I’ve been working full-time since 1980 and in that time only once have I had a three-week vacation.
Like most workers my age, when I started working full-time, my time-off allowance (if I had any) would only cover sick days for the occasional cold or flu. Later, as I developed my career, I accrued enough hours to take a week off during the year, as well. About twenty years ago, I had sufficient seniority at my firm to take two-week vacations. Bliss! Two weeks was enough to spend a week powering down from the stress of the daily grind, and still have a week to really enjoy the time off. Eventually, that time-off allowance grew large enough that I was able to manage an entire three-week vacation. That was about ten years ago, and it was the only time in those forty-three full-time worker-bee years that I had such a stretch of time away from the work-a-day world.
Today, though, is a milestone, as I am 200 days away from a very long vacation: on April 1, 2024 I will retire from my firm, after working there for 33 years.
There’s a lot wrapped up in that because in addition to retiring soon, I’m also turning 65. As I mentioned last week, we’ve been quite busy this year preparing for the transition, and yesterday was a big one: we met with our Medicare Guy.
I’ll tell you at the outset, when it comes to Medicare, seek advice (and not just from friends and family). Seek advice from a professional. Find an independent broker* (i.e., someone who isn’t tied to a single insurance provider). Find someone who is responsive, experienced, and able to assist you in navigating the myriad of options available. I tried four different brokers before I found “our guy,” who will help us not only sign up, but will provide ongoing advice through the years as plans and policies change.
Yesterday, we had a two-hour meeting with him, and we came away from it frazzled, fuzzy-brained, deluged with information, but ultimately much more comfortable and confident that we can do this.
We still have a lot of work ahead of us, and many decisions to make, but we have greater knowledge now, knowledge that will help us make better decisions. And—more importantly, for our peace of mind—we also know that whatever decision we do make, it’s not written in stone. If it turns out the choice we made isn’t working or (crucially) if our situation changes, we can change our coverage options to accommodate.
All this is very boring, not at all artsy or creative, and has nothing to do with what I usually bang on about here, but wow, I cannot tell you how much it helped. And it’s a lesson that can be applied in other areas.
Asking for expert advice is not a sign of weakness or failure. It’s simply an acknowledgment that I don’t know everything (gasp!). Just as I ask a doctor about medical issues and don’t rely on whatever advice the TikTok algorithm sends my way, so too will I ask a professional about areas in which I have little or no expertise. This only makes sense.
So, that’s today’s totally boring and very un-entertaining post. I’ll get back to more creative stuff, hopefully soon.
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* This advice holds true also for financial advisors. Pick an independent advisor, who isn’t beholden to a specific financial institution. They cost more, but the difference is you get totally unbiased assessments and recommendations, because they make their money from you, and not from some financial institution in the background.


In 500 days, I will retire. In more ways than one.
