I’ve told these stories enough times that a few people — mostly parents around my age — have asked me to write them down and share them. Given that another Dads-’n’-Grads season is upon us, I figured now was the time.
Strap in, Pennyheads. We’re breaking the previous word-count record for this one.
This is the story of the higher-education trial-and-error that led to my career.
The Beginning
I was a bookish metalhead coming out of high school, perhaps with dreams of becoming a writer or a professional philosopher.
College was, for me, an expensive and strangely curated four-year exercise in figuring out what I didn’t want to do for a living.
I was a bookish metalhead coming out of high school, perhaps with dreams of becoming a writer or a professional philosopher. Marshall McLuhan and Joseph Campbell really inspired me in those days, thanks to a media ethics course I took senior year. I was also a co-editor of my school paper, whose editorials didn’t make me very many friends in the school’s administration.
I was deeply fortunate to come from a family that had the wherewithal to put me through school. That, plus a GPA just high enough to knock loose a small scholarship and priority class-selection privileges, led me to Saint Mary’s College of California, a liberal arts school nestled in the hills just east of Berkeley and about 40 minutes from where I grew up. Turns out, SMC was my second choice as University of Puget Sound didn’t come up with those benefits.
SMC had a kind of college-within-the-college called the Integral Studies Program, into which they coaxed the overachieving undecided. Think Dead Poets Society as taught by Indiana Jones’s dad in the flashback sequence of The Last Crusade. (“Count to twenty… In Greek.”) In other words, this was a perfect curriculum for someone whose career aspirations more or less amounted to “Professional Brain.”
College was, for me, an expensive and strangely curated four-year exercise in figuring out what I didn’t want to do for a living.
The Integral Program focused on The Great Books, as they are called. The mathematics curriculum was based on Euclid’s geometry and progressed through Kepler, Copernicus, and so on. (In my third and final semester in the Program, we engaged with, and together mathematically disproved, the notion of a geocentric solar system.) The literature seminars started with the Greeks and, by senior year, deigned to include important texts from the then-current century. The language requirement was, you guessed it, Ancient Greek and I was surprised that I got pretty good at it; my freshman final was translating the first chapter of the Book of John and defending my choices in front of my class. Instead of a midterm, students went through a ritual called the “Don Rag,” wherein your professors would discuss your academic performance as if you were not in the room. This would feel like attending your own birth or your own wake depending on how well you handled the sophistication and sheer volume of the material.
Now, of course, this bookish metalhead needed other outlets, so I started volunteering at the campus radio station, KSMC-FM. Persistence and a deep-enough voice landed me a Friday-afternoon airshift where I played pretty much whatever I wanted to a campus that was listening to, well, pretty much anything else. Highlights included a two-hour tribute to Testament — then, as now, the best band in thrash metal — a marathon of ‘80s-‘90s goth, and a lunchtime Ray Charles career retrospective that I blasted into the quad, earning the seething enmity of the campus housing office below me. (My last song before I eventually got shut down: “Busted.”)
Persistence and a deep-enough voice landed me a Friday-afternoon airshift where I played pretty much whatever I wanted to a campus that was listening to, well, pretty much anything else.
Over time, however, I started to get worried about where my chosen academic path led. Whenever I asked a junior or a senior in the Integral Program what they planned to do when they graduated, the answer was invariably “more school” — gradschool, law school, med school.
That was not really in the cards for me. I didn’t have much saved up from the job at the plant nursery and, later, the campus bookstore. I didn’t want to take on debt, and I wasn’t going ask my parents to extend my education runway.
But this broadcasting thing. It seemed alright.
Changing Courses
The most adjacent department to this new path was Communications, a major that had only recently evolved in its national esteem beyond its perceived status as the track onto which they shuffled over-recruited athletes. After three semesters of the Integral Program and persistent, if erudite, concern-trolling on the way out, I embarked on my new course of study — one that would still allow me to graduate in four years.
