I've been thinking about and planning the transition, and it's very scary.
I had a similar experience in 2005: I had spent 5 years aggressively paying down debt and avoiding some of the more lavish spending I did to get into debt. When I finally became debt-free I found myself worrying about spending and even how/where to save.
For a brief time it was more stressful to me to have 'extra' money because I had so many potentially wrong decisions I could make with it. When you're in debt up to your eyeballs there is little question what to do with income!
What helped me a lot was that I took control of my money future in 2000—as opposed to making money choices on the fly and being willing to pay more later for enjoyment now—and having participated in forums like this so I understood the choices.
A more specific thing I've found helpful very recently is to make a decision matrix. What is in my power to do, which of those am I potentially willing to do, and what is the outcome? Makes the decision a hell of a lot easier.
I also addressed worries independently. The self-FUD tends to multiply amorphously. I literally made a list of each fear to pin it down. Some fears were obviously silly and reactionary. Others I realized I had already planned for and knew what to do if the feared result came about.
Well heck, here is an actual such list I made 13 months ago and updated last night. The journey from then to now has been fraught but well-guided by this list. The subject is my desire to retire and the fears and/or good reasons blocking me from doing so at the time.
- Have to pay back $<redacted>k signing bonus if I quit before 12 months. Feb 12 was my start date, so the 15th, 22nd, or 28th are candidate last days, or maybe into March depending on how they count service months.
- Bonuses. I'm under the impression the yearly bonus is bigger. No idea if it's worth sticking around for. Basically I'd optimize by leaving just after a quarter or year ends, so early October, January, or April. Nah. Not a factor, although if I give 2 weeks' notice now I'd get into October
- Avoid any negative mark on my manager by sticking around at least a year, so see the first item's dates
- Fear - catch-all for income, portfolio survivability, market concerns, and similar I think I'm over the fear, and I know generally what I need to do if all things go poorly over the first 18 months.
- Uncertainty - catch-all for sequence (do this before that, e.g. medial checkups) I'm now convinced anything I need to do can be done more easily when not working. My only uncertainty is health insurance over time.
- Money - items that don't fit into the previous two such as wanting to do expensive home fix-ups Have that covered with an extra $<redacted>k over my 2x$<redacted>k/year cash pile
- Inertia / social pressure - This may become a problem, but maybe this doesn't even belong on the list Nope. It will be socially awkward to leave as usual, but inertia is no longer a blocker.
In this case, my fear of running out of money too quickly is assuaged by my cash stash and the knowledge that I can go back to work if I need to, which also covers health insurance worries. I can choose to maybe go back to work in 18-24 months (if market crashes right after I retire and I don't find a way to generate semi-passive income), or I can definitely keep working now. Choice seems much more straightforward!
When separated and analyzed one by one the fear is much easier to address than when vaguely wondering about worst case scenarios.
