You've done the outer work. Congratulations! Now it's time to do some inner work. For me, this is similar to the obstacle I had to overcome 3 years ago before FIREing. What happens when you do imagine pulling the trigger? What scenarios and feelings come up? Follow those feelings, especially ones of fear. Examine any fearful scenarios that might be holding you back and ask yourself what you could do to prevent the scenario from happening and also what you would do to help should that scenario arise.
You mentioned several ways your job serves you and several ways it does not serve you. So, no wonder you are ambivalent about leaving it. This is very common. How much do you value those things on each side of the ledger. Every difficult decision in life is an exercise in clarifying values.
Is it actually unhealthy/redundant/ridiculous to keep repeating things you have become an expert at. Some people value mastery above all. Where is mastery in your priority of values? Perhaps it is unhealthy/redundant/ridiculous to keep working your job for possibly other reasons you have?
Tell us more about the "pull to a new life." What is it? How much do you want it? Why do you want it? How much are you willing to give up to get it?
Working is not an identity. Working is just something you are doing or not doing. Who are you if you are not working? Who does society or your friends and family say you are if you are not working?
Be careful of the assumption that you should stop working just because you reached your FI number. Mostly people here make that assumption because of the implicit goal orientation of this community, which is great for support. I love that about this community. But challenge yourself on if you want to quit working, quit this particular job, or quit doing certain things in this job.
Good luck, my friend!
Thanks
@MadBikePoet for posing these great questions! I'll attempt to lay out some responses.
Regarding fearful scenarios that come up when I consider pulling the trigger, there's "what if I'm making a HUGE mistake leaving a good job that I worked my ass off to get to?" There are some vague fears around not really trusting the math of RE, and some nerves around pulling off the 'stash vs. contributing to it. I also fear I'll let my colleagues down by leaving. I know that's a bit narcissistic, but it will have been 9 years when I pull the trigger so there's some element of "family" there. I'm also afraid they'll try really hard to convince me not to go, and end up caving into some other arrangement.
I do absolutely value mastery, but have come to a place where I'm no longer growing and feel the need to challenge myself if a new way. Although my job is complex, I can pretty much do it in my sleep at this point. In addition to mastery, "learning" is a key value that I'm just not getting anymore.
The "pull to a new life" is somewhat vague, but I feel like it's about independence and greater risk. There's a lot of safety in being an employee vs going it alone. I've had 2 new bosses in the past year, and I'm just at a place where I don't want a boss anymore. I feel like I'm too old to be explaining myself! I know we all have to answer to some one, but I'd prefer it be a client rather than some corporate manager. I also have one big project outside of my job that I'm planning to throw myself into. It's risky and therefore kind of scary, but it could also end up being really fun. And if I fail, I won't have to worry about not making money off it.
I've got some work to do I "who I am/who does society/friends/family say I am when not working." I'm not sure I can answer that right now!!
I don't really want to stop working entirely, but I do want a nice long extended break so I can chart the next few years, do some extended traveling, and work on that big project I mentioned. It's entirely possible I'll do some consulting or take jobs on a project-by-project basis, rather than being tied to the hamster wheel.
Thanks again for these thoughts to ponder!