Tag: #OverthinkingOutLoud
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By Ken Hollow, unwilling gardener of corporate metaphors If one more brand manager tells me to “pick the low-hanging fruit,” I’m going to climb the corporate tree and throw the whole orchard at them. Business metaphors are the empty calories of corporate speak — they sound nourishing, but all they do is rot your brain…
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By Ken Hollow, survivor of 4,000 Slack pings and counting I have seen the face of hell, and it is a recurring calendar invite labeled “Quick Sync.” There is no such thing as a quick sync. There is only the slow death of my soul as six people talk in circles for 45 minutes, then…
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By Ken Hollow, unwilling financier of the attention economy Here’s what I wanted from social media: to post a picture, scream into the void, maybe share a meme that will haunt me for five years. Here’s what I did not want: to be coerced into setting up a digital wallet every time I try to…
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By Ken Hollow, unwilling caretaker of expired social logins Remember Threads? Of course you don’t. And if you do, it’s only because the app is still haunting your home screen like an ex you forgot to delete from your contacts. The icon’s just sitting there, silently judging you for not “engaging in meaningful conversations” while…
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By Ken Hollow, professional overthinker and part-time emoji decoder Feedback is supposed to be constructive. Helpful. Collaborative. Instead, it’s often delivered in the most emotionally ambiguous format possible: the single “LOL.” When a client replies “LOL” to something I’ve sent, my brain doesn’t hear laughter. My brain hears: 🔹 The Problem With Digital Tone Tone…
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By Ken Hollow, professional tab juggler and part-time actual worker Every freelancer has their own productivity kryptonite. For some, it’s TikTok. For others, it’s the sudden urge to reorganize the spice rack. For me? It’s the client group chat. Slack. WhatsApp. Facebook Messenger. One client even insists on using Telegram “for the vibes.” They call…
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By Ken Hollow, freelance by choice, regret by default When I quit my last real job, I walked out of the office with a box full of succulents, pens I definitely didn’t buy, and a smile so wide it bordered on manic. Freedom. Finally. No more dress codes. No more awkward team-building exercises. No more…
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By Ken Hollow, professionally lost and brand-consistent There was a time when I had a job title. Graphic designer. Easy. Understandable. You say it and people nod politely and think of logos and Helvetica. Then came the pivot.Then came Instagram.Then came the bios. Now I write things like “Creative strategist for emotionally burnt-out brands,” and…
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By Ken Hollow, emotionally available and algorithmically punished It happens every time. I post something real. Vulnerable. Messy. The kind of caption where I admit I’m not thriving, I’m just hitting deadlines with a pulse and a prayer. And without fail: Let’s unpack why honesty is the fastest way to torpedo engagement. 🔹 Aesthetic >…
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By Ken Hollow, certified human (barely) There was a time when I scoffed at AI-generated content. “Oh please,” I said, adjusting my ethically sourced hoodie. “People want real voices. Authenticity. Personality.” That was before I found myself, at 11:47 PM on a Tuesday, staring blankly at my 19th carousel caption of the week, whispering, “What…