Vacation: No Laptop Required! A Cautionary Tale for Over-Achieving Workaholics with a Fear of Failure

I come from an immigrant culture of color and so my parents taught me to work hard. Very hard. Work hard and then work some more. Get a job, a second job, and a side hustle. Hustle on both sides. Oh hell, just make it a 360 degree hustle. What I didn't learn, was how to slow down and relax without feeling lazy.

When my Dad retired he had accumulated so much sick time from The City, they couldn't pay him for all of it. His dedication to The Job - dragging himself into work even when he was very sick - lost him money. My mother was no different. She had a regular job and still cleaned the house, did laundry, cooked dinner, and took night classes at the local college.

With all that hustle my parents more than earned a vacation. Too bad they never took one. But their parents never took one either. I think their journey to America was the only trip my grandparents ever took. If alcoholism runs in families why not workaholism?

Although I've damn near circumnavigated the globe, I've never been on vacation. Work was always waiting for me when I got somewhere. I'm not complaining because I love what I do. But I rarely took the time to appreciate where I was, judging my off hours by how clean the hotel or how free the wifi.

Yes, I have a strong work ethic and accomplishments I'm proud of but there's a downside. I'm intimidated by my own To Do List. I believe it's become a sentient being with very sharp teeth. I'm a manic multi-tasker yet it's difficult for me to see long-term projects to completion. I regularly fall asleep in front of my computer. Actually, it's more like passing out, which yields a lower quality of sleep than taking my ass to bed at a reasonable hour and purposely putting head to pillow.

Being a live-action Energizer Bunny isn't cute. The constant expenditure of energy without pause to review and refresh has ultimately made me less productive and creative. I needed a vacation, badly, but I didn't know how to take one. I never understood how people find the time and money. Sit on the beach doing nothing while sipping an adult beverage, watching the waves? You lost me at beach. Sand is just pretty dirt.

Family vacations are an even bigger mystery. Seriously, why would anyone travel with children under the age of 30? I've observed many family vacations and they have a common theme: "We argue so well at home, let's take it on the road and see what strangers think."

But as the saying goes, when the student is ready, the teacher appears. One of my best friends is an international tour manager who specializes in Italy. She had been trying to get me to go for years. This summer she rented an apartment while studying Italian at the University of Perugia. She said if I visited I could stay with her. Now, the expense of a hotel was not an excuse, but I immediately thought of others:

"But, I have work," I said. But this summer has been slow. When I checked my calendar for the dates I'd potentially be away I saw that I only had one gig in Delaware.

Delaware?

Italy?

Now, if I was looking to spend the summer incorporating, the D would be the spot. Otherwise, not so much.

To rule it out, since my inner/outer/all around workaholic was still resisting, I checked my frequent flyer miles and found that I had more than enough for a round-trip ticket to Rome. The tipping point came when my friend said, "You know, the President of the United States takes a vacation. If the leader of the free world can take some time off, why can't you?"

"Because he has a staff," I thought, but I kept that to myself.

I got the tickets.

At first the trip was just another project on my To Do List. I was hell bent on figuring out how to unlock my iPhone, finding wifi, and making sure I had the right electrical power converter for my laptop. You heard me. Laptop. I was going to bring it with me to Italy. I say "was" because a friend gave me a serious talking to. He said, "Leave. It. Home. You. Don't. Need. It. You're. On. Va-ca-tion. I know you don't know what that means but it's a Latin phrase for: Leave your laptop home."

And I did. Well, I compromised and took my iPad. Baby steps.

To get myself into the spirit of things I crafted my first out of office email:

I've run away from home and I have limited access to email. If this is an emergency are you sure I'm the person you should be contacting? I have no money, medical skills, or power of attorney over anyone or anything. In the meantime, I hope you're having a great summer. If you're not, it's not too late to change that. "We walk this way but once." Go out and get some good stories to share at the old folks home. #ticktockticktock

The trip didn't stop being a project and start being a reality until I was walking down the jet bridge to board my overnight flight. I thought, "This is happening? I'm going on a va-ca-tion? Work is not waiting for me on the other end of this flight?"

What was waiting for me was 10 days of hanging out in the old country with one of the most experienced tour guides in Christendom. We spent time in Rome, Perugia, Assisi, and Florence. We drank wine with lunch. We drank wine with dinner. I would've had wine with breakfast if I'd ever gotten up early enough to eat it.

Did I occasionally check my email, post pictures on Facebook , and jot down ideas for jokes and stories? Of course; this is one of them. But I also relaxed ... a little. It was uncomfortable at first but I kept at it. I relaxed a little, I relaxed a lot, and then I relaxed some more. And when I was done relaxing, I had another glass of wine (a quartino, grazie) got totally relaxed, and enjoyed my first - but not my last - real vacation. I'm putting my next one on a much shorter to do list. My grandparents would be horrified.