Introduction: What Alan Watts Saw That Most Entrepreneurs Miss

If you’ve ever felt like you’re running in circles—working harder, building more funnels, posting more content, but still not feeling free—you’re not alone.

Alan Watts, the philosopher who made Eastern wisdom accessible to the West, nailed this paradox in just 10 minutes: the more we strive to “fix ourselves,” the more stuck we feel.

This isn’t just a spiritual puzzle. It’s the daily reality for creators, coaches, consultants, and solopreneurs:

  • How do you build a business without burning out?

  • How do you grow without becoming obsessed with endless growth?

  • How do you “let go” when you’ve got bills, clients, and goals breathing down your neck?

In this post, we’ll explore Watts’ insights and connect them directly to the challenges of modern one-person businesses. We’ll see why chasing certainty leaves us anxious, why “positive thinking” often backfires, and how to find a middle way that fuels sustainable growth.

Section 1: The Human Predicament

Watts begins with a blunt observation: life feels unpredictable, tragic, and full of suffering. No matter how much success we gain—money, power, or tech comforts—we’re never satisfied.

Sound familiar? For solopreneurs, it shows up as:

  • Getting your first sale… then immediately worrying if you can repeat it.

  • Growing an audience… then stressing about engagement drops.

  • Hitting a revenue milestone… then lying awake at night thinking about taxes, churn, or competition.

The lesson: It’s not your circumstances. It’s your mind.

Creators know this intimately: the external game is never-ending. If your peace depends on “fixing everything out there,” you’ll never rest.

Section 2: Why “Fixing Your Mind” Doesn’t Work Either

Watts points out that the usual advice—positive thinking, affirmations, “just relax”—feels hollow.

Because deep down, you know you’re hypnotising yourself. You’re still trying to “control the mind with the mind,” which leads to an infinite loop:

  • You’re stressed → you try to calm down → you get stressed about not calming down.

  • You want to let go → you try hard to let go → effort blocks the letting go.

As solopreneurs, this looks like:

  • Obsessively tracking metrics, then getting paralysed when they dip.

  • Buying more courses to “fix” yourself, but only feeding the sense that you’re not enough.

  • Trying to force creativity, which kills the very playfulness you need.

💡 Connection to IMMachines: This is why tools like Chaos to Clarity GPT exist. It’s not about piling on more tasks. It’s about clearing noise and helping you focus on what actually matters.

Section 3: The Rascal Inside Us

Watts calls it the “irreducible rascality” inside us—the part of us that resists being improved.

For creators, this is the inner rebel that:

  • Procrastinates on finishing that sales page.

  • Rejects rigid productivity hacks.

  • Sabotages with perfectionism when it’s time to publish.

We all carry that inner rascal. And here’s the kicker: if you, the flawed human, are also the one in charge of fixing the flaws, you’re stuck in a paradox.

It’s the same as asking: who polices the police?

Section 4: The Trap of Endless Improvement

Watts exposes a problem most business owners feel but rarely name: the self-improvement treadmill.  ( Yes, I have read many self-improvement books so I know this treadmill well!)

You try to transform your “lower self” (ego) with your “higher self” (spirit). Sometimes it works, but mostly it leaves you asking:

  • “Is my ego too strong?”

  • “Is my higher self too weak?”

  • “Why can’t I just get it together?”

For solopreneurs, this shows up as:

  • Always chasing the next strategy, platform, or system.

  • Never feeling like your funnel, copy, or offer is “enough.”

  • Thinking freedom is just one more launch away.

💡 Connection to IMMachines: The £3K GPT is designed to cut through this cycle. Instead of chasing shiny objects, it focuses on simple systems you can repeat.

Section 5: The Yin-Yang of Business and Life

Watts uses a powerful metaphor: human consciousness only knows things by contrast—yes vs. no, light vs. dark, success vs. failure.

We want “yang without yin.” In business, that’s:

  • Wins without losses.

  • Clients without rejection.

  • Productivity without rest.

But reality doesn’t work that way. You don’t recognise a bestseller unless you’ve written a flop. You don’t know loyal clients without difficult ones.

Instead of fighting this, creators can learn to embrace it:

  • Every flop is part of the portfolio.

  • Every unsubscribe sharpens your audience.

  • Every failed product is data for the next MVP.

💡 Connection to IMMachines: Tools like Content Repurposer Pro turn “losses” (unused drafts, forgotten posts) into wins (paid products, new content).

Section 6: Desire and the Paradox of Non-Striving

Watts turns to the Buddha’s insight: desire is the root of suffering. So maybe the answer is to eliminate desire.

But try it, and you’ll see the problem: you immediately desire not to desire.

For solopreneurs:

  • You want to relax about money… but then stress about not stressing.

  • You want to “be more present”… but then check if you’re being present.

  • You want to stop striving… but you’re striving to stop striving.

It’s the ultimate paradox.

💡 Connection to IMMachines: Frameworks like SLICE or VIRAL LOOP (- see this post to understand more about frameworks -) help you avoid over-striving. They turn one idea into a week’s content, or one post into discovery traffic. You’re not “trying harder,” you’re letting systems carry the load.

Section 7: Non-Doing and the Creative Flow

Watts introduces the Taoist idea of wu wei—“non-doing.” Not laziness, but effortless alignment.

For creators, this is flow: the sweet spot where work feels natural, like you’re surfing instead of swimming against the current.

But here’s the paradox again: you can’t force non-doing. Try too hard, and you miss it.

So what’s the path?

👉 Systems. Frameworks. Containers.

When you have simple recipes to guide you, you don’t have to “force” productivity. You just show up, follow the steps, and flow emerges.

💡 Connection to IMMachines: Frameworks like MAGNET (for lead magnets) and ROPE (for emails) give you structure so creativity can flow without pressure.

Section 8: How to Apply Alan Watts’ Insights in Business

Let’s make this practical. Here’s how creators, coaches, consultants, and solopreneurs can use Watts’ wisdom today:

  1. Stop Chasing Perfection. Accept the yin with the yang. Launch the product even if it’s not perfect.

  2. Use Systems, Not Willpower. Instead of “trying harder,” lean on frameworks like MVP, CORE, and HOOKMAP.

  3. Build Rest Into the System. Flow comes when you balance effort with release. Tools like Chaos to Clarity GPT help you prioritize and drop the noise.

  4. Redefine Success. See failure as contrast, not disaster. Each “loss” sharpens your next move.

  5. Practice Non-Doing. Let your systems do the heavy lifting. Your role is to show up consistently, not control every outcome.

Section 9: The Spiritual ROI of Letting Go

Alan Watts’ real gift wasn’t in giving quick answers, but in reframing the problem: maybe the issue isn’t you. Maybe the striving itself is the trap.

For solopreneurs, this is freeing. It means:

  • You don’t need to be perfect to create value.

  • You don’t need total control to build a business.

  • You don’t need to force growth—momentum builds when you stop strangling it.

This doesn’t mean passivity. It means trusting your frameworks, trusting your systems, and trusting yourself.

That’s the heart of IMMachines: creating simple processes that reduce friction so you can finally let go and grow.

Conclusion: From Chaos to Flow

Alan Watts reminds us that trying to “beat life” by striving only deepens the struggle. The path forward is paradoxical: embrace both sides of the coin, accept the rascal within, and lean on systems that let you create without forcing.

For creators, coaches, consultants, and solopreneurs, this means:

  • Use frameworks to guide your output.

  • Accept failures as part of the process.

  • Let systems carry the load so you can focus on the human part—connection, creativity, presence.

Because when you stop striving for perfection and start flowing with the process, your business (and your life) becomes lighter, freer, and far more sustainable.