I think my interview/offer ratio is somewhere below 1%.

Keep your spirits up, and be mindful that there are tons of job adverts out there that don’t actually have a real job position to fill, and are only used by recruiters and consulting companies to harvest CVs and meet their internal quotas. 1% sounds about right

The title made me think you’d been using Windows XP for the last 20 years.

I’m a similar boat. Diagnosed with ADHD recently but later in life, and it’s likely why I never settled into a single domain. I consider myself a strong software engineer but tend to fall apart in interviews, particularly with unstructured things like being asked to “tell me about yourself.” I am also planning a shift into a management role.

My main regret in life is spending a lot of time trying to apply advice that seemed reasonable and how Other People did things. Only adopt things that work for you.

• I highly recommend at least trying stimulants. I inadvertently self medicated with caffeine for years, which might work in a pinch. My secret sauce is frankly 90% Concerta and 10% behavior modification things like carrying a notebook around.

• I would not mention that you have ADHD to interviewers since you can’t count on anyone to properly understand it. Showing weakness is just blood in the water. Hopefully this won’t be an issue for future generations. Yes, I am extremely bitter about this.

• Approach this as doing whatever you have to do to get yourself over the finish line, and know that trying harder at a failed strategy never works. Don’t limit yourself to how things are supposed to be done.

• Security requires a flexible mindset and attracts square pegs. Data centers are where all the real weirdos hang out so devops might be worth considering. I’m confident most scientists I’ve worked with have ADHD, and prototype R&D work is definitely more ADHD friendly.

• Insist on knowing the structure and expectations of each round of an interview. I pitch this as “I need to know how I’m being evaluated so I can properly prepare and demonstrate my abilities.”

• I’ll be honest: the interview process is mostly nonsense and should be treated as such. Anything that puts a thumb on the scale in your favor is fair game, short of unethical behavior like lying. Telling people what they want to hear is a great way to counter dumb questions.

• I’ve built up an Obsidian ‘database’ of bullets to help during interviews, including a prepared statement of why I have it and need to have it available.

  • “Tell me about yourself”, “what type of role are you looking for”, “why do you want to shift into management” open ended questions. The key thing is respond in a coherent, organized way without showing any negativity or weakness. Yes this is ridiculous, but it’s how it is.

    • Turn your generalist background into the strength it is. I use: software engineering is a problem solving role, everything else is a means to that end. Solving problems is what I do; I’ve done so in a wide range of fields and domains and always drive them to completion. What I’m looking for is a great team to join, which is independent of industry or tech stack.

  • “Tell me about a time” behavior questions. I like the STAR format. I do well on these but need an outline to work with. Make sure it’s polished into a coherent narrative. Put an emphasis on what you did, but also how you enabled your team. Numerical data points are great if you have them

    • If the company posts their values or principles then that’s likely want they want to see out of these. Match your scenarios to the values beforehand. The idea is previous behaviors indicate future ones.

  • System design questions. I have my own checklist of questions I go through since I don’t like the popular format. I expect this is where you shine, maybe just need a bit of scaffolding to help organize your thoughts.

  • Leetcode programming tests. Like it or not, it’s part of the game.

• If you are serious about going into management, you’ll need a prepared philosophy of how you see the role and will approach it.

  • This is also a great question to ask hiring managers. The best indicator of what the job will actually be like and you can’t wiggle out without raising red flags.
  • The two books I like are The Manager’s Path by Camille Fournier and the classic First, Break All the Rules by the Gallop folks. Again, not all advice is good so only take away what you think will work for you. Worth reading if only to understand what you should expect out of a manager.
  • Do not make the mistake of feeling like you need to go into a people management position. Shifting into project management is perfectly fine. Topping out at a senior or staff software engineer role is also perfectly fine. Frankly, topping out at a mid level engineer is fine, just watch out for ageism.

• I also have check lists for all sorts of random things. Even dumb things like how to respond to a question I didn’t prepare for: repeat the question, write it down, jot down what I think they want to hear, write down points, and give them an order.

Changing that much was probably a bad thing,

I’m a generalist and this gets me too.

For many jobs the ones doing the hiring are thinking of their domain, so more experience in the domain means a better worker. But a software developer who has developed CRUD apps 50 times on-budget and on-time over 20 years is almost certainly going to be a fantastic candidate alongside the dev who specialised in the health insurance (or whatever) domain for the entirety of their 5-year career.

