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 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.


Comment feed for ongoing:Comments feed

From: John M. (Feb 19 2017, at 00:32)

Thanks for posting this. I found out this week that my current contract won't be renewed due to cash flow problems at the small Japanese company I've been working at for over a year. I helped build large parts of their system (which uses lots of AWS BTW), and no longer being part of their small team definitely hurts.

I'm considering my options, trying to decide whether to remain freelance, apply for a job at a "big co.", or leave tech. Your post is a useful data point. 🙇🏻👍🏼


From: Ade (Feb 19 2017, at 09:54)

Missing: Should you work in academia?

(Yes, definitely. Education needs good technical people, and research needs good ideas. Plus, screw all that corporate bullshit - although it's a creeping menace in the sector.)


From: Brian (Feb 19 2017, at 10:37)

For government, don't forget the NASA and the Department of Energy/National Labs. Very big computers, very hard problems, and a bit more of a "professional academia" vibe with a some of the standard government crap mixed in.


From: Kevin Dangoor (Feb 19 2017, at 10:55)

I have worked at 3 non-profits in my career thus far, and my experience is that they have a different feel. There is a lot more talk about "the mission" and how things that we do support the mission. How the org is doing financially does come up, but it comes up a lot less often in the non-profits I've worked in.

I will say this, though: all three of the non-profits I've worked for (JSTOR, Mozilla and now Khan Academy) are pretty well capitalized organizations. I suspect money would be a bigger topic of discussion in non-profits that are less well established.

Anyhow, I am at Khan Academy specifically for its mission ("free world class education for anyone, anywhere"), and this is true for everyone we hire. For-profits can certainly have that, too, but I think the motivations are less universal at most for-profits.


From: sm (Feb 19 2017, at 11:48)

I find it problematic when people try to straddle the line between engineering and management.

An engineer might think they want to report to a technical manager and the manager might think it's important for them to write code. But at some point a conflict of interest will emerge in dividing work between the manager and his reports.

There is no escaping the reality that a manager buried in meetings doesn't have as much time to develop their technical skills, but as they continue to have technical input and be able to override their reports the arrangement becomes counterproductive.

If you really want to be a manager do it wholeheartedly and honestly.


From: hawkse (Feb 19 2017, at 12:22)

Working in a non-technical company has its upsides. Not being directly involved in the day-to-day grind removes a lot of pressure and it can be immensely satisfying using tech to solve real world problems close to the coalface.

In a small enough company one also tends to get a very good understanding of all aspects of the business as IT today really is the backbone of most companies.

There are some downsides though; the pointy haired boss is real. Be prepared for lot's of "how hard can it be?" and working hard to keep those consultants wasting the tech budget OUT.


From: Twirrim (Feb 19 2017, at 14:47)

> The good news is that it doesn’t get hard­er ei­ther.

It's good to hear that. I'm heading in to my late 30s and every now and then I find myself wondering how long I can keep up with the pace of change in the industry, and if it's even feasible for me to do so.

It always feels a little like I'm sort of scrambling along, surviving, rather than rushing ahead and thriving. Yet I'm managing to have a successful and productive career, and have no end of opportunities for other work presenting themselves, so I'm clearly doing well enough. I guess I just keep expecting that I'm going to fall off the wagon somehow, soon :D


From: Michael R. Bernstein (Feb 19 2017, at 16:11)

Re: nonprofits: "I nev­er have, and I re­gret it."

It is never too late! Check out organizations like

You are right that the technical issues can be rather pedestrian (since as you noted, the tech is *so* much better than it used to be), but the pain you'll be saving users (whether NGO, public service, or the public) from are *very* satisfying to solve, and sometimes the technical issues *are* quite interesting as a result of extreme resource constraints.

Seriously consider it. There are many non-profit organizations tackling really important problems that you probably care about quite a bit, at practically any scale that would suit you.


From: Rob (Feb 19 2017, at 19:30)

"I sus­pect that the tech­nol­o­gy prob­lems and so­lu­tions are pret­ty mun­dane."

