In the last few months, I've submitted over 130 job applications. Somewhere around number 30, I started noticing a checkbox at the bottom of most forms. Something like: "I'd like to opt out of automated screening and request a human reviewer."

I used to check it every time. I thought I was being smart.

I wasn't.

In this episode I dig into what that checkbox actually does, where it came from (spoiler: lawyers, not HR), and why checking it almost always moves you out of the working pile and into a waiting room nobody's staffing.

I cover:

• Why the opt-out exists — NYC Local Law 144, built for employer liability, not candidate protection
• What actually happens when you check it — the three most common outcomes
• The documented AI bias that makes the opt-out tempting — and why opting out doesn't fix it
• The five specific cases where opting out is actually the right call
• What works better instead

If you're job searching right now, this one's for you.

Full post: https://jakehallman.com/opt-out-box-ai-screening-trap/

You raised your rates. A client you'd worked with for years went quiet. No blowup, no email — just gone.

And somehow, you felt relieved.

That's where this episode starts. When I bumped my prices 25%, a steady client disappeared within three weeks. On paper it looked bad. In reality it exposed something I should have seen coming: they weren't loyal to me. They were loyal to the old number.

In this episode:

• Why your price isn't just a transaction — it's a diagnostic tool that tells you who actually values your work
• What good clients are really buying (it's not hours or deliverables)
• Why cheap prices send the wrong signal and train clients to treat your time as elastic
• How to raise rates without apology — give notice, say it once, stop talking
• What happens to your calendar and stress level when the wrong clients leave

If you're still charging what you charged two years ago, this one's for you. Spoiler: the ones who leave were already gone.

Full post: https://jakehallman.com/expensive-clients-are-just-clients-who-didnt-quit-yet/

You're good at something. You actually enjoy doing it. So when someone asks what you charge, your brain does a thing — and the number that comes out of your mouth is too small. You know it's too small. You say it anyway.

That's what this episode is about.

There's a trap built into loving your work. The internal logic goes something like: "I enjoy this, so it doesn't really cost me anything, so I should give them a deal." It feels generous. It feels humble. It is quietly costing you thousands of dollars a year.

In this episode, I break down:

• Why creative people and educators systematically underprice their work (and there's actual peer-reviewed research on this)
• The "passion paradox" — how caring deeply about your craft becomes a lever in someone else's hands
• The real math: a $400 project that eats 20 hours isn't meaningful work, it's $20 an hour
• Why teachers are especially primed for this trap, and why the same logic that gets exploited Monday through Friday follows them into their weekend freelance gigs
• How to price based on time and skill instead of how the project makes you feel

You can care deeply about what you do and also get paid fairly for it. Those two things coexist just fine.

This one is for every educator running a side hustle, every creative saying "it's not a big deal" when they know it is, and every freelancer who's done the math afterward and cringed.

Read the full article: https://jakehallman.com/the-lie-you-tell-yourself-about-charging-for-work-you-actually-like/

Years ago I watched a part-timer in the newsroom resize senior portraits one at a time in Photoshop. Open image. Click. Type. Save. Close. Open the next one. I lasted about four minutes before something in my brain gave out.

She wasn't doing anything wrong. Nobody had shown her the better way, and nobody had stopped long enough to ask whether this was a problem a computer could solve faster than a human.

That moment gave me a rule I've used ever since: if I'm doing something the same way for the third time, I stop and ask whether I should automate it.

In this episode I get into where that rule came from, why repetition costs you more than time (it costs your judgment, which is the expensive part), and how I've used it lately to cut a 45-minute YouTube upload workflow down to a few minutes using Google's Antigravity. You don't have to be a software engineer anymore to make this stuff work. You just have to notice the thing you're doing for the fourth time and decide maybe you shouldn't have to do it a fifth.

If you're sending the same email with tiny tweaks, filling out the same form every Friday, or moving data from one place to another like a glorified data mule, this one's for you.

My niece Lucy was three the first time she watched a cat food commercial and called it a mini-movie. Kitty was hungry. Kitty got food. Kitty was happy. The end.

That's a complete story. And it's better than most of the 30-second spots people are making on purpose.

In this episode I get into the mini-movie rule — why the best commercials aren't crammed with logos and features. They're the ones that tell a tiny, complete story. I walk through the three questions that'll carry almost any spot. I talk about a holiday commercial we did that dropped the audience straight into Santa in a dressing room. And I explain why three-year-olds might be the most honest critics you'll ever have.

If you've ever stared at a brief full of talking points and thought "there's no story in here," this one's for you.

I've got friends who are pro photographers. Some of them have portrait photography – headshots – as an integral part of their businesses. Those photographers are about to have the metaphorical rug pulled out from under them by artificial intelligence.

So how can they adapt? By co-opting the process, making it so the client doesn't have to do any heavy lifting, and turning AI photos to their advantage.

Mornings in my world are spent teaching A/V classes to a bunch of bright-eyed teenagers in a rural high school that's as small as it is full of character.

You might wonder what the scariest part of this routine is. For me, it's the chill that runs down my spine when administrators grace the classroom with their presence for observation. But for the students? It's the stark terror of facing the infinite possibilities of a blank screen (or page, but honestly, we rarely actually write anything).

Much like "Plan 9 from Outer Space," there's media out there that so terrible, so awful, so poorly-done that it flips around the scale back to being good.

In films, you have "Plan 9" and "The Room." Commercials featuring the late Billy Mays (OXICLEAN!) and Vince Offer (The ShamWoW guy with the jaw). Or any commercial featuring a spokesperson with the title "Crazy." Music brings us the phenomena of William Hung, "Barbie Girl," "Achy Breaky Heart" and a lot of the disco produced in the 1970s. Literature has "Fifty Shades of Grey" and the "Left Behind" series.

Not even presidents are immune. H. L. Mencken said that Warren Harding's English was "so bad that a kind of grandeur creeps into it."

At some point in your career, you'll hit upon the idea of making something bad on purpose, hoping to get the so-bad-it's-good magic that'll make your production (in)famous.

DON'T DO IT.