We entered retirement in phases. Came up with a five-year plan of maxing our contributions to retirement plans, paying off all debts, selling things, and getting ready to live in paradise.
Bought a fixer-upper house in the Caribbean and moved there in our early 50s, and lived there about nine wonderful years. We left behind the high stress and long hours of Washington, DC, and had part-time jobs in the US Virgin Islands that paid less but gave us much more satisfaction and control over our days. We made lifelong friends and had great experiences. With a lot of sweat equity, we sold the renovated house at a great profit. Moved back to the mainland US due to poor 3rd world health care down there and to be closer to aging parents.
Back in the US, we continued enjoyable part time jobs on our own terms with lots of flexibility to allow travel. We've made a lot of long bucket list trips, including many in our RVs. Never regretted leaving the big salaries behind because life has been so rich ever since. Now about 20 years later we are almost fully retired and do the occasional assignment for fun. Still traveling.
I think this was an ideal path for us to retirement. No sudden change from work to empty days, and freedom to reinvent our career paths into things we had long hoped to do for a living.
A big key to retiring young and being able to pursue your long-held job interests or hobbies IMHO is to be debt free and have some savings that can grow.
