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I'm a software developer working for several years in same company.
However, I've been stagnating technically speaking, as the other devs were higher level and older in the team, they were given all the core tasks.
So since all years I've been working on routine tasks and didn't change the tech stack at all(which is becoming extinct).

Now the time to leave the company is approaching and I'd like to evolve somehow, as a developer. What would you recommend? Or perhaps other ideas?
Or is it too late to get back on track?

1. work on a startup project

I've worked on multiple project ideas during these 5 years. Did some prototypes but neither reached maturity.
Been able to get something working for personal purpose but didn't find a way to scale it or go around some possible legal issues with it(related to scraping websites).

Advantages:

• if I'd be able to scale it and launch it, I could get hired easier at next dayjob (as startup probably needs time to mature, etc. - and become a financial support)


• if I use some tech that is common like NodeJS and React, I could more easy get hired at next dayjob


• if I'd use some open-source components, perhaps I could contribute to their code => OpenSource contribution => good reputation for getting a dayjob

Disadvantages:

• time required to build it and scale it
  could easily loose focus as startup world involves much more than just focus on one technology or a specific stack.
  It is also focus on infrastructure, tooling, etc.
  I could forget the aim of financial support(get dayjob) for my family and get sidetracked.


• mental and financial stress of working on it without a dayjob


• mediocre architecture as I've no point of reference (like working on an open-source project)

2. work on an open-source project

Advantages:

• learning a specific tech stack


• high-level architecture from which I could learn (?! much more than on the startup project)

Disadvantages:

• zero financial gain and mental stress from it


• family doesn't agree

3. read books/do sample projects/interview questions/tutorials on a specific tech stack

Advantages:

• probably fastest way to gain experience for a dayjob?!


• apply to jobs quicker

Disadvantages:

• shallow experience gain, with focus to only pass the interview


• impostor syndrome - as no real experience with the tech stack

4. apply for remote jobs

Advantages:

• independence of location and working hours - I could accept this and be ok with the lower salary

Disadvantages:

• lower salary range


• they seem to have much higher acceptance bar versus the dayjob


• could spend quite a while before getting accepted

Preparing to get your dream job for a long time may not be the worst idea, but you shouldn't do that at the expense of not having a job and income. You have a family you have to support, and that should be your main concern.

I was in a similar situation a few years ago, where I had to switch my field of expertise. I had surprisingly good feedback when I was just honest and said in my interviews that I want to switch my field of expertise and needed some training on the job. Of course it depends on your situation and the companies you are applying to, but for a lot of companies I know it is more important that the applicant fits into the team, is motivated and at least competent enough that it is worth investing into him. You may have to accept some salary cuts, but if you do well, it should rise again quickly.

This way, you can try to get a job with the new technology stack that you want to work with and gain experience with it, so that you can work on your side projects a little more efficiently. And if you succeed with it and your startup idea matures, you can work on that later.

The first thing you want to do is polish up your resume and start applying for Jobs. Finding the perfect job can take a long time, and the longer you aren't looking for your dream job, the more potential dream jobs you are missing.

So dust off your resume, polish it up and actually apply for Jobs. You will find that there are a huge range of jobs available online, and you should narrow your search down to something that interests you, but is broad enough that there is a steady supply of new jobs being posted (if you choose extremely specific field, you might find that the requirements are extremely strict and job applications are few and far apart). So get out there, see what the market is currently like.

Once you have an established routine, then you can work on extra tasks. By extra, I mean that you should keep your current job and work on anything you can in your free time. Having a Job and steady income can be extremely important to your family and having a Job can also help you secure future employment.

There is no sense in preparing to look for a job, without first looking for a job.