Around this time, I had exhausted my patience with my campus bookstore evening shift and the alternately starry-eyed, viciously entitled students from the college’s graduate education program. “What! do! you! mean! you don’t have a copy of the third edition of New Age Organic Magical Child in stock!?!” they would scream, their branded tote bags transmitting the righteousness of their causes (World Wildlife Federation) or their perceived status among the cultural elite (NPR listenership) in ways that were similarly loud and performative. (Today, those nocturnal customers of mine are teaching your kids. Sleep well.)
“What! do! you! mean! you don’t have a copy of the third edition of ‘New Age Organic Magical Child’ in stock!?!” they would scream, their branded tote bags transmitting the righteousness of their causes or their perceived status among the cultural elite.
So, I took on an associate sysadmin job at the school library, overseen by a patient and preternaturally calm director of information systems. (“That was… ungood” was his measured response after I accidentally deleted the patron database during a weekly backup while suffering from both pneumonia and the codeine prescribed for it.) As my dad was among the very first in his industry to use computers, I had grown up around them and generally knew how they worked. For two-to-four hours per day, $6.05-per-hour, four days per week, I got to do everything from building Linux servers and ensuring service uptime to writing automation scripts and vacuuming dust-bunnies out of creaky 286’s.
This technology thing. It seemed alright.
Pounding the Pavement
Fearing I had no time to waste on this new path, I started my internship hunt early.
The school’s career development center was a great place if you happened to major in business administration or finance, less-so if you were studying, well, pretty much anything else.
Just ahead of my junior year, I leafed through the three-inch-thick “D”-ring binder that contained the various summer jobs and internships on offer. The pickings were slim, but there was one sad, dog-eared job description hanging on to the binder by its last punched hole.
It was for something called “public relations.”
I didn’t know what the hell that was. SMC’s communications curriculum did offer a public relations course, but it was taught by a grizzled international wire-service reporter who had nothing but awful things to say about the trade and its allegedly Svengali-like practitioners.
However, what I did understand from the abused job description was that the three-person boutique agency specialized in wine and food clients.
The pickings were slim, but there was one sad, dog-eared job description hanging on to the binder by its last punched hole. It was for something called “public relations.” I didn’t know what the hell that was.
With obnoxious levels of follow-up and perhaps some clever soft-pedaling of my youth, I found myself in possession of an internship at Brown-Miller Communications of Martinez, Calif., which has since transformed into a successful public-affairs and cause-marketing agency.
That summer, I would spend two days per week at Brown-Miller and the other three at the college library keeping things running. It was the summer of the “Low-speed Chase,” Forrest Gump, and the United States’ unlikely hosting of the World Cup. It was also the summer where I learned how to pitch media, write copy, manage events, and work with clients. The stories from those three months could fill another overlong post by themselves.
This public relations thing. It seemed alright.
“Turn In Your Geek Badge, Sir.”
Now, I sought that particular internship for one reason only: marketable experience in some communications field. But Communications majors could also take an internship for credit, which I went ahead and did. After all, why settle for one internship when you could have two at about twice the pay?
My broadcasting ambitions had led me to become very interested in audio production. It turned out that the Skywalker Sound division of Lucasfilm and its THX team was looking for an intern to test audio components that were submitted for certification.
One thing led to another and I found myself at the Lucasfilm HQ in Marin County, driving past an Endor-esque campus of Victorian-looking buildings with charming 19th-century façades that I imagined housed hyperdrive, Death Stars, AT-ATs, or Rancors. Eager beaver that I was, I showed up forty-five minutes early, figuring that I could take the guy at the security gate at his word and just chill in the parking lot until my appointment.
I was there maybe two minutes before a security guard knocked on my window.
“You can’t be here.”
“It’s cool, ma’am. The guy at the gate said I could wait here until my appointment.”
“Sorry, but we can’t let you do that. I’ve informed your appointment and they’ll be here to get you soon.”
Great. I’ve already ruined my interviewer’s day and I haven’t even left my car.
I awkwardly tried to make conversation as I clambered out. “So… Security’s pretty tight here? I guess?”
“See that hill over there?”
I nodded.
“The other day I had to get in my vehicle and chase off some kids who set up a high-powered telescope.”
“Oh.”
At this time, LucasFilm would have been deep into pre-production for what was to become Star Wars Episode One: The Phantom Menace, a film that, if anything, probably could have used a few more external eyeballs.
