2026-04-03 00:30:00
Adam Smith, the 18th century economist, wrote that it’s not uncommon to meet a mother in the Scottish highlands “who has born twenty children not to have two alive.”
That was life. And it hardly mattered whether you were rich or poor. Queen Anne of England had 18 children, not a single one of whom made it to adulthood. American president James Garfield died in 1881 in part because the best doctor in the country was not yet a believer in germs. Two weeks before his death, Franklin Roosevelt’s blood pressure was 260/150, and his doctors could hardly do a thing; basic blood pressure medicine didn’t exist.
If you could show any of these people a modern grocery store, they would faint from disbelief. They could not comprehend that the biggest challenge of grocery shopping is deciding which of the 19 brands of jelly to buy, or that in January you can buy papayas in Minnesota. But most shocking would be the pharmacy in the back, which they would find magical.
And what would their response be?
I don’t think it would be, “You are so amazing.”
It would be along the lines of, “You are so spoiled.”
They would watch us getting frustrated at having to wait in line at the pharmacy and scoff at how unappreciative we are for the magic pills that await us.
They couldn’t fathom that we complain about the price of food rather than being gobsmacked at the mere possibility of abundance.
The irony is that every generation toils and innovates to create a more prosperous world for their heirs. But when you watch those future generations interact with their world, your feelings can shift from pride to disappointment. Our kids won’t suffer in the same ways we did, and they won’t even appreciate it.
It’s a common problem. Wealthy families wonder how they can support their kids without them becoming spoiled brats. Whole societies have a long history of feeling disappointed in youngsters who look lazy and entitled relative to their elders.
I’ve been thinking about this as I contemplate money and my own children. Here’s where I’ve landed.
I had a conversation with a guy a few months ago whose immigrant parents came to America and worked tirelessly in low-wage jobs to make ends meet.
Those kids are now adults, and this guy – as I understood it – felt a sense of shame that as a college-educated white-collar worker he would not have to suffer the same way his parents did for him. His parents instilled in him the lessons of frugality and grit. Would his own children learn the same from him if they watched their father live a comparatively easy life?
He gave an example: when he was a kid, all books were borrowed from the library. Now his young daughter demands (and gets) to purchase $15 Taylor Swift books that pile up in her room.
My response was that if we talked to his immigrant parents, I would bet they would say: that was the goal.
The entire reason they worked so hard was to catapult the family’s standing to a point where one generation must grind to get food and the next can indulge in Taylor Swift books. The granddaughter’s spoiled appearance is not a side effect of wealth; it was the goal.
To put it differently: The goal of some parents is to work so hard that their kids and grandkids get to live a life that appears spoiled by the standards of previous generations.
Like wealth, there is no objective definition of what counts as spoiled – everything is just relative to someone else.
I can look at my own kids and see how spoiled they are relative to my own childhood.
But couldn’t my grandparents do the same for me? They had to worry about polio, scarlet fever, and a host of other things that never cross my mind.
And couldn’t their own grandparents do the same? Their transportation was limited to horses, and a bad crop could mean losing some of your children – a life inconceivable just a generation or two later.
What’s common to miss here is that when one generation’s life becomes comparatively easier than before, their life does not become objectively easy; they just move on to worrying about higher-order problems that were previously deemed not urgent enough to worry about.
One generation worries about how to get food and shelter.
The next doesn’t have to worry about food and shelter but frets about security.
The next has security but worries about disease.
The next tackles disease but worries about education.
The next gets education but worries about work-life balance.
On and on. It’s the classic John Adams line, which I’ll paraphrase: “I studied war so my kids will have the liberty to study engineering. They will study engineering so their kids can have the liberty to study philosophy, whose kids can have the liberty to study art.”
I hope my kids and grandkids won’t have to worry about cancer in the ways we do. I hope they have incredible technology that makes their jobs easier than ours. I hope that everyday frictions we deal with today disappear. I hope their energy is so abundant they consider it unlimited.
Is that spoiled? I suppose, but when you frame it like that you might think of a different word – perhaps “lucky,” or, “fortunate.”
Or perhaps, “beneficiaries of the accumulated hard work of those who came before them in a way that leaves them able to spend their days solving new problems.”
Which is what you and I are today.
