There are some mornings when you sit down…
Look out at the horizon…
And you know exactly what to write.
The thoughts come quickly.
And the words just flow.
* * *
Then there are other days…
When it’s hard.
When you need to dig deep…
And you need to push yourself…
To find that new, novel (and useful) original idea that you know somewhere desperately wants to break through…
For me, today was one of those days.
1 | So what does one do on days like this?
Well, I don’t know about you…
But for me, there are a few goto “moves” I’ve learned to help me get unstuck…
Like a brisk solo-hike in the cold winter woods…
Or a long, hot shower to clear my mind…
Often times on days like this…
I’ll also look back at my notes from what I’m currently reading or listening to (Soulcraft by Bill Plotkin, PhD at the moment…) and the connection it has to the projects I’m currently working on…
I’ll also look back at my calendar from the past week and review the most impactful conversations I’ve had, like:
- The “Contrarian Ideas for 2025” presentation I delivered for the amazing Alex Cattoni‘s Copy Posse group and the ensuing discussion that sparked an idea in my mind around “Authenticity, Deception, & Self-Deception…”
- The conversation with my friends Jon Vroman and Jason Lee about a Front Row Dads book on fatherhood that we’re exploring possibly writing together, and the importance of starting with “First Principles Thinking…”
- Or the discussion with my colleagues Jayson Gaignard and Charlie Hoehn about artistry and craftsmanship; carving your own path instead of chasing the algorithm; and being the “Lighthouse for the Change” you’re looking to make…
I could go on and on, but I think you get the point :-)
Another thing I’ll do when I get stuck like this is look back at a weekly Evernote file I keep called the “Cutting Room Floor…”
Like the screenshot below, this is a weekly file I keep that contains all my raw notes of everything that did not make the cut into that week’s issue of The Digital Contrarian.
As you can see, my weekly “Cutting Room Floor” is often a motley collection of half-baked ideas, resources that have been recommended, messages that I’ve written, (as well as a fair bit of “throat-clearing” that needed to be clipped from that week’s newsletter, but which I didn’t have the heart to discard…)
This weekly file will also sometimes contain a few “hidden gems” that didn’t quite fit into the content of that particular issue – but which I believe could warrant deeper exploration in some future work…
So it’s often fertile ground when digging for ideas worth writing about…
* * *
All that said…
When it comes to ultimately deciding what I’m going to write about in a given week, my absolute non-negotiable is this:
It needs to be something which I’m deeply fascinated by in this moment, and which is making me think about some aspect of the world in a new and different way.
And I’ve learned to trust that by starting with something that fits this definition, it will yield insights that are interesting to both me and more importantly (at least some of) my readers.
(Hopefully today that includes you :-) )
And then almost invariably, once I start getting into it, eventually it happens:
That once seemingly-elusive “new, novel, and (hopefully useful) original idea that wants to break through” somehow emerges in the writing process itself…
It’s often not what I intended to write about when I first started, but it’s nevertheless the idea that shows up…
And that brings us to the focus of our discussion here today, which begins with the following…
2 | Why "Over-Indexing" is Both the Single Biggest Secret to Success (& Reason for Potential Failure) in Your Business.
The idea of “Over-Indexing” came up in my investment peer group meeting this month, when we examined a highly-concentrated investment portfolio comprised of just four (4) public stocks and a large position in BTC.
(A very atypical level of concentration in our group…)
And this led me to reflect on some ideas that I think are worth considering not just in terms of investing…
But in terms of your business (and perhaps life) more generally…
* * *
Now, before we go too much further, let’s begin with a quick definition of “Over-Indexing” to set the stage…
Within the context of an investment portfolio – ChatGPT offers the following:
Over-indexing refers to allocating a disproportionately large share of assets to a particular sector, asset class, or market, often to capitalize on perceived opportunities, but at the risk of reduced diversification and increased exposure to volatility.
(Or in other words, putting a huge percentage of your net worth into BTC, for example…)
But over-indexing is not just a concept limited to thinking in terms of how you invest.