This morning of interviews started with that breach in protocol, featured a small gauntlet of interviews with the Skywalker Sound team, and ended with a Deeply Unhappy HR Director.
“We hire very few interns full-time! And if we do hire you, don’t even think that your compensation will include stock! This company is one-hundred-percent owned by The Founder.” I don’t remember anyone there saying “George Lucas,” “Mr. Lucas,” or even “George.” It was “The Founder.” You could hear the capital “T” and the capital “F” spoken in reverential tones.
“We hire very few interns full-time! And if we do hire you, don’t even think that your compensation will include stock! This company is one-hundred-percent owned by The Founder.” - A Deeply Unhappy HR Director
I drove home convinced that I’d blown it. However, I resolved to keep pounding the pavement until I secured an — hell, any! — internship.
This Lucasfilm thing. It…
[record scratch]
Around this time, one of my mentors suggested that I contact a company called StarPress, Inc., a publisher of games and reference titles on CD-ROM that was acquired by Great Bear Software and, later, Graphix Zone. By this point, my mentor knew that I was passionate about the potential for this thing called “The Internet” and StarPress was looking for something called a “webmaster.” (Pennyheads might remember the story of my early Internet-related campus activism, such as it was.)
I knew enough HTML (Windows Notepad) and graphic design (Paint Shop Pro) to be dangerous, so I went for it. One BART trip to Market Street and a brief meeting with Cindy Mascheroni, and I was in. They wanted me working for them immediately.
Then I got the call from Lucasfilm.
They had left a message while I was at my library shift. Turned out I hadn’t blown the interview after all and they were eager to have me start ASAFP.
I wrestled with this decision for two agonizing days, going back and forth about the pros and cons of each. In the end, my roommate Eric, his Kathy Ireland poster, and I decided that StarPress was the way to go.
Lucasfilm was… Lucasfilm! It was the metaphor-fountain of our generation. But even though I’d have the Lucasfilm name on my resume, so the reasoning went, the tasks were likely to be more tedious and conventional and not exactly career-building. StarPress, however, had the cachet of exploring a technology frontier that was still brand-new.
I returned Lucasfilm’s call to find out from the Deeply Unhappy HR Director that no one — no one — turns down Lucasfilm for an internship. I was making the biggest career mistake of my life. How many young adults would kill for the opportunity I was throwing away!?
The school’s career development center was a great place if you happened to major in business administration or finance, less-so if you were studying, well, pretty much anything else.
I lamely eked out a “thank you” and hung up, mildly shaking from the dressing down I got from a Voice of The Founder.
“Alright,” Eric said. “Turn in your geek badge, sir.”
In the end, it was the right choice: Starpress got a website, I learned how to take feedback in a corporate setting (“<frame>
is great for the product catalog. Please don’t use <blink>
again.”), and I can even today duct-tape a webpage together with a text editor if I had to.
The school even decided to highlight my internship in the yearbook, presumably because having someone out on the “Digital Frontier” made for good marketing. However, editorial sloppiness with the spellcheck turned “Starpress, Inc.” into “Strippers, Inc.” within this feature. At first it made me angry (“I’m sure you’re pulling out what’s left of your hair” Eric said), but the bad copy only made my early career in tech look far more scandalous — and perhaps vastly more lucrative — than it actually was.
But, this Internet thing. It seemed alright.
Seeking Safety
Throughout all of this, I still had a lot of anxiety about having a job lined up when I graduated. No real reason, to tell you the truth. My parents would have let me stay at home as long as I needed to, but I very much wanted to get out into the world.
So I participated heavily in the campus recruitment process and signed up for everything that I was even remotely qualified for.
Andersen Consulting (now known as Accenture) were very active on-campus recruiters, sometimes taking up multiple offices and conference room spaces when they really got going. Of course, I knew less about management consulting than I did about PR before the Brown-Miller internship, but that didn’t stop me.
I made it through the first screen, mostly by way of my associate sysadmin work at the library. That and showing up with a tie probably checked all of their boxes. The next step would be a one-on-one interview with one of their consultants.
