Why I Went Freelance Instead of Applying for Another Web Design Job

1 minute

I applied for a web design job once that asked me to create an account, upload my CV, then manually retype everything on my CV into their system.

Name. Education. Work history. One job at a time.

It took 40 minutes.

I never heard back.

Not even an automated email. Just silence. The digital equivalent of someone taking your CV, nodding thoughtfully, and then binning it while maintaining eye contact.

The social contract is broken

There used to be an unspoken deal with job applications. You put in the effort, they at least pretend to consider you. A rejection letter. A "we'll keep your details on file." Something.

That deal is gone.

Now companies want you to treat applying like a part time job. Multi-stage processes. Personality assessments. Take-home tasks. All for a role paying £28k that lists "5 years minimum experience" as a requirement.

For £28k.

The audacity is genuinely impressive.

Cover letters are a joke

You have my CV. You have my portfolio. You can see exactly what I've built, who I've worked with, and whether I can do the job.

And yet.

"Please attach a cover letter explaining why you want to work at [Company Name]."

Why do I want to work there? Because I need money and this job seemed fine. That's why everyone applies for every job. Nobody is sitting at home thinking "I've always dreamed of being a mid-level UI designer at a SaaS company in Leeds."

The cover letter exists to filter out people who can't be bothered. Which is fair. But when you also have a portfolio that took years to build, asking for a cover letter on top feels like making someone show ID after they've already passed a background check.

The mortgage application problem

Some application forms look like you're buying a house.

Previous employer. Dates of employment. Reason for leaving. References. Emergency contact. Do you have the right to work in the UK. Have you ever been convicted of a crime.

Mate. I'm applying to redesign your pricing page.

And here's the thing nobody says out loud. There is a 99.999% chance I will never hear from you again. That is just statistically true. Most applications go nowhere. So you are asking me to spend an hour of my life filling in what is essentially a government form, on the off chance that I am the one person out of hundreds who gets a reply.

It's not a fair trade.

So I stopped

Going freelance wasn't some bold entrepreneurial move. It was more like... refusing to keep playing a game with rules that only benefit one side.

One client. One conversation. One project. No accounts to create, no cover letters to write, no personality tests to fail, no 40 minute application forms that lead to nothing.

Just someone who needs a website and someone who can build it.

Turns out that's a much better deal for everyone.

If you're a web designer still grinding through job applications wondering if it's supposed to feel this demoralising, it isn't. The process is just broken.

Going freelance won't fix everything. But at least when it goes nowhere, it's your own fault.

About

With 10 years of hands-on experience I’ve learned most of what I know by doing. This blog is a collection of my personal insights and general musings on the craft of web design.

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© 2026 Chris Monks Design All rights reserved.
© 2026 Chris Monks Design All rights reserved.