An Advent of Christmas Movies and Business Lessons

Written at Dec 25, 2023 5:00:00 AM by Dave Connors

I love Christmas. I own an absurd amount of Christmas Jumpers, and if you see me in December I’ll probably be wearing one. I also love Christmas movies. I watch them almost unironically. While there is no need to find an excuse to watch a Christmas movie in December – just grab yourself a Hot Chocolate or an Irish Coffee and get watching – if you do feel that you need a fig leaf of justification, did you know that a lot of Christmas movies have business lessons you can take? And some of them are particularly relevant to InsurTech.

Not convinced? Well, I’ve compiled a list of 24 Christmas Movies and the lessons you can take from them. distriBind’s gift of an Advent Calendar of cinematic goodness for you to enjoy, and learn from, this December. Merry Christmas.

  1. Die Hard

You need to watch this right off the bat, 1st of December, the main reason being that some people will tell you it’s not a Christmas movie, and you need to identify these people and cut them out of your life quickly. You can’t have that sort of negativity around you at Christmas.

John McClane is only at Nakatomi Tower because it’s Christmas… he’s visiting his estranged wife to be with his kids for Christmas. It’s a Christmas Movie. Now that’s out of the way, let’s move on to the lesson.

Die Hard is a paean to start-up culture, an object lesson in what an under-resourced yet highly motivated and nimble team can achieve even up against those with bigger budgets. John McClane is a founder.

  1. Die Hard 2

    Watch this on the 2nd December, because Die Hard 2 is objectively not as good a movie as Die Hard, so anyone who overlooked their reservations over whether Die Hard is a Christmas Movie, definitely won’t keep quiet two nights in a row. Seriously, you don’t need this in your life.

    What Die Hard 2 teaches us the importance of instinct, as John McClane senses things are off early, and ignores the appeals to authority from Carmine Lorenzo and his attempts to keep our hero out of the air control tower. I like to imagine Carmine as the London Market worthies telling us how important common data standards are while keeping them securely behind ACORD’s paywall, and lacking the self-awareness to realise they’re continually losing relevance to the main proceedings

  2. The Nightmare Before Christmas

    The story of Jack Skellington’s disillusion with the repetitiveness of life as Halloween Town’s Pumpkin King and his desire to try life as “Sandy Claws” after he stumbles in to Christmas Land. Lacking the expertise to pick up on the finer points, Jack’s attempt to play Santa goes horribly wrong.

    This movie teaches us that specialism matters. There’s no harm in concentrating on one task when you’re the best at that… there’s a lesson here for customers and buyers too, you need solutions that are designed to do the job you need.

  3. Elf

Before we get on to the business lessons of the story of Buddy the Elf, I have a philosophical question about the world of Christmas Movies like this.

In Elf, Santa is real and he brings the presents. But most older kids and adults don’t believe in him. So, in the universe of Elf and movies like it, who do the parents think is giving presents to their children? Are the kids getting 2 PS5s and sneakily selling one on eBay, or do the parents get blackout drunk and wake up hungover on Christmas day, see the presents and go “oh yeah, I did that”? I often wonder about this.

Elf teaches us about team building and culture. The Elves at the North Pole support Buddy and help him find the tasks he’s good at. When Buddy goes to New York, his positivity impacts those around him too. Find the right people and support them.

  1. Surviving Christmas

The story of Ben Affleck’s spoiled and lonely rich businessman hiring a family to spend Christmas with, this movie is mainly memorable for James Gandolfini sending up his Tony Soprano hardman image, though has a few other funny moments too.

This is a bit of a stretch to draw lessons from (and I’m only at number 5…) but this does tell us about the value of approaching partnerships in the right way, and the balance in client vendor relationships.

Affleck’s character Drew starts off very demanding and transactional, riding roughshod over the “vendor” family and making unreasonable demands. As the movie progresses, the communication becomes more open and equitable. What we see here, is while the “budget holder” may have the power, the provider is also delivering something they need; a relationship based on mutual trust, respect and acknowledgement of the dynamics and needs is key to a successful and lasting partnership.

  1. Deck the Halls

Maverick Danny DeVito winds up the straight-laced Matthew Broderick by covering his house in an absurd number of Christmas lights in an effort to make it visible from space. Only after several mishaps and both men falling out with their families do they finally come together and make everything alright.

Think of DeVito as InsurTechs – unconventional, disruptive, chasing a seemingly-unrealistic dream; and Broderick as “the Industry”… conservative, hidebound by tradition, unsure about the newcomer and their new ideas... actually it turns out they need each other.

Insurance can be too conservative and restricted by tradition “because that’s how it’s always been done”… but while InsurTech can help them do some things better, InsurTechs need the support of larger corporates to realise their dreams.

