Career Crossroad – Need Advice Please

It sounds like you have a ton of relevant experience -- I would love to work with you -- and your main hurdle will be the interview process. Never fear, this too can be engineered :)

Some thoughts:

* Practice makes perfect. Practice your story, say that you're looking to a more exciting startup environment. Practice with friends or your computer camera.

* You're probably going to have to move when you start the job. Not a lot of startups are remote-friendly. I would recommend SF or NY. You're a painter in the Renaissance -- if you want to stay on top of cutting-edge techniques, best move to Florence.

* When you're talking to startups, don't mention the word IT, and change your title from "Director of IT" to "Infrastructure Lead" -- it makes you sound more like an IC (individual contributor) w/ a DevOps role.

* Don't mention you'll take a huge pay cut. That sends a bad signal, even if it's true. It's like putting a sign on your back that says "KICK ME."

* Apply for lots of jobs. Make different versions of your resume, with a PO Box with a local address on the top. No one will likely check (though you can get the PO Box if you want) -- and it will make recruiters far more likely to call you. If they ask about your location, say "I am currently working in Houston, but looking to relocate to [TARGET LOCATION] as soon as possible, for personal reasons."

* This is something I did that got me a lot of interviews very quickly: https://medium.com/@calcsam/outsource-your-job-search-3e9909...

Thanks for reading, everyone. I'm hoping to gain some insight from other IT folks out there as to where I can go from here. I'm really burning out and could use some solid advice.

Cheers!