Ask HN: After 20 years of programming, what do I do now?

I've been programming for 20 years, the last 12 in ASP.net webforms (I know, I know). In every job, I've been told I was the top dev at the company. I kept my current job because of the money and flexibility they gave me to stay, but now that working here isn't worth it anymore, I'm feeling that remaining in this job has soured my career. I'm not sure where to go from here.

I've held management positions, and while my projects were successful, I'm not interested there. The monotonous consulting-services work I've been doing for the last 5+ years hasn't lent itself to exploring new technologies, so I don't have the breadth for an architect job. I've tried the solo-business route, and while my app is loved and has sold copies, it's only breaking even and won't sustain me now.

Almost all of the jobs I am interested in (remote or product-based) want newer technology. SQL Server's been a big part of my entire career, but it feels like that is losing relevance with the ORMs/EFs of the world. I've only worked with MVC on personal projects, but even if I brushed up on it, I'm guessing managers would feel I am an expensive hire without any advantage a junior dev who worked with MVC their whole career.

Do I try to build a MVC portfolio, since that seems to be the popular MS technology? Or work on a JS portfolio (my web style today is already JS calling JSON services) and try to rebuild myself on the front end?

Do I take a big pay cut and try to rebuild my skills with a company open to a senior dev without the exact experience?

Do I try to gamble and find myself a newer technology to reinvent myself into, hoping it sticks around?

Or am I just at the natural point in my career where I'm supposed to be working for another services company?

Anyone refactor themselves into something new at a similar point in their career? I'd love to hear your advice. RefactorCareer@gmail.com in case you have any private advice.

Being a senior dev doesn't mean 20 years of experience on every part of the stack. It means you deliver value even when things get tough. MVC is so ridiculously simple compared to WebForms I don't even know why you wouldn't sell yourself as top of the bill senior for projects that are MVC based.

I have interviewed a fair number of people for different positions over the years, here's my 2p:

1. I would look at your CV and see your narrow focus but I would still be wondering based on your experiences whether you could move to the technology we use.

2. Good/great developers seem to be in short supply, if you can prove your ability to understand code, build robust things and ship you would be just fine in my interview.

3. I think you would find a lot of very similar technology in the Java field and it wouldn't be a huge hurdle for you to pick that up if you have a good and deep understanding of how you currently deliver apps using ASP. If you could show on your portfolio how you have picked up Java/Ruby/Python/whatever based on your 20 years of experience and show you understand "how things work" rather than the nitty gritty of a the language then you would beat a lot of the people we interview.

In short, if you came to an interview for a Java job I would be more interested in how easy you would be able to learn what we do with Spring etc and how much and how deeply you understood the stack you were working with rather than worrying too much about you not have "5 years of Spring MVC" or whatever other blurbs HR stuck on the job description. I've interviewed a lot of people who have no clue whatsoever how MVC works and have no notion about how things fit together to make a system, they just fill in the gaps in the Spring/Hibernate/library config and write a few lines of code and "it just works". If you have the deep knowledge I think you can easily take a senior/architect role in Java-land.

Let's talk, emailing you now...

Study up on Microsoft SQL Server and present yourself as someone to fill a DBA role. Pay attention especially to the basics: backup, restore, migration, import and export of data and Microsoft Report Services. Read the fine print about SQL Server version differences (nobody else will).

SQL Server is in high demand and most programmers have little interest in the DBA role, yet it is crucial (read "highly-valued") in most organizations.

Organizations want young programmers/developers. But when they think of DBAs they want someone with experience. So grow a beard!8-))