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Ask HN: How to reskill without losing income?

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Ask HN: How to reskill without losing income?

#1
I am making a good living with a niche skillset. It's a fairly old technology and there's less and less work in that area. I'd like to move to another technology stack - it's not too hard for me - different keywords etc and I've actually done some hobby projects already. I think if I applied for a job I'd get rejected as there is no track record of being able to work with that tech. Best get case I could probably apply for a junior job which would pay well below my current. It will probably take years to get to the same level of pay, assuming that particualr tech stack takes off. Is there any eascape from this? Are there any companies that would be willing to hire a grumpy 30-something and recognise his/her experience as something reusable?

Re: Ask HN: How to reskill without losing income?

#4
Maybe start by attending user groups or meet-ups on the tech you're interested in. That might lead to some potential freelancing gigs or even just some open source work in that field.

But, in general, I think many, many companies are willing to hire 30-somethings with experience. Perhaps seed-funded startups aim for cheap low end labor, but enterprises and well-funded startups consistently value experience over skills with a specific stack or language.

Re: Ask HN: How to reskill without losing income?

#6
> I think if I applied for a job I'd get rejected as there is no track record of being able to work with that tech.

This is a big assumption, that is simply not true for a lot of opportunities out there. If you are able to show proficiency in what they are looking for, many companies will take you seriously as a candidate, even without 5+ years on the resume in said technology.

Worst thing you can do for yourself is to not try and apply. Worse case is you get a "no thanks" and you move on to the next application.

Re: Ask HN: How to reskill without losing income?

#7
If you have an employer, this is usually a pretty easy sell. Approach your boss about transitioning Aging Product X to a new technology stack because the current one is becoming defunct. Of course this will require some training for you, but it is easier to teach you a new skill set than to hire someone with that skill set and get them to learn about Aging Product X.

If you aren't employed and are contracting/freelance, it is just as easy. Since your skill set is niche, not everyone has it, and you can charge more for that niche. Up your rates enough that you can cut 10 hours a week out to study something new.

Re: Ask HN: How to reskill without losing income?

#9
Thanks a lot for asking this - I'm in a similar boat¹ and will follow this thread with interest.

Good luck from another 30-something.

① For me 'niche tech' is one thing, and 'investing a lot of time in the bowels of the corporate product over 10 years' the other one - the latter just WILL go away if I switch and is absolutely not useful elsewhere

Re: Ask HN: How to reskill without losing income?

#10

If you have an employer, this is usually a pretty easy sell. Approach your boss about transitioning Aging Product X to a new technology stack because the current one is becoming defunct. Of course this will require some training for you, but it is easier to teach you a new skill set than to hire someone with that skill set and get them to learn about Aging Product X. If you aren't employed and are contracting/freelan…

Is convincing employers to transition technology stacks really something that is generally considered easy (or even doable)? I'm stuck maintaining 'enterprise' software running on VB6 and ColdFusion 9 and the idea of getting my employers to sanction a migration to something newer is laughable.
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