Geek Career Paths

Suppose you’re doing technology, and like doing technology, and your career’s going well, and you find yourself wondering what you’re going to be doing in twenty years. I’ve been down several of the roads you might decide to take, and it occurs to me that talking them over might amuse and inform.

Thanks are due to Andre Leibovici, who tweeted Is it possible to be in a sr. leadership position and still be hands-on w/ tech & code? For geek leaders out there... how to juggle? and got me thinking about this.

Q: Should you stay in tech-related work? · Seriously, this is the most important question. I know of knitting-store owners and carpenters and luthiers and microbrewers and doctors who walked away from tech life. Their reasons were good: They wanted to engage with life physically, to get away from rows of desks, to be outside, to be around women.

Me, I was never tempted; I’ve liked computers for their own sake for decades and still do. But I’ve watched people do this, and I’m pretty convinced that if you’re going to, it’s never too late or too early. When you’re young you can get by on less, have more energy, and have lots of years to flail around till something works. When you’re older, you probably have more money, which can be used to solve a remarkable variety of problems, and more experience as to how the world works.

For the purposes of this piece, let’s assume you’re staying on the tech train.

Q: Should you stay technical? · The bad news that it’s a lot of work. We’re a young profession and we’re still working out our best practices, so the ground keeps changing under you; it doesn’t get easier as the decades go by.

The good news is that it doesn’t get harder either. Once you learn to stop expecting your knowledge to stay fresh, the pace of innovation doesn’t feel to me like it’s much faster (or slower) now than it was in 1987 or 1997 or 2007. More good news: The technology gets better. Seriously, we are so much better at building software now than we used to be in any of those other years ending in 7.

And another thing that may not be obvious: It’s not a one-way door. I stepped off the technology train, spent years in startup management and technology evangelism, and climbed back into engineering life without too much pain.

It hurts me to say this, but there are gender issues here. There is a pernicious tendency for smart women to get streamed away from actually doing technology to, well, almost any of the alternatives I’m going to talk about below. I’ve been in the room when it happens: “She’s great with customers and super-organized, let’s encourage her to look at a management role.” Not that there’s anything wrong with a management role, but the engineering ranks need women too.

Q: Should you go into management? · I tried it, was a CTO and a CEO. I liked being on the spot for everything that mattered, and rarely having to wait for someone else to make a decision. Also, of course, getting the biggest paycheck.

But I hated lots of things: finding investors and dealing with them, managing cash-flow, being pulled in a thousand directions every minute, the really hard shitty HR problems that get to the top, and never being able to say anything that wasn’t on-message. I also disliked the company of my fellow CEOs, because they are people who can never say anything that’s not on-message.

A lot of the best executives started out as engineers. And there are really no barriers. In every tech company I’ve been in, if you’re a competent engineer and also a good communicator, and show evidence of seeing the bigger picture, then if you tell your boss you’d like to try management someday, that day may come a lot faster than you expect.

Q: Should you go into Product Management? · FYI: Good product managers are really hard to grow and hard to hire. So if you combine those technical, business, and communication skills, you won’t have any trouble finding work.

But it’s probably not a good long-term choice; most companies don’t have much of a career path for PMs. That may not be a problem; many PMs transfer to management or marketing positions after a while, without obvious strain.

So while it might be a good choice right now, you’re probably not going to be a PM in twenty years.

Q: Should you go into sales? · I’ve been on a lot of sales calls, and closed a couple of big deals all by myself, which is one of the most insanely satisfying things you can get paid for (and you can get paid a lot). It’s easy enough to find out; most technology companies’ salespeople regularly need geek support and well-run ones are happy to send engineers out on sales calls. If you like what you see, give it a try.

Yes, there’s the risk of ending up in Glengarry Glen Ross. And that remorseless pressure to close is implicit in the profession. But a lot of really successful sales people are ex-engineers; is the remorseless pressure to ship that much better?

Here’s a hint: All the truly great sales pros I’ve known have been people people; would genuinely rather hang out and shoot the shit all day than anything else. If that’s not you, then probably not.

Q: Should you go into marketing? · Marketing is at the center of everything. You probably know why you’re building the technology you’re working on, and what it’s good for, But it turns out that figuring out who out there needs it, what they’d use it for, and how to explain it in simple enough terms that an overworked non-geek can get it quickly, is really really hard.

There’s a range of marketing roles, from tech-oriented ones like “developer advocate” or “evangelist”, all the way over to full-time business strategist. Every one of them is accessible in principle to a technical person who wants to change lanes.

