How is one supposed to feel as they approach their retirement? And what does one do with their free time LOL?

Grab your old boot camp / basic training duffel bag, and SpaceA around the world. At least that’s my plan,

Best advice I was given, so at least one productive thing a day. If you have no hobbies pursue some. I always liked photography but never did much. Now I enjoy wildlife photography, especially birds. Volunteer for a group that interests you. A became involved with the VFW. when you go shopping go on off hours. No lines and easier shopping. Foremost, enjoy life !

CMSgt James Nolan retirement depends on what you want. If you are retiring from the service, do you want to work in the civilian community? If retiring from a second or third career, that is also different.
I was given an early retirement from the Air Force, I walked into a civilian position the day I retired from the Air Force. I worked a total of 17 years in my field atn2 different hospitals. When I retired from anesthesia I taught at a University for 4 years, to help ease me into retirement. When I had enough, I resigned. I still enjoy life. I am involved in volunteering my time a certain amount each month, involved in church activities, my grandchildren, working around the house, riding my bicycles, and traveling. There are many opportunities out there when you retire.

Sgt (Join to see) this will be to proverbial “toe dip” into the pool. 2-3 yrs and hang up the Law Enforcement spurs and then it’s completely on (or off HA, depends how one looks at it) but yes sir. There’s fish that need catching.
We do intend to do some traveling, because unlike while working, nobody is telling you to be back at work on Monday....

Hope your retirement is going as well as I would like to think mine will sir.

CMSgt James Nolan Retirement is a major life change and is something to look forward to. For me, I worked 33 years on the Space Shuttle Program and was probably too invested in my career. Even though I knew the program was coming to an end, it was still a shock to my system when the end did come. I retired one month after the last Space Shuttle flight, and felt the loss for two year afterwards. I like to travel and read in my free time, and manage to stay busy, and I am never bored. In Florida, I would look at the fishing opportunities that you have there, and also travel. Good luck.

This is an easy fix, Chief. All you have to do is stay in.

Haven't discovered the free time thing. Retirement is one of the busier jobs I've had. You're best mentally orienting yourself like I did. That's saying you live multiple lifetimes within one. This one is closing and you're off on the next one. That time is past. Don't deny the "it's time" feeling. Don't go with herd mentality. Live, play, and do what interests you. For us, it was getting away from stop lights. Rural, acreage, monthly Costco run. Why? See the Milky Way at night. Nature at the doorstep. Quiet. Clean air. My only hard requirements were good local beer, getting a Gator, internet, and the XM works fine so I don't have to listen to Country Crap. Stick with your habits. Your eyes open at 0500; that's OK. Beautiful sunrises. Other advice is not to "help" your new place get better by mucking with local politics. The major purpose of retirement is to reduce stress. Why invite it? Some people can't seem to quit and keep involving themselves in stuff to stroke the ego. That'll take years off your life. Don't be in a hurry to die.