In the fwiw dept. I just posted this to FB, and will share it here in case it is useful.

Some things I've learned in the process of getting ready to retire that might be helpful to many of my friends who aren't that far behind me, especially for those of you who are of moderate/modest means, as am I.

1. Apply as early as possible. You can apply for Social Security 3 months in advance of your retirement date. The same is probably true if you are vested in a state, federal or local government retirement plan. Neither Social Security nor other pension plans will likely be able to nail down the exact amount of your monthly pension until you actually apply and specify the date of retirement. That gives you some time to plan and save up to get through from your last pay check until you are receiving your full monthly retirement checks, gives as much advance notice as possible of what your monthly income from pensions will be so you can plan not just short term, but also longer term and contemplate any cuts in expenditures you may need to contemplate going forward. Look
at a calendar and figure out when your last pay check will come and when your first pension check(s) will come.

2. You will need to have some savings to live on before your first checks arrive. Plan on having the equivalent of 2 months take home pay saved and designated for living expenses until you begin receiving your retirement pensions, so that you don't start your retirement "in the hole" financially.

3. Apply for Medicare 3 months before you are age 65, even if you plan to continue working. Realize you will be billed for the premium and plan accordingly. If, like me, you are also retiring at 65, which is a year earlier than my full retirement age, also plan on paying the first 3 months premiums out of pocket and save up for that. Medicare eligibility begins the month in which you turn 65. In my case, I am eligible for and have applied for Medicare effective November 1. I will not be 65 until the latter part of November, however. If I also retired November 1 the amount of my Social Security pension would be based on a retirement age of 64. I will receive 8% more per month by retiring Dec. 1, after I have attained age 65. Since I am applying for benefits a year before my full retirement age of 66, my monthly benefit amount will be 8% less than had I worked another year.

4. Some of the above I knew before I applied for retirement, some I did not. I'm gonna be OK with it because I am frugal and already have savings. Had I known all of this before I applied, I perhaps (but not certainly) would have put off retiring for another 1 or 2 months in order to save a bit more to maintain what I consider my minimum cushion in a savings account after the above noted expenses that will need to come from savings.

5. If you have dental or vision insurance through your employer, get vision and dental needs taken care of while you still have insurance. Since most dental and vision plans still don't come close to covering the cost of lenses, glasses, crowns, etc. also plan on having the money set aside to pay off your share without having to put it on a credit card before your retirement date. You don't want to go into retirement with unplanned credit card debt.

Hope the take away is that if you don't have money saved, the transition from full time employment to retirement income is not seamless in terms of cash flow, but thinking, planning and saving ahead can make for a smoother transition - or at least not leave you surprised.