Don’t Squander Opportunities. Work Hard. Over Deliver.

by Jack Shedd, Co-owner and “chief nerd” of Mess, a web design and digital marketing agency in Chicago.

By trade, Jack Shedd is a software developer, but, as he tells us, he has worn “every hat that can fit on the hat rack: user experience, branding, design, copywriting, business development. All of it.”  He is also a Lumity STEM Talk speaker extraordinaire. Here’s just a snapshot of Jack’s career path and the advice he shares with students.

Find Your Passion 

Lumity: Each corporate volunteer with Lumity has reasons for sharing their stories and advice with students. What are yours?

Jack: These kids are me. I know what it’s like to go to an underfunded school. A single mother raised me, and we were just barely middle-class. People discount that college is legitimately not an option for some students; it wasn’t an option for me, for numerous reasons. However, what I found was that I could still have a good job and a really, really good life, thanks to the accessibility of creative technology. I want students to know that they can too if they have a passion for technology and are willing to put in the effort.

Lumity: You share with students that you didn’t have an easy time during or right after high school. What were those years like?  

Jack: I dropped out of high school my junior year—with no GED, no certification from a high school that said I was employable. I didn’t go to college. I took one community college class when I was 12, but I never attended a single day of university. I thought I was going to be a comic book writer. I was living on my own and working in a movie theater job. I got fired from that job. Got another job—and was fired from that one. Rinse and repeat a few times.

After one particularly horrible firing, I applied at CompUSA for a sales job. While I wasn’t much of a traditional “nerd” in high school, preferring loud rock and delinquency to academics, I was a devoted Mac fan. My mother had, somehow, managed to buy me a Performa 400 for Christmas one year. It was absolutely not top-of-the-line. It constantly broke, often without my help. But still, at a time when being a “Mac guy” was rare—this was almost a decade before the iPhone—I thought I’d do fairly well selling them.

The Power of Grit

Lumity: So, applying for a sales job was your first step into the tech world. How did it go?

Jack: During the interview, two things became clear; they didn’t need another Mac sales guy, but they were looking for someone who could fix Macs. Without much to lose, I straight up lied and said I could do that.

Not to be outsmarted by some 16-year-old, CompUSA forced any potential hire to do what’s called a “bench test.”  They marched me back into the repair area and set me down in front of four broken Macs. All I had to do to secure the job was, you know, fix them. Foiled!

I got immensely lucky during that test. Two of the Macs weren’t broken at all. One had a simple extension conflict—common and easy to resolve—while the other just needed its desktop rebuilt—all things any amateur would know how to do. The third machine had a broken CD-ROM drive. The fourth nearly ended my career. I had no idea what was wrong with it. I’d never seen the problem it was exhibiting, had no idea how to fix it. I just sat there, for what felt like hours, hitting buttons hoping something would magically happen. In what I rank as my second luckiest moment in my life, one of the techs in the room heard me talking out loud and blurted out a solution. Behold, I was hired.

That Friday, I drove around to all the libraries, checked out every book on computer repair, and spent the weekend trying to read them. I couldn’t cram eight years of learning into one weekend. So, I put the books in the back of my car. Then, at work, when I couldn’t fix a computer, I would pretend I wanted a cigarette, go outside to my car, leaf through the books, and then go back in to try it. I just kept doing that until I found the answer. I basically faked and lied my way through the job.

From Tech Repair to Tech Entrepreneur

Lumity: You say that you “faked and lied your way through the job,” but, in reality, you weren’t faking anything. You were teaching yourself an immense amount of skills and knowledge. Continuous learning is a theme in the STEM Talks you give to our students—and something you’ve done your whole life. So, how did it take you from CompUSA to your current role?

Jack: The job at CompUSA led to being hired by Deb Turpin, a Kansas City entrepreneur who was starting an IT consulting business just for Macs. I drove around Kansas City, figuring things out while I went, sleeping in clients’ offices and working non-stop. Eventually, Deb hired me as the full-time IT guy at her creative agency, River City Studios. After I’d mostly automated my job, I began to teach myself graphic design, illustration, and user experience. When the studio needed someone to learn ASP, I pretended I already knew it. That meant teaching myself web development.

A few years later, I’d move to Washington D.C, where I’d get a job as full-time web developer and designer. A few years after that, I moved to San Francisco to run a friend’s design team. Then, of course, Chicago, where I started working for Mess leading their development team, while my best-friend ran the creative department. A few years after that, after the company imploded, the two us took it over.

Lumity: It sounds like you had some lucky breaks, but you clearly made the most out of your opportunities. 

I absolutely got lucky. I just happened to be a Mac guy back when being a Mac guy was rare. I got incredibly lucky in that interview. I was lucky to meet Deb, and lucky, she took a chance on me. Honestly, who hires a 16-year-old? 

I never took any of that for granted. I over-worked myself. Terrified of failure, and perhaps more terrified someone would realize I wasn’t as capable as they thought, I just constantly worked. I’d often be up for more than 24 hours. I’d sleep at the office. I actually rented a room above the office just to be closer to a real bed. I worked my a#$^% off. 

The Many Paths to a Tech Career

Lumity: There are many lessons to be learned from the career path you took. It could be a tricky story to tell students—the majority of whom do and will benefit from high school and college. How do you balance this?

I tell them, “The numbers are against you” [if they don’t finish high school] and, if you can go to college, go to college. If you can’t, there are other paths you can go down that are unique to STEM; as long as you put in the time and energy, you can do it.” You won’t be a civil engineer without a degree, but you can become a game designer or web developer. Tech is one of the most accessible careers that exist. Demand is high, almost insatiable, and the wealth of resources available to you is unmatched in any other field.

It won’t be easy, but if you show up, if you’re willing to put in the work, and if you don’t squander whatever opportunities you’re given, you can have a great career. I mean, I do, and I’m honestly not that smart.

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