2026-03-31 19:00:00
We are in the early innings of a fundamental shift in how we understand the human body. The current medical model is reactive and episodic — you feel sick, you see a doctor, you get a snapshot. But your body is a complex machine running 24/7, and it deserves a software layer that can actually keep up.
That’s the idea behind what founder Will Ahmed from WHOOP calls the Health OS: continuous monitoring, proactive intelligence, and personalized coaching — all built on one of the most comprehensive longitudinal health datasets in existence. WHOOP has collected over 24 billion hours of continuous physiological data from more than 2.5 million members. That data, combined with a new medical-grade device and a generative AI coaching layer, positions WHOOP to bridge the gap between consumer wellness and clinical healthcare in a way no one else can.
This is why Collaborative Fund is leading a $575 million Series G round in WHOOP at a $10.1 billion valuation — our largest investment ever. Below is a lightly edited version of the cover letter to our term sheet:
Dear Will:
From the time Nicholas Negroponte introduced us back in April 2013 and we met at Grey Dog Cafe to talk about Bobo Analytics, I’ve been a true believer in your mission. We invested early, making WHOOP one of the core positions in our second Fund.
Empowering people with meaningful insights into their health is one of the most significant ways to improve human life. WHOOP represents exactly why I started Collaborative Fund: to back founders who push the world forward. You and your team have built not just an exceptional company, but an outstanding global brand. The awareness-to-purchase ratio is the best in its class, and it keeps growing because the product delivers.
In 2020, during the chaos of Covid, I remember telling you how much I was relying on WHOOP to monitor my respiratory rate and spot early signs of infection. That experience only deepened my conviction. We followed on in the Series E through our Opportunity Fund. Then in 2024, after my father’s heart scare, I bought him a WHOOP so I could track his recovery each day. Now we compare stats all the time using the community feature. It’s something that brings us both peace of mind and connection.
WHOOP stands apart as the only founder-led company in the health and wearable technology space, and it shows. The craftsmanship and attention to detail from your design and product teams are unmatched. The user experience is elegant and intuitive. The new medical-grade device positions the company to expand meaningfully into healthcare and even Medicare markets, bridging consumer and clinical worlds in a way few others can.
You and the team are building a generational company. I feel lucky to have had a front row seat, and I’m confident in making a firm‑defining investment as WHOOP enters its next phase of growth.
This opportunity has the full commitment of Collaborative Fund. We have attached a detailed term sheet outlining our proposal.
We’re proud to anchor a global syndicate that includes the Qatar Investment Authority, Mubadala Investment Company, Macquarie Group, Abbott Labs, Mayo Clinic, and cultural icons like LeBron James and Rory McIlroy. Together, this group will fuel the company’s international expansion across Europe, the GCC, Latin America, and Asia.
WHOOP is at a true inflection point. The opportunity ahead is bigger than wearables, and bigger even than wellness. It is to build the software layer for the human body: a system that helps people understand what is happening inside them, respond earlier, and live with more agency over their health. With unmatched data, exceptional product instincts, and a long-term vision, Will and the team are in a position to define what that future looks like.
You can read more about the deal in today’s New York Times: Whoop, a Wearable Health Device Maker, Raises $575 Million
2026-03-17 23:33:00
Everyone wants to be successful. Successful in our careers, our families, and our communities. I’ve certainly felt this way, that is until this past fall after attending two events, the first being a speech from someone who is more than a decade younger than I am.
In October I attended The Mario St. George Boiardi Forum for Ethical Reflection at my high school, The Landon School in Bethesda, Maryland. The forum celebrates the values my friend George exhibited as a student-athlete at Landon and then Cornell University before passing away on this day exactly twenty-two years ago after being struck in the chest by a lacrosse ball during a game.
This year’s speaker was Connor Buczek, the head men’s lacrosse coach at Cornell, which had recently won the University’s first national championship in any sport in close to five decades. Of even greater significance, it happened 21 years after George passed.
Halfway through his speech, Buczek turned to this topic of success.
Now, if I am being completely honest, I was expecting Buczek to echo the narrative you almost always hear in these scenarios — work hard, follow your passion, etc. and you will dramatically increase your odds for success. So, when he instead implored the room to chase something other than success, I perked up. After all, hadn’t he just defined success by reaching the pinnacle of his profession at the ripe old age of 32?