It actually has far deeper implications when we think about it in terms of the decisions we make in our business – and within the context of life more broadly…
Here, ChatGPT offers up a much more relevant definition for our conversation:
Over-indexing refers to allocating an outsized amount of focus, resources, or effort to a specific area, often to achieve extraordinary results or gain a competitive advantage, sometimes at the risk of neglecting other priorities.
(Like for example, building your entire business around a specific skill – or a piece of technology…)
Remember Clubhouse, anyone?
Now of course, there’s the obvious “don’t put all your eggs in one basket” cautionary tale that over-indexing evokes…
And if you take a moment to examine your own life and business and ask yourself:
What’s one area (if you’re totally honest with yourself) that you may be over-indexing for right now?
You probably already know what it is.
But the tension lies in the fact that, at the same time, over-indexing is also a necessary prerequisite for success.
In fact, by definition, achieving extraordinary results in any field, market, or vocation requires going deeper (and investing more effort, focus, attention) than the majority are willing to go…
The key lies in the difference between:
Unconscious Over-Indexing:
When we overly focus on an area without realizing it, potentially leading to blind spots or imbalance.
And…
Intentional Over-Indexing:
A deliberate, strategic focus on an area to achieve mastery or outsized results, recognizing the trade-offs and potential risks.
With respect to the latter (which is our focus here today) the question is naturally:
How do you know what to intentionally over-index for in your business to maximize your chances of success?
Or in other words, how do you learn to identify the Bitcoins while at the same time learning to stay away from the Clubhouses…
The answer to this question lies within becoming a student of…
3 | Megatrends.
First, what is a megatrend, exactly?
(And what makes it different from a plain old regular trend?)
Well, according to Wikipedia, a megatrend is a substantial, long-term shift that influences a wide range of activities, processes, and perceptions, often on a global scale.
And unlike regular trends, which may be short-lived or confined to specific sectors, megatrends are pervasive and enduring, affecting multiple aspects of society, including politics, economics, environment, and culture.
The term “megatrend” was first popularized by futurist John Naisbitt in his 1982 blockbuster bestseller, Megatrends: Ten New Directions Transforming Our Lives.
And in his work (which was groundbreaking at the time) Naisbitt identified significant shifts, such as the transition from an industrial to an information-based economy.
Now, you might be wondering…
What are some examples of the biggest megatrends reshaping our world today?
Well, a few notable ones include things like:
- Food Tech Innovation (e.g. precision fermentation)
- Longevity & Healthspan (vs. Lifespan) Extension
- Specialized (vs. General) AI Augmentation (e.g. law)
The “Return to Real Movement” we discussed in-depth in [Issue #028] of The Digital Contrarian would qualify as a response to the megatrend that we might describe as “Digital Saturation” & The Search for Authenticity…
Speaking of which by the way…
I wanted to let you know that the upcoming “Return to Real” in-person Mastermind that I’m hosting in March is officially 100% Sold Out.
(Spots went much more quickly than I expected – in less than 24 hours of the email I sent out announcing dates and details.)
All that said, there is clearly interest to do more of this sort of thing. So I may do another one of these later this year.
And if you’re interested in being notified the next time I do one of these in-person Mastermind Experiences, you can get your name onto the priority waitlist by clicking this link here below:
Okay. Now, in terms of megatrends, there are of course many others beyond the ones I’ve listed above…
But the key is this:
By over-indexing your business around one or more of these megatrends, it can create asymmetric opportunity for you because you’re aligning your business with the future and riding the wave of inevitable, compounding growth…
But all that being said…
It’s not enough to just throw yourself into the river of one of these megatrends and passively float your way to the promised land of success…
There’s an additional ingredient that’s critical to the equation, and that is…
4 | Layering Contrarian Thinking.
You’ve probably noticed that one thing I place a high value on is craftsmanship and originality…
(Sometimes to a fault, to be honest…)
And in world that’s obsessed with better, faster, cheaper… more, more, more… and quantity over quality…
This is largely a contrarian view that’s often at odds with the rat race that the majority is running…
ZIG when they ZAG.
