Have you ever looked around your workspace and realized… you’re grinding your way through tasks you’d never choose if money weren’t involved?

Alan Watts’ sharp observation cuts to the core of why so many solopreneurs feel burnt out despite technically being “free”:

“Most people are working at tasks which they hate so that they can make enough money to stop doing it and play.”

This isn’t just a commentary on corporate life. It’s a trap many midlife solopreneurs accidentally recreate in their own businesses.

We leave our jobs to escape someone else’s schedule—only to become our own harshest boss. We chase scalable offers and productivity hacks while silencing our original joy for what we do.

Work as Play vs. Work to Escape

When you design your business around tasks you tolerate—just to make money—you’re postponing joy.
But when you design it around tasks you love—you create a self-renewing engine for purpose, profit, and personal fulfillment.

That difference is massive.

Working to “get to play later” delays your best life.
Working “as play now” brings that best life forward, right into your daily to-do list.

The Midlife Advantage: You Know What You Hate

Here’s the gift of age: by now, you’ve lived enough to know what drains you and what energizes you.

You’ve probably tried things “for the money” and realized it doesn’t sustain you. You’ve seen how your body and soul respond to joyless obligation versus creative alignment.

So why not design your business to make money doing what you’d want to do anyway?

That doesn’t mean you’ll love every second. But it does mean your core business model is rooted in personal resonance—not forced obligation.

Turning “Play” into Profit

How do you begin?

Start by asking:

  • What do I enjoy doing so much, I’d do it for free (or already have)?

  • What transformation have I helped others achieve, even casually?

  • What would my 20-year-younger self find impressive about how I spend my time now?

Then ask: How could I package, teach, demonstrate, or sell that?

Whether it’s through a micro course, cohort program, group coaching, or digital products—the modern creator economy lets you monetize what lights you up.

You’re not stuck. You’re actually more equipped than ever.

A Path Forward

If you’re stuck in “tolerable but lifeless” business tasks, here’s a midlife reframe:

  • Don’t build a business to escape work.

  • Build one that lets you enjoy your work.

  • Monetize from a place of clarity, not desperation.

  • Play now. Profit follows.

You don’t need a million followers or a VC-backed platform.
You just need to love what you’re doing—and design it so someone else benefits from that love.

When your work becomes your play, your audience feels it. They trust it. And they’ll pay for it.

CTA:
💬 What part of your business feels most like “play”? What feels most like “escape”?

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