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.

How I Became a Writer

How many times have you created a goal and never achieved it? We’ve all done it. Most of us set new goals every January and by March we know that we’re not going to achieve them.

In January I set a goal to start writing a blog. My goal for the blog was to help me become a better a writer, create content for my customers and increase my visibility on social media for new opportunities. If you’re reading this piece on my new website and asking yourself, “Well, you did it, so what’s the problem?” 

The problem was that I made the exact same goal in 2019 and didn’t write a damn thing.

What could I do to make sure that 2020 was not going to be a repeat of 2019?

I first needed to determine what went wrong last year. I set the goal to start a blog to use as a tool to share product stories and gain meetings and sales with my customers. I came up with a lot of good ideas but never really wrote much.

So what could I do? Luckily for me I found a book that said you shouldn’t set goals. Problem solved.

The New Year can’t officially start until you’ve made your resolutions and purchased a new self-help book. After doing some research it seemed the options were to Unfu*k Yourself or Start Building Good Habits. I went with the latter because it talked about not setting goals and focusing on a system, and I already had a therapist for the former. The book I’m referencing is “Atomic Habits” by James Clear

Early in the book, I was really struck by what the writers refers to as the three layers of behavior change: a change in outcome, a change in your process, or a change in your identity. Outcomes are concerned with the results, process revolves around habits, and identity is concerned with your self-image. Clear states that identity is the true behavior change and the only reason you’ll stick with a new habit is if it becomes part of your identity. If I wanted to be successful this year then my goal shouldn’t be to start a blog but to become a writer. That was an identity I hadn’t considered.

The more I thought about it the more it made sense. Becoming a writer didn’t have to mean becoming an award winning author, but if I wanted a blog where I consistently put out quality content then I would need to act and work like a writer to see myself as one. So I needed to write more to be a writer but the lack of writing is mostly what held me back in 2019. I was confident in my ideas for blog topics and the overall approach of how it would help me and my customers, but I only thought of myself as a decent writer who could use some help with grammar. I would also need some tips on writing a blog for business. 

I discovered “Everybody Writes” by Ann Handley with a simple Google search for books on business writing. This book seemed to be on everyone’s best of list and after a quick read on her website I knew it was the book for me. Ann talked about how everyone was already a writer because of emails and social media and even though I did those things I didn’t feel like a writer. But it was her approach to writing that showed me I could be one. She emphasized how a good piece or writing was assembled and not written. She outlined how to put the blog post together with instructions and even recommended not doing it all in one sitting. 

Armed with this new outline, other solid writing tips and no pressure to feel I had to write a masterpiece in one sitting I didn’t feel as overwhelmed. Maybe I could be a writer? The next writing expert helped me put the final pieces of my writing identity puzzle together and also provided some unexpected business advice.

Dorie Clark has appeared on a few podcast episodes that I’ve listened to so I was familiar with her story — a story that many of us find ourselves in today due to the COVID-19 pandemic. She was let go from her journalism job around 9/11 and had to find a way to re-invent herself and make money. She decided that she needed multiple revenue streams and even wrote a book titled “Reinventing You.” I didn’t read the book but instead took the online course on her website called, “Rapid Content Creation Masterclass.” 

The course became the perfect set of instructions I needed for writing a business blog. She simply gave me all the rules I needed to follow to write a blog post. There were helpful tools for creating topics, testing the title’s strength, and ways to bolster each paragraph. The Rapid Content Creation Masterclass allowed me to create my own blog writing template that made it easy for me to sit down and finally start writing—a template that I one day plan to refine so I can share with others who would like to start a blog to help their sales career or business.

Even though I made myself an easy-to-use template and the writing seemed to be coming more naturally I just wasn’t writing enough—especially if I planned to put out content on a regular basis. You see, I had created an awesome template that helped me write but I still didn’t have a system that would make me a writer. 

Next up is my post on creating a plan around my new schedule that helped me find the time to become a writer and discover an even more important identity.

I Needed a New Plan

My writing habits were improving but I wasn’t writing enough. Potential blog posts were being worked on but not completed. I’d schedule time to write but when the time came I’d usually just focus on other things for my job. 

