How do you handle a multi-year employment gap as a developer?

Also curious what responses you get. Kind of in the same boat but not a dev but pm.

Hi, I had a similar gap in my experience - I was doing web development, after that some project management, then I went back to university and then I went back to programming.

At first I couldn't find a job because I was looking for web development jobs, and at that time that's what everybody did (2011). I figured out I will never find a job like that, so I decided to start doing something that not many people were doing but looked like it had a future - Android mobile programming. Also, not many people had experience with it so even having a few months experience could position you heads and shoulders above the rest.

Long story short, in 3 months I had published 3 apps in the market and then I started looking for a job - and got 10 interviews scheduled in 14 days.

So the advice would be - don't do the same thing everybody else does, but invest a few months in something more niche that has a future. At the moment, data science looks the most promising (to me).

If you are proactive in your job search you would not need to worry about changing your resume since you’d be tweaking them as you apply for jobs. Think of your self as a product and your resume as a marketing ad.

As a founder, I would expect to see the truth. In addition, founding experience is incredible for startups that are hiring because it means that you are capable of doing your job and figuring out how to solve problems on your own without being a burden on your teammates. Don't be embarrassed about your past. It's way more valuable to show you are able to learn from your mistakes, and own up to the risk you took, while showing you can handle that risk.

As a developer, your skills are most highly valued if you can show your work and prove you get work done on schedule. When hiring developers, I ignore most everything else, since the work ethic and skills to get the job done are the reason I'm hiring you. If you can get the job done on time, and work in an organized manner, I couldn't care less about whether or not you spent the last 5 years in retirement (but that would be a red flag since the likelihood of that timeline is ~0... That's not relevant in your case though!)