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> I'm at an inflection point these days on whether I want to push forward on the management path or go for the third path, as you mentioned above.

FWIW, the few folks I know who tried to stay on purely technical paths ended up regretting it many years later. While the ones who went into management merely lamented the loss of their hard earned technical skills.

Anecdotal, and I know there are lots of people on HN with counter anecdotes, but think forward 10 or 20 years and see if the things you don't like about your role are things you can continue to tolerate or not. The grass isn't greener on the other side, but sometimes new problems are easier to handle than the same old problems over and over again.

Also, don't make the mistake of thinking going into management will give you more agency as an employee. From a non-management position it feels like those "higher" than you get to call the shots, but quite often a good manager is creating space for you to get to run your day-to-day and is boxed around almost daily by those higher than they are.

> FWIW, the few folks I know who tried to stay on purely technical paths ended up regretting it many years later.

Why?

I think a lot of it was career envy.

You see people who you hired as young developers end up, years later after going the management track themselves, in regular face to face interaction with the CEO or senior corporate executive VP or whatever.

Their peer group seems to have more control over their own destiny or more power or however you want to frame it, while they're still stuck bootstrapping yet another CRUD framework for the nth time and answering to a department head who's now younger than they are and getting younger every day.

I think, when that inflection point comes, you have to decide if you're okay with being in that position, and if working with the tech is enough for you...for some people, they honestly don't care about the careerism bit and just simply enjoy the bit twiddling and never get tired of doing it. You really have to decide if you're one of those people and it can be really hard to do so.

One mistake I see often is people, hitting that inflection point, conflating the pride they have in the effort they put into gaining the knowledge they have as being the same thing as the love of the art. And also the fear of jettisoning that life-style (and yes, development quickly becomes a lifestyle), for something entirely new and different with an entirely different set of skills that often have to be learned from scratch.

Big companies try to have career paths for technical people. They claim "Distinguished Engineer" is the equivalent of a VP. However, it's really hard to get promoted to the few coveted DE positions, whereas a fresh batch of VPs are anointed every Monday.

I've gone the 'third' path as described here over a year ago, and in my late 30s. I can't recommend it enough to you since you said "but getting into the politics of management is unappealing".

You're contradicting yourself when you say on one hand you're used to having jobs thrown at you and then saying it's clearly a lot riskier. From my point of view there's way too many management/analyst types trying to get those management positions. The politics is no joke. You have to be really good at it and in some ways you have to have no soul.. just kidding! ok maybe a little ;-)

anyway, going solo and starting your own thing, if done right, is more rewarding on all levels. less politics, more tech stuff you love, better pay (that totally outweighs the cost of having to pay for your own insurance), better hours (however you define better hours for yourself), not having to do any "company contribution" for someone else's company, the clients treat you better because they know you're the expert, etc etc.

Granted, it took me almost 15 years working at bigger consulting firms before I wised up and went independent. And maybe I could have done it sooner, who knows. But I highly recommend it since you don't like "the politics of management". The trick is to find one good solid gig. Just one. And there are enough of those going around.

I don't think this life is for everyone though. One thing people often don't consider when going freelance is that your job shifts. Instead of just being a developer, you are now a developer, marketer, business owner, accountant, project manager, office manager and more.

Some people don't mind that, or even enjoy it. For others, having to deal with all the tasks that go along with running a business, in addition to being the sole developer, can make life much less enjoyable. Especially if you're not fairly well set financially and would have a hard time enduring lean periods.

Not to say it's bad, it's certainly rewarding to run your own business and you gain a lot of freedom. But it's a tradeoff, and one that might not suit everyone.

that also really depends on what kind of gigs you get.

for example here in the DC area there are lots of independent contractors that have steady multi-year contracts. as long as you're not total dead weight you do the hourly thing for a long time. many years. It's more rare to find those folks that go from solo gigs to having other subcontractors going through them too. That's when all your points become really important. But you can be solo and not have to deal with a lot of that stuff you mention.

Folks keeping score at home should note the successful DC area contractors in this thread. DC is full to the gills with easy, good-paying software work from budgets that need spending. But I don't think that it is a good place to be for your career if you are interested in the technology, unless you are able and willing to get a TSC, and to perform the sort of work that requires one. I recently relocated from the DC area to California for this reason.

What is a TSC and how do I get one?

It's a "Top Secret Clearance," a certificate saying that you are trustworthy to perform top secret government work. Based on what I've heard from others, getting one includes taking a lie detector test, having family members, neighbors, and colleagues interviewed, and hopefully not too many other probing things. My impression is that any warm-bodied US citizen who doesn't have much of a record, and who knows the right things to say, can get a TSC unless their nationality gets in the way.

Cool, thanks.

personally I haven't seen nationality get in the way. Actually, I've seen many folks that are either 1st or 2nd generation US citizens. But the rest of what you say is right, though not all clearances require a polygraph. Relatively few people get those if you include regular Secret and Public Trust positions.

Wikipedia has a decent breakdown of the various clearances btw: http://en.wikipedia.org/wiki/Security_clearance

You get a clearance by having your employer or client sponsor you. It inactivates when you switch jobs, but can be reactivated fairly easily within 24 months. Beyond that, you need to be re-investigated. Standard Form 86 [1] lays out the information you need to provide.

[1] https://www.opm.gov/forms/pdf_fill/sf86.pdf

The tradeoff to that is that DC has a horrible commute and exceptionally high cost of living. How many of these contracts would allow primarily working from home?

I would be worried that the "politics of management" would be substituted by the "politics of marketing." Did you not find this to be the case?

> The management path seems to be the path of least resistance, but getting into the politics of management is unappealing.

From a non-management type, I have loved working for managers who can play the politics part, in a level headed way that keeps awareness of and effects from politics out of my individual contributor's life, and at the same time understands what I do and what can reasonably be done.

I've been working for more than 20 years (still an individual contributor), and I can think of two managers in my history that fit that description. If you think you can do it, you'll improve the lives of a lot of developers.

+1. You're lucky you've had 2. In my 20 years, I've had one. I was about to start making the transition to manager via tech lead, but after working with my most recent manager...ugh...I felt dirty after going to meetings with him. I spent more time parsing his double speak than concentrating on what really needed to be done.