My Pathless Path Into Technology, Design and Beyond
How a liberal arts kid becomes a brand strategist, an engineer, a designer and whatever's next
Et ignotas animum dimittit in artes, naturamque nouat
Ovid, Metamorphoses, VIII, 18
I’ve published 68 pieces since I started Better by Design last year. I’ve written about design, technology, and ways to level up your craft, but one thing I haven’t done is introduce myself. I haven’t told my story. So today I want to take a step back and share my continuous prototype of a career with you. Aswould put it, I want to share my Pathless Path.
I want to tell you how a liberal arts kid gets a gig at a prestigious creative agency with no advertising experience. How I broke down and quit 18 months later without a plan B. How I pivoted over and over despite the confusion of my friends and family. And how I’m pivoting again right before your eyes.
I want to tell you the real story. Not the tidy, linear timeline you see on LinkedIn. The real deal: the doubt, the struggle, the relief, and the joy.
While I don’t know how applicable my experience will be to whatever you might be facing, I hope that you might know me a little better and feel a little less alone on your own winding journey.
The liberal arts season
Artsy kid doing liberal artsy things
I spent my college years at a small liberal arts school called Davidson College.
I majored in Political Science with a focus on political philosophy, which meant I spent an ungodly number of hours in the library reading some of the densest writing you’ll ever see (read one paragraph by Immanuel Kant and you’ll see what I mean).
While I enjoyed the philosophy part of my major, I picked Political Science mostly by default; it was perceived as one of the more challenging social science majors and I liked what that said about me.
I spent most of my free time participating in the arts; I sang in an acapella group and acted in plays and musicals. I always felt especially alive when I was performing. If I had been honest with myself (which frankly, is pretty hard to do when you’re 19), I should have just majored in theater or music, but I couldn’t handle the social pressure to conform to something more standard. It was hard enough to answer the dreaded question “What are you going to do with that major?” with my PoliSci degree. How could I answer it with a creative one?!
The deep motivation of not moving home
When senior year rolled around, I got struck by a deep motivation to find a job simply out of fear of the prospect of having to move home to rural, central Pennsylvania with no end in sight. While most of my friends were applying to jobs in consulting and banking or heading to a professional grad school (law or medicine), none of those felt right to me.
I was curious about business but wanted to do something “creative” which led me to explore advertising. The career counseling office wasn’t much help in my pursuit, but I was able to get connected to three or four alumni working in the field to start having conversations. I cold-emailed them, set up phone calls, asked about their experience, and always ended by asking who else I should talk to.
After a few calls, I decided to target brand strategy as my discipline and got advised to create a portfolio to showcase my thinking. Since I didn’t have any official projects to highlight, I started a Tumblr blog where I analyzed ad campaigns and talked about what I thought was effective and what I might do differently. In retrospect, it’s kinda what I’m doing now with Better by Design, just written by naive, little 22-year-old me.
By the time I finished my search, I had talked with over 50 people and written a dozen or so pieces. Eventually, right after graduation, a recruiter from Leo Burnett reached out to offer me a spot in their internship program that became available because another more experience candidate dropped out. I had already received an official rejection from Burnett a couple of weeks earlier, so this was a big surprise! I got the nod simply because I had taken the initiative to talk with a half dozen folks in their strategy department, so I guess they figured that if nothing else, I had some hustle. I took the offer, briefly went home to PA, and then headed off to Chicago.
The advertising season
My hands-on “master’s” at Leo Burnett
After the internship, I landed a full-time gig as a junior strategist. I worked on projects for a few accounts but spent most of my time focused on Esurance, the online insurance platform owned by Allstate (another Burnett client).
My experience was trial by fire. As you might expect, I was in over my head.
In retrospect, the entire concept of a “junior” strategist feels ridiculous to me now. How was I, a 22-year-old kid, supposed to advise decorated creative directors on strategy when they had more years of work experience than I had in life?
Thankfully, everyone I worked with at Burnett was not only A+ talent, but also A+ people, and the more seasoned folks helped me get up to speed and get by. I now consider this experience to be effectively my “master’s” degree in brand and communications strategy; I learned a ton in a short period of time from some of the best in the biz.
