Cheek turned five this month!
My five biggest lessons growing an independent media company
It’s been a hard year. I haven’t come across anyone with a sentiment that differs greatly from this. At a personal level, I’ve grown up a lot faster and copped more personal attacks than ever before. Perhaps most significantly, I feel Cheek has gone from being viewed as an underdog platform to one that genuinely threatens mainstream mastheads. The result of that threat hasn’t just been defensiveness, but a lot of commentary about me personally. I’ve had to move through my own emotional response to these experiences at a pace I didn’t know I was capable of. I’m truly proud of the person I’ve become, and the person I’ve remained through these sticking points.
When I write reflective pieces, I’m always considering whether I’m speaking from the wound or the scar. At the end of gruelling periods, it is seductive to narrow your perspective in on the pressure point and resentment that oozes from the mark. Discomfort, complex topics and mistakes are ever-present in the world of news and politics.
Instead, I try and begin my writing by considering how I still feel towards my work and the feelings that emanate. When I think of my job, what are the first three words that come to mind?
Impact. Clarity. Fun.
As we look to the close of the year and celebrate half a decade since my first baby (business) was born, I know there have been three serious occasions where I’ve wondered if I’m doing the right thing and Cheek can and should continue. Reflecting on the above three words are the reason I know the answer is yes, every single time. I’m onto a fucking good thing.
To mark five years, here are five lessons from me that have stuck.
1. The 60-day test (and the 85% rule)
My best trait is having a bias for action. I don’t like sitting on things for too long wishing they would come to life. I plan, organise and execute in both my professional and personal life. I am also not a perfectionist. Cheek would not survive if I approached every thought I had for a post or a big change with a mindset of fear. When implementing something new, there are two approaches I find helpful for Getting Shit Done.
The 85% Rule: When you’re 85% sure you want to do something, start. Women stop themselves from proposing changes at work, starting businesses, asking for a pay rise, applying for a new job or throwing ourselves into new social environments because we question and diminish ourselves more than men. Don’t ask me for a stat on that, I’ll send you the graphs depicting how many men think they could land a plane in an emergency or score a point against Serena Williams. Sigh. Doubt exists in the 15%. It’s risk management and aversion, predicting failures and mitigating harm. We should be more than 85% sure of some decisions before making them (medical professionals necessary disclaimer I feel), but when it comes to submitting an application, trying a new hobby, starting a side hustle or asking someone if they’d like to grab coffee - if you’re 85% sure - fucking do it.
The 15% where things go wrong is the magic. A fuck up is a lesson. A rejection is a new pathway commencing. We need to feel the burn of that unknown.
The 60-Day Test: This one applies heavily to social media content, but I think is a great test criteria for a lot of new systems. When thinking about Cheek’s content strategy, there’s less than 10 ‘pillars of content’ you’ll come across. When you follow a business or organisation online, something that builds loyalty is repetition and routine. People want to know the product and what they can expect. If you love a podcast that has no consistent scheduling, you’ll lose trust and your listening routine pretty quickly. It’s quite similiar with Instagram. If I were to ask you what kinds of posts you expect to find on Cheek, I hope at least half of our audience would be able to identify our external contributor pieces, explainer carousels, what we call a ‘dual photo post’ (two photos with a tweet between them), reels, meme dumps, and a few others. This creates familiarity.
When adding a new pillar, I used to freak out if the audience engagement was low on the first three attempts. After five years, I know audiences take two months to get into a rhythm with new themes and material. It might be increasing the frequency of posts, introducing external contributors, or trying a new style of video - but do not measure success in a week or even a month. Give it two. You need to practice, and the audience needs to see it a few times too.