  1. Jingle All the Way

I might be the only adult male in the world who has watched Jingle All the Way more than any other Arnold Schwarzenegger movie. It’s objectively terrible: camp, corny and just horribly acted; I love it. This is the one movie on the list I definitely don’t watch unironically. I’ve tried but it’s impossible. The bit at the end when the mum thinks her son is about to fall to his death and he’s saved at the last minute and she takes us through the entire emotional range of mild concern to supreme indifference, is sensational. Arnie is the best actor in this movie. It’s amazing, but true.

The story of a dad who forgets to buy his son the year’s “must have” toy, and tries to find it in busy stores on Christmas Eve, this has a couple of lessons for us.

Firstly, there’s the lesson of appropriate delegation from the real villain of the piece, the Mum. So far as I can tell, she’s a stay at home mum, so what the hell is she doing getting her overworked husband to buy the present, and only checking with him that he’s got it on the 23rd December? Finding the appropriate person to do a task, setting appropriate deadlines and checking in with them in a timely manner is important.

But the key lesson is “know your audience”. Santa doesn’t seem to exist in this movie, certainly not in the “he’s real, and he brings the presents” sense. Yet it’s mindless and cheesy and corny and slapstick, obviously aimed at kids. Who was this made for?

  1. Home Alone

8 year old Kevin McCallister battles the Wet Bandits to protect his home after his horrific family (really, objectively awful people) leave him at home and fly off to Paris.

Home Alone’s lesson is one that experience is not the be-all and end-all and that given an opportunity to flourish people can achieve amazing things. Kevin goes from one of “les incompetents” to a meticulous planner saving his house from being burglarised and flooded by the nefarious Wet Bandits.

At distriBind, some of our team didn’t have a lot of experience when they joined but they are resourceful, hard-working and intelligent and amongst the very best people I’ve ever worked with. Hopefully, they won’t smash me in the face with an iron.

  1. Home Alone 2

    Kevin’s family are still terrible. He’s on his own again, this time in New York. The Wet Bandits are now the Sticky Bandits and they’re on the loose and up to no good.

    The lesson here is one about growth and expansion. When your company grows, maybe expands into new territories, you’ll face some similar challenges and some new ones. Hopefully the new ones will be more of the regulatory regime kind, and not obviously paedophile Hotel Receptionists. (Seriously, Tim Curry sees a 9 year old boy in his hotel and sneaks into his room at the first opportunity – what the hell?)

  2. Bad Santa

The story of Billie Bob Thornton’s mean-spirited, foul-mouthed, drunken, womanising, thieving Department Store Santa Willie T. Soke and his exploitation of the gullible Thurman Merman, this is a world away from a lot of the family-friendly movies elsewhere on the list.

But, for all the NSFW content, there is a business lesson here, honest. (Well… there is if you’re prepared to go with me… come on, it’s Christmas!)

Remember, this is still a Christmas movie, so of course there’s a happy ending / redemption arc of sorts. One that has an object lesson for startups.

It is, of course, the art of the pivot and taking opportunities when you see them open up. In his eventual determination to deliver Thurman his pink stuffed elephant, Soke is the founder who sees the opportunity to keep pushing forward when things might otherwise seem lost.

In his drinking, swearing and womanising though, he’s not like any founder I know…

  1. A Christmas Carol / Scrooged

    This is a double header. Firstly, you must watch the 2009 Disney Animated version with Jim Carrey to learn the right lesson. Of course, you can watch any version of A Christmas Carol to learn the corny lessons around second chances, learning from mistakes and “it’s never too late”, but you’re not here for that.

    No, it’s crucial to watch the Jim Carrey version, because while it’s mostly faithful to the source material there’s also an absurd chase scene inserted that is so obviously only there to make use of the then-current 3D craze. It’s not particularly suspenseful and it holds up the narrative. It’s shoehorned in painfully. But, 3D was the shiny toy… it was the future. We were all gonna have 3D TVs at home… right?
    The lesson is that not every innovation works, especially if it doesn’t have the killer use case, or there’s friction on uptake (as with 3D specs). 

    The parallel with the current enthusiasm for AI is not precise but there’s no doubt the blanket use of AI regardless of the benefit of the use case will see “AI” in some applications being discarded like 3DTV. I recently posted about my washing machine using AI to decide what cycle to put on – this is obviously nonsense. I also have my doubts about Large Language Models being used in document processing, at least for as long as the user still needs to write prompts.

    Then, you should watch Scrooged - an updated version of a Christmas Carol, so you can watch it to learn all the corny lessons I wouldn’t let you learn in the Disney version, but there’s Bill Murray so you don’t have to hate yourself.

  2. Daddy’s Home 2

    I first watched Daddy’s Home 2 on an aeroplane on the way home from Singapore, and it immediately became one of my favourite Christmas movies.