There I was, ten minutes early for my three-o’clock interview, my resume sheathed in a sturdy envelope, my body in my One Good Suit. Across the hall from my chair where I waited, were two doors behind which Andersen Consulting interviews took place simultaneously.
Three o’clock rolled around. Then five minutes past. Then six.
At ten minutes past, the door opened. Out walked the interviewee, suitably dressed for the meeting as if she were ready for the cover of Forbes. She exchanged a crisp handshake with the recruiter and parted ways.
No sooner had she turned on her designer heel, I stood up immediately, offering my hand to the recruiter, who briskly held up his own hand in response.
“Woah! Okay. You need to wait a minute. I need to confer with my colleague for a bit.”
I sat back down. Through the door, I heard my supposed interviewer high-fiving his colleague because the previous candidate — with whom the interview was extended for ten extra minutes — was none other than that year’s crowned winner of the county beauty pageant.
I was furious — for her and me — but I was also prepared to exact revenge on behalf of both of us. You see, one of the advantages of the emerging Internet was that it was very easy to share useful information like… the interview questions certain companies tended to ask.
After his moment of brohomie was over, my interviewer called me in. He started by talking about how he and his colleagues loved their eighteen-hour days solving the most impenetrable problems for big companies through, I imagined even then, equally impenetrable methodologies. With his gelled black hair, five-o’clock shadow, slightly loosened tie, and the top button of his shirt undone, he looked more like an extra from the newsroom in All the President’s Men than someone to whom one would entrust billion-dollar decisions. He must have used the words “culture” and “strategy” fifteen times in five minutes.
Then came the question. The one that the Internet prepared me for: “How do you get a giraffe into a refrigerator?”
This question is meant to assess a candidate’s ability to look at a problem from the simplest possible perspective and not make too many unnecessary assumptions, in this case, the size of the refrigerator. My interviewer wanted me to say “Well, you open up the (really big) refrigerator and herd the giraffe in.”
I was prepared to give that answer but, as I said, I was pretty irritated that my interview was delayed by someone whose eighteen-hour days had probably meant he had opted to maximize, through the mild coercion of an employment opportunity, the rare chance to talk to a pretty girl.
Stroking my chin and staring off wistfully over his left shoulder, clear in the knowledge that I would rather work, well, pretty much anywhere else, I outlined my solution to the problem.
“Well… First of all, you need to be humane: Tranq that giraffe with about 75cc’s of sodium pentothal. Then, you gotta stop the heart. I think potassium chloride is probably the way to go. From there, you’ll want to cut up the giraffe into manageable pieces, use an industrial blender to puree those pieces, allow the puree to dry so as to reduce mass and size by more than 65%, I figure, and then pack the pulp into uniformly rectangular vacuum-seal bags. Compress those bags with a hydraulic press, using a filter that should extrude that last bit of moisture as well as reduce the overall volume while keeping the solid mass. Now, vacuum and heat-seal those bags, trimming off any excess plastic. Once done, you should have no problem fitting an entire giraffe into an average GE or Whirlpool product. Is there something wrong, sir?”
Stroking my chin and staring off wistfully over his left shoulder, clear in the knowledge that I would rather work, well, pretty much anywhere else, I outlined my solution to the problem.
About halfway through my procedural overview, he went oyster-cracker white, having realized his late afternoon had gone from supermodel-to-psychopath in about $100 of otherwise billable time.
After he patiently explained the desired answer, the interview limped along a bit further before ending — on time — with a perfunctory handshake. In the few minutes it took for me to walk back to my dorm room, and in an age before cellular connectivity was very widespread, I already had a message on my answering machine from a human resources representative: Andersen Consulting would not be continuing the interview process, but wished me the best — really… The! Best! — luck in my ongoing search.
This management consulting thing. It seemed…
Nope. Sorry.
Wither Broadcasting?
Throughout this whole time, though, I was still entertaining the notion of becoming a broadcaster. I would use my show at KSMC-FM as live-taping sessions for my audition reels, dubbing the best bits together, sending them out, and reliably generating patient rejections like “I look for a certain style. I did not hear it on your tape.”