In his words,
“We are all chasing success at some level. We all want to be good at what we do. We want to be well regarded by our peers. However, how you do this is really important. Success often happens in a vacuum. We are so dead set on the outcome — Am I going to get into this college? Play this sport? Have this leadership role or win this accolade? Yet, being successful in this world isn’t all it’s cracked up to be. Rather we should aim to be significant, which means accomplishing things together. We want to make an impact on the people around us and bring people along with us. Success is meaningless unless we are being significant.”
This was particularly relevant because George’s life embodied significance, as evidenced by the fact that by my count, more than seventeen of his friends and teammates from high school and college have named their sons “George”.
Which brings me to the second event I attended.
A couple months after the Ethics Forum, Landon hosted an annual event that honors two graduates – one for having a distinguished career (either through service to his profession, community, or country) and another for outstanding service to the school.
While the criteria for each award are uniquely different, each year it is often difficult to distinguish which alum is winning which award based on their resumes alone. This year, though, the award winners seemed more obvious… at least on paper.
The alum who won the award for a distinguished career served in the U.S. Navy after attending Stanford in the late 1960s, has been a successful venture capitalist for more than two decades, has been a NVIDIA board member for even longer, took three companies public, and sold a fourth to Sun Microsystems.
Meanwhile, the winner of the award for outstanding service to the school has been a physical education teacher at the school for more than four decades, while also leading the weightlifting program and serving as the offensive line coach for the football team.
Yet, for as different as these two alums’ careers seemed on paper, my new appreciation for this issue of “success versus significance” made me realize that their impact on people is more similar than I may have thought in previous years.
The first served his country, created many jobs as a founder, generated meaningful investment returns for countless investors as a venture capitalist, and has helped change the world as we know it during his time at NVIDIA.
Meanwhile, the second alum also touched a lot of lives, albeit in a very different way. A way that I hadn’t fully appreciated until he explained why he chose to pursue the career he did.
He explained by saying,
“The reason I chose this career is because after graduating from college, I came to the conclusion that I could have a bigger and more long-lasting impact on students through teaching physical education, coaching sports, and working with them as a strength coach than I could as a classroom teacher.”
I loved his rationale,
“See, helping a young boy avoid always being the last one picked in a game or helping an unathletic or small boy gain coordination, speed, strength, and most importantly confidence, brings long-lasting effects. As a mediocre athlete myself, I knew I had to work hard to improve physically in order to play. In doing so, I learned that self-efficacy is the most valuable lesson that I can teach because it helps kids develop work ethic, character, and the ability to handle challenges long after they leave the playing field.”
In essence, this alum’s goal was to help young men who weren’t as strong or talented as people like George have the opportunity to share the same field with them. To be their teammates. To be their friends.
Considering how many young men had passed through that weight room over the years, I knew he had helped hundreds, if not thousands, of young men over the years. What I didn’t fully appreciate was how. That is until I had lunch with another alum a few weeks later.
This alum graduated a few years after I did, spent more than fifteen years in the Marine Corps, and looks every bit the part, standing 6’2 and 190 pounds with a short and tapered haircut.
During our conversation I told this Marine the story about these two award winners and, as I did, I witnessed a huge smile emerge across his face. Naturally, I asked him why?
His response?
“Because when I was in high school, I was the smallest kid in my class at 5’ 6” and 125 pounds, and didn’t hit my growth spurt until I got to college. As a result, it was difficult for me to make varsity sports, but Marty saw something in me. So, with his help in the weight room, I ended up occupying the 126-pound weight class for the wrestling team. Later, after being cut from the varsity lacrosse team in high school, I went on to not only make my college lacrosse team as a walk-on, I eventually was elected a captain as a senior. Then, with more to prove after college, I joined the Marines. Marty’s confidence in me was a big part of the reason why. When I was the smallest kid in my class, he was the one who instilled in me the confidence to know I could do anything. I owe him a lot. It’s the reason he and his wife were at my wedding a few years ago.”
Impacting lives quietly along the way. George did it in his own unique way, as did the two other alums.
Now that’s significance.
2026-01-16 04:56:00
Today, NBC Sports owns the rights to many of sports’ “crown jewels,” including the Super Bowl, the NBA, the Premier League, Notre Dame Football, and of course, the Olympics. Yet, it hasn’t always been this way.
