General Expert, Major Havoc

Is it better to go wide or to go deep in your tech career? One industry old-timer weighs in.

Major Havoc was an interesting game. This 1983 Atari vector-graphics arcade title was not really a hit, and I guess my criticism of it would be that it had too steep a difficulty curve, and some questionably-sensitive jumping mechanics. But the idea was cool, that being you were this Commando invading an enemy base, planting a time bomb, and trying to get out before it exploded. To get there you went through a series of different mini-games, that each required you to use a set of unrelated skills, like shooting ships in space, targeting a landing pad, or navigating a hazard-filled maze.

If you think I am setting you up for some metaphors about work, you are right. Partially anyway — because to be honest, I needed a Major to go with my General in the title, and this was the Major that came to mind first. But I am really determined to shoe-horn some Havoc into this article if need be, so stay tuned.

If You Want to get Specific, I’m General

I wanted to share some thoughts about whether it is better for your tech career to find some problem space or domain and become the recognized expert in it, or whether the best thing is to gain a broader set of diverse skills, but spend less time learning and working in a specific area.

And I’ll start by spoiling the ending, and say that there is no right answer here. I can tell you how it worked for me so far though, and we can compare notes. The other thing I’ll say is, I am very much a generalist. I would assume it is probably how my brain works overall, but certainly when it comes to work, this is how it turned out for me over the past 35 years.

I cannot claim that I planned it that way. But for whatever reason, I rarely spent longer than five years on a project or job role, before moving to something completely different. For instance, I spent the first five years of my career designing chips, but switched for the next five, and designed systems and printed circuit boards. I moved to developing software after that, and spent five years writing software, followed by five years of managing software engineers. Back to programming of totally different software after that (GUI design) for another five, and so forth.

These transitions were sometimes of my own making, but more often than not, the result of some external sequence of events that either opened a door for me, or necessitated change. Which brings me to my first observation, which is that being a generalist is about liking change, or at least being good at adapting to it when it comes.

Change is not everyone’s thing, and I should also point out that not all change is welcome - there’s a Dilbert cartoon making fun of that tired “Change is Good” aphorism in a strip about a worker throwing that expression back at a boss who used it a lot, but was now going through the change of getting laid off.

Layoffs not withstanding, change is usually compelling to me — so I often just let it happen. I think if I were a ‘deep’ minded kind of person though, I would have made very different decisions in my career, to keep on a specific course relevant to my previous experience, rather than let the wind blow me where it will.

For instance, I started out my hardware career in IC chip design, but when the time came to move on from the group I worked for, I accepted a job offer doing something completely different, PCB and Systems design. If I wanted to become a more experienced and eventually expert chip designer, I would have turned down that offer and looked or waited for another more relevant chip design one. I know several people I worked with over these years that did in fact stick with IC design, and went on to become very senior people in very big-name companies. They most certainly ended up making a lot more money than me, were more famous, and probably have more instantly-recognizable accomplishments under their belts.

So my next observation would be, if you are shooting for the moon, then specialization, at least to some degree, is the way to go. There’s that metric about it takes 10,000 hours of practice to gain mastery at something. Another tired saying if you ask me (and a bit simplistic) but it gets to the heart of it. You need to spend a sustained period of time doing something not only to become good at it, but to be recognized as someone who is good at it — and being known as an expert in something can create opportunities.

I have easily spent more than 10,000 hours working as a computer engineer, which qualifies me as being an expert at… something. Being a generalist, it becomes hard to say what, exactly though. This very much came into play once a few years back, when I was considering joining a startup. I was approached by a former coworker who had started a company with a new product in a similar area to those of the company I worked for, and they were poaching engineers with relevant experience.

Giving a Generally Vague Impression

I was not actively looking for a job, but I was open to the idea of going to work at a startup. I had worked for one previously, but was hired just after they were purchased by a larger company, so had the startup work environment, without the equity. Sounds like the worst of both worlds I know, but it was actually a good job working with great people, and I had learned a lot from it. What got me to go meet the founder of this new company was that the opportunity was the real, with-equity thing, so we set an after-work meeting at a location unlikely to be frequented by anyone from the office.

At the time I remember being fairly optimistic about my chances of being hired, because I had such a wide set of experiences under my belt. A little hardware design, a little software design, a little bit of management experience, some GUI design experience. All of which, this company needed.

