The startup holidays

How does something become a big name national holiday? How does a holiday go from the start-up tier (think National Taco Day or National Talk Like a Pirate Day) all the way up to that rarefied air of Christmas or Thanksgiving. Or, not even that, how does a startup holiday climb the ranks to reach the Columbus Day or Groundhog's Day level?

To get started, let's breakdown the holiday hierarchy.

Tier 1 - National Day off + acceptable to take the whole week off 

Holidays include: Christmas, Thanksgiving, 4th of July, New Year's

Have you ever tried to book a meeting with someone in mid-November? The response is always something like, "Well, we've got Thanksgiving coming up, then it's Christmas, and New Year's, so let's look at February."

And we accept that as a being reasonable answer when really it's three days being referenced. That's why Christmas will always be the G.O.A.T; no other holiday can make it reasonable to shut things down for 2+ weeks.

Tier 2 - National Day off

Holidays include: Labor Day, Memorial Day, President's Day, MLK Day, Columbus Day, Veterans Day

This one has gotten interesting over the last 10 years. To make it into this tier, you first have to be recognized as a national bank holiday. From there you have to get out and campaign to stay nationally recognized. There's no guarantee a holiday will always remain in this tier.

For example, Labor Day and Memorial Day are both on solid ground, MLK Day is on the rise, but Columbus Day is on the hot seat. Abe Lincoln and George Washington's birthdays used to be their own things, but were absorbed into President's Day. It's not crazy to think that in five years the 4th of July will buy up both President's Day and Veterans Day, making room for two more holidays in this tier.

Tier 3 - Hide it on a weekend

Holidays include: Easter, Mother's Day, Father's Day, Super Bowl Sunday

These holidays played it safe and put themselves on a Sunday. Would they have made it into Tier 1 or Tier 2 on a Monday? We'll never know.

Tier 4 - Eh, they're out drinking

Holidays include: St. Patrick's Day and Cinco de Mayo

Socially acceptable to take these days off, but it's hard to convince your co-workers that Guinness and mid-day margaritas are not involved.

Tier 5 - Nationally recognized, but no day off

Holidays include: Halloween, Valentine's Day, Groundhog's Day

Halloween has gradually taken over October. There's a scary movie playing every night. Costume parties every weekend. Part of Columbus Day's decline is because people are now saying, "October is Halloween." There's no room for another holiday.

Halloween is getting close to being a day off. It started with company-wide costume contests. Decorate your desk contests. It expanded into trick-or-treat in the office, bring in your kids. The afternoon is basically off and the morning is incredibly light on work. Halloween could be five years away from a Tier 2 holiday.

Keep an eye on Valentine's Day too. They have a sneaky plan in place to become a national holiday. It all started with companies one-upping each other on maternity and paternity leaves. You give six months? We're doing a year for our employees... full pay! The next logical step is a company saying, "Alright, we see your one-year full pay and raise it with 'Our employees get Valentine's Day off.'" Other companies will adopt this as well to try and keep up and Valentine's Day steadily climbs the ranks.

Last but totally least would be Groundhog's Day. If you ever tell a friend, "Yeah, I think I'm gonna take off Groundhog's Day," the response will be filled with concern. "Really? Is everything ok at home?" 

And that's it. Everything below Tier 5 is in the startup category. But, of this startup group, there are a few top-performers who have set their sights much higher. The question is, will any of these days become the next Uber or AirBnB of the holiday space? Let's dive in.

Super Bowl Monday

This is an ambitious expansion play from Super Bowl Sunday. The Super Bowl is looking for the double-play similar to how we have Christmas Eve and Christmas Day, Thanksgiving and Black Friday, New Year's Eve and New Year's Day.

Super Bowl Monday's best bet is shooting for Tier 4. Instead of "Eh, they're out drinking" the assumption is anyone calling in sick or "working from home" on this day is nursing a hangover or combating the chili con queso with a Pepto Bismol bubble bath. In order for this plan to work, football still has to recover from the national anthem and concussion/player safety controversies, but if the NFL can re-establish themselves at the popularity level they were at just five or six years ago, we could absolutely see Super Bowl Monday as a Tier 4.

Lunar New Year

This one had surprising momentum in 2019. I was seeing Lunar New Year posts everywhere.

The downside to this holiday is the date bounces around like crazy. This year it was February 5th. Last year was February 16th. Next year is January 25th. The lack of continuity isn't a deal breaker, just look at what Thanksgiving and Easter have been able to do, but it's a much tougher path than having one set date. Especially as a startup holiday.

Sweetest Day

Trying to be the Valentine's Day of October. And it's not looking good.

I think Sweetest Day needs to regroup, maybe even rebrand. First, they've got to get out of October. Halloween's momentum is not slowing down. You can't expect someone to buy a Pennywise costume one day then flowers for their girlfriend the next. Gotta get out of October.

As for the rebrand, I say call it "Maternity Day" or "Maternity/Paternity Day." Try to sneak past Valentine's Day for the corporate sponsorship. Move things up to August because 1. There's no other big holiday to compete with and 2. This is the time of the most pregnancies.

They could even consider becoming "Pawternity Day." Be the go-to holiday for dog and cat owners, stop competing with Valentine's Day altogether.

The route to a Tier 5 or Tier 2 is definitely there, but it's not gonna happen as the current Sweetest Day.

Election Day 

This one seems to have the most momentum and companies are already starting to give the day off or make this a no meeting day at work. But I don't see it climbing any higher. I think the government is afraid to make this a national holiday because every two years people will weigh staying home to vote vs. "You know, I could really turn this into a 4-day weekend..."

May the 4th 

This is my sleeper pick to make a surprising climb up the charts. With the new Star Wars movies, there's another generation of fans. With Disney buying Star Wars, it's now got the marketing powerhouse behind it. And with nerd culture becoming more and more cool, it's totally normal for people to openly greet each other with a, "May the 4th be with you" and do a quick light saber battle in the company kitchen.

One aspect to keep an eye on, with Cinco de Mayo right next door, there's the potential for a holiday merger. Could we see a May the 4th + Cinco de Mayo double play in the next five years? It's not out of the question.

First Two Days of March Madness

Reports say the U.S. economy loses $4 billion a year from lack of productivity during March Madness. Businesses might finally cave and say, "You know what, stay home, but can you give us like two hours of true heads down focused work before the games start? Please?"

But I don't see this happening. I think part of the thrill of March Madness is sneaking a look at your bracket or having the game streaming on a separate browser tab. And it's hard to beat the camaraderie in the break room when everyone's turned into the biggest Loyola or UMBC fans.

For now, you really have to remove your wisdom teeth or schedule a hernia surgery to enjoy this holiday from home. And there's not really a Tier for that.

This is the rare Wednesday post on Medium Rare. Just ran out of time on Monday. I'll have another installment of the "Please, Take This Idea" series on Monday highlighting a startup idea that combines the barber shop with your favorite bar-b-q restaurant. In March I'll be taking a break to focus on my sister site,, as well as a couple other projects. I think I'll do a post in a few weeks to share what's all in the works. 

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