In the early 1990s, NBC Sports was in trouble. After losing Major League Baseball, the network faced a 32-week hole in its programming schedule, which represented an eternity in sports television. With no obvious answers and little margin for error, NBC turned to Dick Ebersol, the co-creator of Saturday Night Live, to stop the bleeding.
Ebersol implemented widespread layoffs and turned to a young producer named Jon Miller. His marching orders were simple, but stark. Fill the schedule, and do it on a shoestring budget.
What happened next didn’t just save NBC Sports. It quietly reshaped sports television for decades to come.
How?
By turning severe constraints into unexpected opportunities.
Given NBC’s state of peril, the moment was ripe for experimentation. In Miller’s first few months on the job, he threw anything he could on the air. This included events like the NFL Quarterback Skills Challenge, beach volleyball, and the National Heads-Up Poker Championship.
Some worked, others didn’t, but a significant revelation occurred. Being starved of money and resources forced Miller to be relentlessly creative. Most notably, things Miller learned from one experiment led to innovation in others.
Look no further than the inaugural Quarterback Skills Challenge. In passing, Miller asked John Elway and Dan Marino if they would be interested in the prospect of playing in a celebrity golf tournament during the offseason.
The reason?
Miller was looking to fill NBC’s massive hole around the 4th of July, so knowing that NFL quarterbacks were the biggest draw in sports and often pretty good golfers, he thought he there might be something there.
After securing two of the NFL’s biggest stars, along with former standouts Joe Namath, Joe Theismann, and Jim McMahon, Miller launched the American Century Celebrity Golf Tournament at Lake Tahoe, an event that would become a runaway success for more than three decades.
Witnessing Tahoe’s popularity, Miller saw room for more unique events. Sticking with golf, he turned to an international match play golf tournament that hadn’t generated much in the way of television ratings — the Ryder Cup.
In 1991, Miller secured the rights to the tournament at Kiawah’s Ocean Course and capitalized on a simmering feud between U.S. captain Paul Azinger and European captain Seve Ballesteros. Combined with the surge of patriotic fervor following the Persian Gulf War, the stage was set for an epic showdown that would forever be remembered as the “War by the Shore.” In the process, Miller transformed a once-overlooked event into the most anticipated tournament in golf, every other year.
This success would spawn several more iconic events, including the National Dog Show (a Thanksgiving Day staple since 2002) and the NHL’s Winter Classic, now the highlight of hockey’s regular season.
So, what explains Miller’s actions?
Psychologists have a name for it — cognitive resourcefulness.
In short, when resources are scarce, humans often bypass conventional thinking and take unfamiliar paths to solve problems. In this case, cognitive resourcefulness caused Miller to reimagine what sports television could be. Without dollars to spend, he truly had to think. To solve. To create.
We see this in all walks of life.
Seinfeld, arguably the most successful television show of all time, was primarily filmed on a tiny set meant to resemble an 800 square-foot apartment on the Upper West side of Manhattan. In reality, the set was less than half that size.
So how did the cast operate within such a tiny space for nine seasons?
As Julia Louis-Dreyfus (aka Elaine) explains, they had to be creative, saying:
“We were always challenged by the size of Jerry’s apartment. It was just so small. What are you supposed to do? You can’t just walk in and sit on the couch every time. This is why I used to do things like go to the refrigerator and just look for things. We were limited, so we had to constantly be creative.”
I witnessed something similar this past summer on our family vacation to the beach. Our boys and their cousins only had a few inflatable toys, two-fold-out chairs, a couple balls, and a rickety goal in the pool. Yet, within minutes, they had invented a game — two points for jumping over a foam noodle and throwing a ball in the goal, five for making it through an inner tube, ten for sinking one into a small basket. First to twenty wins. Limited resources sparked limitless ideas.
Whether it’s an NBC executive, actors in a sitcom, or a group of high-energy kids, if you give someone limited resources and a clear challenge, odds are they will find a way to solve it. Most importantly, they will be infinitely more innovative than if they had unlimited means.
Just look at our economy.
Is it a coincidence that some of our most iconic companies were born during economic downturns?
I doubt it.
As access to capital during the 2008–2011 financial crisis dried up, entrepreneurs were forced to improvise. Airbnb turned spare rooms into a global hospitality network, while Uber built a transportation empire using existing car owners instead of buying a brand-new fleet. Meanwhile, Venmo and Square set out to solve everyday problems with lean, tech-driven models.
