It’s officially the end of an era.
In case you missed it, Microsoft announced that Skype will be shutting down on May 5, 2025.
Yeah, Skype.
The category-defining behemoth that MSFT purchased for $8.5 Billion (that’s “Billion with a B”) back in 2011 is being shut down in the next 60 days.
Like Xerox… Skype, which at one point had over 300 million monthly users, was once simultaneously both the product and the verb we ubiquitously used for more than two decades…
This press release was a sobering reminder (and for many, a wake-up call) that in business – almost nothing lasts forever, no market, no business, no platform, no product…
No matter how dominant or essential it once seemed.
And during the AI Boom we’re in right now – where it feels like the ground is shifting beneath our feet and the rules of digital marketing change virtually every single week…
A question that’s worth taking a moment to reflect on is the following:
But… what (if anything) doesn’t change??
1 | The Nature of Change vs. The Anchors of Permanence...
Lately, I’ve been thinking a lot about the skills I want to pass on to my sons.
Not the ones that are trending right now. Not the ones that will help them get ahead next year – but the ones that will serve them for a lifetime.
The skills that will still matter in ten, twenty, fifty years, no matter what new technology comes along.
Many of the roles we play in life are fleeting. But as I’ve written about previously: Fatherhood is Forever.
(Which is a phrase that is incidentally tied to a book project I’m quietly working on in the background with my friend and founder of Front Row Dads, Jon Vroman, pictured below…)
My friends Jon Vroman (left) and Justin Donald (right) – two amazing fathers – pictured with yours truly looking admittedly a little rabbi-esque with the long curly hair and beard :-)
It’s clear that the pace of change in this world is accelerating – not just with AI and technology – but in the very fabric of how we work, communicate, and do business.
Yet, in the midst of all this, there’s a contrarian truth:
What’s not changing is often more important than what is.
* * *
Jeff Bezos put it best when he said:
“I very frequently get the question: ‘What’s going to change in the next 10 years?’ … I almost never get the question: ‘What’s not going to change in the next 10 years?’”“And I submit to you that that second question is actually the more important of the two—because you can build a business strategy around the things that are stable in time.”
And I’ve been thinking a lot about this recently.
You can build an entire business around things that don’t change.
In fact, this is something that came up when I was interviewed by Alex Cattoni (founder of CopyPosse) this week for her YouTube Show (The episode of which is going live in a few weeks. Stay tuned…)
In the case of Amazon, Bezos’s thesis was that customers would always want lower prices, faster delivery, and more selection.
(Which so far has proven to be true…)
But the idea of “Anchors of Permanence” applies not just to business – but to skill-building, identity, and even how we spend our time.
In [Issue #021] The Life-Changing Magic of “Strategic Obsession” I wrote about Charlie Hoehn – arguably the #1 expert in the world on “how to sell a million copies of a non-fiction book”.
And one of the things I’ve learn to appreciate from Charlie – is the importance of making your work both timely and timeless.
Charlie Hoehn and I connecting recently to talk book strategy, while wearing apparently what is the only shirt I own based on practically every recent video and photo taken :-)
This is true whether that’s a book, a business, or a body of work that speaks to the moment but remains relevant decades later.
(BTW – This is one of the reasons why “Evergreen Market” is one of my “Five Market Must-Haves” when choosing the right market for your business, as detailed in my second book, Choose: The Single Most Important Decision Before Starting Your Business…)
So…
What does “timely and timeless” mean in practice?
It means cultivating skills that don’t expire. Skills like…
- Curiosity.
- Strategic thinking.
- Resilience.
- Adaptability.
And one skill I’ve been reflecting on more than ever:
Taste.
2 | The Role of "Taste" in the Age of AI.
AI can generate endless content, but it cannot discern what’s good.
That’s where taste comes in.
Taste is the ability to recognize what deserves to exist.
My friend, Jason Lee, recently forwarded an excellent article from The Sublime (a Substack publication by Sari Azout) that does a great job of exploring this idea in more detail, if you’re interested in diving deeper.
* * *
As AI floods the world with mediocre, derivative content, the rarest and most valuable skill will be knowing what’s worth keeping.
(e.g. Is this AI-written headline for your client, a bit too… cheesy? Is this AI-written Facebook post for your own business a bit too… schmaltzy? AI can’t answer those questions – But this is where taste comes into play.)
In other words, while the nature of the work involved in copywriting, communication, and marketing may be rapidly evolving… the skill of developing good taste remains as timeless and essential as ever.
* * *
What does this have to do with permanence?
Well….
I believe taste is a timeless skill because it’s a way of seeing the world. It’s an ability that only grows (and is refined) through experience, observation, and curation.
(And it’s one of the few human traits that AI *may* never be able to replicate because it lacks context of the full human experience – failure, struggle, love, and heartbreak…)
So if some things are timeless, and others are fleeting, how do we distinguish between the two?
Well….
This is where the concept of “The Scale of Permanence” can serve as our guide…
3 | The Scale of Permanence: A Framework from Permaculture...
When I began deeply studying the discipline of permaculture several years ago, there is a core concept that had a deep impact on my thinking:
The Scale of Permanence.