But as we talked over drinks at a dreary hotel bar, it became apparent that my Whitman’s Sampler of experience did not pass the bar for any one opportunity they had available. They wanted to hire a CTO, but after discussion we kind of mutually agreed I was not a good fit, having neither extensive management experience, nor deep knowledge in the area of their product. The open programming jobs were also meant for specialists, such as an opening for someone experienced in writing machine code generators, pretty specialized software than can create other software.

My pre-conceived notions that a startup would have a limited number of engineers and thus would seek to hire people with generalized experience, and who could work in many roles at once was obviously way off target, at least for this company. A coworker friend, whose management and technical experience was much more limited in scope than mine, got the job offer. Rather than generalize, he had spent his time mastering that specific area of machine code generation and associated low-level programming skills, and could probably recite the Intel instruction set from memory. It was just the thing they were looking for.

So I came to understand this different, “startup logic”, which is that if you only have a limited number of hiring dollars, you want to spend them on getting the very best at whatever areas are key to your success. And this one is definitely a win to be chalked up for the specialist, because startups (like all companies) want to be differentiators and therefore want to hire people who are differentiators, which often precludes those well-rounded but non-expert sorts.

The Specific Danger of Expert Typecasting

There is a lot to be said for the idea of pursuing your passions in life, and devoting yourself completely to something you care about. It is advice that can be used by generalists and specialist alike, with perhaps the only difference being the length of time involved. Where a person who was inclined to stay specialized might devote a very long period of time, even a lifetime, to a specific area of expertise they are passionate about, a generalist might pursue it to an equal degree, but for a shorter period of time.

Or perhaps, the non-specialist may also devote extended time to a field, but in a wider capacity, exploring different facets of it, or taking on a job that has multiple roles related to the area. I think that last one is a common pattern for entrepreneurs, who may start a company based on something they love and want to focus on, but in their founder role, take on a widely-varied set of responsibilities from financial, to technical, to marketing and so on - but all related to a specific thing.

This is the type of person who fits the “General Expert” category from the article title, and I’ll return to the idea of general vs. expert not being a mutually-exclusive choice in a bit. But there are most definitely people who are “Specific Experts”, whose field of interest and preferred job role are both narrowly defined. This is a very common pattern in academia, where someone might pursue a major in a specific area, then a masters, PhD, post-Doc degrees, and become a professor or teacher, all in a very specialized domain.

I don’t know what percentage of Specific Experts choose to remain in the academic world, but I can definitely see the attraction, since that world provides a good environment for extended specialization. If we were to create another (somewhat false) dichotomy between academic and entrepreneur type person, I would self-identify as the latter. On the whole I would guess that there is a strong correlation between the entrepreneurial-minded people and the generalist-minded ones, but it does not preclude the Specific Expert type people from being successful in the working world.

In my current job, I have coworkers who have been working in relatively small, but very complex code bases for decades. Having an expert at your company to own and drive complex parts of your product can be invaluable, and doing it right often involves deep knowledge that cannot be easily replaced. This can be a form of job security for the Specific Expert, providing the area they work in is something that does not become obsolete or unneeded later.

And I cannot emphasize this last point enough, because if there is one thing I have seen time and time again in my 35 years of computer engineering work, it’s high-profile and seemingly-crucial technology or projects suddenly vanish without warning. When this sort of thing happens, a lot of time the Specific Expert associated with it vanishes too, either because the company can no longer find a job for them that justifies their salary, or because they are not interested or able to change job areas to something completely new.

Hollywood calls this “Specific Expert” thing typecasting, and just like the tech world, it can be imposed by the management above, or a self-selected choice. Vincent Price relished his lifelong typecasting as the creepy horror villain, for example. So it is not necessarily a bad thing, but a choice that comes with positive and negative consequences.

General Stability and Private Ryan

I wrote earlier about how my generalist experience precluded me from consideration for a startup job. I would also go on to say, that the fact I moved around to different job roles frequently rather than staying in a specific domain also has to some degree prevented me from reaching higher levels of technical seniority, even after spending 25 years at one company. While it is sometimes hard to see other less-senior people be promoted above me, I can take comfort in one thing, and that is the job stability and ‘stickiness’ afforded by having a broad set of skills to draw from, whenever the technological landscape changes.

I have had the good fortune never to have been (so far anyway) laid off in my career. While this is certainly a matter of luck to a good degree, I would say at least in some cases, I can chalk it up to my generalist nature saving me. My closest call was in 2009 during the big recession. I was working as a manager, with about eight or so reports. It was a pure-management position, with little individual technical contribution needed in the job.

