A stranger on the internet is dangerously close to convincing me I’m interesting.
They’re liking the photos, reading the articles, and cheering on my adventures like we survived middle school together. Keep this up and I might start believing in myself. Then we’ll all have to live with the consequences.
Meanwhile, someone I actually know: “I don’t really do social media like that.”
Fair enough. Fortunately, I’ve built a website for people who want to support me without getting caught enjoying social media. Actual articles. Complete sentences. You can read the whole thing in silence and emerge with your mysterious offline persona fully intact.
And I actually benefit financially when you visit, so reading about my questionable decisions helps fund future questionable decisions. Finally, a sustainable business model built around me leaving town.
But all this encouragement raises a concern: what happens if I get too confident?
Because I’ve spent decades with a surprisingly effective system for keeping that under control.
I had a conversation with a friend about weight loss recently, and I joked that always being a big guy had probably kept me humble and out of trouble. Knowing my taste in women, my choices, and the opportunities I would have enthusiastically pursued, the confidence I imagine having with a six-pack could have taken me down quite a path.
Apparently, my waistline has been providing adult supervision. An unexpected service, but here we are.
Wayne Gretzky said, “You miss 100% of the shots you don’t take.” Inspirational advice. A trim Garrick would take that as a personal challenge.
Give that man a six-pack and suddenly he thinks every unanswered DM is just a missed scoring opportunity. Calm down, buddy. Wayne was talking about hockey. You’re in the grocery store, and she asked whether you were using that cart.
And the waistline’s duties extend beyond my dating life. Being a big guy has also kept me from signing up for some of the more reckless adventures I might otherwise have talked myself into: skiing, high-level whitewater rafting, ziplining, skydiving, hiking some ridiculous mountain, or scuba diving in what my dramatic self would call “shark-infested waters.” The sharks probably just call it home. Either way, I’m down there trying to remember the instructions while wondering whether I look like an appetizer.
You know, activities where “this should be fun” comes with a waiver and my family asking why a scenic overlook wasn’t enough.
Apparently, somewhere underneath all this is a guy who thinks jumping out of a perfectly functional airplane sounds like a lovely afternoon. Thankfully, the current management has mostly steered him toward boat tours and lunch.
Get me in shape and suddenly we might be adding “Does my insurance cover this?” to the itinerary. For now, I’ll continue risking it all by ordering something I can’t pronounce.
Then I hit my thirties and my hair started thinning. Because apparently being the big guy wasn’t enough character development. My hairline also needed to explore other opportunities.
Between the waistline and the hairline, staying in my lane has been a remarkably well-managed operation. Multiple departments. Excellent communication. Somebody is always available to humble me.
Even now, if I start feeling a little too confident, I just let my hair grow out a bit to nerf myself. And when I say “a fresh haircut,” I mean shaving my head. We’re not blending a fade over here. We’re clearing the property.
A freshly shaved head lets me pretend this is all an intentional styling choice. Let it grow for a couple of weeks and the remaining hairs stand far enough apart that you can see the budget cuts.
Then there’s the beard. It’s there. I’m growing a beard, not starting a rumor. Could it be fuller? Absolutely. The plan is “bald and bearded,” and while the beard has reported for duty, I wouldn’t object to a few more employees on the schedule. We’ve got coverage. I’d just prefer less daylight between departments.
Suddenly the bathroom mirror is asking, “Are we sure we want to send that message, handsome?”
Fair point, scalp. Let’s save it to drafts.
Some people meditate to keep their ego in check. I just skip shaving my head.
Besides, I prefer traveling solo, so a little humility helps protect the itinerary. I can’t be getting too confident and answering the few women in my DMs. That’s how “Where should I go next?” turns into “What do you mean you don’t want to go there?”
And yes, I said a few. Let’s not confuse a couple of notifications with a waiting list. Nobody needs crowd control.
Still, one flattering message on a freshly shaved head day and suddenly I’m considering somebody else’s availability. Absolutely reckless. Grow the hair out. Restore order. Book the solo cabin.
But underneath all the jokes is someone who spends a ridiculous amount of time getting in his own head.
The funny thing is, I do have confidence. It just shows up in very specific places, apparently on its own schedule.
Booking a trip? That’s where I shine. Give me a destination, some available PTO, and a flight that looks reasonable after I’ve stared at it long enough, and suddenly I’m a man of decisive action. I can second-guess a text message for an entire evening, but apparently I can authorize my own departure to another continent.
