Career September 5, 2026

Applying for a Job Is a Black Hole. I Know, I Built One.

Every remote role we posted got 2,000 to 3,000 applications in a few days. Then AI arrived and made it worse. Here is what actually works instead, especially if you're changing direction.

7 min read
Two people in conversation across a cafe table, one holding a copy of The Art of Reinvention

It was our weekly team meeting, and I could feel something was off.

Elena, who ran our recruiting, was visibly tired. Red eyes, almost like she'd been crying. I asked what was wrong and she struggled to get the words out.

"I just can't do it anymore. There are just too many applications."

It looked like she was about to resign. She'd built her whole identity and pride on being a great recruiter, and she couldn't handle the pressure any more. It was in no way her fault. Our reality had changed almost overnight, and we hadn't worked out how to solve it.

We were in hyper growth and desperate for people. Almost thirty open positions.

But our problem was the opposite of what you'd assume.

Too many candidates, almost none of them real

We'd open a role and within a couple of days we'd have 2,000 applications. Sometimes 3,000. Occasionally we had to shut intake down before the weekend so the system wouldn't fall over.

And on paper they all looked amazing. Perfectly written, every one of them adapted to the job description.

Then we'd interview them and almost nobody met the bar. Many wouldn't even reply or show up.

We were fully remote and accepting applications from everywhere. Previously we'd get a handful per role, of wildly varying quality. You could see who had put the effort in and who hadn't. We'd interview the top few and get someone on board fairly quickly.

Then the world changed. ChatGPT went mainstream.

Almost overnight, candidates started using AI to find roles and tailor their CV and application to the exact job description. People began applying to hundreds of roles at a time. For remote roles the applications came from everywhere on earth. The volume became unmanageable.

Imagine you're the perfect candidate for a role, but you only see it on day three. Too late. You wouldn't even be able to submit. We'd never see you.

Now let's say you're fast and you make it in before we shut it down. You're smart, so I imagine you use AI to sharpen your CV. I'd recommend it, honestly. But so did everyone else. Including the not-even-close-to-qualified.

You're now competing for attention in a pool of several thousand applications that all look equally perfect. Our AI would score them, and 90% got discarded without poor Elena ever laying eyes on them.

Your chance of being considered is close to zero.

These days, applying for a published role is like sending your CV into a black hole.

I don't particularly enjoy admitting that. I owned the process.

And it gets worse if you're changing direction

Here's the part that doesn't get said enough.

Your CV points backward.

It's a record of what you've already done, often very successfully. Every line on it proves you were good at the last thing.

Now you're asking someone to believe you'll be good at something slightly different.

On paper, you're unproven. That's true no matter how senior you are. Actually the more senior you are, the more clearly your CV argues for the life you're trying to leave.

So the filter isn't just noisy. It's pointed the wrong way. It's matching a document about your past against a description of somebody's future need, and when you're reinventing, those two things don't line up. No amount of polishing fixes that.

What I did instead

When I came back to Stockholm after years in the US, I didn't know what I wanted next. I had skills, a network, and no map.

So I didn't apply to anything. I had lunch.

I made a list of fifty people I admired. Old colleagues, authors, friends of friends, people who looked interesting on LinkedIn. Then I sent each of them the same invitation, and the framing was deliberate.

"I'm not asking you for a job. I'd love to hear your story, and I'd love your perspective on what I should be applying myself to next."

Almost everyone said yes. Asking someone to share their story is flattering. Asking for a job is stressful.

I'd spend the first half of each lunch listening. The second half I'd flip the table and walk through me. What I'm good at. What I'd happily be paid to do.

A pattern showed up inside the first ten.

And two of those people called back weeks later. They'd been quietly thinking about something they needed done. I matched. They invented the role around me.

That's the move. The job did not exist before the conversation. Nobody else was in the running. I wasn't candidate 1,847 in a stack of 3,000. I was the only person in the picture.

If you want the full method, I've written it up as how to do your own 50 Lunches.

Now go back to your list

Here's what most people miss.

If you've been doing this properly, you already built the thing you need. You've had the conversations. You showed people what you were figuring out, asked questions, collected introductions, and slowly worked out where you might fit.

At the time I'd have told you specifically not to ask those people for a job. The moment you turn an exploratory conversation into an interview, everything changes and you lose the honesty.

But something has changed. You've made a decision.

So go back to that list. Start with the people you actually met. Tell them what happened since you spoke. I promise they're curious. I would be.

When we spoke, I was still figuring things out. I've now decided I want to move into X. And I'm looking for Y.

Then make it easy for them to help you.

Don't say you're looking for something at the intersection of strategy, leadership and impact. I'd have no idea what to do with that. Neither will they.

Do the research first. Be specific. Make a list of five actual open roles and be ready to explain why each one fits the new you.

If one of them is at your contact's company, tell them before you apply. They'll get a referral fee and your application skips the black hole entirely. For roles elsewhere, check their LinkedIn to see who they know there. "Can you introduce me to Anna at Google about the analyst role" is a much better ask than "I think I'd like to work at Google."

Warm intros are worth gold.

Then keep going down the list, one at a time. Make it personal. Ask for specific opportunities. Ask for introductions. And then ask the question that keeps the whole thing moving:

Given my new direction, who else should I speak with?

Break the rules

My author friend Jordan Carroll writes about landing remote work in his book Remote for Life: How to Find a Flexible Job and Fast Forward to Freedom. If a remote job is what you're after, that book is your best investment. After this one, of course :)

His main idea is that you should decide what life you want first, then go find the companies and roles that make it possible.

But the reason I gave him the unofficial title "The Rockstar of Remote" is his approach to positioning yourself. Jordan likes to break the rules.

His ideas are counterintuitive and then obvious once you hear them. Don't obsess over reaching HR. Reach the person who would actually manage you and benefit from your work. And then don't explain how great you are, because they've heard it all before. Give them something that proves it.

Say you're moving into marketing. Instead of writing that you're strategic, spend an afternoon analysing the company and send the CMO a set of updated marketing assets.

Moving into people leadership? Look at their careers page and their role descriptions, and send the CPO your improved drafts.

Going after a commercial role? Identify a few potential customers and explain why you think they fit. Better still, reach out to one of those customers and make the introduction yourself. If you bring a paying customer through the door before you've even applied, ignoring you becomes a career limiting move.

Conventional wisdom says don't spend unpaid hours working for someone you haven't even spoken to.

I say forget conventional wisdom. It's much better to do unpaid work and get noticed than to spend the same unpaid hours throwing applications into a black hole.

This is the whole point

Look at what that approach actually does.

It replaces a document about your past with a demonstration of your future. The CMO doesn't have to imagine whether you can do marketing. They're holding the marketing.

That's why it matters more for a career changer than for anyone else. Someone moving up in the same field can let their CV do the work. You can't. You have to show it instead.

So start by proving yourself. Then, when you get the interview, and you will, lean on everything you already worked out about your own story. Why this? Why now? Why you?

Answer those three properly and you'll be ten times more interesting than the next candidate. It's also a much better story than pretending you've secretly wanted this exact job since you were twelve.

None of this requires you to beat the algorithm. It just requires you to stop feeding it.

If you're between two chapters and trying to work out what's next, the Life Report will show you where the friction actually is. And if you'd like someone in your corner while you do this, that's part of what coaching is for. :)

The full arc, from noticing something is off through to living the new life, is The Five Stages of Reinvention, the framework behind my book The Art of Reinvention.

From the 50 Lunches Podcast

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