How about in the depths of the dot.com bust?
Would you believe me if I told you Palantir and Tesla both were founded in 2003?
The same is true in investing.
Personally, I cringe when I hear that individual investors are “disadvantaged” because they don’t have access to things like private equity and that the only answer is to provide them with access through the “democratization of finance.”
Why?
Because the answer to a lack of resources is not to follow others. Rather, the answer is to be different. To be creative. To think outside the box.
This is why I shake my head when people recommend that average investors should follow Yale University’s David Swensen or Berkshire Hathaway’s Warren Buffett. While Swensen and Buffett had large balance sheets, a supremely talented team, and a network around the world that was second-to-none, you likely have none of these.
However, a lack of resources means you have something they don’t — a license to be creative. It means you have the chance to play your own game, do things differently, and adhere to a game plan unique to you.
So, when should you think about putting a plan in place?
Now is as good a time as ever.
Fifteen years into a bull market with deregulation underway, interest rates being cut, credit widely available, corporate earnings continuing to surpass expectations, and investments in artificial intelligence booming, things feel pretty darn good.
The problem though, as Hyman Minsky was fond of saying, is that,
“Stability breeds instability. The more stable things become, and the longer things are stable, the more unstable they will be when the crisis hits.”
So, what should an investor do?
Go to cash? Run for the hills?
Not exactly.
Rather, it begins with focusing on what you can control. This means positioning yourself and your portfolio to be ready for the next crisis, whenever one hits, so that you can see it as an opportunity rather than a threat.
An opportunity because crises create scarcity and pressing problems that demand solutions.
An opportunity because crises are what spawn companies and innovators who rise to solve them.
An opportunity because you’ll likely be in a position to supply the capital that empowers these folks to succeed (and at much more attractive entry points than we are seeing today…).
For me, this has meant taking a few chips off the table recently and rotating capital from some richly valued parts of the market into lesser trafficked areas (e.g., REITs, biotech, select parts of international markets, etc.).
More importantly though, I have dusted off Dan Rasmussen’s “crisis investing” framework and started thinking about what I will do when a crisis hits. This has meant determining what companies, funds, or parts of the market I will want to invest in and what will trigger those investments (e.g., a specific percentage sell-off, credit spread limits, valuation triggers, etc.). It has also meant making sure I am completely comfortable with what I currently own, so that when things do crack, I will be able to hold them through to the other side.
The fact is, I have no clue when the next crisis will occur. No one does. Yet, it is hard to deny that we are closer to one than we were 1-, 3-, 5-, and certainly 10-years ago. This is especially the case given the S&P 500 has compounded at 20% over the past six years and annually at 14% for fifteen (the NASDAQ has been even more pronounced generating an annual return of 27% for the past six years and 18.5% over the past fifteen).
The reality is that when one of these moments does come, things will feel uncertain, even dangerous. Future prospects will look grim. As a result, most investors will turn bearish, retreat, and de-risk. However, that’s when the instinct should be to do the opposite. That’s when you should turn to the playbook you built when things felt more stable.
The reality is, these are the moments when innovators and visionaries like Jon Miller, Brian Chesky, and Elon Musk don’t just survive — they reinvent the game. And when they do, that’s when you need to invest.
2026-01-07 04:09:00
Things I’ve been thinking about lately …
I broke my back skiing when I was a teenager. It’s still screwed up and I occasionally tweak it, leaving me in agony for a few days. When I’m in pain I’ve noticed: I’m irritable, short-tempered, and impatient. I try hard to not be, but pain can override the best intentions.
One lesson I’ve tried to learn is that whenever I see someone being a jerk, my knee-jerk reaction is to think, “What an asshole.” My second reaction is: maybe his back hurts.
It’s not an excuse, but a reminder that all behavior makes sense with enough information. You can always see people’s actions, but rarely (if ever) what’s happening in their head.
Here’s a related point: Most harm done to others is unintentional. I think the vast majority of people are good and well-meaning, but in a competitive and stressful world it’s easy to ignore how your actions affect others.
