"When is the best time to retire?"
Never is the best time to retire.
I was asked that question in an idea list about why I think the retire early aspect of FIRE is a terrible idea. I'd tell anyone who would listen to forget about ever "retiring." Focus instead on the next step or next chapter and using you're earlier professional years to create a transition to a post retirement period that is very active and potentially lucrative.
I was asked that question in an idea list about why I think the retire early aspect of FIRE is a terrible idea. I'd tell anyone who would listen to forget about ever "retiring." Focus instead on the next step or next chapter and using you're earlier professional years to create a transition to a post retirement period that is very active and potentially lucrative.
1. "What would you do if money was no object? Do that."
2. Pay your dues
A good financial base or emergency fund that could cover a couple of years worth of expenses could provide fantastic optionality at a pretty young age. I got laid off at 35 but we had about a year and a half's worth of expenses set aside that we could have used before taking the desperate step of tapping my 401k.
The job I got laid off from was a pretty good job and it definitely helped me build both types of bases mentioned above. I then spent another year building these bases before moving on to my next and current professional chapter as a self employed investment advisor.
3. Freedom
I don't think of myself as retired, I moved on to something that gave me more flexibility, more ownership of my time to do what I want. Some will call that retired but it was actually the beginning of a period where my workload increased dramatically building a much more rewarding career than I ever would have had as a W2. I was unambiguously freer than I'd ever been as an adult but working hard than I ever had.
4. You might need an income after you "retire"
5. Seeking out new professional endeavors
Writing though did become a new endeavor in terms of what it led to. I was a regular outside contributor at TheStreet.com for eight years. It also led a pretty great side gig at ETF provider, AdvisorShares. Writing also gave an opportunity to go on stock market television many times over a 5 or 6 year period. That was a fun thing as a unique set of experiences. Where writing led to lucrative opportunities in the past they could do so again so I continue to write for that optionality but more importantly because it is fun.
6. Immerse in hobbies or other areas of interest
A non-creative hobby, like stamp collecting. There are people who essentially know everything there is to know about stamps because it interests them and is fun for them. Same with other collectibles. Although time consuming, this is a path to an income stream too. Even though these sorts of things are time consuming people have a blast with time spent this way. Even if there is no income stream to be had, this is a productive use of time, productive because it is enjoyable.
7. Teaching or coaching
8. Actively volunteering
9. Don't just wait to die
The point in idea number 3 is that I started this transition in my 30's, very early as per idea number 4, after building the base I needed in my 20's, paying dues. As the years have gone on I've been adding ideas and endeavors into my life such that if I ever stopped being an investment advisor (seems unlikely) I would just be giving up one thing in my life out of many things going on which isn't all that disruptive or difficult.
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