Ask HN: How to reskill without losing income?

Hiring managers, you are going to get what you ask for.

1) You have experience in a corporate environment. You know the kinds of things that terrify them, and you know the kind of experience they expect from the companies they interact with. This knowledge and perspective is incredibly valuable to any startup in the b2b space.

2) The problems you solved - while maybe specific to the corporate product - generalize well. There's a better-than-even chance you had to deal with managing data from multiple inputs, scaling and performance, build management, testing issues (even if experience in pain of not having it), product delivery, and/or user experience. These things are not as different as you might expect.

Reference: I spent many years working for a Large Bank developing in-house software before transitioning into the startup world. THe biggest problem I had faced was my complacency - somewhere along the way I gave up on pushing to do things better, and it took me a while to get that back. In that way I was fortunate that I came to work for a company that gave me the time I needed to do that.

1) You have experience in a corporate environment. You know the kinds of things that terrify them, and you know the kind of experience they expect from the companies they interact with. This knowledge and perspective is incredibly valuable to any startup in the b2b space.

2) The problems you solved - while maybe specific to the corporate product - generalize well. There's a better-than-even chance you had to deal with managing data from multiple inputs, scaling and performance, build management, testing issues (even if experience in pain of not having it), product delivery, and/or user experience. These things are not as different as you might expect.

Reference: I spent many years working for a Large Bank developing in-house software before transitioning into the startup world. THe biggest problem I had faced was my complacency - somewhere along the way I gave up on pushing to do things better, and it took me a while to get that back. In that way I was fortunate that I came to work for a company that gave me the time I needed to do that.

Taking a less-senior position for less-senior pay in the new tech stack is probably going to be more money per unit work, and my experience has been that you can get people to work with you on titles and that nobody actually knows what you got paid at your old jobs.

I mean, sure, if you really are that good and actually get things done regardless, your way might be better. My experience has been that good contractors going direct get a little more money than you can get through a body shop or as an employee. But... I'm talking like top 5%. Most of us aren't there. If you are mediocre... if you are merely 'good enough' - being a "real" contractor is difficult and under-remunerated. (to be clear, it's under-remunerated for the top 5%, too... but those people work like crazy all the time, so it's not like the customer is expecting more out of them.)

If the antiquated tech you have experience in is more complex than the new stack (antiquated tech usually is), it sometimes works as a positive: you have a perspective 'native' users of the stack don't.

At least in my experience as a contractor, people are looking for contractors because they have lots of experience in this technology but don't have the resources or time to devote to their project full-time. So if you have little experience in a tech stack, you may have a hard time finding this kind of work.

I simply built a side project (I did this with Rails) and then got hired full-time at a startup to do Rails work. As with everything, YMMV.

I did this with a twist, if you can swing it.

1) Find a local client that is looking to do a project on the cheap - someone who has an Elance budget but is uncomfortable dealing with someone remotely.

2) Propose to do this project pro-bono if they budget the availability of a sr. resource for mentorship - say 5 hrs a week.

3) Put in reasonable constraints AFA availability, estimates, testing, etc., that befits your jr. status. Ultimately you want your mentor to guide you as much as possible and the client to understand this relationship. It shields you from unreasonable expectations.

Doing this, a) you get to work on a real-world project (it pushes you forward faster with issues that a side project usually doesn't... if for nothing else you're interacting with others on their schedule, their whims), b) you get on-hands training, and c) you get access to the networks of your mentor/client if the relationship is fruitful.

I did this back in 2012 - the only work I had done prior to this was going through the Hartl Rails Tutorial. The initial project lasted for 4 months @ ~20hrs/week and I was paired with someone who was an early engineer from Gilt Groupe. During this time I continued to work my day job.

Toward the end of that project my mentor brought me the opportunity to bid a long-term gig. I quit my job the day the that contract was signed w/ about 3 months of financial runway. A few months later he brought me another, and that work kept me going for over a year at an overall cashflow greater than I had made at my enterprise job. Toward the end of these engagements I started consulting for a local startup which converted into a FTE situation for a year and a half. Now I'm back consulting on another long-term project by way of a recommendation from the design team on one of those earlier projects.

The one thing I will say about consulting is when you're starting out communication is more key than technical skill. Just be open w/ the client, you're both making concessions in such a situation.

Occasionally however I run into people who have absolutely no side projects and have been doing the same stuff for 10+ years. I'm a Java expert (or .NET or C etc.), they claim. When I ask them if they've tried anything else besides that one thing they've been doing over and over for a decade, perhaps a side project, a toy product, some contribution to OSS in the new paradigm they apparently really want to work in, I get responses along the lines of "I'd never work on something I'm not being paid for, I'm a serious professional that's irresponsible".

Er.. ok. So I'm supposed to hire you, take a huge risk not knowing if you can pull this off or not, train you for a year to do something you have 0 familiarity with, and then you might peace out right about the time when I'm starting to recoup the onboarding costs? I'll pass. Candidates who already demonstrate a lot of interest, side projects, and desire to learn outside of their 9-5 will win any day of the week with me.

I emailed him and asked if he wanted to do the thing he was clearly passionate about full time.

He aced the interviews, came out and built our app. About a year later one of our founders left to start a new company. The founder recruited this guy. Within 18 months, their company sold for a few hundred million and now instead of writing the C# code he hated, he has now helped build an awesome company, build a whole new skillset and built his leadership skills. Not to mention the fact that his wife and child are basically taken care of for life because of this decision.

I was hired into my original position here knowing absolutely nothing about the language or the technology. Like you, my manager just wanted raw talent that could be retrained and it worked out for him. That's probably colored my interviewing practices over the years, but an awful lot of people don't want to take that kind of a risk.

I would have just looked in man pages for the switch that I required or the usage. For commands I would hardly ever use even on a production system. He told me my Linux skills were weak ha. It may be true, but at least I could find the answer without google. The hosting company I interviewed at told me to feel free to Google it, "I'm good I just need man pages."

It's like knowing how to spell. Just because you don't know how to spell a word doesn't mean you don't know how it's used in a sentence. If you know how to locate the word in a dictionary you have the right answer.

Yes, they do. Moreover, you don't even get a junior position because you don't have adequate education and/or experience.

There are different things you learn when you've coded in a mix of C/C++, Java/C#, Ruby/Python, and perhaps something functional. But having all your experience in one of these buckets is more a sign of a junior developer, or the old "one year's experience ten times".

For example.

If you are a C# programmer who has never done Java programming. It takes you 6-12 months to get reasonably up to speed with the JVM, standard libraries and idiomatic coding. Let alone any dependency injection, web framework etc. libraries.

Why would the Java shop pay you the same as a developer who has spent the last 5 years doing Java full time who can be productive in Java right away?

That said, I think reverting someone to junior status is too extreme. A slightly lower salary or requiring an 'ace up your sleeve' to compensate is probably fair.

You get an up vote for that.

He was a fast learner and had no issues getting up to speed in a reasonable amount of time.

I like to talk to people with a variety of skillsets and interests in their background and try to figure out how to leverage those towards the work we do.

Bonus: having a huge diversity of skills is kind of like having a deep bench to work with