These other things kept me busy but deep down I knew they didn’t have the long term potential for future gains and earnings that writing and the blog would provide. 

I really enjoyed the writing but the fear of what others would think was holding me back. 

When I was researching to become a better writer and develop better habits I noticed that all of the books, blogs and podcast had a similar message. Focus on the identity of who you want to be, establish the habits that type of person would have so you can start to see yourself in that light and find someone who will help to hold you accountable.

For me that meant, in order to view myself as a writer, I needed to consistently write to consider myself a writer and have someone to hold me accountable and help edit my writing. Luckily I married into a family of talented writers; my wife included. My sister-in-law Colleen is a published writer, former college writing professor and a director of marketing. She was perfect and most importantly, willing to help me out. 

I knew Colleen would provide me with constructive criticism, new ways to approach topics and the confidence to overcome my fear of appearing stupid. Soon after I was finishing posts and hitting my goal of one new draft a week.

Unfortunately the COVID-19 pandemic hit and now I was self-isolating at home with my wife and two sons under five. Since no one had anywhere to go I figured I’d have more time to write. I quickly realized that being home with two kids left me with less time than I had before. 

That’s not to say I didn’t have time to write I just needed to figure out when the best times were. 

My first inclination was that as long as my boys were being quiet then I could write. The younger one doesn’t stay quiet or still for less than ten minutes so that was a mistake. I just ended up getting irritated and blaming them for not writing as much. I knew it wasn’t their fault and I was starting to become pretty moody toward everyone. 

I needed to rethink my new situation as a whole because there were a lot of other things I wasn’t taking care of either. I wasn’t working out, doing household chores or enjoying the time I had been given with my wife and kids. I came to the sudden realization that there were certain times of the day that were better suited for certain tasks or projects.

To see how I could fit the projects into my new life I broke down the days into the natural time blocks our kids were dictating without factoring in anything that I wanted to do:

  • 6 – 8am: Boys wake up and get settled into morning 
  • 8-10am: Breakfast and playtime
  • 10-11am: Zoom school meetings
  • 11am — 12pm: Bike ride with the boys or destroy basement
  • 12-1pm: Lunchtime
  • 1-3pm: Youngest naps and older one has quiet time
  • 3-5pm: Playtime, outside time, practice numbers and letters
  • 5-7pm: Family and dinner time
  • 7-8pm: Boys go down for bed
  • 8-10pm: Relax and hang out with my wife

Now that I had the day broken down into its natural flow I could see what times were best suited for certain projects and allow me to be present for my family. I made a list of what I wanted to accomplish during the week: writing, developing website, working out, household chores, learning/research and my own personal downtime. Then I cross referenced those tasks with the daily schedule and started to put the new puzzle together (puzzles were a popular activity during the pandemic). 

  • 7-9am: Workout – My wife and I could switch off during this time. The morning is better for me because I lose all motivation to work out after 10am.
  • 9-11am: Learning/research or chores – This time was perfect to listen to podcasts, read books & blogs, or clean part of the house. The boys are pretty active during this time but I realized I could work on things that I could easily put down and walk away from. 
  • 11-1pm: Bike ride or playtime with boys and lunch together.
  • 1-3pm: Writing, web development or errands.
  • 3-8pm: Family time, chores and dinner.
  • 8-10pm: Time with my wife or open for tasks (Tiger King, The Last Dance, etc.)

Once I started following this new schedule I instantly saw better results in my projects and mood. I was enjoying my time with the boys, writing and reading more, working out, well the working out wasn’t happening as much but there were plenty of enjoyable bike rides. 

This new system simplified my days because I knew exactly when I could get certain things done. And if something didn’t happen on a given day I wasn’t angry because I knew I had the time tomorrow. 

However, when I looked back on my week I noticed that I was working on some things more than others. There really didn’t seem to be a proper balance for what I was working on. One morning listening to a sales podcast, at the designated time, I discovered a new system that would change everything. Check out the next blog on a system that showed me a way to feel balanced and fulfilled at the end of each day and week.