Q: Should you go into Venture Capital? · Please, please don’t. With the exception of a very few top-tier firms, it’s a shitty business that delivers a lousy return to its investors. A large part of your job consists of saying “no” to people, then watching most of the people you say “yes” to fail anyhow.

In my view, most of the pathologies that infect the tech sector, starting with self-absorbedness, arrogance, and lousy diversity, are joined at the hip with VC culture.

Q: Should you work for startups? · Absolutely, yes. I have, twice. The best reason is that you’ll get to see all the different parts of a business up close, how they work, and if you decide you want to pitch in with something that looks interesting, you may not encounter much resistance, particularly if you turn out to be good at it.

The white-hot team intensity, the feeling that you and a few others are moving the world, is just not something you’re going to find elsewhere.

You might make a lot of money, but do bear in mind that most startups fail, and there are a lot of ways for a startup to succeed where most of the money goes to the VCs and almost none to foot soldiers.

Q: Should you work for a BigCo? · Yes; you might not like it, but you should try it. Particularly, in a well-run company, when you get to see what high-quality marketing and legal support is like, and what classes of problem can be solved by throwing money at them, and maybe most of all, how to build systems and processes that are sustainable in the long term.

The flip-side of that coin is that you’ll likely also see institutionalized stupidity, toxic politics, and pathological caution. But I think the rewards make up for it.

I should also point out that you can make serious money working for a BigCo too, particularly if you get lucky with the share price. I speak from experience here.

Finally, suppose you’ve tried managing people and you just don’t like it, but you still want a senior job. Most big tech companies have a position called “Principal Engineer” or “Distinguished Engineer” or some such, which it usually takes decades to grow into, but is pretty well the ideal job for someone like me. You get to work on the most interesting problems and feel like you’re part of the leadership team, and have the chance to move the needle.

Fintan Ryan of RedMonk just published On the Myth of the 10X Engineer and the Reality of the Distinguished Engineer, which I think overstates the wonderfulness of the position, but does hit a few key points.

Q: Should you work for a government? · Up till maybe five years ago, I would have said “No way, run screaming in the other direction.” For decades governments as a matter of policy hired no software developers and based all their projects on outsourcing, usually to loathsome blue-suit operations whose core competencies are winning public-sector bids then cashing in by charging for every ripple coming out of those classic waterfall projects.

In recent years, led initially by the UK organization now called the Government Digital Service, a few governments have clued into the fact that information processing is an essential core competence for the public sector, and started pulling it in-house.

Remember when the Obama administration wrested control of healthcare.gov out of the hands of the consultants, aimed a bunch of competent geeks at it, and rescued it? I’m thinking that kind of work could be among the most rewarding things you could load up a technical career with.

There’s a sub-question here: How about a job in the inteligence community? I’ve never had one, but I’ve sold them technology and worked with them. They have the biggest computers and maybe the hardest problems, and I firmly believe that effective intelligence makes the world a safer place.

But the people I know in the community always seemed more stressed out and less happy than your average geek, and I heard persistent grumbling about work-culture problems. So I’m not sure I’d recommend that path.

Q: Should you work for a non-tech company? · I can’t help you here very much; never done it. Since I’ve been working for AWS I’ve got in face time with a lot of IT people from outside the geek-o-sphere, and they seem to be pretty happy. But then, the ones I’m talking to are the ones mixed up in the move to the cloud, which is absolutely the most interesting single trend in IT these days.

Obviously, you’re probably at slightly higher risk of a pointy-haired boss who hasn’t the vaguest idea what it is you actually do.

Q: Should you be a consultant? · This is really two questions. First, should you be an independent consultant, working for yourself? I have, and it was OK, and paid pretty well (although both the startup and the BigCo did better). You have to be willing to market yourself aggressively; conference speaking slots work best, in my experience. Then, after the gig, you have to hassle your customers to get paid, which really isn’t fun. Finally, you’re going to be spending a lot of time on the road.

I had fun, and several remarkably interesting customers. Two things got on my nerves. First, you get to work on the hard problems, but you never get to stick around and ship a product. Second: A lot of times you end up telling management exactly the same thing their own smart geeks were telling them, but they listen to you, not their own people

The second question is, should you go work for a big consulting company? I’d offer a firm “No”, even though the pay is good. These companies work their people insanely hard, and in my opinion, based on thirty years of observation, charge too much and deliver too little. They are definitely Part Of The Problem, and you should stay away.

Q: Should you work for a nonprofit or charity? · I never have, and I regret it. Obviously, this is not a ticket to the 1%, and I suspect that the technology problems and solutions are pretty mundane. But I’d hope there would be other, more important, rewards.

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