I’ve been working on Maybe A Weekend as a side hustle/hobby since 2019.
And by “working on,” I mean occasionally giving it my full attention, occasionally ignoring it for months, randomly redesigning things nobody asked me to redesign, writing travel stories at questionable hours, and repeatedly convincing myself that this time I’m definitely going to be consistent.
Several years later, here we are.
The website exists.
The social media exists.
People occasionally visit both.
Money has been spent.
Very little money has been made.
So basically, business.
I’m practically a CEO.
I Have No Problem Failing
There’s a thought that has bounced around in my head for years:
“I’m not afraid to fail. Failure is a learning tool, so keep failing until you succeed.”
Very motivational.
Put that shit on a coffee mug.
But I actually believe it.
Failure doesn’t bother me that much. I’ve failed before. I’ll fail again. You try something, it doesn’t work, you figure out why, make some questionable adjustments, and launch yourself directly into the next failure.
Eventually something works.
Probably.
That’s basically science.
But while thinking about this recently, I realized something considerably more disturbing.
I might actually be afraid of succeeding.
Well, shit.
Failure Is Actually Pretty Comfortable
Here’s the beautiful thing about Maybe A Weekend failing:
Nothing happens.
I wake up Monday morning.
Go to my regular job.
Collect my paycheck.
Pay my bills.
Look at airfare during work breaks like a responsible adult.
Book another trip.
Take too many pictures.
Come home.
Write about it.
Repeat until death.
It’s a perfectly functional system.
But what happens if this ridiculous little project I started in 2019 actually works?
That’s where things get uncomfortable.
Because success means maybe someday I’m not just a cog inside somebody else’s giant machine.
Maybe I’m standing on my own two feet.
Maybe I’m running something I created.
My ideas.
My decisions.
My money.
My responsibility.
My complete inability to blame anyone else when everything catches fire.
That’s terrifying.
Failure lets you shrug your shoulders and say:
“Well, I tried.”
Success looks you directly in the eyes and says:
“Congratulations. Now don’t fuck this up.”
Then I Decided to Fight the Instagram Algorithm
Recently, I decided Maybe A Weekend needed more Instagram followers.
Naturally, I approached this with a carefully researched social media strategy developed through extensive market analysis.
Just kidding.
I started making stupid reels.
I threw caution to the wind and decided that instead of trying to make polished influencer content where I dramatically stare into the distance while inspirational music plays, I would just put the thoughts already bouncing around inside my head onto the screen.
Travel.
Sarcasm.
PTO abuse.
Questionable financial decisions.
Not wanting to work.
Wanting to disappear to another country.
Being willing to temporarily sell out if someone wants to fund my reckless vacation behavior.
You know.
Wholesome travel content.
And something incredible happened.
Almost nothing.
My Instagram following barely moved.
Mission accomplished.
Another failure successfully completed.
Except Facebook Apparently Didn’t Get the Memo
Here’s where things got weird.
Those Instagram reels automatically posted to Facebook.
I wasn’t really thinking about Facebook.
Facebook was just…there.
Like that drawer in your kitchen filled with batteries, expired coupons, three screwdrivers, and a charging cable for a phone you haven’t owned since 2014.
Useful occasionally, but mostly ignored.
Except people started watching the reels.
Then more people started watching.
Then people started following.
And the number kept going up.
Excuse me?
THAT WASN’T THE PLAN.
I was trying to become mildly more relevant on Instagram.
Instead, Facebook apparently wandered into the room like:
“Hey, I heard you idiots were giving away followers.”
So now the audience there has grown considerably more than I expected while Instagram continues looking at my content like a disappointed parent.
Fantastic.
But Apparently Nobody Wants My Free Stickers
Naturally, with all this newfound social media momentum, I decided to capitalize on my rapidly expanding media empire.
I made a reel advertising the free Maybe A Weekend stickers available through the website.
FREE.
Not discounted.
Not “free with a $75 purchase.”