By now, I was in my senior year. This story now takes me to one of the rarest of Friday nights during that period.
I had a date.
Okay, that’s not entirely true. While I didn’t really date in college (or high school, really) I just kind of had girlfriends. I was slowly emerging from the smoking crater that was the most recent such relationship, a recovery process that included Tower Records retail therapy, the accidental purchase of medieval Portuguese requiem masses on CD, and sinking further into that crater while binge-listening those masses in my room on a rare solo Saturday night when absolutely everyone was out of town.
As I was putting on a shirt with a big-boy collar and my one good tie, my phone rang.
“You need you to come down here right now. My producer is a no-show. Probably drunk, for all I know. I need help. We’ll pay you double.”
My buddy Matt had an airshift at an adult-contemporary station in Pleasanton, a little more than a half-hour south of the campus. During “Friday Night Fever,” he would spin disco’s greatest hits until well after midnight. Matt urgently needed "talent support” — someone who could grab the various songs, bumpers, and advertising spots when required so he could focus on putting on the show.
Evening plans cancelled, I tempted the moving-violation gods all the way to Pleasanton. As soon as I got there, someone handed me an inch-thick, dot-matrix, continuous-feed printout that went something like this:
20:00:00 — Play Station ID
20:00:15 — Talk
20:00:45 — “Staying Alive,” The Bee Gees
20:04:33 — “Love Rollercoaster,” The Ohio Players
20:08:12 — Advertisement for auto dealership
20:08:42 — Advertisement for amusement park
20:09:12 — Talk
20:09:57 — “I’m Coming Out,” Diana Ross
“This is broadcasting?” I asked.
“Um. Yeah.”
“This tightly programmed?”
“Give or take, but yeah.”
“At KSMC I could follow Ray Charles with Slayer! It was even encouraged!”
“Heh. Yeah, no. Can’t do that.”
This broadcasting thing. It was…
Well…
Trying to Put It All Together
“I swear to god that I am never going to work for that freaknest!”
“So, I like this PR thing. I like this technology thing. Broadcasting is out and professional philosopherdom is in my rear-view mirror. I wonder if there are PR firms that specialize in technology?”
In retrospect, this was a gloriously naive thing to ask myself in 1996, living just a couple of area codes from South Bay and Peninsula and with the dot-com boom already building up its momentum. Still, at this stage, the phone book was a more reliable and comprehensive research tool than the web services of the time. From there, I’d check to see if the so-called “tech PR firm” had a website. This simple filter eliminated a number of candidates that both surprised me (prior to entering the trade) and didn’t (after I spent any amount of time in it).
I then very nearly carpet-bombed the remaining firms with my resume and got two solid bites: The California outpost of Boston-based Weber Group and global powerhouse Edelman.
My run at Edelman started with the most surreal of panel interviews. My assessors were a middle-aged account director with a short, curly white-gray mullet and a much younger account executive. The director struck me as the kind of character unique to Silicon Valley who likely started as a hippie and just sort of fell into tech. I was certain that his sock drawer hid both an Apple Newton and half of a long-ago-burned draft card. The account executive gamely laughed at our jokes and our nerdy references with a kind of forced, brief, staccato bark.
“I wonder if there are PR firms that specialize in technology?” In retrospect, this was a gloriously naive thing to ask myself in 1996.
Things were going pretty smoothly until, from behind me and to the left, the door clicked open and an absolutely stunning woman strutted into the room. I imagined her as a T-1000 Terminator sent by Skynet to eliminate John Connor at a black-tie gala — a mimetic polyalloy assassin that poured into a short black cocktail dress and flawlessly mimicked every detail except, perhaps, the one that might suggest it wasn’t very customary to wear such attire at ten-o’clock in the morning.
Upon entering, she runway-walked the length of the table behind my interviewers, approached some framed press clippings leaning against the wall on the floor, inspected the frames, left them where they were, turned, gracefully retraced her route, and exited without a word.
My interviewers said nothing, appearing to not notice her. At all.
My God this is some weird test, I thought to myself, my twentysomething failure with which is now, nearly three decades later, painfully evident to all Pennyheads. I nevertheless managed to finish either the answer I was giving or the question I was asking. I remember that detail less vividly.
