Changing careers: website maintenance or technical illustration?

Hello, everyone! I’m hoping to get some advice on how to make a career in the technical field without any advanced technical background.

Just to show how little technical background I have: Website creation was more of a hobby than a path to a job (mostly because my family discouraged it). I’d spent most of my working adult life in retail and customer service. After quitting my job a couple of years ago, I used the extra free time to become better acquainted with my hobbies: website creation and art.

Rather than return to the drudgery of retail, I want to use these minor skills to build a career I actually love.

The minimal experience I have:

  • I’ve done HTML and CSS coding since the mid-90s for personal websites.
  • I occasionally use Javascript and PHP for snippets like showing the date for copyright purposes and including files so I don’t have to repeat code.
  • I have a few self-hosted Wordpress sites. I’ve edited theme code, created child themes, created backups, and changed passwords through the MySQL database.
  • As for art, it’s comics and illustrations, but I can adapt to most styles and art software.

Here are my main questions:

  1. Would it be easier to get into website maintenance or technical illustration? Which has a minimal barrier to entry?
  2. What kind of work or portfolio would I show for website maintenance? Would it matter if my portfolio consisted of my own websites?
  3. What do hiring managers look for in technical illustration portfolios? (How many pieces? Do they have to be very technical? What about help manual illustrations or step-by-step instructions?)
  4. Is it going to matter that most of my work history is retail? To be honest, it’s not something I’m very proud of, especially at my age.
  5. Since getting a job anymore is more about who you know, where I can find other website managers and technical illustrators?

Thank you for your input!

In not sure that “website maintenance” is really a much of a job; companies don’t really hire people specifically for a role like that because either it’s an admin who updates company websites as a minor part of their job, or it’s a developer (/designer/copywriter/etc) who works at creating websites/web apps. There used to be “webmaster” as a job category, but that was a very long time ago (~20 years ago, ish).

Web development, yes. It’s hard to get a first job, often very hard, after that becomes much easier.

Both that & illustration place more far more emphasis on demonstrable ability rather than qualifications. However both also place very strong emphasis on experience, which makes getting first jobs difficult: there are lots and lots of people with basic skills. Illustration is naturally a lot easier to demonstrate ability in. There are many more opportunities for programmers. Programming pays significantly more.

You’re trying to demonstrate skills, so in that respect no. However, the flip side of that is it doesn’t really demonstrate anything about working with and for other people and it makes it a little bit difficult to assess ability.

Need a portfolio, has to be only top notch work. You’re wanting specific work, so needs to reflect that, so either technical illustration work you’ve done for others or mocked-up stuff to show it in context. For general (editorial/advertising) work, normally an ability to work across a variety of styles and applications (of the work, not computer applications). That’s not necessary, can work in one style, it’s just helpful to be somewhat chameleonic. Note I’ve known two people who each did one specific type of technical illustration in one style: one was originally a biologist & one an engineer, and their technical work was based respectively on scientific & engineering/CAD knowledge. More specialised, more chance of being stuck if jobs dry up.

Being able to design is more than useful. Being able to animate is more than useful. Being consistent is incredibly important (this is experience). Self-promotion is incredibly important.

Yes if you’re going for first job working full-time for one employer. Not so much if you’re working independently (no-one is really asking in the latter case). No for jobs after you have experience.

Probably Reddit for a start, go from there.

[edit: experience – for degree specialised partly in illustration, then worked as a designer and illustrator for several years prior to settling into programming as a career]