At a certain point in 2019, 
internet 
users 
in 
both 
the 
drama-filled DeuxMoi and the 
aspirational New York City-
esque digital spheres were once 
again pulled towards Caroline 
Calloway. She has lived through 
multiple digital selves and has 
survived multiple news cycles of 
hatred and ridicule over the past 
decade. The Cambridge blogger-
turned-scammer is now best 

known for her confessional, often 
chaotic Instagram presence — 
but for better or worse, the chaos 
is intentional. In a tweeted 
response to a critique of her 
behavior, 
Calloway 
summed 
herself up with ease.
“I’m chaotic. I love my work. 
My work is writing, painting, 
photography, posting on social 
media, 
and 
living 
inside 
a 
Truman Show of my own making 
— performance art. Most ppl do 
not consider what I make to be 
art. More chaos ensues.”
In 
spite 
of 
the 
hatred 

associated with her name alone, 
Calloway has found repeated 
ways to rebrand herself into 
a persona that thrives off of 
whichever 
news 
cycle 
she’s 
currently a part of. Her life has 
turned to chaos for one thing: 
a life of falsities worthy of a 
memoir.
Act One: The creation of 
Caroline Calloway, Cambridge
According to Calloway, she 
first joined Instagram in 2012. 
At the time, the social media 
app seemed revolutionary: a 
photo-based platform promising 

connection 
and 
marketing 
towards young, hip users. The 
app was unique in its ability to 
create curated images, filtered 
vignettes 
and 
distinct 
user 
brands. From the very beginning, 
the app was made to commodify 
and create followings. Influencer 
culture on Instagram has stayed 
relatively married to the same 
principles since its creation — 
dominate the attention economy 
and build a brand worthy of 
advertisement partnerships — 
with the only notable difference 
being the extremes that are 

now required to stay relevant. 
Instagram influencers have been 
running in this rat race since the 
beginning — Calloway included. 
Calloway’s 
Instagram 
origins 
aren’t 
particularly 
unique 
— 
her 
page, 
titled 
AdventureGrams, 
was 
a 
conglomeration of aesthetically 
pleasing travel photos, selfies 
and documentation of a deeply 
curated life abroad. Photographs 
in Sicily, Venice and other 
European tourist traps during 
the summer of 2012 brought 
in her first audience. Then 
in 2013, she accomplished a 
life-long 
dream: 
transferring 
to Cambridge to finish her 
undergraduate 
degree. 
Her 
platform faced a harsh pivot 
here, and soon her page became 
dedicated to the academic life of 
lavishness she lived alongside 
her wealthy, beautiful, British 
peers. Calloway was not born — 
she was created and recreated.
Calloway, however, had one 
unique quality that shifted the 
way Instagram users connect to 
their audience and commodify 
their life stories: long, personal 
Instagram captions. In an article 
by The Cut, Calloway’s college 
friend and frequent collaborator 
Natalie Beach wrote “… the 
internet felt like the future of 
writing … Instagram is memoir 
in real time. It’s memoir without 
the act of remembering. It’s 
collapsing the distance between 
writer and reader and critic.”
Her 
page 
became 
more 
of a series of diary entries 
accompanied by a photo of a 
beautiful Cambridge student, 
living a life of deeply curated 
beauty 
and 
adventure. 
This 
was an early predecessor of the 
“radical vulnerability” approach 
to garnering Instagram fame, 
and it successfully launched 
Calloway 
into 
being 
the 
aspirational 
and 
vaguely 
literary influencer she had been 
attempting to become since the 
beginning. 
Act 
Two: 
book 
deals, 
workshops, NYC party girl
The decision to create this 
account 
would 
ultimately 
change 
Calloway’s 
entire 
future, just as she intended 
it to. She amassed a cult-like 
following through her digital 
diary and quickly became one of 
the first influencers to acquire 
a book deal. This, largely, was a 
result of her careful branding: 

adventurous, intellectual and 
effortlessly perfect. At age 23, 
her book deal was accepted — 
only three years after she joined 
Instagram — as she amassed over 
300,000 
followers. 
Calloway 
had finally nabbed her dream 
project through an accepted 
proposal with Flatiron Books 
reportedly worth $375,000; of 
course, it was a memoir. True 
to brand, this process was 
documented through a careful 
lens of updates, snippets and 
behind-the-scenes images being 
shared online. But Calloway 
quickly lost interest in writing 
the book — she claimed that 
publishers didn’t want her life 
story, and that she instead sold a 
story of her life that was purely 
defined by the men she dated. 
Her book deal was dropped in 
2017, and she was hundreds of 
thousands of dollars in debt. The 
first echoes of hatred, ridicule 
and “scammer” criticism began 
in this era — the vaguely literary 
brand she had made for herself 
was strewn in artifice.
After the book deal dissolved, 
Calloway still had her following 
despite 
a 
new, 
negative 
connotation attached to her 
name. During this point she 
became 
increasingly 
candid 
online: 
A 
new 
brand 
was 
created, but this time it relied 
on being beautifully artistic in 
a deeply unhinged manner. Her 
online life showed two, deeply 
interwoven sides: her life as a 
party-filled, fun and beautiful 
New York creative; and being 
emotionally candid online, to 
the point of deep oversharing 
of 
her 
mental 
struggles, 
judgment-worthy 
anecdotes 
and hourly Instagram story-
posting. This branding became 
what she was ultimately known 
for, and garnered nearly as 
much ridicule as her failed 
book deal did. Additionally, 
this era marked her sharing 
her deeply personal story of 
Adderall addiction. Throughout 
the writing process and her 
final 
years 
at 
Cambridge, 
Calloway shared her reliance 
on the stimulant and her overall 
mental decline during what 
was perceived as the best years 
of her life. Her previous image 
had shattered, but Calloway 
still rode the momentum of the 
attention she was receiving. 

A comprehensive history of Caroline Calloway

HUNTER BISHOP
Senior Arts Editor

AVA BURZYCKI
Senior Arts Editor

Desgn by Avery Nelson

Read more at MichiganDaily.com

4 — Wednesday, March 22, 2023
Arts
The Michigan Daily — michigandaily.com

Do you ever feel as though nothing is real anymore? Do you 
find yourself looking for something natural, only to discover 
that everything has become a copy of a copy of a copy of what 

came before it? Do you fear a future of Artificial Intelligence 
and androids and losing ourselves in our technological 
advances? If so, welcome to the Artificial B-side.

puzzle by sudokusnydictation.com

1
2
3
4
5
6
7
8
9
10
11
12
13

14
15
16

17
18
19

20
21
22

23
24
25

26
27
28
29
30
31

32
33
34
35
36

37
38
39
40

41
42
43

44
45
46

47
48
49
50

51
52
53
54
55
56
57
58

59
60
61

62
63
64

65
66
67

SUDOKU

WHISPER

“One day ~~~ 
Day one……. 
You decide.”

“March Mad-
ness.”

WHISPER