Let's first make two simplifying assumptions: first, you have, through personal responsibility or choosing the right work situation or just darn good luck, accumulated sufficient financial resources to continue to do the things and live in the style that you lived in the day before you retired. You're not suddenly wealthy or suddenly poverty stricken. If you are suddenly wealthy, then stop reading this and good luck to you, you fortunate SOB. Send me your contact information.
Second, you have no special health concerns that you didn't already have before you retired. You may not be quite as fast or quite as slim or have quite as much hair as when you were 25, but hey, you're doing OK.
You have no doubt had some vision of what your new status would be like, and probably even made some tentative plans -- I did. My vision went something like this: I will have all this new time on my hands! And more important, my waking hours will now finally be released from the many work-related constraints, that include having to get up in the morning and dress up and go to work, enduring the deadening 45-minute commute that never seems to get better. And then at the office I go to meetings with whiney colleagues that last at least twice as long as they should and never really resolve anything, and I do stuff which makes no real difference but does seem to matter to my average-at-best bosses. And I deal with people ranging from somewhat to very much younger than I. These are "colleagues", by the way, who don't know who the Beatles were, although I suspect that they do gossip behind my back that I don't know who Katy Perry is (who is she, anyway? Is she one of those ultimate fighter women, or is that Mohammed Ali's kid?). And they write "btw" and "LOL" in their emails. And I have to get a sandwich at the local deli and eat at my desk to catch up on reports and other industry stuff I am supposed to be up to date on, even though it's mostly repetitive and badly written. And then commute home, eat dinner, watch TV, go to bed, and then do it all over again the next day. Yes, I will be free from all this, and therefore I have many plans!
I will exercise more, both cardio and weights, every day, and also take long walks as this is proven to stimulate creativity. I'll have to bring a small note pad and a pen with me to jot down insights.
I will learn a new language or at least polish up an old one. Either something useful like Spanish or French, or something that will impress others like Arabic or one of the Indian dialects, but not something really hard like Chinese.
I will take up the guitar and learn to be the life of the party. Who doesn't love "Don't Think Twice, It's All Right?" or "Michael Row the Boat Ashore?" Or maybe try to learn the ukulele which is easier.
I will travel extensively to exotic places to which none of my friends have gone. Except they have to have a Four Seasons to stay in, or at least a Sheraton, and no current State Department warnings as to terrorist activity or amoeba that eat your brain when you swim in the polluted river next to your tropical paradise hotel.
I will keep up my contacts in my industry and keep up to date on whatever matters are important, mainly by chatting up my old buddies and by reading the numerous free industry newsletters that I never had time to read while I was actually in the industry. Probably people will ask me to join Boards or consult extensively in my specialty, once they learn that I'm now "available."
I will write my memoirs, a humble but compelling story of my career and the leadership I exercised in many important business situations. It will be laced with pithy observations and doses of modest humor. While it may not be quite the best seller that Jack Welch's was, it will be much less arrogant.
Well, that's quite an ambitious plan, I think you'll agree.
Here's what really happens.
Exercising is a real pain in the ass. Just like it always was. And I no longer have the company facilities to use, or the discount at the fitness club near my former offices. And even if I did, all this stuff is still 45 minutes away from where I live, and wasn't I planning on ever I repeat ever driving down that goddamn freeway again. So I have to find a place nearer to the house, or start using the exercise bike in the basement, the one that has been doubling as a clothes drying rack. And since there is no longer any urgency about this (I don't need to squeeze my work out in before work or at lunch or after work) then there's no real hurry. I can surely have a cup of coffee first and read the paper....
Learning Arabic is a great idea, and very trendy, and useful if I'm ever captured by ISIS. Maybe first I should learn "God is great, and he doesn't want you to cut my head off." No, too dark. But learning Arabic requires something like a book to study, or some tapes to listen to. However, I find that they don't make tapes anymore, "Btw," so I had to down load something onto my computer, and I don't have an IT department to help me any more so this wasn't so easy. Then I thought maybe I could go to my local community colleague and take a class. But probably not in Arabic. Maybe in Spanish. And it's a community college, so I don't exactly have London School of Economics quality teachers, and the rest of the students turn out to be either retired like me (but older looking, naturally), or young kids who really aren't very smart. And since I don't really need the language in my daily life, what's the point of this? It's a lot of work, and takes a lot of time if you're serious, and I've got other things to do, like work on my memoir. Which is not going to be written in Arabic or Spanish.
