IMHO, if one is concerned about having enough money to last during retirement, try to stay employed until can qualify for Medicare. Sometimes a big age gap between spouses may not have that possible for both - but the health care exchanges available are a help beyond COBRA time frame.
Many on this thread have not ācounted onā Social Security income, but at least know what makes sense for your situation on when to draw the SS.
Be sure to take advantage if you have some age 65 savings - sometimes with certain home property tax costs (for us small amount, but it is a savings); we actually get a 10% senior discount on our city water bill. At certain restaurants, getting a discount on meal (Dennyās, AARP 10% off, and DH also has a Dennyās ap) - I tip extra at places like Dennyās because the help works hard and deserve a good tip. A friend sent a huge list of what use to be places with Senior Discount - a lot of that has gone away, but some is still there.
Gas/expenses on work commute are easy to add up. We definitely use less gas generally too - we can plan shopping trips and use less gas on errands.
Having a newer car at retirement is also a good thing, as it delays a car replacement.
Once DH no longer wants to keep up the yard (1/2 acre, but some of it is wooded) is also about the time he will give up his local hobbies and be willing to move near the grandkids (another state). I have a fund building up to do some home improvements, so when it is time to sell the house, the work has been spread out over years. Baby steps. Once we have spring weather (it was 67 degrees today, but we will surely get cold again - and in our area, best to wait until after April 1st) I will add some more ācurb appealā perennial plants - desire to have different things blooming at different times with good looking spring/early summer (which is the target time for selling our house, but years down the road I believe). This is the 3rd year for doing the extra with spring plants, and DH has been helping me with this task too.
One has to know their income stream after retirement. So will they have a pension, will they take money out of 401k or other investments, do they have annuities set up with taking monthly cash out w/o penalty, do they have income properties that are generating income?
For us, it took a little time to make all the transitions with health insurance/Medicare, social security, setting up annuity monthly cash payouts - DH and I retired at different times. I took SS and Medicare when I retired, and DH retired months earlier but started Medicare B at same time I retired. DH also delayed his SS till some months later, at the same time we had annuities making the monthly payments. At first we started taking a certain amount from annuities, but this year we are maxing what annuities will cash out each month w/o penalty to build up funds for home improvements. We have a separate investment account which is our money/not retirement funds, which also can be used for home improvements and other expenses.
SWAN - sleep well at night. Do the decisions that do not have you stressed out.
Some people want to travel right away when they retire - and they set up a budget for that and a source of funds for that. DH wants to be a home body after having to travel a lot for work, globally and nationally. That keeps most travel expenses to just me, and I have just one overseas trip planned and one airline trip planned for helping with the grandkids. We will have a few gatherings out of state that will be road trips/generally lower cost.