Or, um, are so stupendously difficult that they are not terribly amenable to automation (there I am, waaaay down at the bottom at 0.0031:

You might know someone who has worked on medical information systems, who may be able to advise you how mundane the problems are.

But yeah, when the choice is between a really cool and totally useful database app, and several weeks worth of food, clothing, housing, and meds for a drug addled & mentally ill malnourished HIV positive homeless teenager fleeing a pimp, well the teenager wins pretty much every single time when budget questions come up.


From: Alan Little (Feb 19 2017, at 23:38)

> Should you work for a non­prof­it or char­i­ty?

My solution to this one is to work at my day job managing machine learning projects for a large telco during the day, and write an administrative system for my brother's church in the evening. It's a mundane little CRUD app in django, albeit with some interesting little wrinkles, and I'm enjoying it immensely.

I wouldn't have had time for this approach when my son was smaller though.


From: Jim Antoniou (Feb 20 2017, at 13:31)

As someone who was given a promotion opportunity a couple years ago to manage the group I was already in and is now actively working on moving back out of management into technical work, this is a good and relevant read for me.

There is a lot of culture shift and transformation - both good and bad - happening in our department these days which has me pausing to think about my next moves or even if I should make any. The move out of management is highly intentional - I was not asked to step down but rather felt my talents would be put to better use not focused on the day to day management - so I'm inclined to stand pat for now to see where the tides take me at this point. Generally speaking I've always had a pretty clear picture of when it was time to move on from a company and I may be approaching that here - or maybe not. I couldn't possibly be more equivocal :)

I will stay in the technical side of things as long as I can - I'm a long-time IT ops and systems/network engineering person - and yes you're absolutely correct: It's incredibly challenging to stay relevant in that always rapidly changing world we live in. I'm in my 40s now so perhaps I'm a little nuts intentionally stepping out of management - indeed it's almost a rite of passage that you're expected to "graduate" out of being an individual contributor at some point in your career - but I have learned a lot of good things being a manager and who knows may end up back there some day.

I'd agree generally on government or public sector work, at least from an outsider's perspective. Every time I've interviewed at a public sector employer - and I've probably done roughly 6 in my career - I've invariably regretted it. The pay is rarely even close to what I'd consider competitive and the weird panel interview process they tend to do borders on infuriating. There's actually what LOOKS like a good public sector job practically around the corner from my house (vs. the 2+ hours a day I spend on the road now) that SEEMS to have the appropriate pay scale and benefits but I just can't motivate myself to apply. Never say never though :) I'm just not sure I could handle the dramatic culture shift that tends to happen in any government/public sector work.


From: Lauren (Feb 20 2017, at 16:44)

A large number of people leave tech because of sexism and/or ageism (which you discussed in, not because they don't enjoy the technology aspects. If the company employing you lays off half their staff, or the entire IT department, there often isn't a ready replacement job available.


From: Dan Sneddon (Feb 21 2017, at 06:03)

I agree with the comments recommending Academia and the Department of Energy. I've worked in large companies, startups, and ran a consulting business, but working at one of the National Labs that was operated by a university was one of the most rewarding jobs I've had (in every way except pay, which was probably 80% of market rate). One hidden benefit is that you get to work on problems that are more theoretical than standard practice (doing things at unprecedented scale, or developing new hardware to solve a specific problem). Another thing to note is that the benefits are better than in nearly any other sector: 40-hour work weeks (and a more relaxed pace); 4-6 weeks time off per year; reimbursement for education costs for the employee (and their children in some cases); generous retirement packages; good healthcare, etc. Depending on how many of those benefits you make use of, you might even end up better off at the end of the year than someone in corporate tech. Finally, there is an immeasurable reward that comes from helping to find answers to fundamental questions of the nature of the universe, developing new science and materials, and working to make the world a better place.