And while it’s true that the majority is sometimes right.
At the same time…
The biggest opportunities in life come from decidedly not following the crowd…
In fact, generating outsized returns and results of any kind – as both an investor and an entrepreneur – necessitates taking a position that…
Most of the world disagree with.
Consensus (or near consensus) agreement on an idea means that there is unlikely to be any sort of outsized opportunity…
From an entrepreneurial perspective…
The opportunity has already been exploited and is now obvious.
From an investment perspective…
The opportunity has already been priced into the market…
To put it another way:
You need to be willing to make unpopular moves – that much of the world disagrees with – if you want a chance at generating outsized returns in your business.
But the nuance here is this:
This is not just about making unpopular moves that most of the world disagrees with for the sake of being contrarian…
You want to be making these unpopular moves within the context of one or more megatrends for the sake of being strategic…
In short:
Over-indexing + contrarianism = outsized results when you combine:
- A.) A deep focus on a megatrend.
- B.) A contrarian approach that the majority dismiss.
Let’s take a look at an actual example to bring this idea to life…
5 | Growing Wealth Inequality & How to Leverage this Megatrend...
In my lifetime, according to the World Inequality Database, the Wealth Share of the Richest 1% in the United States has increased from 24.5% to 34.9% in just the last 40 years.
If you’re curious, you can check out the Original Source of Data.
Now, the current wealth concentration of the richest 1% in the United States (34.9%) is still considerably lower than the 1929 high (48.7%), but the fact remains:
The vast majority of people in the United States (and much of the world) are experiencing the greatest concentration of wealth in their lifetime.
So how can we think about this megatrend?
And how might we use it to potentially inform a contrarian approach in our business that the majority dismiss?
Let me give you an example:
I had a conversation recently with a Private Client who charges $100,000+ for an engagement…
Now, this same client was charging just $30,000 a few years ago, essentially for the same service…
And in our conversation, we started to entertain a provocative question:
What if they were to charge $1 Million per client?
Now, on the one hand this sounds crazy. But on the other hand, this is exactly what one competitor is doing (meaning there’s precedent…)
And more importantly…
If a megatrend playing out in the world is a radical concentration of wealth in the hands of the 1%…
Then a business model that aligns with this wealth dynamic would be to give away for free (or at a very low cost) everything you do to serve 99% of your market…
And then charge a radically high price (10x or 100x the norm in your industry) exclusively aimed at the remaining 1%….
Because here’s the thing:
There is a segment of every market that is not nearly as price sensitive as you think.
And if you aim to serve that market segment, your biggest risk is actually undercharging for what you do…
Like for my client, when compared side-by-side against the competitor who charges $1M per engagement, buyers want to know why my client is so comparatively so cheap.
The secret to the 1% strategy is simple:
Solve big, acute problems for players with money.
Or in other words:
“Scratch the itch of the rich within a niche.”
(Feel free to quote me on that one :-) )
Then, you can serve the remaining 99% of your market which is price sensitive, by giving away everything else you do (or making it available at a comparatively low cost…)
This for example, is exactly what Esther Perel does in her business.
Now, if you’re not familiar – Esther Perel is a Belgian-American Psychotherapist whose work centers around relational intelligence.
(Side Note: I actually had a chance to meet and spend time with Esther a few years ago – and the conversation we had about the dynamic of spouses who also partner together in business had a big impact on me at the time.)
Now, most of Esther’s work is available for free or very low cost, like her book Mating in Captivity….
And her course on Masterclass.com:
But in the session I hosted earlier this month with my business partner in ScoreApp, Daniel Priestley, we talked about Esther Perel and what she charges to work with clients…
And while most people might think the “limit” to what the market will pay to work with a psychotherapist with Esther’s credentials is maybe something like $500 per session…
In reality, Esther actually charges a minimum of $100,000 to work with her as a private client.
