Follow Your Weird: My Career Advice

In my last several of my roles, I’ve spent time mentoring early-career engineers. Reasonably enough, they ask me questions like “Did I join the right company?” or “Did I start in the right role?”

I answer: “You did.”

Sometimes they ask me this question in reverse: “Did I waste my time by learning this language” or “Did I miss out on my optimal career trajectory because I didn’t do such-and-such program at such-and-such school?” or “Did I doom my career by not starting in a team with some buzzword in its name?”

I answer: “You didn’t.”

In their position of vulnerability and youth, they don’t have the background to understand my gnomic replies. Oftentimes, our relationship is still new and they don’t know me well enough to simply trust me. So this post is an attempt to tell everyone that your career choices will be the perfect provided you follow one simple rule: follow your weird.

---

Said Kierkegaard:

life must be understood backwards. [b]ut … it must be lived forwards.

– Kierkegaard Journals IV 164 A

Today as I write this, I have an amazing job that feels uniquely tailored for me, my competencies, my background, and my interests. Per Kierkegaard, looking backwards, I see how, to steal a phrase from The Wire, all the pieces mattered. But living forwards, I couldn’t see that those pieces were creating steps, pulleys, rungs, rails, ladders, and ramps to where I am now. Let me provide three chains of experiences that made this outcome possible and, in retrospect, seem designed to bring about my current state.

The Three Chains

A Calculator for a Toddler

Ultimately, the story of my present could be unwound to somewhere where I wanted a “calculator” like my Dad’s (HP 12C-era, reverse Polish notation (RPN)).

My mom saw this and bought me a Little Professor ™ calculator and was told that a tot like myself (3 or so) would break it. But I didn’t. I still remember the tactile feedback on its number pad. When, later, I’d use a 12C myself, the tactile resistance was the same. The aesthetics of the tactile response were excellent in those days of American electronics. I didn’t abuse it or break it. I was careful with it and its red LED display.

Run time forward and see my Dad showing me how reverse Polish notation worked at a beach house on Galveston island through the follow-along projects in the manual. Run that way forward and see me reading a Lisp book that described functional application to lists and going “Oh, like Dad’s HP calculator.” Run it forward to now, and the idea of meaningful educational experiences that teach concepts is what I do.

A Taste for Modems

In high school in the mid-90’s, my family got a computer. Included in the computer was a 2400 baud modem. One day I grabbed the newsprint computer times periodical by the exit at one of our area software or electronics stores (Circuit City, Babbage’s, Egghead). I read the articles and was intrigued about their reviews of software and programming trends. But then I found pages of phone numbers at the back. These were the phone numbers of local bulletin board systems (BBS). I don’t know why I cared, or why I bothered, but I called out and – slowly – a computer somewhere in town started printing out what we would now call a forum. Eventually I would find other BBS-ing teens and we would play online games, send messages, talk music videos, talk about what our school was like, etc. Time would see me upgrade from 2400 to 14.4 and experience the first real thrill of an upgrade.

And then one day, I saw someone’s signature text on a post include something like someName@nasa.gov. I asked him what that meant. He explained that it was his “e-mail” address on “the internet.” I asked whether it was like a BBS or something and he explained that it was just machines that you could visit if your computer was connected to the “inter-net.” I was intrigued. On my next visit to the local Bookstop, my mom bought me “Whole Internet User’s Guide and Catalog” by Ed Krol. It introduced me to the state of the art of the pre-GUI internet.

It also introduced me to the programmer culture of the south Bay area: somewhere between the Grateful Dead, the Electric Kool-Aid Acid Test, and Fairchild semicoundcutor. It was the same tradition that would birth my slightly-older cohort icons like Steve Jobs, Nolan Bushnell, and Bill Joy. It also served as a friendly and fun guide that put fun and exploration front-and-center in electronics. It was a lot less oscilloscope and a lot more digital dumpster divers with pocket protectors. This irreverence and thrill is another aspect that I take into curriculum design in my current role.

In any case, it definitely made me think about heading West post-college. I did, and had many, many adventures there that lead to the moment when DevBootcamp moved me to New York.

“High-Tech Lowlifes”

The title refers to the readership of the old Usenet newsgroup alt.cyberpunk.

With the “Whole Earth Internet User’s Guide” in hand, I went searching for an internet provider. Windows of that era didn’t even ship with a TCP/IP stack, so it was impossible for me to work on the internet directly. You might find it hard to believe, but in 1992-3 era Houston, there were 2 “dial-up shell” providers. Basically, you dialed up their bank of modems like a BBS, but instead of it dropping you into a BBS, you were dropped into a Unix “shell.” So I got my account (thanks Dad for taking a risk and doing the unthinkable – using your credit card to pay for something over “the inter-net”).