Roy Baumeister writes in his book Evil:
Evil usually enters the world unrecognized by the people who open the door and let it in. Most people who perpetrate evil do not see what they are doing as evil. Evil exists primarily in the eye of the beholder, especially in the eye of the victim.
One consequence of this is that it’s easy to underestimate bad things happening in the world. If I ask myself, “How many people want to cause harm?” I’d answer “very few.” If I ask, “How many people can do mental gymnastics to convince themselves that their actions are either not harmful or justified?” I’d answer … almost everybody.
An iron rule of math is that 50% of the population has to be below average. It’s true for income, intelligence, health, wealth, everything. And it’s a brutal reality in a world where social media stuffs the top 1% of moments of the top 1% of people in your face.
You can raise the quality of life for those below average, or set a floor on how low they can go. But when a majority of people expect a top 5% outcome the result is guaranteed mass disappointment.
I think the majority of society problems are all downstream of housing affordability. The median age of first-time homebuyers went from 29 in 1981 to 40 today. But the shock this causes is so much deeper than housing. When young people are shut out of the life-defining step of having their own place, they’re less likely to get married, less likely to have kids, have worse mental health, and – my theory – more likely to have extreme political views, because when you don’t feel financially invested in your community you’re less likely to care about the consequences of bad policy.
Every economic issue is complex, but this one seems pretty straight forward: we should build more homes. Millions of them, as fast as we can. It’s the biggest opportunity to make the biggest positive impact on society.
I heard someone say recently that the reason so many people are skeptical AI will improve society – or are terrified it will do the opposite – is because it’s not clear the internet (and phones) made their life better.
That’s a subjective point, but it got me thinking: Imagine if you asked people 25 years after these things were invented whether life was better or worse because of their existence: Electricity, radio, airplane, refrigeration, air conditioning, antibiotics, etc.
I think nearly everyone would say “better.” It wouldn’t even be a question.
The internet is unique in the history of technology because there’s a list of things it improved (communication, access to information) but another list of things it likely made worse for almost everybody (political polarization, dopamine addiction from social media, less in-person interaction, lower attention spans, the spread of misinformation.)
There aren’t many examples throughout history of technology so universal with so many obvious downsides relative to what existed before it. But the wounds are so fresh that it’s not surprising many look at AI with the same fear.
This is more hope than prediction, but I wouldn’t be surprised if in 20 years we look back at this era of political nastiness as a generational bottom we grew out of.
There’s a long history of Americans cycling through how they feel about government and how politicians treat each other.
The 1930s were unbelievably vicious. There was a well organized plot to overthrow Franklin Roosevelt and replace him with a Marine general named Smedley Butler, who would effectively become dictator. The Great Depression made Americans lose so much faith in government that the prevailing view was, “hey, might as well give this a shot.”
It would have sounded preposterous if someone told you in the 1930s that by the 1950s more than 70% of Americans said they trusted the government to do the right thing almost all the time. But that’s what happened.
And it would have sounded preposterous in the 1950s if you told Americans within 20 years trust would collapse amid the Vietnam War and Watergate.
It would have sounded preposterous if you told Americans in the 1970s that within 20 years trust and faith in government would have surged amid 1990s prosperity and balanced budgets.
And equally absurd if you told Americans in the 1990s that we’d be where we are today.
Cycles are so hard to predict, because it’s easier to forecast in straight lines. What’s almost impossible to detect in real time is the same forces fueling public opinion plant the seeds of their own demise. When times are good, people get complacent and stop caring about good governance. When times are bad they get fed up and say, “Enough of this.” And I think we’re not far from that today.
I have a theory about nostalgia: It happens because the best survival strategy in an uncertain world is to overworry. When you look back, you forget about all the things you worried about that never came true. So life appears better in the past because in hindsight there wasn’t as much to worry about as you were actually worrying about at the time.
2025-12-17 06:44:00
People often ask me where I get ideas for this Substack. The simple answer is everywhere, even a Christmas tree lot on a cold night in December.
When my brother and I were kids, each year we would make the annual trip with our dad to pick out the family Christmas tree. But when we left for college, he was left to make the selection without us. That is until recently when we decided the old man needed some help.
Now, one might conclude that we did so because at 78 and a shade under 5’4, wrestling a nine-foot tree off the car roof had become a nearly-impossible task. While true, our rationale ran deeper — we thought he needed “air cover.”
Air cover?
Yes, air cover.