Not “just pay $14.99 shipping and handling.”
Literally free.
You ask for one.
I send you one.
Simple.
The response was overwhelming.
Two people requested stickers.
Two.
At least now I know exactly how many people are willing to go through the tremendous inconvenience of filling out a form in exchange for free merchandise.
To be fair, I did put possibly the most annoying background music imaginable on the reel.
So maybe the marketing campaign actually worked perfectly.
Apparently the strategy was:
“FREE STICKERS! COME GET YOUR FREE—”
Annoying music begins.
“Actually, never mind. I’m good.”
Demand successfully controlled.
Supply chain crisis avoided.
I remain fully stocked.
For anyone brave enough to endure my marketing decisions, there are still free Maybe A Weekend stickers available through the website.
Please.
Take them.
I bought these things.
Maybe One Day I’ll Actually Sell Something
I’ve also had some Maybe A Weekend merchandise made over the years.
Nothing resembling an actual merchandise operation.
Mostly stuff I had made for myself and friends because apparently the natural progression of creating a travel blog nobody asked for is eventually putting its logo on things.
Shirts.
Random branded stuff.
The usual signs that someone owns a domain name and has started getting ideas.
For now, I’m not launching the Maybe A Weekend International Lifestyle Apparel Corporation.
But if this thing ever gets popular enough?
Who knows.
Maybe I’ll actually put some merchandise up for sale.
Then I can experience the entrepreneurial thrill of spending $2,000 creating merchandise and celebrating when somebody buys a $24 shirt.
BUSINESS.
Again, practically a CEO.
But first, apparently, I need to figure out how to give away the stickers.
Baby steps.
A Toast to Random Internet Strangers
There’s another weird thing I’ve learned through all of this:
Sometimes random people on the internet will hype you up more than the people you actually know.
And I don’t necessarily blame my friends or family.
I try very hard not to be that person.
You know the one.
“Hey, check out my website.”
“Did you see my new Instagram post?”
“Follow my Facebook page.”
“Here’s my TikTok.”
“Did you watch my reel?”
“Did you LIKE my reel?”
“Did you SHARE my reel?”
“WHY AREN’T YOU SUPPORTING MY DREAMS, PEOPLE?”
Nobody needs that kind of pressure.
So I generally avoid constantly bombarding friends and family with links to Maybe A Weekend, Instagram, Facebook, or TikTok—which, for the record, currently has a very small following.
TikTok has apparently reviewed my application for internet relevance and decided:
Denied.
Fair enough.
But while I’ve been intentionally trying not to annoy everyone I know, complete strangers have been showing up.
They watch.
They like.
They comment.
They share.
They follow.
Some of them have promoted Maybe A Weekend more than anyone I actually know.
There’s something both hilarious and genuinely cool about that.
Some random person sitting hundreds or thousands of miles away can stumble across one of my sarcastic travel reels, think:
“This idiot makes a good point.”
Then hit share.
Suddenly Maybe A Weekend gets introduced to another group of people.
Then somebody else shares it.
Then somebody follows.
And somehow this weird little thing keeps moving.
Meanwhile, people who have known me for twenty years are probably scrolling right past my reel thinking:
“Yeah, that sounds like Garrick.”
Honestly, I respect it.
So here’s to the strangers on the internet.
The people who don’t know me but decided to follow anyway.
The people sharing my posts.
The people leaving comments.
The people feeding the mysterious algorithm gods on my behalf.
The people helping Maybe A Weekend slowly escape from my immediate circle and wander unsupervised into the larger internet.
You’ve promoted me more than almost anyone I actually know.
And I appreciate the hell out of you for it.
If this ridiculous little project ever actually becomes something, just remember:
It apparently wasn’t nepotism.
It was strangers.
Beautiful, chaotic, algorithm-feeding strangers.
Cheers to you.
And since you’re already making questionable decisions by following me…
There are still free stickers.
Nobody Panic, I’m Still Not Famous
For clarification, I’m not Instagram famous.