    The Christmas-themed sequel to a non-Christmas movie, this sees Will Ferrell and Mark Wahlberg’s blended families staying together over Christmas, and the tensions that ensue.

    This teaches us important lessons about effective communication and its impact on team cohesion and how the balance can be thrown off by having the wrong people around. Mel Gibson, who play’s Wahlberg’s dad, is a bit of a dick who enjoys bringing to the surface anything Wahlberg and Ferrell may be “harbouring”, and Ferrell’s dad John Lithgow is keeping his own secret…

    Lots of analogies to office politics, especially if you buy in to the conceit that companies that say “we’re like a family around here” are often the worst. It’s also really funny.
  1. Christmas Vacation

Chevy Chase is never not funny, and while the story of the Griswald Family’s disastrous Christmas isn’t one of his classics, it still has some decent laughs.

This movie has probably the most overt business-focused message of any, since the main narrative revolves around Clark Griswald’s plan for his Christmas bonus, and the calamity of not getting it.

The movie teaches business leaders to beware the impact of their decisions on the members of their team.

  1. The Santa Clause

    Tim Allen’s divorced Dad accidentally kills Father Christmas and after putting on the Santa suit for implausible plot reasons actually becomes Santa.

    Like Elf, and so many others, this is another universe where Santa is real but no adult believes in him, so again I ask, who the hell do they think is bringing all the presents? How does the economy work? If all the kids get 2 Nintendo Switches, the re-sale value is gonna tank. How drunk are the parents, and can I get a glass of what they’re having?

    The lesson of The Santa Clause is about adaptability in the face of new and unexpected challenges. Tim Allen’s character learns to embrace the new role and challenge of life as St Nick. This is particularly relevant to life in a start-up, where you have a lot thrown at you and often have to wear many hats – though not usually a red one with white fluffy trim.

    Talking of being nimble and adapting to unexpected circumstances… did you know Tim Allen was once facing life imprisonment for cocaine smuggling, and snitched on everyone to get a lighter sentence. While I’m not sure we should draw lessons from that, it does put a different spin on the term “White Christmas”.

  2. The Holiday

    Insufferable couple Vince Vaughan and Reese Witherspoon have to spend Christmas with their even worse families, teaching us the valuable lesson that however annoying that one co-worker is, the new starter is probably worse…

    It’s no surprise that the parents of both of the main protagonists have divorced, because imagine the strain bringing up these self-absorbed idiots must have put on their marriages. If they were just a little less annoying, maybe they’d only have to have two Christmases…

    Aside from the “it can always get worse” message, this film also teaches us about changing priorities and effective communication, especially communication between team-members. While not one of my favourites, this is worth watching for when Vince Vaughan’s character gets beat up by his brothers.

  3. Arthur Christmas

In this animated Christmas tale, there isn’t one Santa but a long line of them. It’s the current Santa’s last year as the main man, before his son “Steve Claus” officially takes over next year. But this is a very disengaged Santa, the son really pulls the strings and has been focused on modernising, bringing a ruthless tech-driven efficiency to the North Pole’s operations. The reindeer have been pensioned off in favour of a turbo-powered sleigh, and the Elves deliver the presents with Mission Impossible style spy gear.

When a glitch happens anyway, and one girl gets left without her present, Steve is nevertheless delighted at a smooth Christmas Eve and convinces Santa that reaching an over 99% delivery rate is an amazingly successful operation.

This leaves his younger brother Arthur and his grandfather the old Santa, to get out the old Reindeer-driven sleigh and deliver the present.

A kid-friendly movie that nevertheless teaches the business world a valuable lesson – tech and modernisation needs to be delivered with the goal of improving customer experience, not as an end in itself.

  1. How the Grinch Stole Christmas

    It’s actually pretty insane to think back to just how big a star Jim Carrey was, and to consider he built a career entirely out of being able to pull a stupid face. As with The Nightmare Before Christmas, there’s a lesson here about finding something you’re good at and riding that pony as far as it will take you!

    But that’s not the main lesson of the Grinch.

    All the Whos in Whoville mindlessly follow tradition and unquestioningly go along with whatever they’re told, whether that’s Christmas is about spending lots of money, or that Green Man bad, mmkay. It is only Cindy-Lou Who who has the courage to stop, think for herself, and ask questions.

    Just because everyone thinks something, or this is the way it’s always been done, doesn’t make it right. You should be inquisitive and ask questions and “why” and “why not” are great ones.

    Like John McClane, Cindy-Lou Who is a founder.

  2. Office Christmas Party

Another of my all-time favourite Christmas movies. Tech company ZenoTech is making cutbacks and one of the branches earmarked for closure is the original home branch of the company’s late founder.

