The Tradeoff Trap…
The Tradeoff Trap: Death By a Thousand Edge Cases & The Myth of Having it All.
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I’m here in Bentonville, Arkansas – just outside of Walmart HQ…
And I’m reminded of a business lesson:
Earlier this week, I was on a call with a plastic surgeon client.
And on paper, he has a great business.
Profitable practice. Multiple seven figures in revenue.
High patient satisfaction scores.
Glowing testimonials.
But his growth has been stuck for the last several years.
A few years ago he hit a revenue ceiling he hasn’t been able to break through.
And when we started peeling back the layers together…
What became immediately apparent was a classic case of what I describe as:
“Death by a Thousand Edge Cases.”
Too many services. Too many SKUs. Too many “80% finished projects.” Too many fringe offerings designed to attract “just this one” client… which, over time, have a tendency to multiply like weeds in an overgrown garden.
Now, as a strategic business advisor, I’ve seen versions of this story play out in dozens of businesses over the years.
And typically, the conditions that lead to this point don’t happen all at once.
It happens slowly:
One “yes” here, one exception there.
A new service offering for a vocal few.
An onboarding sequence for that one “opportunistic” lead source.
A resource added to the website that 7 people asked for on Instagram.
And before you know it, what was once a clean, sharp, streamlined business starts to feel bloated and unrecognizable – even to the person who built it.
This in turn, becomes a prison.
And that’s what today’s issue is about:
The hidden cost of trying to have it all…
The psychological agony of choosing…
The business consequences of not choosing…
And why the hardest part of being a contrarian isn’t going left when everyone else goes right…
It’s having the guts to go only left when your heart wants to sprint in every direction.
If any of that feels uncomfortably familiar…
You’re not alone.
Let’s dig in.
1 | The Myth of "Having it All"
We love the idea that we can “have it all.”
That with the right systems, the right planner, the right stack of apps, the right mindset – we can be wildly productive andfully present…
Build a thriving business and stay perfectly balanced… explore every curiosity and go deep on our craft.
But it’s a lie.
What we rarely admit is that every yes is also a no – and often, I find that most people aren’t fully honest about what we’re saying no to.
Take something small and personal:
Lately, I’ve been playing a lot of pickleball.
It’s been fun. Competitive. Social. And a great excuse to get out of the house early in the morning after writing and wrapping morning farm chores.
(And yes, I really am that sweaty….)
But what I haven’t been doing?
Lifting weights.
And it shows – especially in my shoulders.
Now, sure – I could do both. But not without giving something else up. Sleep. Family time. Writing hours. Something.
And that’s the point.
“You can have anything you want. But not everything you want.”
And the same is true in business.
Every new product dilutes focus from your core offer.
Every new audience segment chips away at your messaging.
Every new channel you add creates more complexity to manage.
I see this most often with polymath founders (myself included).
You have range. You have ideas. You have a dozen frameworks on your whiteboard and half a book in your head. You’re curious, capable, and interested in too many things.
Which of course is both your gift and your Achilles’ heel.
Because in a world that rewards specialists, there’s a cost to your multidimensionality.
And that cost is focus.
2 | A Tale of Two Clients: Examples of REAL Tradeoffs in REAL Businesses.
If the plastic surgeon’s story in the open is a cautionary tale of too much…
Let me introduce you to another private client – a successful CPA with the opposite problem.
He’s built a remarkably focused firm. Eighty-five percent of his revenue comes from a single type of client, in a single vertical.
In many ways, it’s a dream setup:
Strong margins.
Tight positioning.
Operational leverage.
But now he’s hit a different kind of crossroads.
That concentration – which has provided a level of strategic focus – is also what’s making him nervous.
He’s not the only firm focused on this vertical.
So there is competition.
And because the TAM is inherently limited, he’s concerned that he might not be able to hit his growth targets focusing exclusively on this vertical…
Additionally, what happens if the industry gets regulated? Or disrupted? Or goes through a downturn?
Right now, he’s considering expanding into another vertical.
(Which, on paper, sounds like a smart hedge.)