Now I’m aiming for more software-focused companies and consultancies since I think I’m more likely to meet people who appreciate that broader experience.

First take some time to actually define the lifestyle you want. It’s very easy in today’s world to get tunnel vision on your career. But once you have financial stability more money doesn’t necessarily make you happier. Trying to move up the career ladder could prevent you from enjoying life. That’s where the saying “money doesn’t make happy” comes from.

But if advancing is important to you there are still ways to achieve this. Consider moving abroad for a few years. Especially the middle east has ton of good job offers and since many people you will work with there aren’t English native speakers your pronunciation shouldn’t hold you back. UAE, Kuwait, Jordan, Bahrain all have a very vibrant expat community. They are more likely to value your experience and offer you a higher position. Then after 2-3 years you can go back with a stronger CV.

Or you can consider picking up a remote job, move to a tropical island and enjoy a more relaxed life. That’s what I did (not as a programmer but still remote work). A salary that barely let’s you survive in the west let’s you have a very comfortable lifestyle. You only have to consider the visa issue but for most countries that means just leaving for 1-2 days every 90 days. And with the extra spare money taking short flights/vacations is easily doable.

Both option obviously depend a bit on your social life.

I only have very limited knowledge about programming. But I do know that some languages are fairly new. So you switching around isn’t necessarily bad. Just focus on something that’s fairly new and then you are on a level playing field.

And if you haven’t done so yet. Spend a few bucks on a professional CV writer. If your interview rate is so low there is a good chance your CV is bad. The job market is crazy at the moment and getting tons of rejections isn’t uncommon. But with 20 years of experience it shouldn’t be that bad.

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Management isn’t the only career path forward, but leadership is certainly part of any role of senior developer or higher unless you have very solid specific domain knowledge. Perhaps an architect role might work?

Having a broad base of experience can work for you in interviews, but you need to present it the right way. You know 20 different ways /tools for doing things and are able to choose the best tool for the job rather than having only a hammer and hitting everything like a nail.

• reinforcing others’ comments – “define the lifestyle you want”
• do you really want to move up to management? – not just social skills, management requires both a different skillset and mindset – there’s no shame staying on the technical/development/engineering side of things
• in your off-time, try out stuff and find what feels most comfortable
  • backend? – there can be more focus on interoperability over performance, plenty of companies trying to get their web frontends working with enterprise backends that they’re never planning on upgrading – ex. there’s still a huge call for COBOL programmers
  • embedded? – between maker communities and self-hosting communities, there’s a big hobbyist community sitting outside the corporate sphere – ex. programming microcontollers/SBCs in C, MicroPython, PicoRuby, Forth/Factor, …
  • 8-bit? – tools, programs, and games for virtual consoles (uxn, Pico8, TIC-80), chiptunes and tracker music (keeping the legacy of Amiga MODs alive)
  • Android? – pick up some Go or Dart/Flutter skills (one of the current maintainers of Dart, Bob Nystrom, has put out Game Programming Patterns and Crafting Interpreters and likes programming roguelikes)

I would advise 3 things: you know your limitations, start by being upfront and transparent with them. In my opinion its already pretty good that you have that understading and that you are working on it. Nobody is perfect, but if you are transparent and start with that, it shows great awareness and also confidence. Second thing is, try to show why do you love programming, Why is it your passion? (Assuming it is) Third, what can you offer? Eg, you might not be a very social person, but as soon as someone gives you a coding challenge you dig deep and figure stuff out on your own! You are independent,etc… (im just guessing, as an example)

I kind of have to opposite but a similar problem. I’m diagnosed autistic, so while I am great at self teaching, I also tend to hyperfocus. This lead me to be a kind of one trick pony, but I’m really good at that one thing. And I think my lack of diversification is killing me. I just don’t have broad enough knowledge to cover a full position. That and well…I’m awkward in interviews, with the no eye contact, reciprocating responses, and tendency to ramble.

One anecdote to illustrate the point: On my last job, I was initially directly chosen by upper management that was my former boss in another company. The HR interviewer blocked me anyway, the higher ups hired me as a contractor for a year, and only them they hired me directly

Have you considered trying the gig economy and picking up contracts on websites like Fiverr as a freelancer?