Some of us are organized and some of us are not and the rest of us are ‘sorta/kinda’ organized. I’m in the ‘sorta/kinda’ organized group.

I am, however, heavily invested these days in teaching others a process to follow when thinking about their future retirement. I’ve created an internet school called Successful Retirement Secrets™ where I’ve written and published two courses on the topic. Look at the image on the right and watch the free previews.

In the meantime, those of you thinking of soon calling it quits, are either excited by the prospect or somewhat uncertain. Fewer jobs have mandatory retirement ages these days and with so many of us realizing our savings are not up to par, are trying to figure out how to develop a positive cash flow when we tell ourselves we’re now officially retired.

Here are a few steps I think you should discipline yourself to follow:

Put together an inventory or financial statement. It doesn’t have to be to the last penny, but documenting what you have that can be used either directly or indirectly for paying for things you absolutely need is very helpful psychologically. Send me an email and I’ll send you a relatively simple form where you can list everything.

Set yourself a note on your calendar to update it periodically. This needs to become an automatic effort as the years roll by. It tells you, and presumably those members of your family, that all is well and there is no need to freak out. Or not. For most of us, retirement is a 25 year trek into an unknown future, and none of us have a clue how it’s going to play out. One way to get ahead of that, at least a few years from now, is with some numbers that document to some extent how well, or bad, you’re doing.

While we’re on the subject of inventories, another inventory you should develop is what you want your life to look like five years from now. Make a list and keep it with the financial inventory. Describe things like your health. Do you need to move to a smaller residence? Are you as busy as you’d like to be? What are your financial goals? None of this has to be definitive like the financial inventory, but an articulation of all this creates benchmarks that will trigger happiness or fear. Since there’s no way to go back in time and try again, the sooner you realize a need to modify your behavior, the more likely you are to have a successful retirement.

Social Security is both complicated and simple. Making the mistake of signing up too soon is something you may not be able to undo. On one hand, there’s a high probability that it will be a critical income stream for the rest of your life and that of a spouse, assuming you have one. On the other hand, discovering at age 64 that you didn’t need to start taking benefits at age 62 and should have waited, makes no difference now. You’re locked in and apart from annual cost of living adjustments, you’re stuck with it. Make a real effort to explore the good and the bad involved in not waiting until your FRA, or Full Retirement Age.

I mentioned health in #3 above. For your life up to this point, health care costs have most likely been covered by insurance. Yes, you may have had some out of pocket expenses but nothing financially debilitating. Retirement brings a new kind of healthcare challenge that up to this point has not affected you personally. Now it could. If you become goofy and your brain is no longer optimal, it might create an expense that isn’t covered by Medicare and the typical medicare supplement plan. You need to figure out in advance how you are going to be cared for if you can no longer look after yourself. If you wait until it happens, it’s too late.

Attempt to create a budget and follow it. For some of us, this is almost impossible. I know it is for me. Again, this comes back to where you are on the spectrum of having more than enough money to last you through 25 years of thick and thin, to clearly not having enough. If you think you may not have enough, then establishing some ground rules for yourself and forcing yourself to follow those rules might mean normal satisfaction with life or it might mean abject failure. Your call.

Tony Kendzior \ June 21, 2019