From the login message (/etc/motd), I learned that the machine was a Santa Cruz Operations (SCO) release 5 (V) Unix system. I remember the login message abbreviated these facts to SCOV. There wasn’t much to see in the shell, but thanks to “Unix for Dummies” (thanks for the bookstore run, Mom), I learned basic tools like pico and then vi. I also learned to do basic builds of C programs to get applications I wanted – specifically extensions for Internet Relay Chat (IRC). Add in a basic terminal mail reader (elm) and news reading software (tin) and I had the majority of the value people get off the internet today back at the bleeding edge – oh and in glorious text, text, text: no images, no ads.

This interest was completely absorbing to me and would wind up defining my early career. Because I had this background, when I was interning 4 years later, I got to work on an internet mail gateway software program. Because I had experience with Unix and builds, when I did my on-university interview with Cisco, my interviewer was surprised I knew anything about what they actually did (versus the Microsoft-heavy curriculum my school delivered) and bookmarked me for an interview. My career as a systems admin/Linux installer/Developer/Developer Productivity/Curriculum person more or less starts as a consequence.

Remixing

What’s interesting to note now is that these threads don’t ladder in a discrete, obvious way (directed acyclic graph) in one direction. They mix and remix in interesting ways (directed (cyclic) graph). It’s more like a fractal soup of ideas than a video game’s skills tree. Examples:

1. The SCO Unix experience meant that when I started doing systems administration work, I was already familiar with the BSD Unix design approach and disk layout. This paid off as a sysadmin and then over a decade later when I came to Bloomberg and encountered BSD-based Unix systems.
2. When I was interning ~ 1998, I was doing support, but doing support is a lot like writing documentation for tools or writing curriculum for classes. It’s a lot like teaching and selling too: extemporaneous speaking, integrating questions in stories you want to tell, etc. The ability to do tier 1 and tier 2 tech support, while ostensibly unsexy, unlocked many doors of advancement that other less rhetorically nimble folks were unable to pass through.
3. Dial up shell and early IRC lead me to meet students from TU Delft and users of xs4all.nl. Chatting with them about their lives in far off the Netherlands and seeing that barely-incomprehensible language they spoke made me curious about Dutch, this would lead me to learn the language and study abroad there. International experience and properly embracing diversity in its many forms is highly valued in my current role. There were also less-abstract benefits: a decade ago I was able to negotiate with Dutch DHL delivery to treat a server I’d ordered in CA but was meeting in Amsterdam more gently because I could address him in the mother-tongue

…and all of those experiences mixed, recombined, and built together. It seems miraculous that all the pieces that I would need in 2024 were being acquired like gem pendants and strung onto a necklace out of the chaos of daily living, but I stand today as a testament for it having been so.

But that’s looking backwards

Looking Forward from Back in History

But now as an exercise in empathy and imagination, go back to those times. Look forward.

• Did it make optimal sense to sign up for a language class for a small Western European country (population 16m) when my own state was literally across from a major trading partner (Mexico)?
• Did it make sense to pursue a philosophy degree also?
• Why did I fill my electives with things like French and Art History instead of more degree-relevant topics?

I don’t think that, back then, I could have explained these choices which don’t look like the “most likely path to optimal outcomes.” The smart or recommended moves would have been taking sandbag electives so that I could pump my in-major GPA and land vaunted internships at Enron and Anderson Consulting. The smart moves would have been blowing out my electives with more CompSci or econ classes. But I was always lucky that my weird interests were tolerated by my parents and then by everyone who has employed me since.

At all of these junctures, I just knew in my gut that I just had to learn these things or later try certain roles. I’ve used all those experiences as they’ve mixed and remixed while being refined, revisited, and redeployed. They’ve allowed me to find novel metaphors; allowed me to approach difficult topics with funny/memorable analogs; allowed me to jouer with the computer.

In short, my career success tracks my weird and my sense of caprice. Do you still listen to your weird? Have you told it to “be quiet” as you follow the recommended path? Maybe it’s time to listen to it again.

The Steve Jobs of it All

Speaking of Think Different…

Shortly before his death, Steve Jobs gave a beloved commencement address at Stanford. It’s available on YouTube.

In it, his advice is to follow your weird heart in a way similar to me. Jobs relates a famous bit of his own self-mythology that because he took a class in calligraphy at Reed college he cared a lot about fonts, and because he cared about them so much he pushed the first Mac to have beautiful, proportional fonts – which we use to this day: Mac, Windows alike.

I suppose I could have just tl;dr’d this whole post by pointing to the YouTube video, but at the time Jobs was speaking, he was a multi-millionaire. He had sold Pixar; he owned land in SF peninsula hills; he had a house in Palo Alto; he drove new Mercedes and parked them wherever he damn well pleased. It would be easy to watch the video and say “easy for you to say.” But I don’t believe he was wrong, and let me say as a less-privileged person:

I am not Steve Jobs, and I don’t think that I’m likely to have a fraction of his wealth before I depart this mortal coil. I work for a salary and I say: follow your weird. Quoting Jobs: “Even when it leads you off the well-worn path…[it] will make all the difference.”

• Career
• Advice

• Next: The Most Important Video Game Ever (For Me)
• Previous: The Killers' "Hot Fuss" 20 Years Later