I’m not Facebook famous.
I’m certainly not TikTok famous.
I’m not even “random person recognizes me at Costco” famous.
Obviously.
I can’t even give away stickers.
Nobody is stopping me at airports.
Tourism boards aren’t sliding into my DMs.
Hotels aren’t offering me complimentary suites.
Airlines still expect me to pay for flights like some kind of peasant.
And cruise lines continue refusing to acknowledge the completely reasonable argument that I should be allowed to cruise for free because I’ll probably write something sarcastic about it afterward.
The disrespect continues.
But…
People are watching.
People are following.
People are sharing.
The message is slowly escaping containment.
Maybe A Weekend is reaching people who weren’t already friends, family, coworkers, or someone I personally harassed into visiting the website.
THE STRANGERS HAVE ARRIVED.
This was the goal.
Which is unfortunately where the problem starts.
Oh Shit, What If This Actually Works?
This is normally the point where my fear of success would kick in.
Something starts working.
I notice it working.
Then instead of smashing the gas pedal, some deeply responsible part of my brain says:
“Okay, that’s enough attention. Everybody go home.”
Lower your head.
Stay comfortable.
Don’t get carried away.
You’ve got a good job.
You’ve got stability.
You’ve got a paycheck.
You’ve got PTO.
Don’t start imagining some alternate universe where this weird travel website actually becomes something.
Except…
Why the hell not?
I’ve spent years telling myself I’m not afraid to fail.
Maybe it’s time to find out whether I’m willing to succeed.
Release the Chaos
For once, instead of backing away from the tiny bit of momentum I’ve accidentally created, I’m going to lean into it.
More reels.
More travel stories.
More photography.
More ridiculous observations.
More promotion.
More experimenting.
More failing.
More accidentally succeeding at something completely different from what I was trying to accomplish.
Maybe even more stickers.
God help us.
I’m going to stop worrying about whether Maybe A Weekend looks like a perfectly polished travel brand.
Because it isn’t.
And neither am I.
It’s travel.
It’s photography.
It’s weekends.
It’s side quests.
It’s water.
It’s outdoors.
It’s random flights booked because airfare dropped $47 and apparently that’s all the justification I need.
It’s occasionally traveling halfway around the world because sitting at home seemed boring.
It’s working a regular job while constantly plotting my next escape from said regular job.
It’s basically my brain with a domain name.
And apparently some people want to follow that.
God help them.
The Timing Couldn’t Be Better
The best part?
Another adventure is less than two weeks away.
Which means another round of airports, questionable decisions, excessive photography, random food, drinks, side quests, stories, and whatever chaos happens between leaving home and eventually stumbling back through my front door.
And this time, there are a few more people watching.
So I’m going to try something different.
I’m not going to hide from the momentum.
I’m not going to overthink whether I’m qualified to do this.
I’m not going to wait until Maybe A Weekend is perfect.
That ship sailed sometime around 2019.
I’m going to make the content.
Tell the stories.
Take the pictures.
Post the reels.
Promote the website.
Try to give away some damn stickers.
Maybe eventually sell somebody a shirt.
And see what happens.
Maybe this whole thing eventually fails.
Fine.
Failure is a learning tool.
Maybe it stays a weird little hobby that occasionally pays for a beer somewhere interesting.
Also fine.
Maybe the Facebook algorithm eventually realizes its mistake and sends everyone home.
Honestly, very possible.
But maybe…
Just maybe…
this stupid thing actually works.
And I think I’m finally becoming more afraid of never finding out than I am of succeeding.
So here’s to the next adventure.
Here’s to more stories.
Here’s to more chaos.
Here’s to the random strangers on the internet who decided to come along for the ride.
And here’s to seeing just how far I can take this ridiculous little idea I started back in 2019.
If it fails, I’ll learn something.
If it succeeds…
Well, shit.
I guess I’ll have to figure out what the hell to do next.
Probably while booking another trip.
And seriously.
Somebody request a sticker.
