How I wound up here: A tale of one UX Designer’s career path

I reflect upon my journey from movie theater busboy to designer, developer, and dad

9 min readJul 10, 2020

At age 16, my Mom arranged an interview for me at the local movie theater.

My first day was during Finding Nemo opening weekend.

Nearly two years later, my girlfriend dumped me.

Trouble was we worked together, most often as the only two reps selling tickets at the box office. I quit without another job lined up.

I applied for and secured a job at the closest Circuit City. I was great at talking to customers. I was terrible at selling computers with accessories. I worked on-and-off between my first two college semesters.

By sophomore year, I was living with three pals in an apartment.

In other words, I no longer had to return home between semesters. I applied for and secured a job at the University newspaper as an advertisement designer. I worked with other designers and ad salespeople.

One of the designers was extremely tech savvy. He showed me some websites he built.

I worked two jobs part-time my last two years at college: a few days at the newspaper, the others at a local grandma-and-grandpa-owned print shop. Both jobs helped improve my graphic design and layout skills. The print shop job helped me acquire a wealth of practical knowledge about the pre- and post-press processes.

Early senior year, I applied at Raytheon Missile Systems. No offer.

Shortly after graduating, I applied again. I gleefully recall getting an offer via phone upon returning home from the interview as I pulled into my apartment’s car port.

I learned a lot while there. I participated in the entire lifecycle of the range of media I designed. I serviced internal clients from a variety of lines of businesses. I received valuable mentorship from my manager and co-workers.

My employment at Raytheon ended abruptly due to my own foolishness.

Seeking continued work as a graphic designer, I applied for an opening at an agency in northern Tucson, AZ. Regardless of how my interview actually went, I was lucky to get an unsolicited reference from a woman I worked with at Raytheon: she was related to the owner of the agency.

In my time there I experienced incredible reward from the work.

I coded my first few websites.
I fine-tuned my photo editing and brand identity design skills.
I contributed creatively to several high-profile clients and campaigns.

Sadly, I also experienced extreme stress due to the toxic environment created by the husband-and-wife owners who seemed at constant war with one another and who used their clients and employees as pawns in their sick game.

Fortunately, my small portfolio, accrued interpersonal skills, and passion for design helped me sell myself to the founder and CTO of a local home security reseller.

I was a ‘team of one’ marketing department.

I ensured that the largely student salesforce had professional-looking marketing material during their daily door-to-door rounds.
I managed the company’s customer and recruiting websites.
I persuaded the CFO to lease a commercial printer so I could design, print and cut almost all material myself.

Before two years passed, my job, the city, and my wife and I’s interests in staying in Arizona grew stale.

We moved to Charlotte, NC.

Having cold-emailed one founder while back in Arizona, I scheduled an in-person interview with both founders of a small ad agency in Southend.

I was in and out of that job after three months. Personality types weren’t a good mix.

Thankfully, two weeks later one of Charlotte’s top recruiting firms helped place me in my first contract at Family Dollar. My passion for working smarter-not-harder oddly annoyed my co-workers and manager. Instead, I found friends among the in-house print designers and photographer.

After a round of layoffs, my team suffered two hits.

But a few roadblocks had been cleared. I continued to express my creativity and passion. Many seemed impressed. One seemed unable to forgive me for a minor oversight related to a campaign she led.

For various reasons, I was uninterested in extending my contract.

I applied for and secured a job as a pre-sales engineer at a SaaS company who was attempting to enter and quickly dominate the US market. Much to my surprise, my creative skills helped me impress the regional sales manager early. He taught me how to sell software, and anything else, really.

He sadly lost a member of his family and soon left the company.

By then, I became more interested in designing software than facilitating sales calls and technical demos.

Unfortunately, the product teams were in Europe.

I applied for but failed to receive any offers for several User Experience Design jobs. This made sense as I had no practical experience designing experiences.

I had, however, designed and built many websites in the time since being employed at that toxic ad agency job in Tucson. Even more to my benefit, most of them were built using WordPress.

This specific experience in combination with the charming and good-natured personality of the hiring manager helped me attain my first job at a bank.

Much like at Raytheon, I learned a lot in my six-month contract at Wells Fargo.

On my first day during a meeting with my manager and his, I learned that any research, creativity or critique I could offer would be met with immediate resistance.
I learned that a progressive marketing campaign caused budgets to shift and several team members to re-apply for their jobs.
I learned that my manager prioritized advanced functionality in the micro-sites that we built, thereby hampering our clients’ ability to independently maintain their new digital property.

I also learned that my co-worker shared my interests, humor, and disdain for the decisions made by leadership.

We continue to enjoy friendly weekly calls.

As my contract neared its end, I received an invitation to interview with another bank. It would be my first formal User Experience design job. It would be full-time. It was an incredible opportunity.

It was my longest-held job: three years.

It was my most rewarding and fulfilling job thus far: among other projects, I led efforts to redesign the company’s background check form.
It helped me realize I enjoy mentoring and tutoring others.
It forced me to master a lesser-known but highly robust rapid prototyping tool: Axure RP.
It positioned me as an interviewer, helping me advocate for increased diversity among my already diverse team.

