Ask HN: How to Break Career Stagnation?

5 years in and I never expected the job search to get more miserable as I gained more experience.

Everyone says the market is great right now and so I’ve begun looking again, but man the jobscape is depressing. I want to increase my pay (I have certain targets of mine), break out of stagnation, and by the grace of gods work on something I find interesting, but it’s just looking so grim. I’m seeing a lot of “senior” level roles mostly in areas I have no experience in. This might mean technologies / languages / working on software of scales that I just couldn’t get at my current company or past companies. This isn’t a matter of “I don’t fit all of the qualifications” more so “the only qualification I meet is general YoE”. To be blunt, I have little experience with modern technologies and what I do have is a little old to be relevant. I’ve never had direct interaction with any clouds/cloud technologies and I’ve never had to do significant system design or work on any software at scale. Though I do a good bit of design work on my perpetually unfinished side projects. I don’t feel comfortable listing many skills on my resume as even the programming languages I’ve built my career on, I don’t feel I know that well, in account of the very little code I’ve written in a professional context. My resume in general feels rather bare, lacking education or a plethora of technologies/programming languages I can confidently list.

I’ve begun categorizing jobs I see in my head into three categories

1) The jobs I could qualify for, but would continue my stagnation. These are pretty easy to spot, my prior experience is typically very relevant, I mostly would look good on paper and could pass the interviews, but they would at best be the same thing I have now, with marginally more pay. They are likely to be boring, and not actually push me any at all and I’d basically just get more tenure with little good experience to back it up. Could probably get a pay increase, but not near my target. If I begin to open up, the recruiters that contact me will almost certainly be from this group.

2) Jobs that seem mostly boring but would meet my pay targets and at the very least slow the stagnation. Not ideal, but would at least be better than what I’ve done in the past and set me up for more success down the line. Some of these pay quite well, but I would be unlikely to pass the interviews or even make it to one.

3) Jobs that look interesting, and also meet my goals for pay. There are really two groups within this. A) Jobs I would never qualify for regardless, save for effectively starting a second career doing significant OSS or side work and B) Jobs that I could qualify for, but with substantial work and a healthy dose of luck. Note when I say qualify for here, I mostly mean on paper. A lot of these tend to be more niche as well, and almost always end up being actual senior level roles desiring domain experts, so I’m still likely out of luck even with some self development.

Interviews are another component. I could probably manage a “take home” type interview because of my ability to figure things out quickly (if I have the motivation), but save for that and the coveted but rare “talk about stuff” interviews. I’d flatline on nearly anything else. Particularly I would never pass a leetcode/white boarding type interview and nowadays I’d probably fail most trivia" interviews given the lack of depth of my experience.

OTOH, I don’t think I’m a complete idiot. I know a little about a lot and am confident in my abilities to ramp up quickly in the correct context. I spend a lot of time reading about all sorts of technologies and can talk my ass off about many things. It’s just that I lack sufficient depth in almost everything to look good on paper or perform in an interview or a senior level role.

I suppose, some gaps could be filled with side projects, etc., but I struggle with contrasting that with my professional experience without downplaying YoE. Only so much can fit in a resume. Additionally, I'm not sure how well this works outside of entry level roles when someone asks me about my experience with X and all I have to say is that I spun some shit up on my laptop one day, toyed around ,maybe made something neat, but never used it in a real world context.

It's effectively the "need experience to get the job, but need the job to get experience", but I no longer can rely on the normal entry-level hacks.

17 points | by the_only_law 996 days ago

9 comments

  • sdevonoes 995 days ago
    > To be blunt, I have little experience with modern technologies and what I do have is a little old to be relevant. I’ve never had direct interaction with any clouds/cloud technologies and I’ve never had to do significant system design or work on any software at scale. Though I do a good bit of design work on my perpetually unfinished side projects.

    You only need a month or so to get up-to-date. It's not that you need to be a master of such technologies; if you have the fundamentals (OS, networking, some architectural patterns on mind) it should be fine to apply for such jobs that ask for such tech stack after a month or so of playing around with the tooling on your free time.

  • ffhhj 995 days ago
    Make a list of the companies/positions you would like to work at, with the crappy/boring ones at the bottom. Apply for interviews in some of the later and record them in video. Fail their tests but get to the end. Deeply study the topics of the tests. Apply for the interesting jobs in ascending order.
  • softwaredoug 995 days ago
    Go deep into one thing

    Sounds like you have a lot of breadth, likely that means great overall instincts. This is a great asset!

    So you feel you’re out of date in your skills? Don’t boil the ocean. Instead go really deep into a specific new, marketable thing. As a side effect you’ll learn adjacent skills. It’s more time efficient and helps you gain confidence.

    You’d be surprised how many people actually have very shallow skills in modern things. They put “AWS” on their resume, when really they pointed and clicked a few times to start a server.

    While you’re going deep freely give away what you learn. Write, speak, whatever. This both better reinforces knowledge you’ve gained as well as advertises your skills to others.

  • yuppie_scum 996 days ago
    I think you are answering your own question here. Not to put too fine a point on it, but nobody just jumps into one of those category 3B jobs without, as you say, substantial hard work and a healthy dose of good luck.

    You say that to get a job in category 3B you don’t have the experience to confidently pass a job interview. So, keep grinding at your current job until you develop the expertise you need. Or take a job in category 2 that will expose you to the things you need to fill the gaps.

    Luckily you have the cliff notes to this test - just look at the job description requirements for the 3B jobs you’re really targeting, and seek opportunities that will get that on your resume.

    • the_only_law 996 days ago
      2 and 3B effectively require the same amount of work, only differing in how common they are and my subjective interest.

      I'm just not sure what sort of work I need to do when my currently job (and company) cannot expose me to what I need and neither can side projects.

      • yuppie_scum 994 days ago
        Well then you need to find out what you need to do to qualify for a job that will expose you to what you need to get to the 3B.
      • PaulHoule 996 days ago
        There is no limit with side projects if you pick the right one.
  • runawaybottle 996 days ago
    Some of this is the industry’s fault. There are many companies still building lame stuff. In other words, they kind of don’t need the new you, they just need the old you (no pun intended). The old you is now easily created in Bootcamps and new grads.

    There are fewer jobs that need the new you. Your dilemma right now is that you have to present this new (older) you as the best older (newer) you. Subconsciously most companies see through this and are making a simple business decision (just get the cheaper stuff, it’s the same old you). Sucks to be you.

  • giantg2 995 days ago
    I feel the same. My only real recommendation is to work on a simple side project in the tech you want to get into. You want to get into Android? Build a simple calculator. It sounds stupid, but focus on the best practices. You'll learn about the different components, basic project structure, localization, accessibility, rendering for different device sizes/orientations, etc.
  • readonthegoapp 996 days ago
    What are two or three titles you'd like to have? assuming a semi-ideal-ish world, or where things just kind of worked out pretty darn ok over the next month or two.

    ps, this is not going to give away your identity.

  • kleer001 995 days ago
    When in doubt, look to take on more responsibility.
  • PaulHoule 996 days ago
    3B work hard like a salmon going upstream.