Now, the reason she can do that:
Number one, because she’s very good at what she does.
But number two, because she exclusively focuses on working with UHNW (Ultra-High Net Worth) individuals who are on the precipice of marital divorce…
In other words…
She solves a big, acute problem for players with money.
And when you take this approach in your business…
99% of people in your market won’t be able to afford your prices.
But that’s not the point.
Because the 1% will.
They’re not as price-sensitive like everybody else.
Instead, they’re looking for the best.
Not the option that’s 20% cheaper.
* * *
Now, is there injustice with the increasing concentration of wealth in the hands of the 1% – and does it pose global problems at a societal level?
Absolutely.
But it’s nevertheless a megatrend that’s occurring in our lifetime…
And we can recognize and complain about it…
Or we can recognize and over-index around it…
Supermax offer for that 1%.
Free (or low cost) for everybody else.
Because when you do this…
You can actually have your cake and eat it too.
You can still have the type of broad impact you’re looking for by supporting the vast majority who otherwise can’t afford the Supermax price tag with your free / low-cost work.
And at the same time, by charging a Supermax price aimed at the 1%, you’re actually helping to facilitate a redistribution of wealth…
(Unless you’re already in the 1% yourself, that wealth is being redistributed to you – which you in turn can choose to further redistribute as you see fit…)
* * *
Now, the vast majority of people reading this right now will balk at the approach I’ve just outlined…
They’ll come up with all sorts of reasons why it won’t work for them and why their market and their business is different.
(In fact, I can practically hear the mental chatter coming through right now :-)
But to quote Henry Ford:
“Whether you think you can or you think you can’t, either way you’re absolutely right.”
And this is precisely why over-indexing your business around a megatrend like this in an unpopular way represents such an opportunity:
It’s a contrarian approach that the majority will dismiss.
Now, is this the only way to run a business?
Of course not.
But it’s an example of how to tap into megatrend in a real and practical way, which brings us to…
6 | A 4-Step Framework You Can Leverage.
So how do we apply this approach of “Over-indexing within the context of a Megatrend” and this type of strategic thinking more broadly?
Well, I asked ChatGPT to analyze what I’d written above and come up with a simple framework to put these ideas into action.
This is the 4-step framework ChatGPT came up with:
- Identify the Megatrend: Choose a trend that aligns with your interests and has long-term inevitability.
- Go Deep (Over-Index): Focus your resources, time, and energy on mastering that trend.
- Take a Contrarian Stance: Look for overlooked or unpopular angles within the trend where competition is low and skepticism is high.
- Build Blind Spot Awareness: Regularly assess the risks of over-indexing, and mitigate them with feedback, partnerships, or diversification.
Pretty straight-forward, right?
But what about applying this framework to Micro-Trends?
In other words, not just to global megatrends (long-term, systemic changes), but also smaller micro-trends (short-term or niche shifts) that might be happening right now within your industry?
Well, that’s exactly what I’m exploring right now in an area I’ve been spending a lot of time researching:
7 | Micro-Trend Example: Short-Form Video vs. Long-Form Content Discovery (LFCD)
Right now, as we all know, one of the biggest micro-trends in social media / digital marketing is short-form video as a primary content format to drive discovery.
It’s fast, engaging, and optimized for increasingly-fleeting attention spans.
And as I wrote back in [#027] How to Design Your “Strategic Content Ecosystem”…
In addition to TikTok, Instagram Reels, and YouTube Shorts, even LinkedIn is jumping on the short-form video bandwagon…
In fact, just this week, with TikTok on the ropes with the most recent US Supreme Court ruling I received the following piece of propaganda *ahem, marketing* from LinkedIn pushing people to switch to short-form video on their platform:
But here’s the thing:
While short-form garners views, long-form is what builds relationships.
