Planning for Not Working.

Here is a great article about not running out of money in retirement.  For our purposes we will consider this the endgame aspect of retirement where after you hit your 60's you may want to slow down from your already long lived recreational lifestyle of teaching tennis or doing whatever it is you like to do best.  There comes a time when you have to face the possibility that you can't generate enough income through your avocation to keep the bills paid.  This means long term planning for not running out of money.

The central aspects of this are being conservative and keeping track of expenses.

One of course is social security though it may someday only amount to a utility bill payment for you if you are in your 20's or 30's.

A private pension in the form of an annuity is one approach that merits a strong look.  I am using that as one form of cash flow in a total of at least six I have planned to receive.  An annuity that lasts your lifetime is a relatively solid way to guarantee income throughout your life.

Laddered annuities for specific periods of say 10 years can also move you further along the timeline until you reach a point where only basic necessities are what you might worry about.  This gives you a higher payback for your money since it is not for your lifetime but a fixed period of time.

A target retirement fund ETF  in an IRA that represents the date you must begin to take withdrawals will allow you to at least have another stream of income come online as the laddered annuities drop off and you have gained the additional time for growth from the balanced investments that are within the target fund.

Stock ownership in a taxable fund that is your long term fallback that if you sell them you will only pay capital gains and you may never actually sell them.

Royalties and rental income if you have intellectual properties or real estate that generates income.

Work that you do to keep busy and enjoy life such as teaching tennis.  I have known many teachers that worked into their 80's since their skills are still evident to beginners and if they have been involved for a long time they have a reputation that will carry them forward.

Finally, here is an article to help you determine if you are ready to retire.  Notice they mention one of the six reasons is that you like your job.  If you like it, it's not a job, and if you love it there is no work involved so you are retired.