With company CEO (and daughter of the founder) Jennifer Aniston closing the branch seemingly to spite her party-animal brother T J Miller, unless they can land a big deal that day, things look bleak. Unless that is, Miller ignores the corporate instructions not to hold Christmas parties, overrules HRs insistence on a “non-denominational mixer”, and throws an insane Christmas party that the prospect is invited to. Seems reasonable.

The lesson here is about fostering morale through togetherness and a common goal, even in tough times. I’m told this doesn’t always have to involve alcohol, but I’m not sure I want to risk it.

  1. Gremlins

My parents bought me Gremlins on VHS when I was about 7. I don’t know what they were thinking, but I guess money was tight and it was probably in the bargain bin of Woolworths. I don’t remember being particularly scared by it, though watching it now I assume I must’ve been.

The story of a teenager who receives a mysterious creature for Christmas, only to discover it multiplies when it gets wet and turns into a violent, murderous psychopath if it eats after midnight, with a narrative pause for a story about a dad dressing as Santa, falling in a chimney and dying and not being discovered for days after, Gremlins is a heartwarming Christmas tale for kids of all ages (endorsement © Mr & Mrs Connors, 1987).

Gremlins has a crucial lesson for Product Owners… don’t ship a product with a fatal flaw that is incredibly easy for users to accidentally replicate. QA is important.

  1. A Bad Mom’s Christmas

    Like Daddy’s Home 2, this is a Christmas-themed sequel to a non-Christmas original, with a trio of apparently “Bad Moms” enduring visits from their own mothers over Christmas and finding them all unbearable in different ways.

    The main arc follows Mila Kunis’ battles with her “nothing’s good enough” mum, but all of the main characters have their own “mommy issues”.

    Obviously, the parallels between parenthood and management are not exact, but you can see archetypes of management styles from overly-critical, micro-managing, and not being supportive. So the lesson is for managers in giving their staff the space and support to flourish. Then, they hopefully won’t flip-out and trash everything.

  2. The Santa Clause 2

    Having fallen foul of small print once, Tim Allen’s Scott Calvin does so again, when he discovers that he will lose his magic and position as Santa unless he can find a lady willing to become Mrs Claus.

    Leaving the North Pole in the control of a strange cyborg Santa, he has to go back to his old life and decides having more or less abandoned his son for life as St Nick, scoring with the troubled boy’s School Principal is a sure fire way to smooth the father / son bond. Seems legit.

    Back at the North Pole, the cyborg Santa goes mad with power and decides all the children in the world have been naughty and they will get coal. (This would have a lot more narrative jeopardy, if not for the fact none of the parents in world believe in Santa, so presumably will be buying the kids presents anyway…)

    The lesson here is about the cult of leadership. The problems stem from the belief that only “Santa” can be in charge. He has good helpers around him, but is unable to delegate leadership to them because of his profile. Leaders – share the burden and the glory with the people around you that enable your success: it will help you in the long run.

  3. Anna and the Apocalypse

    A Christmas Zombie movie musical… what more could you want?

    High-schooler Anna and her friends are caught in a Zombie Apocalypse when they are already dealing with pressing matters such as planning a gap year, struggling with school work and handling part time jobs

    Sean of the Dead meets Scream meets White Christmas, this is not your average Christmas movie.

    What we can learn from this, however, is the importance of adaptability in crisis management, and being prepared to roll-your sleeves up and get stuff done. You may not want to decapitate a Zombie snow man (or whatever your equivalent is), but sometimes you just have to.

  4. The Star

    Christmas Eve Eve is my favourite day of the year. All the excitement is still ahead of you, but it’s close enough to the big day to justify breaking out the chocolates and opening a bottle before the sun is over the yard arm. What better way to get in the festive mood than to watch the only religious movie on my list?

    The Star tells the story of Mary and Joseph’s journey to Bethlehem not only through their perspective but also the perspective of Bo, a donkey that has escaped from a mill and is travelling with them, and his animal friends including Ruth, a sheep that’s left her flock to follow the star.

    With everyone following the star, this movie teaches the importance of focus on a goal, and working together to achieve that goal.

  5. The Night Before

It’s Christmas Eve, so what else are you going to do other than watch a movie about Christmas Eve?

Ethan’s parents died one Christmas Eve, so his 2 friends vow to always spend Christmas Eve with him and party. During the years that follow, they hear about the mythical “Nutcracker Ball”, but can never get tickets.

Fast forward some more years, and the death of Ethan’s parents means he cannot commit to relationships because plot reasons, but his other friends have moved on and are ready to end the tradition. Meeting for a final Christmas Eve, they finally get tickets to the Nutcracker ball.

There’s a major lesson in this movie of the importance of being open-minded, and able to embrace new opportunities when they present themselves.

Merry Christmas from all of us here at distriBind.

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Dave Connors