Every so often someone gets dragged through the mud online, and one recent casualty was the writer and Instagram influencer Caroline Calloway, who had been selling $165 tickets to a series of creativity workshops in the US and Europe.
It’s not a particularly controversial thing to be doing, but Calloway was widely mocked online after a thread of “scammer updates” — screenshots of her posts, tweeted by journalist Kayleigh Donaldson — showed her struggling with the practicalities of delivering the workshops. She eventually canceled (and later uncanceled) her tour.
I found the whole thing irritating, and not just because I’m a fan of Calloway and have enjoyed her writing for the last few years. Her public berating is a symptom of a wider problem on the internet today, where traits like hustle, determination, and entrepreneurship are celebrated in the abstract, but often ruthlessly attacked when put into practice.
It’s easy to laugh at or even actively dislike the culture of influencers, especially the ones stuck on middle ground — those yet to reach Kardashian/Jenner fame, but who are beginning to figure out how to monetize large audiences and make a living. But before snickering too hard or throwing the first rotten tomato, consider what they really are: young people, not that different from you and me, who took at face value the aspirational, entrepreneurial narrative that permeates almost every aspect of our culture.
We live in unstable, unsure times, and if you’re a millennial or younger, life is hard — and Anne Helen Petersen’s essay on millennial burnout captured it well. We enter a workforce that looks completely different from the one our parents inhabited, and we have to work every minute of every day, all to earn less. We’re told to be innovative and entrepreneurial — to show that all-important hustle — and that should, in theory, be easy, because we have access to technologies previous generations could never have imagined. The pressure is enormous, the student debt staggering, the economy precarious, and the constant criticism draining. With rubble in our hands, we’re asked to build palaces.
So, we use what we’ve got. We build our brands, harness our audiences. Become influencers. Engage with fans. Post consistently. Maintain presence. Use the tools. Stay online. Do all the bullshit influencer things that even we sometimes know are bullshit, but we’ve already accepted that this is how it works nowadays, that this is how livings are made.
Then, when it doesn’t go exactly to plan, we’re promptly mocked and jeered by people who seem incapable of dismounting from their high horses. Previous generations of people also built businesses, and they also got it wrong all the time. They sometimes couldn’t deliver what they’d promised, or had to refund money for bad products. They went bust, sometimes unable to even pay their own staff. Filed for bankruptcy. Sent out apology letters. Lost millions. But none of it happened in the public eye, so it was acceptable and even forgivable.
Today we live in a society that consistently perpetuates the narrative that to try is the most important thing. To shoot for the moon because even if we fail, we’ll land among the stars. To try, try, and try again. To fail fast and double down. To learn from the mistakes. To keep challenging ourselves because that’s how we grow. To live with caution and not fail is a failure in itself. To never give up. That trying and failing, and consequently learning, is the honorable thing to do.
So, the influencers and the Instagrammers and the bloggers and the young millennials who stare out across a bleak career landscape, with constant instability and absurd housing prices, look down at the tools they’ve got and get to work. They try, try, and try again. They do the things we’re all supposed to, which is exactly what Caroline Calloway did. She had an idea and quickly ran with it. Tried to create something different, something distinct from the old-school motivational seminar or corporate conference.
This is how it’s meant to be done, right? You have an idea overnight and then start the business out of your bedroom the next day, get into debt, fail about four times, start four other new businesses, and eventually make it onto some Forbes list and tell your story in Entrepreneur magazine, all while the world pins you up as the latest millennial entrepreneur and starts putting your quotes about failure and success on their Instagram captions.
Caroline Calloway is yet to reach that hallowed ground. She’s still in her “failing and learning” stage, but she’s just done it publicly, and the media was kind enough to document her every mistake and miscalculation.
Our culture demands that young, privileged millennials try harder, at everything. That we must juggle the jobs and the inboxes and the LinkedIn content and the social profiles. That we must eat well and become vegans. Carry metal straws in our bags and save the planet. That we must settle for less pay, stop eating brunch, and get on the property ladder. That we must never, ever, stop working and above all things, keep trying — and if we mess up, our failures can be amplified to an absurd level, broadcast to the world like a modern-day Enron scandal. It’s contradictory and confusing and constantly emotionally draining.
I’m not sure I know how to do any of it. It feels hopeless and bleak, because no matter how many emails I send to clients and how many hours I work, it’s never enough. The work never stops and the to-do list just keeps getting longer. But in the middle of all this, when we do try, with all our courage and gumption, and we do squash our hearts and souls into tiny Instagram squares, we are brutally and painfully shot down if it doesn’t come off perfectly. We’re creating an arid world in which failure and human error is no longer an option and where an army of people are waiting in the wings, always with thumbs poised, ready to document your every blemish, flaw, and mistake.
That’s not a world I want to be part of and not one I will actively contribute to. I stand by everything Calloway did, and other influencers like her. If they find brand affiliations that match their morals and framework, then they absolutely should take the money and use it to pay the never-ending bills. If they spend time and energy building an audience that wants to pay hundreds of dollars to show up in the same room as them, they 100% should sell the tickets. If your knowledge, skill, and experience has built you a following, you’re well within your rights to sell your knowledge back to them, and it’s their choice whether they want to buy it or not. The mason jars may be empty, but it’s only because the generations before us left them so, and we’re doing anything we can, any way we can, to fill them back up again.
Salma El-Wardany is a half-Egyptian, half-Irish writer. She is currently working on her debut novel, building her own marketing business, and writing and performing spoken word poetry across the US and UK.