As I said my goodbyes, the account executive warned “Not so fast! There’s the writing test!”
“Writing test?”
”No one told you?”
“Hrm. No.”
“Okay. Sorry about that. Just sit here at this desk and write a press release about a pencil. You have one hour.”
They sat me in the noisiest-possible cubicle between the copy machine and the intern pool. Believing the assignment inane, I decided to write something nearly as ridiculous — a launch announcement for the Woodworks, Inc. (NASDAQ: WOOD) Smarter-Than-God Mega Pencil(TM). This technological wonder featured variable-hardness graphite, electro-shock spellcheck, and (my favorite) the Oliver North Signature Correction Fluid that would squirt out of a tiny hole near the point and spontaneously shred any paper product it splashed. The boilerplate of the release mentioned that the Woodworks’s president and CEO won the company in a poker match. (“He was bluffing.”) I saved the file to my own folder on the computer’s desktop as instructed, said my goodbyes, and left.
“How’d it go?” Eric asked upon my return to campus.
“I swear to god that I am never going to work for that freaknest!”
Of course, most people know how that turned out. For those who don’t, I would join that “freaknest” almost a decade later and build quite a career over thirteen years.
The Weber Group interviews, in contrast, were pretty standard. I would find out later that my distinguishing characteristic besides a uniquely eager persistence was that one of the office’s leads thought that my senior thesis on Cold-War-era science fiction film and television (“Green Fingers on Society’s Pulse”) at least demonstrated that I had critical thinking skills in an area that might endear me to their nerdier clients.

In the end, Edelman offered an internship but Weber offered me a job. This “account coordinator” position at Weber came with $21,000 per year, a ninety-minute commute each way, and the right to brag that I had the same billing rate as Shaft: “Fifty bucks and hour, plus expenses.” And it ruled.
I managed to miss the whole dot-com boom because, well, it just didn’t excite me very much. So, The Weber Group would put me on the most deep-tech clients possible, most notably SRI International and Hitachi Semiconductor. The lessons learned there launched a career — and passion — for decades to come.
This technology-public-relations thing…
The Road Once Traveled
So, I’ve kept you, dear Pennyheads, for long enough. Now for the obligatory bits of advice prescribed by, hinted at, or placed completely independent of the tales told here.
The best path is the unpredictable one — To be honest, I richly envied fellow freshmen who showed up on Day One believing that they one-hunner-per-cent knew what they wanted to do with their lives. My own path was neither straight nor predictable, marked as it was by false starts, unexpected opportunities, and a quest for "alright" in the absence of what some might say was a “calling.” But I felt that the path I took was as unique as I am and, in retrospect, I wouldn’t have it any other way. This is my biggest hope for any recent or imminent college grad reading this. At the very least, you’ll have a story to tell. At most, you’ll have a successful path that only you could have taken. The ability to forge your own idiosyncratic way is vital.
You make your own luck, for yourself and others — Whether it’s via 10,000 hours of focused effort or some other number, what people perceive as “luck” really just comes from how long you consistently and thoughtfully have your arms in some discipline — a widely held concept by now. What’s less-discussed is the importance of becoming the source of other people’s luck — helping colleagues make two-plus-two equal five. Colleges teach and encourage individual achievement, but the working world forces you to work in a broad ecosystem whose members often have conflicting interests. They don’t teach this in school. You’ll want to learn this quickly.
You don’t need all the answers right away — We’re in an era where we demand certainty in even the most mundane things. Movie trailers give away some of the most important plot points, because we the audience have signaled, consciously or otherwise, that we want to know precisely what we’re paying for. More and more of us who aren’t hearing-impaired are watching TV with the subtitles on, even in languages we know well an in contexts (like comedy) where vocal timing is an essential part of the experience. Millennial and Gen-X employees show up to performance reviews with specious salary surveys and career-pathing checklists. But, as the joke goes, there are two kinds of people in this world: Those who can’t process incomplete information, and….”
Be the latter.
So, best of luck to the Class of 2024 and beyond, however you got there and wherever you’re headed.