In 1999, I applied for a title-related job at one of the big underwriters.

HR actually called me. Because back then, HR wasn’t an AI auto-rejection bot with the emotional warmth of a parking meter.

And yes—I got hired.

Just not for the job I applied for.

The woman from HR was starting a side hustle and spotted “web design” on my resume. She asked a few questions. I answered like a normal person.

Boom. I had my first client.

That is basically my whole career in a nutshell:

I show up for one thing, and end up building a system for something else because someone’s business is on fire.

And right now? Web and graphic design fires are everywhere.

Not because there aren’t talented designers. There are.

But because most small business owners were never taught how to:

This is about helping you use what you paid for and get the outcome you wanted in the first place whether you choose to hire me or someone else.

So let’s make sure you don’t get burned.

This guide will help you:

✅ Evaluate designers before you hire them (so you don’t accidentally buy dependency or chaos)
✅ Communicate your vision clearly and confidently (without jargon or “make it pop”)
✅ Avoid common and costly missteps (revision spirals, platform traps, scope creep, vague contracts)
✅ Build a professional working relationship that actually works (with respect and boundaries)

You’ll find short stories and blunt truths… and a whole lot of checklists.

Most small business owners don’t shop for a web designer.
They panic-buy one.
The site is outdated or non-existent.
Someone told them they “need SEO.”

So they set out to choose someone and it goes like this…

“My cousin ‘does websites’ but I asked him to change this one thing 6 months ago and he just keeps putting it off.”

“I got this $399 deal on Fiverr. It seemed legit.”

“I found this new start-up who is offering free web design to build their portfolio. It’s only going to cost me $100 per month for ‘hosting and maintenance.’”

And because web design feels mysterious and technical, people default to price instead of fit. That’s how you end up paying cheap prices for expensive problems.

This guide exists to stop that cycle.

This is not a sales pitch.
It’s not a technical manual.
And it’s definitely not another vague “you get what you pay for” lecture.

This is a clear, practical, quick-reference guide that teaches you how to think before you hire a web designer—so you can make a smart decision the first time.

It’s the guide I wish every business owner read before spending money on a website.

A good website isn’t cheap.
A cheap website isn’t good value.
And the most expensive website is the one you have to build twice.

The magic isn’t in the pixels.
It’s in the thinking behind them.