[kelseyhightower]

1) The answer to this lies in the question. Agile is a practice and it'll take some to get up to speed. One path I took was taking jobs in tech support, answering phones calls, and finding opportunities to engage with the product teams. You can start by giving feedback on the top issues you're seeing and breaking down ways the product can improve to reduce related support calls. And Boom, you are now apart of the Agile process, providing a feedback loop that helps development teams incrementally improve the product. You also help reduce support cost; don't worry, if you automate yourself out of a job, there will be a better one waiting for you.

That's how you open doors for yourself. Many great Q/A and operations engineers started in tech support where they honed their troubleshooting skills.

2) Yes, I use to get those questions. My answer was, "I'm starting a family, and I'm looking for something a bit more stable, and bigger challenges than the ones I was getting on my own".

It's all about being able to demonstrate your skills. Some times it's whiteboard coding exercises or logging into a live system and "making it work". My IT certifications helped me earlier in my career and now things like GitHub and blog posts are a great way to showcase your skills.

3) Remember, you can always tailor your resume for the job you want. If you want to avoid looking over qualified, then re-frame your experience to align with the job requirements. Instead of "I ran a business doing X,Y,Z", you can re-frame it, "As a _ I did X,Y,Z".

During the interview you can show off your full skill set by giving deep answers demonstrating your understanding of the big picture and how to make a business impact.

If you ever want to discus this stuff further, shoot me a DM on Twitter, I've been where you are, and I know what's possible.