In my free time, I started taking improv classes at The Second City in Chicago. It felt great to perform again and be surrounded by the pure creative energy of my fellow improvisers. After completing the core program, I got accepted into the musical improv conservatory where I continued my study.
As time went by, I started to realize that advertising wasn’t a good fit for me. I enjoyed certain aspects of it (like doing research and learning about people’s psychology) but I felt unhappy with the output of my work (pushing people’s buttons to make a sale). I also didn’t like that I was disconnected from the actual making of the creative work. I synthesized the strategy and presented it to the creative teams and then they went off and made the ad.
Coming to terms with the realization that advertising wasn’t for me left me deeply conflicted because I knew I should feel lucky to have found my way into this highly sought-after job. But I also just wasn’t happy. To cope, I started spending more time doing improv and disconnecting from my work. Ultimately, this decline came to a head in a tearful discussion with my boss where I decided to resign.
Zen and the art of becoming technical
Just like that, I was jobless. However, I don’t remember feeling scared about the prospect of my unemployment. Instead, I remember feeling a great weight lift off of my shoulders. I had freed myself from something that wasn’t right for me, no matter how desirable it might have appeared to anyone else.
After leaving Burnett, I thought I might make improv and acting my main pursuit, but I also realized that I didn’t want to have to wait tables to survive. I knew I would be miserable doing that kind of work and that it would kill my creative energy while also not giving me a reasonable income or a skillset I was interested in.
Right at that moment, I read the book “Zen and Art of Motorcycle Maintenance” and it removed one of my major limiting beliefs at the time. While I had written off the idea of a technical career, the book opened me to the possibility that I could expand that side of myself. It convinced me I could learn to be technical if I could change my mindset.
Soon after reading it, I started going to a local coffee shop and teaching myself how to code using Codecademy. I enjoyed the experience and was excited by the prospect of growing a high-value skillset that might also enable me to work part-time or freelance to support my other creative interests. After a few weeks, I decided to commit to becoming a professional programmer. The concept of code boot camps was just getting off the ground in 2013, but I found one I liked, got accepted, and moved to NYC to start my next chapter.
The technology season
Eat, sleep, code, repeat
I arrived in New York with a singular focus: learn to code.
To finance this endeavor, I used my limited savings, some money I inherited from my grandmother, and took out a personal loan. Taking the loan seemed somewhat risky, but I felt it was worth betting on myself considering the potential upside.
I lived in a sublet room on the 6th floor of a walk-up building in the lower east side of Manhattan and walked the 20-30 minutes to Union Square in the cold each day for my classes.
I lived, breathed, and dreamed code during this time.
I was learning fundamental programming concepts for the first time and basically just banging my head on the desk until I understood them (not an ideal or sustainable learning methodology btw).
As the program progressed, I gravitated toward building the front end of web apps. Probably in part because I needed more time for the true software engineering concepts to sink in, but also because I’m a visual person by nature.
At the end of the program, two job opportunities surfaced: the first, a more traditional front-end engineering role with a tech startup, and the second, a hybrid front-end role on a design team at American Express. At the time, I thought I wanted to go deep into engineering, so I preferred the first option. However, I was only offered a position by Amex, so I took it.
I didn’t know it, but the fates had my back big time here as that job would introduce me to many incredible people and start my long journey of learning to design.
Learning by osmosis
My job title at Amex was “Experience Technologist”; basically a UI developer focused on prototyping in code throughout the design process.
As a technologist on the team, I would partner with designers from the earliest phases of discovery to the end of our prototyping implementation. I learned so much by osmosis, just watching the senior designers do their thing, seeing how they made their decisions, and collaborating with them to build their designs.
I had a great time at Amex and stayed until the company decided to reduce our business unit to its bare bones and laid off 80% of the design team. At that point, I had been in NYC for a couple of years and it felt like the end of an era: I was unemployed again, my roommate was moving out to go to business school, and other friends were getting married and moving away.
I took a trip to LA for a wedding and decided to move to California upon returning home. A couple of months later, I moved to LA without a job, trusting that my skill set would help me find something quickly. I worked with a recruiting agency and got placed as a UI developer at a small fin-tech startup in about 6 weeks.
