Patrick Whitson didn’t stumble into WordPress last year — he’s been working in tech since long before websites were the main event. His career started in the U.S. Navy, moved through decades of I.T. work and contracting, and eventually landed in freelance web design when he decided corporate life wasn’t for him anymore.
In this profile, Patrick shares how a career that started in the U.S. Navy evolved into decades of hands-on I.T. work, contracting, and eventually building a long-running freelance business focused on helping local businesses show up and compete online. He talks candidly about the traps we all fall into (overthinking, over-tweaking, over-planning), why follow-up is still one of the most underrated growth tools we have, and what it means to still be standing after 15+ years in business.
If you appreciate perspective that only comes from time in the trenches — and advice that’s equal parts practical and self-aware — you’ll enjoy Patrick’s story.
What kind of work did you do before your current business and what did you bring with you into this career?
I joined the U.S. Navy out of High School. Six months after landing on my assigned post (U.S.S. Saipan LHA-2) I transferred to the S-7 Division as a Data Processor. For the remainder of my tour I learned computer operations, started to learn programming & database design.
At my shore duty station, I supervised a team running the mainframe operations for the Office of Naval Intelligence (ONI) with a top-secret clearance. I helped create and run the help-desk support system for the building, learned computer networking, how to build/repair PC’s (at the time, Zenith) and other administrative tasks.
In 1994, I was honorably discharged and started contracting through technical staffing companies for clients, such as, GM, Ford, Chrysler, MSX, Intl., Saturn, Toyota, Detroit Edison, and many others. I began by converting WordPerfect documents over to MS Word 6, then moved into application development, programming, n-tier development, website design / development, database design / development and eventually data warehouse design. This was all learned through “on-the-job” training, courses and classes I took either from the company I contracted for, the GI Bill or from home after hours.
I completed working as a contractor in October of 2009 after I was let go.
What got you into WordPress and how long have you been using it?
Around August 2010, I went through a 7-day training on WordPress and shortly after won a ticket to a weekend seminar in Indianapolis, Indiana on building a business using WordPress.
During that seminar, I met a practicing dentist (I’ll keep his name anonymous) who was wanting to build websites for dentists and do their digital marketing. Our meeting is what launched me into using and working with WordPress for local businesses.
It worked out great as he needed someone to handle the “technical stuff” and he would do the selling to bring in the clients. A match that paired well for many years.
I also worked with many people I met, didn’t meet, and their friends from that seminar to help them build or improve their websites using WordPress.
So, I’ve been using WordPress for nearly sixteen years. I started off using the Thesis theme by Chris Pearson. Then, I migrated to Genesis (by StudioPress / Brian Gardner), to Thrive Themes to Astra/Elementor and now settling with Bricks/ACSS/Frames stack – which I really enjoy using.
What part of the website creation process is your favorite to work on and why?
Coming from a drawing, and graphic design background, I really enjoy the design process the most and seeing either a new site coming to life or a redesign taking on a new look and feel. Not only that, but observing or hearing the client’s excitement when they see their website launched on the public internet.
What motivated you to start your own business, and what keeps you going when things get tough?
Mainly, I needed to bring in money to pay bills as I was let go from my work and I no longer wanted to work in the corporate arena. I also saw how local businesses were being left behind in technology and having an online presence. This motivated me to want to help them build websites that sell for them and grow their enterprises.
What’s your biggest frustration with running your agency or with our industry?
From my experience, there isn’t just one hard lesson, but if I were to give one, it would be stop paralyzing yourself through analysis. This is a REAL thing, not just for website designers, but many entrepreneurs.
Let’s take our own website’s for instance. I mean, how many times do we need to tweak, spin, twist or fiddle with the layout, content, speed, etc. before we launch. STOP! I’m speaking to myself as much as anyone reading this.
I’m not advocating that we just slap something up without any kind of forethought or research. We need to do that – to a point – and then get er’ done, launch it and then you can modify things as you move along.
Also, and I believe this goes hand-in-hand with the above lesson, don’t get so bogged down into finding the PERFECT target market. I’ve put myself so far into the sand I couldn’t figure out the difference between the sand and tumbleweeds. Whew!
Get out there, talk to normal, everyday business people – shut the pie-hole and open up the satellite dishes (your ears) and L-I-S-T-E-N. You’ll be amazed how much further along you’ll get. Through a process of time, you’ll figure out those red flag 🚩 projects and the ones that are worth it.
What’s your biggest frustration with running your agency or with our industry?
The statistics state that most new enterprises fail within the first five years. I’ve been doing this for 15+ years and in the I.T. Industry for over 35. I’m well pleased that I beat the odds and am still going.
What’s a book every agency owner should read?
MJ DeMarko’s “The Millionaire Fastlane”
What’s a WordPress plugin more people should know about?
What’s your favorite tool, accessory, or gadget on your desk?
My headset
What’s your favorite non-WordPress tool or software?
