How to Go on Vacation

More of a question than a how-to, actually.

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I am terrible at planning and taking vacations. I’ve never had the means to simply book a full-price trip to somewhere great, so I’m always bargain-hunting, which is exhausting and dicey. Because I find the whole enterprise mystifying, I tend to put it off until it’s too late to score decent deals, and I have no choice but to settle for dreck. So a couple of times a year I find myself in some weathered, seedy place, too dissatisfied and overcome with self-recrimination to be able to enjoy the time away.

Some of the rotting wood on the deck outside our room at a shitty place we stayed in Lake George a few summers ago.

For instance, two weekends ago I brought my extended family to a tired, waterlogged old inn in Connecticut where, for 48 hours, we were exposed to an arresting level of mold and mildew (ten days later we all still have sinus congestion), had to waste our time repeatedly dumping water out of a dehumidifier so it wouldn’t shut off and stop doing its job, were stuck with a broken fridge that ruined the food we brought, and dealt with toilets that didn’t properly flush. We grossly overpaid for it, and I am fighting to get our money back. Now I need another vacation to help me destress from that one.

Thanks to Rumikub, Jenga, and my bluetooth karaoke mics, we made the best of it.

We were singing “Hey Jude” here.

I’m also just overdue for a break from all I’m doing at Botton, Ink, where recently I’ve made a couple of errors that attest to how fried I am. (Please enjoy this corrected Sober Oldster Q&A featuring the wonderful

Chris Wells

.) Fortunately, being so busy with the next pieces to publish made me realize I didn’t have time to keep beating myself up about the errors. (I’m also dealing with a weird variety of grief after the death, last month, of a difficult family member, who’d alienated pretty much everyone in her life. You don’t expect to have your heart and mind scrambled by the loss of a person you didn’t particularly like, but, surprise!, that’s part of what’s happening with me and my already-aging-addled brain.)

***

I’ve made a healthy first step toward taking a holiday, blocking out a two-week period on my calendar. But I get twitchy every time I sit down to scheme a plan. The other day I came to the realization that I derive so much comfort and stability from (over)working, that taking time off terrifies me. I’m tired of my surroundings, so a staycation is out. But visiting new places brings with it so much uncertainty, and too many choices (where to stay, how to get there, what to eat, what to do, how to make the most of my time), absolute torture for a Libra.

I don’t remember what I enjoy doing other than (over)achieving, which naturally makes it difficult to pick a place to go. This brings up the matter of workaholism, and whether I suffer from it (probably) and whether I want to do anything about it (probably not).

The actual travel part always feels like a clusterfuck, even when flights leave and arrive on time. And almost everyone I know who has flown this summer has gotten Covid, the prospect of which makes me reconsider a staycation, but then again, nope.

Also: I don’t remember what I enjoy doing other than (over)achieving, which naturally, makes it difficult to pick a place to go. This brings up the matter of workaholism, and whether I suffer from it (probably) and whether I want to do anything about it (probably not). There are days I worry I’ve got a problem, but others when I think:

I have created for myself a demanding day job doing work I love, according to my own imagination and self-direction. It pays me enough to live, and enough to pay contributors, at least nominally. What’s so bad about that?

Maybe both are true. There’s no doubt I could stand to strike a better balance between work and not-work, but who couldn’t? And I should say “no” to requests for my time and energy more often than I have been—something I’ve been backsliding on, always hard for me.

I need to reacquaint myself with activities other than work that bring me joy—plus maybe find some new ones. Since Brian and I both love to sing, and enjoy doing that together, one idea I had was visiting Nashville, and hitting some open mics, including one on Mondays at the legendary Bluebird Cafe. We could do some of the standards and pop covers we’ve worked up over the years, plus some of the songs on Brian’s new EP.

But the whole MAGA movement of the past eight years, and that scary 2017 Unite the Right rally, have turned me off to all things Americana and the idea of visiting the South. Brian didn’t love the idea either.

Is there some kind of vacation you can take where you draw with crayons all day, then jump in a lake or a pool, and later sing songs around a campfire? Is there some kind of arts and crafts camp for adults? No, really—does this exist? If so, please tell me, because it sounds like my idea of a good time.

What else brings me joy…? Hmmm. Writing, but that’s also my job, and I have a three-day writing retreat planned with a few friends/colleagues in October that I’m looking forward to.

Is there some kind of vacation you can take where you draw with crayons all day, then jump in a lake or a pool, and later sing songs around a campfire? Is there some kind of arts and crafts camp for adults? No, really—does this exist? If so, please tell me, because it sounds like my idea of a good time.

I heart crayons. Drawing by me.

Maybe a do-nothing vacation, to a beach or a lake, is what I’m describing. We’ve only done that once, traveling to Rincon in 2010—with a small travel guitar and crayons in tow. Maybe we should go back there. But then I wouldn’t be expanding my horizons by trying someplace new, which somehow feels like something I “should” do.

***

Once I manage to get us somewhere, I’ve got another challenge to overcome: my tendency to pressure myself to get the most out of every second of my vacation, something I also do to myself when getting a massage. Like:

Are you enjoying yourself yet? Because this is going to be over soon! Are you enjoying yourself NOW? How about now? Only three days left…two days…one day… ENJOY YOURSELF ALREADY, DAMMIT.

Please wish me luck taking some much needed time off and actually ENJOYING MYSELF.