Shifting roles from developer to designer
The company I joined employed no full-time designers, so as one of the main UI builders, I started creating my own designs. A few months into the job, the company went through a round of layoffs, cutting back its engineering headcount. Since I had been doing double duty on UI development and design, I was given a choice: either switch full-time to design or get laid off for the second time in two years.
I chose to switch to design.
While I liked programming, I had started to notice that I didn’t care as deeply about the minutia of the implementation as the other engineers I worked with. Instead, I cared more about the minutia of the experience I was creating. So while my switch to design was a forced choice, it was something I had already been considering; Design felt like a better day-to-day fit for my interests and skill set.
I stuck around at that company long enough to build my design portfolio and then began seeking out jobs where I could be a part of a larger team again. I needed to learn how to operate as a designer in that context and be around more senior designers who I could learn from.
As luck would have it, I landed a job off of a random Linkedin application. The universe, once again, led me to where I needed to go.
The design season
Finding a team & learning the day-to-day of a designer
In my first official design role, I joined the team at Tenable as a mid-level product designer.
I shared some last week about how that team’s approach to establishing a design system was ultimately a bust, but my overall experience there was good and important for my development. The impact was twofold: 1) it let me establish myself as a legit designer on a legit design team and 2) it introduced me to the cybersecurity space where I’d find a fruitful niche.
Like many jobs, it was good until it suddenly was terrible. About 18 months in the team got restructured and I started looking for new opportunities. I interviewed with a couple of companies in the bay area but ultimately took a position with a local LA cybersecurity startup called Signal Sciences. I hit it off with the team immediately and hit the ground running.
Expanding expertise and a wakeup call
At Signal Sciences, I expanded my design toolkit in the context of a very high-functioning and talented team. I went deep into designing a very technical security product and got to flex a lot of the design muscles I’d been developing over the prior few years.
Again, things were awesome until they suddenly weren’t. Despite feeling pretty entrenched in the company and putting a lot of heart and soul into the product, I got laid off in the early days of the pandemic. Compared to the Amex layoff, this one stung a lot more. Like many people in 2020, I was suddenly both isolated and floating without a job. Not a great combo. I took some contract work to get by and then, in a strange twist of fate, Signal Sciences got acquired by Fastly and then Fastly rehired me to resume my old job.
I took the Fastly gig mostly because I felt like I had unfinished business to attend to but quickly found that my future there wouldn’t be a simple return to the good times. It turns out that the kind of work that follows an acquisition is just 100% unappealing to me. After only 8 months, I started to entertain recruiting offers from two other companies. Against my better judgment, I fell under the golden glow of being recruited directly by the CEO of one of the two, took his offer, and quickly realized I’d made a terrible mistake. I pivoted immediately, and thankfully the other option was still available, so I pounced on it.
Following that brief snafu, I joined JupiterOne in the summer of 2021. My third cybersecurity company in a row.
I reunited with my former team lead from Tenable with the plan to take our learnings from designing other cybersecurity tools and apply them to help J1 become a best-in-class software product. We’ve faced unique challenges this time, but I think we’re living up to our expectations. Though the progress can feel slow, we’ve made massive strides in the past two years.
I view J1 as a kind of capstone project for the last six years of my career as a product designer focused on cybersecurity tools. I want to leave my best effort out there before I hang up the post-its and move on to my next season of growth.
The next season
Since this post is already nearing 3000 words, I’ll spare you my detailed thoughts on the future for the time being. The gist is that, while I’m still in a good spot job-wise, I feel something bigger brewing.
Ever since I decided to leave Leo Burnett and pick up coding a decade ago, I’ve had it in the back of my mind that I would one day give myself the space to pursue my own creations. And thanks to the weird, winding road I just shared with you I now have a wonderful complement of skills that can be useful to a wide range of people.
As I start to close out this first year of publishing on Substack, I can honestly say that the future is looking as bright as ever. Thanks for being a part of my ongoing journey and I hope that I can help you on your own path!
PS. If you know anyone who has also been a brand strategist, then an engineer, then a designer, please introduce me to them!!
If you got a little value from this post, consider subscribing, sharing, or following me on Twitter. If you got a lot of value, consider pledging to support my work with a paid subscription in the future.