It validated my hunch that the culture there was not one meant for me.

Five months before my 3-year work anniversary, my wife had our first child.

Thankfully, the bank offered four months paternity leave. I took them all.

While joining my wife in our hospital room, I knew I didn’t want to go back to my bank job. But I had no other viable options to make a decent living. The start-up I helped build had developed incredible technological solutions, but we had no paying customers yet. The small businesses I provided design and technical services weren’t hiring.

I had an idea for a business: 1-on-1 coaching for junior developers.

I bought a domain.
I designed and published a landing page.
I got my first recurring client within days.

Throughout the next four months during my son’s naps, I tutored that client in frontend development. I joined a few slack communities and offered free coaching sessions as an introductory step towards acquiring new clients. I applied to 1–3 jobs each night.

I struck out in all three ventures.

My client’s company withdrew funding for our coaching sessions
No new clients enrolled,
and no job offers were extended.

There was one success.

I persuaded one of the small businesses to pay me a small monthly sum in exchange for serving as their quasi-CTO. I accepted responsibility for improving and automating several aspects of their operations.

One month before my 3-year work anniversary, I returned to the office. Aside from a few new faces in different cubicles, nothing noteworthy had changed. My inbox had accrued only a few hundred messages. They were a mix of email chains, system-generated notifications, meeting cancellations, and inter-team memos.

It was abundantly clear: I was no longer interested in fulfilling this role.

My wife and I agreed that as foolish as it was for me to voluntarily withdraw my job security, resigning was unavoidable.

Surprisingly, moments after notifying my boss, I received a call asking if I was still available to interview for a job I applied some weeks prior. It was at another business within the last bank.

I was sold on an opportunity to be mentored by an expert in web accessibility and work directly with several product teams in effort to help them update their software to meet important accessibility benchmarks.

After one week, I felt duped.

My manager and would-be mentor moved to a different team prior to my start date. My primary job was to routinely re-evaluate web applications, emails and PDFs for accessibility defects. I lived exclusively in Excel and VersionOne, an Agile project management tool. I listened to designers over-explain arbitrary constraints imposed by software developers and their overly-complicated solutions to seemingly trivial user tasks.

I was grateful for the job, but the limited scope of work had me feeling grossly undervalued.

After meeting the newly-hired Southeast Regional Customer Experience Design Manager for a fully-remote consulting firm, I was convinced that I would soon be doing the work I most enjoyed: rapidly prototyping complex web applications for clients spanning a range of industries.

Sadly, there wasn’t enough work yet to offer me the job.

Then, everything froze due to covid-19.

Work screeched to a halt. Few new jobs were posted. Extracurricular events were cancelled.

I didn’t freeze, though. In fact, I felt more encouraged than ever to speed up.

I continued to publish a short article each morning on LinkedIn.
I updated my resume at the start of each month.
I redesigned my online portfolio to better communicate my skills and value to prospective employers.
I wrote several case studies describing recent side projects and the work I had done for the start-up and small business.
I completed nearly 20 frontend challenges to validate and improve my skills.
I built a game that helps junior developers self-teach frontend.
I reached out to people who expressed difficulty learning frontend in the slack communities I previously joined, and helped several of them focus their attention on a small list of free resources, including the game I made.

Oh, and I started recording myself tying a variety of knots. It seemed like a great hobby that I could do with my son.

Eventually, a recruiter contacted me about an exciting position in a new industry, healthcare. An application was submitted on my behalf. A few weeks later, I was informed that the position was put on hold.

A month later, the same recruiter contacted me again. That position had re-opened. I confirmed my interest and availability. Better still, another position opened within a different team at the same employer. I expressed equal interest.

I had two interviews the same day.

One seemed to go poorly due to a miscommunication. The other seemed like a great match within minutes.

Later that week the recruiter called to extend me an offer for the second opportunity.

I accepted with excitement and without hesitation.

In the time between accepting the offer and starting, I read three books on the subject that I would be expected to demonstrate expertise in: data visualization.

I’m doing what I enjoy again.

I interview senior leaders about the data they need and the stories they are expected to tell.
I prototype data visualizations that I think would most effectively help leaders tell their stories.
I work with software developers to ensure my prototypes can be built within the allotted time and budget.

In essence, I use my accrued knowledge in sales, interface and experience design, software development, marketing, visual communication, rapid prototyping, accessibility, and data visualization to help leaders make smarter, data-driven decisions.

Beyond the day job, I use these same skills to build a start-up, scale a small business, and mentor others who are somewhere along a similar path to the one I described throughout this article.

Even with where I am and what I have experienced, I foresee a career path filled with many twists and turns.

I remain anxious to learn new skills related and unrelated to the job.
I remain committed to helping junior developers discover and focus on the most effective outlets for self-teaching.
I remain in search of other start-ups who need help improving operations and removing friction from their customers’ experience.