But here’s the rub:
The moment he adds a second lane, he risks diluting his valuation and undermining the very clarity and strategic discipline that’s made his business so successful (and attractive to a potential acquirer) in the first place.
The tradeoff here isn’t just between one client vertical and another.
It’s between optionality and focus.
Between breadth and depth.
Between short-term diversification to chase revenue growth and long-term brand equity impacting business valuation.
In other words, it’s not about whether you can do both.
It’s about what doing both says about who you are – and how that message lands in the minds of your market.
So in this section, we’ve seen both ends of the spectrum:
One business strangled by too many “fringe cases.”
Another facing a potential identity crisis by diversifying away from its core.
And the real question in both cases isn’t: “What should I do?”
It’s: “What am I willing to give up?”
That’s the sharper edge.
That’s the harder question.
And that’s what we’ll unpack next.
3 | Why Tradeoffs Are So Damn Hard.
We like to think we’re rational.
We tell ourselves we’re making logical, strategic choices.
But most of the time?
We’re just trying to avoid the pain of letting go.
Because choosing isn’t hard because we don’t know what we want.
It’s hard because of what choosing forces us to confront:
1. Loss Aversion
Psychologists Daniel Kahneman and Amos Tversky famously found that we feel the pain of loss twice as strongly as the pleasure of gain.
That’s why killing a product, walking away from an audience, or cutting a feature – even one we know isn’t working – feels like amputation.
2. The Illusion of Reversibility
We keep doors cracked open, telling ourselves we’re being “strategic.”
But the honest truth?
It’s just a stall tactic.
We confuse postponing the tradeoff with avoiding it.
And in the meantime, we carry the weight of unresolved tension.
3. Identity Entanglement
The deeper reality is that many tradeoffs aren’t logistical – they’re personal.
When you cut a service, walk away from a platform, or narrow your niche…
You’re not just changing your strategy.
You’re saying: “That’s no longer who I am.”
And that can feel like death to the ego.
(I’m feeling this in a very major way right now in terms of my identity as a farmer, because we’re considering scaling back what we’re going to pursue this growing season on the farm – while we balance other emerging priorities for our family…)
4. The Paradox of Choice
As Barry Schwartz argued in his now-famous TED Talk, and which we explored together in Issue #008: Cycles, Patterns, & The Choppy Waters Ahead – more options do NOT equal more freedom.
The abundance of choice can be paralyzing.
More options = more anxiety.
This is why the most successful founders I know often operate from the place of constraint.
Not because they lack opportunities.
But because they understand that clarity comes from “Addition by Subtraction”
(My favorite kind of math :-) )
In the next section, we’ll look at some of the most meaningful tradeoffs we’ve explored in past issues of The Digital Contrarian to identify how this might show up across multiple dimensions of your business and your life.
4 | "Zigging" as a Tradeoff Strategy.
We often think of “Zig When They Zag” as a contrarian stance.
And it is.
But it’s also something more powerful:
It’s a strategic decision to play a different game entirely.
Yes, it requires courage. Yes, it comes with tradeoffs.
But the upside?
It’s how you build real advantage in a noisy, crowded, increasingly lookalike world.
In Issue #020: Going Analog – The Ultimate Zig??, we explored how embracing analog – writing by hand, sending physical newsletters, or gathering people in person – creates a type of resonance that digital just can’t replicate.
That decision comes with cost. BUT it also buys you trust, intimacy, and memorability.
And that’s what zigging earns you:
You stop chasing after algorithmic crumbs and start forging your own path.
You stop blending in and begin building real traction with the people who matter.
You stop reacting – and start leading.
And we’ve explored variations on this theme again and again in past issues:
I. Zig Within the Megatrend
In Issue #027: How to Design Your Strategic Content Ecosystem, I argued that the smartest contrarians don’t fight the trend – they ride the current, but steer differently.
Don’t want to chase AI-generated content like the rest of the internet? Great.
Use AI strategically to amplify your originality, not automate more mediocrity.
II. Meaning > Convenience
In Issue #035: Why the Struggle is the Solution, I talked about raising our own food and the deeper satisfaction that comes with choosing effort over ease.
Doing Hard Things is an essential component to feeling fulfilled.
