentioned below 🫠

Another big change and addition to my newsletter this year has been the chat. When Substack first starting introducing these social media-type add-on’s, I was pretty resistant. However, one of the top reasons I started a Substack was to build community. It was going pretty well just in the comment sections, but readers were restricted to just responding to the post in question. Last October,

Jasmine Sun
(who was then a Product Manager at Substack) got in touch to offer support in setting up chat and I decided to go for it. With chat, paid subscribers can post a question anytime and get input from me and other readers on their style quandaries. One of our most popular threads is our regular Favorite Outfit Friday thread, and as much as I’d like to take credit, it was actually Jasmine’s idea!

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Available in the Substack app and on web

In December, I took inspiration from

Virginia Sole-Smith
and decided to do a reader survey. Hundreds of you responded and I now have a never-ending list of content ideas you’d like to see! Also in December, I was a guest on
Christy Harrison, MPH, RD
‘s podcast, something I’d been hoping to be able to do since I first became familiar with the anti-diet space. Over the last year, I also collaborated with a bunch of other Substackers:
Virginia Sole-Smith
and
Corinne Fay
for our unflattering x Burnt Toast style challenge last spring, and
Lindsey Stanberry
,
Untrickled by Michelle Teheux
,
Pauline
,
Heather Boneparth
, and
Dana Miranda
for my series on clothing spending. I contributed to Living Small with
Laura Fenton
, Nebula Notebook with
Heidi Fiedler
,
Corinne Fay
’s Big Undies,
Lindsey Stanberry
’s Division of Labor,
Pauline
’s Money Feelings,
Intuitive Style
(here) and
The Pleasure Lists
(here).

unflattering
ways to "do" ethical fashion that don't cost (as much) money
Just a quick reminder that the unflattering chat is open and active! This is an added benefit to all subscribers, who can respond to threads, and paid subscribers get the added bonus of being able to ask the community anything! Need help styling something or recommendations for a niche item? It’s all there…
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9 months ago · 145 likes · 18 comments · Dacy Gillespie

Plans for year 3

In the next year, I want to make the unflattering community even more of a part of the regular content on the newsletter. I’d love to have readers submit their own essays about style and bodies and clothes. I’d love to have some posts with reader outfits. Maybe we could have an question column where readers give their advice? Still mulling over all the possibilities. I’d love to hear your thoughts as well!

Unsurprisingly, considering my money habits in the rest of my life, I have trouble spending money in my business. It’s hard to want to spend $4-6,000 for photos and design when that’s a chunk of change that could go toward something in my personal life like our kitchen renovation. However, the last headshots I had taken are FIVE years old and I the only graphics I’ve ever paid for was $35 for my business logo in 2013 😳 (it was to a professional graphic designer I knew in person, not a fiverr type site, and that’s just what he charged me!). I’d love to hire someone to create a logo and graphics for unflattering. If you know a great graphic designer, please let me know!

unflattering
my clothing budget was $0
I was raised in a family without much money. My parents were labor organizers before I was born, my mom working and organizing in a sewing factory, and my dad working and organizing in a shipyard. My mom stopped working when I was born, and then had two more children, my sisters. My dad was seriously injured at work when I was 8 and wasn’t able to work after that. My mom went back to school to get her teaching certification and was the “breadwinner” (I put it in quotes because a teacher’s salary in Alabama in the 80’s wasn’t really winning much of anything) for the rest of my childhood…
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4 months ago · 245 likes · 34 comments · Dacy Gillespie

The numbers

Ok, here’s the part everyone’s curious about. And yes, this is where I’m going to put the paywall.

BUT! To celebrate my Substack anniversary, I’m offering a sale: subscribe at the current rate (monthly subscription rates will be going up this weekend to $6/month) plus a discount - only $3.33 a month - before then! The discount is only for annual subscriptions1

Get 20% off for 1 year

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