I thoroughly enjoyed my time at that DoE job, and left only because the cost of living increased in the last 10 years and I needed to have a market rate job to put away any savings. The math would have worked out differently if I had a family to take advantage of the benefits, but as a single person I couldn't take full advantage. I would love to go back into a similar position when I'm older and planning more for my retirement than my future career. I miss the conversations with Nobel prize winning scientists at the coffee machine, and it was nice never having to think about revenue or profits.


From: Dave Duchene (Feb 21 2017, at 06:19)

This is advice is timely for me. Thanks for writing.


From: Doug K (Feb 21 2017, at 21:15)

on staying technical - "It’s not a one-way door."

I beg to differ. It is a one-way door for most of us. As you mentioned in Old Geeks, most companies would have to make a special exception to hire James Gosling, because he's perceived as too old for technology now. For those of us that didn't invent Java or XML or Atom, there is not much hope of staying technical following any layoff after 40. Bigcos might hire, but chances are good you'll be the old horse walking in circles on the legacy maintenance mill.

My wife was laid off from a tech job in her mid-30s. She hasn't been able to find a job in the field since. She works for the church now, loves the job and does good every day, making just slightly more than minimum wage.

I really don't see that there is a career path for coders. There are a number of exit strategies as you outline here - marketing, sales, consulting. Consulting only works if you have a good network and some marketing skills.

In my 30s when trying to figure out how to stay employed in the IT business I read a book by Ed Yourdon IIRC, covering this ground. That added training/teaching software and tech support to the list. The training jobs have mostly disappeared into online tutorials and hopelessly optimistic MOOCs. Tech support is still there and is how I've been earning a crust since the coding jobs stopped returning my calls. It has its consolations and I get to write scraps of code in a large variety of dialects, which is kinda fun. When the layoff comes I hope to be able to scavenge another such employment somewhere.

Military intelligence - worked on IT systems and codebreaking for the quaintly-named department of Electronic Warfare, many years ago. Hard and interesting problems, but also real emergencies that involved life and death. That's been my standard for responding to customer crises in tech support - "is anyone actually bleeding to death ? No ? then we can fix this.."

Government - Worked for State of California government for a while, remediating a truly awful system from the blue-suit brigade, worst code I've ever seen including in labs for first-year students back in college. It was spectacularly awful. Working for the new US government IT at looks like it would be fascinating and rewarding, at least until the new administration closes it down. That was a spinoff of the rescue operation, which I was remotely connected to. Their problems were my personal top priority whenever they called in..

Universities - worked in the Witwatersrand University IT department while part-timing a graduate degree. I loved that job, good people doing good work, decent pay and good benefits. Since then applied for jobs at NREL and NCAR but came second each time (or so the nice hiring interviewers said).

Startups - have to be young and without dependents, or old and rich already, to be able to afford to work for a startup. It's the same problem as exiting from tech really.


From: Juergen Hoffmann (Feb 23 2017, at 07:01)

Should you go in­to man­age­men­t? I dislike the term management. I think you should rephrase it to Leadership. Especially being an open leader ( could be a very rewarding role...


From: Kiran (Mar 04 2017, at 22:50)

I am a senior qe in one of the fortune 500 organizations in the cloud/virtualization/storage area. I do see a path for qe till principal engineer.after that I do not see any.many we will go to management position after the principal engineer position . Do you have any other idea for qe?


From: Thom Hickey (Mar 25 2017, at 09:25)

I worked for a non-profit most of my life and, at least in the library world, there are (still) some interesting tech problems.



From: Brett (Mar 29 2017, at 07:23)

I've had a 20 year career as a developer. I've learnt to take the day job money and build a nest egg, and not care too much about trying to change the world.

My last project failed because they wanted me on my own to compete with a 3000 employee company. I am smart but not that smart. These days it's hard to have a hit if you're just one person, much like what we saw when the computer games business turned into a vast industry.

The project before that was good technically but the pointy haired boss should have talked to the pointy haired accountant earlier in the project.

My long term gig before that was easy work - the boss never delegated anything.

It is weird that the most successful things I've worked on have generally been my own.

I suppose I should do something else, but there are so few Python people around that I'm always preferred for this rather than anything else.


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