Beware of Your Personal Brand

I had enough content to start my website, but I needed a personal brand. My friend Ryan, who was helping me with the graphics, told me that my signature was unique and maybe he could create a logo based on it.

I always thought I had poor penmanship but you know what—he was right—my signature was unique. I was unique. My site was going to be unique. So I started writing my name over and over again like a sixth grader with a crush and a new pen.

Jason D Dempsey

Jason D. Dempsey


In the end I just sent him my regular signature, the exact same one that many bank tellers and waitresses have received throughout the years. 

We discussed the idea of creating the logo around my initials (JDD) because I wanted people to see there were two Ds in the website name. I took because it was available and my business cards always seemed to say Jason D. Dempsey—so why not?

Not only is Ryan a talented designer, he’s also a published writer. He started asking me about my vision for the site, what I wanted to convey to the readers and what three adjectives would best describe my logo and website?

I couldn’t come up with anything so I just started babbling about the phases I saw the website going through. 

  1. The first being a way for me to improve my writing, learn more about online marketing, SEO and showcase my skills as a sales and marketing person.
  2. Give me another way to connect with customers and share other people’s stories to gain meetings and sales.
  3. Showcase my new experiences and allow me to have other new opportunities I hadn’t even dreamed of.

After my ten-minute stream of consciousness he just looked at me and said, “I’m hearing the words authenticity, voice and authority.”

I said, “Exactly.”

I then got really excited about what this could mean and with a new rush of creativity and I quickly drew a crude logo that I thought would definitely be the one.

My wife overheard me, saw my crude drawing and said, “Don’t be that client.”

I lowered my head because I immediately knew what she meant. When I was in marketing and we were working on the creative components of a campaign or product launch, the product and business managers would always have a ton of ideas for the tag lines, ads or other fun parts. 

I can’t really blame them—they were the fun parts and some of their ideas were very insightful—but it always came across as, “Anyone can do marketing.”

Later the following week Ryan sent me back a bunch of awesome logos in different color schemes and ways they could work on the website. One of the best parts of working with an artist is how they can take your simple idea and create something that totally surpasses your expectations. He definitely did that and my site would not be where it is today without his creativity and hard work.

Ryan did humor me and created a logo that looked a little like my drawing. I never saw the similarities when I drew it but here it was as clear as day. My initials, name and reputation were just one strategically placed dot away from becoming a penis. 

Here it is in all its glory. 

I like to think he did it to teach me a lesson—maybe he didn’t—but it did allow me to see myself for how I was behaving.

If we went with my idea then the real question would have been who’d be the first person to place that strategic dot on my new logo? One of my brothers or friends?

Lesson learned. 

I focused on a couple of the logos that worked better for my messaging and in the end we went with the logo you see on the site today.

The logo is simple, emphasizes my middle initial and also is the perfect size to use for thumbnail images. I also wanted to incorporate some other parts of my life in the site. 

You’ll notice the other icons on the site are a record player and bicycle paired with my logo and the words Listen. Apply. Process. The three icons and words represent how I approach every sales meeting, my writing, and the development of this website. I’m also an avid biker and love listening to music, going to concerts and I’m a volunteer for CHIRP Radio in Chicago. 

My intention for the site was to share success stories from my job, talk about biking in Chicago, and incorporate my love for music and happenings at CHIRP.  Even though some things have changed in regard to my employment, this whole experience has become so much more. 

It has been an incredible exercise in listening to myself and others, discovering what I want out of my life and career, examining how I present myself to the world, processing that information and applying my knowledge and skills to the best of my ability. 

I hope I just don’t come across as a you-know-what.