Don Ho ("Tiny Bubbles," remember?) is long gone, and the ukulele is not exactly making a comeback, although you can buy a cheap one at Costco which is not made in Hawaii but guess which large east Asian country. And it was cheap, so I bought one. In my enthusiasm I momentarily forgot the general problem with musical instruments, which is that while you can learn the theory easily enough (there are only eight notes, not counting sharps or flats), you never get really good unless you practice. And maybe I will practice and eventually get good and coincidentally get invited to a party. I wonder if my host is going to welcome me bringing my "uke" along unbidden? Perhaps I will just look even stranger than I usually am. Are my kids going to ask me to "play a couple of songs" at the holidays? Are my grandchildren going to put aside their cell phones and tablets and game-boys while I teach them the words to Kum-ba-yah? Sure they are. It will make those long and solitary hours of chord repetition seem all worthwhile, that 30 minutes a year around Christmas when at least the family listens to me play and, god help us tries to sing along with songs that they haven't ever heard before.
Travel is good. But now I no longer have an assistant or a company travel agent to take my vague guidance -- "Paris, a mid price hotel, use mileage for the tickets, a week or so in mid-May" -- and turn it into a full blown itinerary, with mileage deducted from the correct frequent flyer account, seats selected, hotel checked out, and passports and appropriate visas all secured. I have to do this myself, and it is not a walk in the park. What used to take two minutes to specify, and then five minutes to review the final product, now takes literally hours and hours of comparing this and that and making sure I get the connecting flights with enough time to connect, and the dates to all match despite time zones and the international date line. Sure, I was a top United Air Lines Secret Squirrel Plus level traveler, but that was before I stopped going to Tokyo twice a month. I don't miss that at all, but United has noticed, and they're somehow just not as solicitous as they once were. To fly also costs real money, and money that I'm paying, not money from the Company. Not small amounts of money. And they really don't want me to bring my ukulele along and practice on the plane flight. I have perforce ended up with a whole new level of respect for the folks who did all this work for me, "before." And it makes me think twice about travel as a good leisure activity.
About those consulting assignments and Board positions. First, I am demonstrably in the "experienced white male" category. This used to be a good thing and probably accounts for at least a portion of my success. But it's not a good thing anymore for Boards of Directors, unless you really were CEO of General Electric or Shell. Diversity is the word of the day. Plus, no matter how many newsletters I read, it's just not the same as being "in the game." I could fork over $2,000 plus travel and lodging to go to industry conferences, but it's now my money not the Company's (see travel, above) and do I really want to walk around the trade show floor with a business card that says -- what? "Retired, but I used to be somebody?"And all those folks in my company who politely asked me to be sure to keep in touch, now really can't be bothered to answer my chatty emails. And why should they? I don't write their performance reviews any more, or help decide who gets promoted. The unfortunate truth is that "gone is gone." I'm gone, and that's how it works.
It is possible to do volunteer work, which usually means engaging in activities that my admin used to do for me. In several cases I have given a nonprofit organization enough money that they decided to put me on their Board. And then I was one of 25 persons sitting on the Board of an organization with a staff of six and an annual budget of $1.5 million dollars, a portion of which I had had to come up with or raise or both, so you really better like what this group does. No one wants to hear that at my last position with the company, I could spend $1.5 million based on my own signature authority.
Writing memoirs is good. It's legitimate, you have complete control of it, you can screw around with the history to make yourself look good, no one is going to fact check it or sue you unless you really do engage in egregious name calling. But then I stopped and pondered this: how much of what I did over the last 30 years do I really remember all the detail of? The names of the people involved, and the amounts at issue, and the technology or the new market or the legal case or the financial transaction or the litigation that I won? I do want to make this interesting, I need facts and color and drama and suspense. I could go back and read the old annual reports, but we all know that they are written by lawyers who are specifically instructed to leave out color and drama and suspense. I did have a good hand with decision memos and trip reports, and everyone said I was a good writer. But how many of those documents did I keep? How about "none?" It is also worth pointing out that writing a two page board paper is way different from writing a three hundred page history of your personal career. It's a lot more words, and few people will be interested in reviewing the draft and critiquing it. And fewer yet in publishing it. Ah well.
One final word of encouragement after all the discussion of hurdles: Everyone that I know who has gone from successful professional career to "retired" has gone through something similar to the litany above. And after a time they have generally worked out a delightful approach that provides for more time with family and friends, some continuing professional and or intellectual involvement in an area where they have the background, even on a volunteer basis, some attention to fitness and health, and some "out of the box" new activities. I admit that I had visions of being the new Renaissance Man in retirement, and I am a bit disappointed that it's harder to pull off than I thought. I would point out that I am now using LOL in my emails, it's really liberating. As for Katy Perry, though, I am still clueless, but content.
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