In short, we needed to witness his selection process so that we could defend him.
See, in what had become a Christmas ritual in the Lamade house, every year for as long as I can remember, my dad would go out, buy a tree, put it up on the stand, and my mom would immediately spot the flaws. Hole on one side. Dead patch in the middle. Leaning hard to the left. An obvious flat top. You name it, we’ve had it.
For years my brother and I would go into full blown “PR mode” after the tree went up, saying things like:
“The tree will look nice once it drops.”
“Dad did his best.”
“It’s Christmas — give him a break.”
But candidly, we kept asking ourselves the same question, how does this keep happening?!?!
I mean, my mom wasn’t wrong. These trees nearly always had something wrong with them.
That is, until my brother and I finally saw him in action on the lot last year. Like the Hardy Boys, we solved our childhood mystery almost instantaneously.
When we arrived at the lot, the two of us prepared to fan out to look for a tree. The goal was simple – find a nine-footer with no dead branches, not too big…not too small, and certainly no flat tops.
Then it happened. Something the two of us had not prepared for. It was akin to the moment as a kid when you find out the whole secret behind Santa.
So, what was it?
Practically the minute we walked onto the lot, my dad pointed to the first nine-footer he saw and said – “We’ll take that one.” Huh? Was this a joke??
Then it all made sense. This is how he had managed to bring home an imperfect tree year-after-year. He didn’t search. He didn’t compare. He didn’t think about how a tree would look after it “dropped.” He simply saw one that looked good enough and bought it. Witnessing what had just happened, the two of us turned to him and said,
“What are you doing? You cannot be serious!?!?”
He then looked at us like we were the crazy ones and said,
“What do you mean ‘am I serious’? Of course I am serious. Your mother will find something wrong with any tree I bring home, so why spend an hour in the freezing cold looking for one?”
Here’s the thing. He wasn’t wrong. But there was more to it.
My dad has always been drawn to the oddball. The misfit. The underdog. The one with “character.” Deep down, I think he liked “rescuing” the ugly tree from the lot. I even think he got a kick out of imagining the moment Mom would see it and deliver the annual critique. The whole thing amused him.
And truthfully, we have laughed about our trees every year. The one with the massive hole. Ole Flat Top. The one that looked like it had fallen over six times. Best yet, after critiquing them initially, almost every year my mom eventually comes around to liking these trees.
Which leads me to the real point.
People think Christmas is about perfection – the perfect house, the perfect photo, the perfect gifts, the perfect everything. But the moments we actually remember aren’t the flawless ones.
We remember the misfit tree.
We remember freezing with our dad in the Christmas tree lot, the uncle who had a few too many adult beverages, and the overly dry turkey.
We also remember the cousin who was allergic to the family dog and almost fell asleep at dinner after taking too much Benadryl (me) and the older brother who shot his younger brother in the rear-end from three feet away with a paintball gun he got for Christmas (also me…the shooter that is.)
Yet, somewhere along the way, we lost sight of this. Perfection, or the perception of it, has become the goal. We curate our lives on YouTube through highlight reels and post our airbrushed photos from vacation on Instagram. It’s why people are increasingly using artificial intelligence to “perfect” nearly everything they do. And yes, it’s why people are increasingly buying artificial Christmas trees….because they are easier to set up, cleaner to maintain, and “perfect” in so many ways.
But here’s the question:
By attempting to remove all the imperfections in life, are we removing the stories? The moments that make us laugh? The mistakes and imperfections that make us uniquely human?
I don’t know. Maybe I sound like the Grinch. Maybe I am overly nostalgic for the past. Maybe I just need to accept that this is what progress looks like. Or maybe, just maybe, there is something special about the tree with the flat top. The one that leans a little. The one with “character.” The one you talk about for weeks, if not years later. The one that reminds you that since perfection is impossible, you might be better off simply embracing life’s imperfections.
UPDATE:
After I finished writing this, I had a work conference in Georgia. As a result, I unfortunately had to miss the annual tree decorating night at my parent’s house, which is a highlight of the Christmas season for all of us, especially the grandkids.
This year, since it was on the same day as my flight, I called my wife when I landed to see how it was going. Her response?
“Ted, you won’t believe it. The tree fell over.”
My reaction?
Now that’s perfect, in every sense of the word.
