For people interested in sailing you could do worse than check out some of the more popular sailing YouTube videos out there. That's how I got started. The first step was realising that "regular" people like me could do it and it wasn't just the preserve of yacht club douch bags (they're still out there I'm sure). The fact that Brian from Delos turned out to be an (ex) programmer was also a pretty big inspiration to me.

Here's my favourites from my subscriptions.

- SV Delos - https://www.youtube.com/channel/UCvLc83k5o11EIF1lEo0VmuQ / https://svdelos.com/ - Ex programmer, may have worked at MS

- Ran Sailing - https://www.youtube.com/channel/UCLYd5EnTTwUKhouIkHoqzMw

- Sailing Uma - https://www.youtube.com/channel/UCXbWsGV_cjG3gOsSnNJPVlg

- Erik Aanderaa - https://www.youtube.com/channel/UCUH6fLsV6J7WKEmf7vJKfAw

- Sam Holmes Sailing - https://www.youtube.com/channel/UCE4vct4tqxSuG4JH6vMVZSA

- Sailing Project Atticus - https://www.youtube.com/channel/UCF45qzioJ_0FVdZVG2NJTWg

- Christian Williams - https://www.youtube.com/channel/UCS6qLhh5YBeL42HRMh3dc1A

- How to Sail Oceans - https://www.youtube.com/channel/UCTmJcC_Yw3IL7Bvtf_7nTLw

- Sailing Yacht Florence - https://www.youtube.com/channel/UCkExLY1E6CE-GPsMCdSjmxQ - The guy is/was an electronic engineer?

- Calico Skies Sailing - https://www.youtube.com/channel/UCGFbz7qMXCm28EPCkZWSMKg

- Sail Life - https://www.youtube.com/c/SailLife - Lots of DIY boat work, but nicely done.

- Sailing Kittiwake - https://www.youtube.com/channel/UCT9U1fPkHj0mJjC4LWGH26g

- Gone with the Wynns - https://www.youtube.com/user/gonewiththewynns

- Sailing Soulianis - https://www.youtube.com/channel/UCRqsOR0Y2zru-jXSzLcMcxg

- Sailing La Vagabonde - https://www.youtube.com/channel/UCZdQjaSoLjIzFnWsDQOv4ww

- MJ Sailing - https://www.youtube.com/channel/UCvJGfEEg7R04-ifkg_FFnaw

- Sailing Ruby Rose - https://www.youtube.com/channel/UC9rRsBE2nFbnUSjtmv6Jq6w (not so keen on this one now, lots of catamaran reviews)

It's important to realise that not everything these people do is always a "correct" or good practice, but watching all of these people /definitely/ helped me get my qualifications down the line, and I still enjoy the escapism of watching someone sail around the Bahamas on a cold winter evening (my boat is up on the hard in N Wales, UK. The Bahamas it isn't).

For me (YMMV) another thing that helped was joining the local dinghy sailing club. I'm really not interested in racing, but it was cheap (they rent out boats, or you can crew on someone elses), and a lot of what I learned about sailing there was directly translatable to the 43ft (13.1m) boat I now sail.

There is also a sailing slack run buy a couple of tech people that you might be able to join if you're interested in getting started and want some more pointers.

https://join.slack.com/t/sailboatguide/shared_invite/zt-g0b1...

*edit* And if anyone is curious, I post about my boat adventures here https://twitter.com/SYSilverGirl