Originally developed by P.A. Yeomans, the Scale of Permanence is a tool used in land design to help farmers and land stewards make decisions based on how permanent each element of a landscape is.
In [Issue #022] How to See Hidden Patterns Others Completely Miss, I wrote about another permaculture principle “The Edge Effect” which I first learned from my friend and permaculture mentor, Ben Falk.
In his book, The Resilient Farm and Homestead, Ben references a Yeomans (Inspired) Scale of Permanence, which you can see here:
At the top of the scale, you have things that barely change over time – like climate, landforms, and water sources. At the bottom, you have things that are constantly in flux – like land boundaries, vegetation, and temporary infrastructure.
The key insight?
If you make decisions based on things that are temporary while ignoring what’s permanent, you build something fragile.
If you build a farm (or a business) around a tool or technology or technique that changes every few years, you’ll find yourself constantly scrambling to keep up.
But if you anchor your thinking to the things that endure, you create something that can adapt without being uprooted.
The same principle applies to business, identity, and the way we navigate change.
Let’s map this concept onto the business world:
4 | The Scale of Permanence for Business.
At the top of the business version of this scale, you have fundamental, enduring principles – things that define how humans have always made decisions, connected, and exchanged value.
At the bottom, you have tactics, tools, and platforms – things that are useful for a time but will eventually become obsolete.
Here’s how a business version of The Scale of Permanence might look:
More Permanent (Long-Term Anchors)
- Core Human Desires (connection, security, status, meaning, convenience)
- Timeless Business Models (helping people save time, improve status, reduce pain, increase happiness)
- Psychological Principles (reciprocity, storytelling, trust, attention)
- Skills that Never Expire (strategic thinking, resilience, taste, adaptability)
Less Permanent (Short-Term & Changeable)
- Marketing Channels (Facebook, Instagram, LinkedIn – As I wrote in [Issue #020]: Going Analog – “Trees don’t grow to the sky and channels don’t last forever…”)
- Technology & Tools (AI software, coding languages, automation tools; Skype being the latest example of this…)
- Job Titles & Labels (SEO Expert, Facebook Ads Specialist, and Twitter Growth strategist – how useful is that now??)
The mistake most people make?
They build their business and identity on the bottom of the scale.
In other words, they anchor themselves to a specific tool, job title, or platform – something that will inevitably change – rather than the timeless human needs and principles that will never go away.
This is why when I wrote about “The Coming Collapse?” a few weeks ago on LinkedIn – for some readers it generated a sense of anxiety, but for others it generated a sense of opportunity…
After all, if you consider yourself to be an “Email Copywriter” – it can feel like your world is closing in right now.
But if you consider yourself to be a “Problem Solver for Your Clients” – it can feel like there is a growing sea of opportunity…
Which brings us to the following question:
If we know what’s permanent vs. what’s fleeting, how do we apply that to our own identity, career, and business choices?
5 | Skills, Labels, and Identity: What’s Worth Holding Onto?
The Scale of Permanence is a way to separate what’s enduring from what’s ephemeral. But knowing what’s permanent is just step one.
The harder part?
Is figuring out what that means for you.
Because in a world that’s changing faster than ever, who you are today might not be who you need to become tomorrow.
And that’s where most people get stuck.
The Problem with Over-Attachment to Labels
When entrepreneurs apply to my Strategic Advisory Group Mastermind and describe themselves and their business when applying, I often see a business description tied to a tool or platform or job title like:
- “I have a YouTube channel…”
- “I run a Shopify store…”
- “I’m an SEO Consultant…”
- “I’m an Email Copywriter…”
- “I run a Facebook ads agency…”
But here’s the brutal truth:
These labels expire.
Even if this is how you position yourself to your customers or your audience in this moment.
These types of labels might serve you for a while, but eventually, the tools shift, the tactics stop working, and what was once your entire career becomes irrelevant.
Ask anyone who built their entire business around “MySpace Marketing”, or more recently, who went all-in on “Clubhouse” as a platform…
The skills didn’t disappear, but the landscape did.
And the same thing is happening right now with AI.
(The fastest way to get left behind is to define yourself by something that very well might not exist in its current form five years from today…)
So what’s the alternative?
Shifting from “Labels” to “Lifelong Skills”
Instead of anchoring your identity to what you do in this moment, it’s far more powerful to root it in the deeper skills that will always matter.
Here’s how we might break this down:
More Permanent (Lifelong Skills to Build Around)
- Storytelling – The medium changes, but people will always respond to great stories.
- Persuasion & Influence – The ability to inspire people to take action is timeless.
- Strategic Thinking – AI can execute, but strategy remains human.
- Resilience & Adaptability – The superpower of those who survive seismic shifts (like what we’re experiencing today)
- Taste & Judgment – Knowing how to recognize what’s worth keeping when AI can generate everything.
- Curiosity & Learning – The ability to re-invent yourself as the world continues to rapidly evolve.
Less Permanent (Roles & Labels That Will Change)
- Specific Job Titles – What’s “hot” now won’t likely be later.
