[wintermutestwin]

>I'm wondering if I should decide on taking the plunge, or at least plan for it... since I do feel the friction in transitioning getting a bit higher as I spend more time in this field.

I spent 25 years in tech before transitioning into non-profit work. The friction/inertia was a bell curve for me and was primarily driven teo things:

Money: For the first 15 years or so, the money/benefits were the archetypal golden handcuffs. At first, the more I made, the more financial responsibilities I took on. But I didn't keep upgrading my lifestyle past a certain point and I kept increasing my savings rate. At the end of my time in tech, my savings allowed me to choose my career without consideration of the money.

Skills: I realized I wanted to do something else and so I shifted my career away from narrow specialization in hands on tech to more strategic roles (product and people management). This gave me a wealth of skills that were more easily translatable to roles outside of tech.

Note that I am not specifically advocating for the path I took, but just giving my perspective on how it worked out for me.