So you’ve made the decision to retire and you’re going to start telling people. I guarantee you that after the initial congratulations you will get asked some variation of “What’s next?” It’s natural. I’ll bet you’ve asked the same question over the years when people tell you they’re about to pull the ripcord.
My mistake was that I didn’t have much of a plan in place when I started telling people. (Of course, only three weeks into retirement, I still don’t have much of a plan – but I have a concept!) So I would get the “What’s next, man?” question and I’d pause, which looks weird because doesn’t everybody know what they’re going to do? Finally, I’d go into a mushy and too long answer about exploring different opportunities, maybe travel, and hey, good thing we’ve got some savings built up, etc. etc. Save that mush answer for your close friends and maybe family who care. For everybody else, which is probably 95% of everybody, you need a short and normal-sounding answer.
For me, that answer became, “I’m getting certified as a mediator for the Virginia state court system.” I was weaker on the follow-up questions; work colleague then says, “Oh, wow, interesting, what will that look like?” Me, “Uh,not sure, I’m still finding out myself.” But at least I had a go-to answer that didn’t kneecap an already perfunctory conversation. Your goal is to get that subtle nod of conversational approval indicating that you sound like a person who will still contribute to society even in retirement and isn’t just going to, say, sit on the couch and add another blog to the Internet.
Second common question: what’s the first thing you’re going to do when you walk out of here on your last day? Or the next morning? Variations of this question start popping up when the retirement countdown is less than a month. Fortunately, I had a pretty good answer to this: we’re going to the circus!
This is not a normal response along the lines of, say, going to a bar and celebrating, but circuses are fun, right? It also had the advantage of being true. I had never been to Cirque du Soleil and they were in town the week I was retiring and so I bought tickets for my retirement night.
As it turned out, the actual very first thing I did after walking out of my agency building was to change out of my work clothes and ride my bike down to Great Falls, Maryland to ride 30 miles on the C&O Canal Trail enjoying an impossibly glorious October 72 degree cloudless blue sky day.

After the bike ride, Mrs. anysecondnow and I ate at fake Florida restaurant Coastal Flats (love their lobster rolls) and then walked across the street to Cirque du Soleil.
(Quick circus review: you will not be disappointed. Everybody should go at least once. Impressive visuals, both the prancing performers and the audience having a great time – except the contortionist; I don’t see how he could be having a great time, we were cringing while watching him.)
Do you have answers to these two questions? If so, you are ready to tell people about your retirement!
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Nice info