And for an introvert, my confidence picks some weird places to make an appearance. Send me to a faraway land where I don’t know anybody, and suddenly I’m having a conversation with a total stranger. Asking questions. Telling stories. Sounding engaging. Who authorized this charming little guest appearance?
Back home, I might be wondering how to start a conversation. Thousands of miles away, I’m already halfway through one, enjoying myself, and realizing afterward that I never stopped to worry about it.
Apparently, my social skills work. They just prefer to be activated outside my home time zone. An expensive discovery, but at least I’m getting photos out of it.
I’ve let the way I see myself talk me out of things before I’ve even tried them. Talking to someone. Getting in the photo. Putting my face in a reel. Telling people, “Hey, I made something. Would you take a look?”
That last one sounds easy until it’s your thing.
I can photograph a sunset without wondering whether the sunset thinks I’m embarrassing myself. Put my own face, words, and personality out there, though, and suddenly I need three business days to approve the post.
Maybe A Weekend keeps giving me reasons to hit publish anyway.
Post the photo. Write the article. Make the reel. Remind people there’s a website without sounding like I’m about to invite them to an exciting presentation about financial freedom.
My pitch is mostly, “I went somewhere, ate something, and took pictures. There may have been a nap.”
And yes, I’d like people to read about it. I put time and money into this, I enjoy doing it, and I’d love for it to help cover its own costs. Ideally before my next brilliant idea involves international airfare.
That’s why the people who show up mean so much.
Someone who owes me absolutely nothing chooses to read an article, share a reel, or leave a comment. They don’t know me from work. We don’t share relatives. There’s no history requiring them to politely acknowledge my existence once every fiscal quarter.
They found something they enjoyed, and they stayed.
Maybe it’s the photography. Maybe they’re planning a trip. Maybe they also have a full-time job and want to squeeze some adventure between responsibilities.
Maybe it’s the sarcasm. Maybe it’s the one out of every five jokes that actually lands. To those of you sticking around through the other four: thank you for your patience during testing.
Or maybe they’re monitoring the situation. Understandable. I also have questions about where this is going.
Despite the opening roast, I know friendship doesn’t come with a contractual obligation to consume my travel content. You can care about me without wanting a detailed account of what I ate in a cruise port.
But when someone does take an interest, it matters. It makes the next post a little easier to share. It reminds me there are people on the other side of the screen enjoying the stories I almost kept to myself.
I’d like to get healthier and feel better in my own skin. I’d also like to stop waiting for some future version of me to give the current version permission to enjoy his life.
There are places I want to see, photos I want to take, and meals I would deeply resent missing because I was waiting to become photogenic.
So I’ll keep traveling, writing, and occasionally stepping in front of the camera. You keep reading, commenting, and helping fund the next questionable decision.
I’ll also be branching out a bit as I flesh out the social media accounts and the website. More of me, more things to try, and probably a few experiments that make us all appreciate the sunset photos. We’ll see what sticks—and how I handle the “fame.”
Yes, fame is in quotation marks. Someone recognizing me in a cruise ship bar would probably sustain my ego for six months. Please don’t let me start referring to a dinner reservation as a public appearance.
If you’d like to help this questionable operation grow, follow, like, subscribe, comment, and share. Pick your favorite button. Get adventurous. Try a second one. Leave a comment so I know who’s here enabling me, and send a post to someone who appreciates travel, sarcasm, or a man publicly negotiating with his hairline.
And visit the website. Read an article. Read another. Share one with a friend. Let’s give the website a proper stress test with actual people reading things. I’d love to find out what happens when the traffic report starts looking less like attendance at a secret meeting.
While you’re there, request a free Maybe A Weekend sticker while they last. Put it somewhere, take a photo, and tag me. Help spread the chaos. I’ve already committed to mailing strangers things; apparently we’re past the point of sensible restraint.
Also, let me know what merchandise you’d actually want in the future. Shirts? Hats? Something else? Tell me what you’d spend real money on so I can make informed decisions before my enthusiasm orders a closet full of inventory. We might as well see whether we can really capitalize on this venture. These questionable decisions aren’t going to fund themselves, and I’d love to turn your support into something you enjoy owning.
Thank you for showing up. You’re helping me get a little more comfortable being seen.
Just don’t let it go to my head.
There’s already less coverage up there than there used to be.
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