That’s a zig.
III. Craftsmanship over Scale
And in Issue #028: The Return to Real, I challenged the idea that success in business always requires scaling at all costs.
Zigging, in this case, meant choosing craftsmanship, character, and creative control – over growth by algorithm.
After all, as I’ve written previously:
The best things in life don’t scale.
And that’s the thing:
Zigging isn’t a gimmick for standing out.
It’s about standing for something.
You should be able to insert the words “I believe…”
I believe…
The Best Things in Life Don’t Scale.
I believe…
Doing Hard Things is an essential component to feeling fulfilled.
I believe…
All Growth Comes with Pain.
Etc.
It’s a strategy that filters.
By running your own race and choosing the road less traveled…
It attracts the right people for you – and repels the wrong ones.
It simplifies decision-making.
And it compounds trust, over time, into something that looks a lot like unfair advantage.
The catch?
You have to be okay not being everyone’s cup of tea.
But in a world where most are stuck in the middle…
Trying to be all things to all people…
Chasing whatever’s trending.
Optimizing for the short-term…
…Being someone who zigged on purpose?
That’s rare.
That’s powerful.
And that’s what can give your work its edge.
5 | What This Means for You
The One Tradeoff You’ve Been Avoiding
By now, you might’ve started thinking about the tradeoffs you haven’t made.
The edge-case offer you keep saying yes to – because it’s revenue you don’t want to turn away…
The product that still gets you traffic, but no longer reflects your best work…
The side project you haven’t shut down – even though it’s not really working (and probably never will.)
Or maybe it’s more subtle:
Maybe you’re trying to speak to two audiences…
Build two businesses…
Be two versions of yourself at the same time.
But here’s the truth:
Most friction in your business isn’t from a lack of opportunity – it’s from avoiding a decision.
Not all at once.
But in slow, invisible drips.
Death by a thousand edge cases…
So here’s the question I’d love to invite you to sit with this week:
What’s one tradeoff you already know you need to make – but haven’t yet committed to?
And to help you get there, here are three prompts:
1. What’s Your 80/20?
Which part of your business drives most of the value – and what’s stealing time and energy from it?
2. What’s Your “Fringe Case” Offering?
Which product, platform, or client no longer fits… but you’re afraid to cut?
3. What’s Your “Maybe One Day” That Needs to Become “Not Anymore”?
What are you still holding onto that once made sense – but no longer aligns with the next chapter?
These aren’t rhetorical.
Write them down. Answer them honestly. Talk them through with your strategic advisor.
Because clarity doesn’t come from thinking harder.
It comes from making the damn decision :-)
And most often, that decision isn’t about what to do next…
It’s about what to walk away from.
6 | Closing: The Courage to Choose.
We opened this week’s issue with a story about edge cases.
A successful practice strangled by complexity.
A founder who is stuck – not from lack of effort, but from too many open loops.
That story isn’t unique.
It’s just usually hidden behind the scenes.
Because from the outside, everything looks “fine.”
But on the inside?
There’s friction.
There’s fatigue.
There’s the quiet knowing that something needs to change – but not yet having the clarity (or courage) to make the call.
If that’s you right now, know this:
You’re not broken.
You’re just human.
Tradeoffs are hard.
But they’re also how we grow.
They’re how we sharpen.
How we clarify.
How we step into the next version of ourselves – deliberately, rather than by default.
And because all growth comes with pain….
I’ll leave you with the same question I’ve been asking myself lately:
What’s one tradeoff you already know you need to make – but haven’t yet committed to?
If you’ve got one that comes to mind, I’d love to hear it.
SHOOT ME AN EMAIL and let me know.
Because sometimes…
The moment you name it, and type the words into existence…
Is the moment you finally reclaim your momentum.
* * *
Have a GREAT rest of your week…
Remember to hug the ones you love…
And until next week,
Ryan :-)
P.S. What am I doing in Bentonville, Arkansas?
On a guys’ trip with my Front Row Dads Band…
Six other dads and I are about to hike through the Ozarks…
Wish us luck! :-)
That one thing I know..... scheduling in time at the library, and getting away from house and fur babies; so I can really focus.