- Tools & Platforms – Today it’s ChatGPT, yesterday it was Web3, tomorrow it’s going to be something completely different…
- Marketing Channels – As discussed, they rise and fall. What’s a traffic goldmine now might be irrelevant in 2-3 years from now.
* * *
So if you (or your business) is not defined by a job title or a product category or a specific product or service, what are you?
Well, perhaps you are actually something bigger:
- Instead of an “Email Copywriter,” perhaps you’re actually a persuasive communicator.
- Instead of a “Shopify store owner,” perhaps you’re actually a strategic entrepreneur.
The former keeps you locked in one place.
The latter keeps you evolving as the world does.
And we effectively have two choices:
Cling to a label that might serve you today, but could disappear tomorrow.
Or root yourself in deep skills, principles, and an identity that will serve you for life.
Which one are you choosing in this moment?
* * *
This brings us to one of the final ideas we’ll explore today which is this:
6 | Expanding Your Time Horizon: Timely vs. Timeless Thinking.
A few weeks ago, I came across an old piece I wrote back in 2010 – the story about how I built my first business from $0 to $25,000/month.
I went back and read it – and while the dollar amounts are outdated (e.g. $25,000/mo in 2010 dollars is the equivalent of $36,000/mo in today’s dollars…) the principles within that piece are just as relevant today as they were when I wrote it…
15 years ago.
This piece – part of a 3-Part Series was titled “Lesson #1: The (True) Power of Kaizen” – And it illustrates a perfect example of how small, incremental improvements – kaizen – can add up to long-term success.
If you’re curious, you can read the full article (for a limited time) through my private Dropbox link here:
* * *
One of the biggest mistakes people make – whether in business or life – is optimizing for the short-term.
They chase what’s working right now – a hot trend, a social media algorithm, a new AI tool – without thinking about whether any of it will still matter in five years.
This is what separates those who build lasting success from those who are always scrambling to keep up.
Which brings us to….
7 | The 10-Year Decision Filter
One way to check if you’re thinking too short-term is to ask:
Would the “future me” 10 years from now be proud of this decision?
Most people make decisions based on immediate outcomes – what will get them paid, noticed, or ahead this month.
But if you zoom out and look at your life as a whole, a lot of things that seem important right now suddenly look trivial.
If I rewind 15 years to when I had written that article some of the things I was obsessing over at the time – like platform-specific tactics or marketing fads – are completely irrelevant today.
But the principles I invested in back then?
(Like Kaizen…)
They’re the foundation for everything in my life today.
So the real question is:
What decisions you’re making today will still matter a decade from now?
8 | The Man-Made vs. God-Made Test
As I’ve been reflecting on the “timely & timeless” core principles of my forthcoming book, I’ve been re-reading Ray Dalio‘s Principles: Life and Work…
And one of the principles I’m exploring in The Return to Real is the importance of God-Made Things vs. Man-Made Things in our lives.
In the digital world, we live almost entirely in man-made spaces – laptops, emails, notifications, screens…
But when we step outside in nature – like here on the farm, I’m reminded that not everything in life runs on a quarterly cycle.
- The maples outside my door don’t care about Skype being shut down…
- The soil sleeping under the snow doesn’t care about GPT-4o…
There’s something anchoring about spending more time with what doesn’t need to be reinvented every year.
This is why the greatest investors, entrepreneurs, and strategic thinkers operate according to longer time horizons:
The best decisions you’re making right now aren’t about the next month or even the next year…
They’re about the next decade of your life.
So a question to reflect on as we wrap today’s issue is this:
If the 5-year period you’re living right now were a chapter in your book – what would be the title of this chapter??
Have a think on that one.
Shoot me a reply to let me know – I read each and every reply you send.
And I love hearing from you.
Remember to hug the ones you love…
And until next week,
Ryan :-)
P.S. If you’re looking for something to listen to this weekend to help reflect on your next decade of life…
I was just interviewed for The AI Grapple Podcast with Kate vanderVoort, where we talk about “The Death of Trust: How to Thrive in a World Flooded with AI…”
This one is worth a listen. You can check out the entire interview here on YouTube:
BTW – Guess what shirt I’m wearing in this interview?
I’ll give you one guess :-)
P.P.S. Speaking of interviews…
If YOU have an audience that you think could benefit from the “Return to Real” message I’ve been sharing here in The Digital Contrarian over the last several months – please shoot me a message…
In just the past week, I Interviewed with Alex Cattoni (CopyPosse), Kate vanderVoort (AI Grapple Podcast), and also delivered a private presentation to Suzi Dafnis‘s and Michelle Falzon‘s HerBusiness mastermind – on top of serving as one of the Keynote Speakers of MMT 2025.
BTW – Below is just some of the feedback from MMT on my talk – and what attendees said to be the most impactful aspect of the event:
I’m lining up my speaking / interview schedule for the next several months – and if you have an audience (small or large) that you think could benefit from what I’ve been sharing here – I’d love to hear from you and would be deeply grateful for the opportunity.
Tell me about your group or audience and why you think it would be a good match, and if it’s a great fit – we can get something scheduled on the calendar.
I look forward to hearing from you! :-)