A 15-second reel might entertain someone, but a 60-minute podcast or a thoughtful essay (or in-depth email newsletter like this one here) fosters trust, authority, and a level of emotional connection…
And I believe that there’s a better, alternative strategy for getting people to discover that we exist, than pumping out a never-ending stream of shallow, short-form social media content…
It’s a strategy I’m beginning to describe as: “Long-Form Content Discovery” (aka “LFCD”)
8 | Cultivating Influence vs. Chasing Attention: A Contrarian Case for LFCD...
In contrast to Instagram, Facebook, and LinkedIn…
Less trendy, deeper-content platforms like Substack and Medium, as well as long-form podcasts (discovered via YouTube) and books (discovered via Amazon) focus on quality over quantity, depth over reach, and loyalty over virality…
Short-form is ephemeral, subject to rapid platform changes and trends. But long-form content like articles, books, and podcasts has an evergreen quality, continuing to generate value years later.
For example: A book or a well-ranked long-form YouTube video can generate visibility and engagement for years, unlike an Instagram Reel which usually peaks within hours.
Furthermore…
Long-form content allows for the unpacking of more complex (and more nuanced) ideas.
LFCD also appeals to a more committed audience – people not just seeking mindless entertainment but meaningful insight.
(The type of people I want to be doing life with.)
And as I wrote in my reply to Greg Hickman (from the “Cutting Room Floor” I shared earlier):
“Shallow content attracts shallow people. Deeper content attracts deeper thinkers.”
Now, the tradeoff is likely fewer (but more engaged) followers.
Long-form content might attract a smaller audience (at least initially). But these individuals are far more likely to become loyal advocates, clients, or collaborators.
Additionally, in some ways, LFCD requires a higher barrier to entry.
Some would argue producing long-form content is harder to create than short-form content (which at the same time, is fast becoming the commoditized domain of AI UGC…)
Whereas in contrast, writing a compelling newsletter, recording an hour-long podcast, or creating a full-length video requires original thinking, effort and consistency.
But I believe this difficulty is a feature, not a bug. It creates a moat against competitors who aren’t willing to commit.
9 | But Ryan, Can't You Do BOTH?!
Can’t you take your long-form content, and cut it up into saw dust in the form of short-form video like so many people advocate?
Perhaps…
But I think it comes at the expense of quality…
Quality of content.
But more importantly, quality of life.
Because it means devoting attention and mindshare to this.
It means spending at least some of your time as a consumer of that medium.
It means watching and scrolling through 15-second video reels to stay on the cutting edge of what’s working…
It means feeding the 15-second dopamine addiction in your brain.
Just.
One.
More.
Video.
And that’s how you get sucked into the vortex.
(And personally, that’s just not how I want to be spending the rest of what Mary Oliver describes as that “One wild and precious life”…)
10 | So, How Does Our 4-Part Framework Apply to this Micro-Trend?
Well, let’s take a look:
Step 1: Identify the Micro-Trend:
Short-Form Video is the dominant form of discovery on social media (and more broadly, in digital marketing) right now. The contrarian micro-trend is Long-Form Content Discovery (LFCD).
Step 2: Go Deep (Over-Index):
Double down on creating long-form content that matches your voice and expertise (e.g. Weekly Email Newsletter). Get really really good until (as Ira Glass has famously written) “Your ability matches your taste.”
Step 3: Take a Contrarian Stance:
While others chase short-term virality on new platforms, focus on substantive content. View long-form as the antidote to digital fatigue: Because audiences overwhelmed by short-form noise are actually craving meaningful engagement right now.
(And you can fill that void.)
Step 4: Build Blind Spot Awareness:
Recognize the risks of ignoring short-form content entirely. Consider complementary strategies, such as using short-form snippets to direct audiences to your long-form work.
(Although I personally am far more attuned to the Cal Newport Approach of eschewing short-form video entirely…)
* * *
And this is exactly what I’m doing right now…
Because for me, at end of the day, the question comes down to this:
“Are you chasing attention or are you cultivating influence?”
I know the answer I’m going for…
What about you?
* * *
Alright, I’ll wrap things up here for today.
Wishing you a great rest of your weekend…
Remember to hug the ones you love.
And until next week,
Ryan :-)
