If You Reply “LOL” to Feedback, I Will Take It Personally
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…
All Guides
Tech Guides by Ken Hollow
Every tech question you've been too embarrassed to ask, answered in plain English.
Burnout Diaries
Burnout Diaries
The Group Chat Is a Full-Time Job
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…
Burnout Diaries
Every Client Thinks They’re My Only Client
By Ken Hollow, part-time diplomat, full-time liar-for-hire Here’s the first rule of freelancing: every client needs to feel like they are your one and only.…
Burnout Diaries
The Algorithm Thinks I’m a Different Person Every Week
By Ken Hollow, freelance chameleon and reluctant trend hopper Every Monday, I check my analytics like a responsible content creator who pretends to enjoy numbers.…
Burnout Diaries
The Client Said “It’s Just a Quick Edit” and Now I’m in Hour Seven
By Ken Hollow, freelance prisoner of pastel purgatory The text came in at 8:14 a.m., right when I was pretending to do my morning routine…
Burnout Diaries
Teaching GPT-5 to Sound More Like Me
By Ken Hollow, AI wrangler, burnout survivor, and reluctant personal brand When GPT-5 dropped, I thought, “Perfect. Finally, an assistant who can handle my tone…
Burnout Diaries
GPT-5 Can Code, Write, and Plan My Day — So Why Am I Still Broke?
By Ken Hollow, now officially the unpaid brand ambassador for AI GPT-5 is here. The internet’s buzzing, tech bros are frothing, and I just watched…
Burnout Diaries
GPT-5 Is Here (And It Might Actually Be Smarter Than You)
So buckle up, because OpenAI just dropped GPT‑5 on us—and yes, it’s as glamorously overwhelming as your last existential meltdown. Official Launch (Suck on That,…
Burnout Diaries
Sometimes I Think My Job Is Just Explaining Things to Software
There’s a romanticized image of “working in digital marketing” that gets passed around on LinkedIn — all minimalist coffee shops, sleek laptops, and people in…
Burnout Diaries
Sometimes I Miss Having a Boss to Blame
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…