In retrospect my decision to take this job was a bad one. I was on track to be promoted in my current technical role, but the management and internal politics of the group I was in had gotten so toxic, that for mental health reasons I needed to make a change. I liked the company overall and did not want to leave though, so I accepted a position from a former boss who was now running a different product division in the company. He needed a manager to manage engineers working on several small unrelated product features, and I accepted.

But when the end of 2008 rolled around, things had changed, and at least one of the product features I was in charge of had been off-shored to a different group in India, and another feature had been dropped. The company was going through financial troubles, and a fairly broad layoff was in the works. My boss came to me and said, “we don’t think we’re going to need a manager position any more for these groups”.

Oblivious to the fact he was essentially telling me that my job had been eliminated, I said, “Well you know me, I’m fine with working on anything.”

To which he replied: “That’s what makes this so hard.”

Only then did it sink in that there was no other thing for me to work on, and that I was being laid off. My wife was working at a dot com startup, and as it turned out, was also in the midst of being laid off as well. A weird twist of fate was in the works though. It turned out that my boss and my wife’s boss actually knew each other, and they discovered over a dinner that not only did they have something in common with the both of us working for them, but also that they were laying us both off at the same time.

The setup kind of paralleled the premise for Saving Private Ryan, where some government clerk realizes one mom had lost multiple sons to the war, and they launch an effort to save the remaining one. The jeopardy to our family was of course not mortal, and even financially we probably would have been able to ride through that rough spot of temporarily losing both incomes. But my boss became alarmed by this revelation nonetheless, and went the extra mile to try to find some sort of job transfer for me.

Four days before the layoff was to happen, I had a one-on-one with my boss, and said something about it being the last time we were going to meet. He said “What are you talking about? You are staying here.” He had found an open Req, a technical position doing GUI design on a new product, in a different branch of the higher-level organizational tree.

My boss and I had met ten years earlier, at another company where I was responsible for GUI design work, and he had remembered this when pitching me to the other manager, who agreed to make me the offer. So I took the job, stayed employed, and shifted from management back once again to a technical role.

This opportunity was afforded to me largely due to my long relationship and friendship with my boss, and you could even say it is a bit of favoritism on his part to recommend me for it to his manager peer. But I cannot discount the role my generalist ways had in making this favor even possible. Had I been a pure manager with no technical background for instance, I could not have even qualified for this job, and in the 2009 market would have likely had a really tough time finding a job that came close to replacing my salary.

A Major Attempt to Return to Havoc

There isn’t anything saying you have to pick between specialist and generalist in your life, and stick to it. Many do of course — I, as said am a hopeless generalist, the bias of which is probably clear in this post. I would love to hear from others who are of the specialist persuasion, and how keeping a sustained focus on something has been rewarding or challenging for your lives and careers.

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But another really smart play in my opinion is to switch it up at some point. Specialize in something for a time maybe when you are new in your career to gain deep experience, but then use that expertise later in a more generalized way, like starting a company, or becoming a manager at a company or product that plays in that realm.

You can also kind of do the opposite. Be general and try many different things when you are younger and more junior, but then settle in on a domain of expertise for a more extended time when you find something that clicks. I guess in rough terms this is a pattern I followed, since my early engineering years doing things like chip design and PCB design were much shorter than my current role, as a software developer in the Electronic Design Automation field. Although my job role has changed a lot within my field and company, it is still a fairly specific field — and might make even me a specialist, of some sort.

Getting back to Major Havoc, (and for those who know my nerdy retro leanings, you were certain I would) there is a parallel to this last idea here, in that this game has you play a few short stages that are largely unrelated to the main, maze-running stage that follows and which consumes the majority of your time. Although those short, early stages require different skills than the final task of getting through the maze and out again, they do kind of prepare you for what is to come, and the whole thing holds together as a cohesive game — even with all the varied experiences. Just like your life and career can, through its various stages. Even the maze-like ones.

Is it my best analogy? Probably not. But mission accomplished, in terms of getting Havoc squeezed into the article! Fine I guess, Mad Ned. But what about the bomb-planting and escaping part? Well, like Major Havoc, the timer is running down to zero on this post, and I will now make my escape. BOOM!

Explore Further

Next Time: We return to the 1982 world of Jim the used car salesman in a gratuitous sequel to my earlier summer job story. Find out what happens when a nerdy teen’s first job is figuring out how to deal with shady situations in: A Teenager’s Guide to Workplace Ethics

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