The 5 Practices to Escape the Grind (and Reclaim Your Life)

A Playbook for Entrepreneurs Who’ve Built Something Successful but Feel Trapped by It

When I was just starting out, my father handed me the family business - a high-end design-build renovation firm in Manhattan. On paper, that sounds like a gift. In practice, it came with $70,000 of debt, no clients, and a staff of one and a half: one full-time employee, and my uncle a master craftsman who worked at his own pace and wasn’t really interested in being managed.

However, I did have two things: The family business’ legacy of excellence, and a stroke of luck. A former client offered a lifeline, covered payroll, and let us work on his apartment week by week with just one rule: “Make it prettier.” Within three weeks, he helped us find two new jobs and we were off to the races.

Soon, my dad returned. My uncle joined full time. And I had partners - two older men I loved, who had more influence than me when it came to the day to day. The business grew. But I didn’t. After a few years, I walked away. There was too much family, not enough business—boundaries blurred, expectations clashed, outcomes suffered. And if I’m honest, I didn’t have the tools back then to navigate that tension.

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The Pattern That Wasn’t Serving Me

It would take a few more ventures before I spotted my pattern. I’d build businesses, find myself unhappy, and then leave. I thought maybe I just liked starting things, but that wasn’t the whole story. This pattern wasn’t serving me, it was holding me back. I was holding me back.

And when I began observing and mentoring other entrepreneurs, I started seeing something deeper. We all had patterns recurring beliefs, behaviors, and dynamics that kept us stuck. Time and again, I’d meet founders stuck in pain—partnership drama, revenue plateaus, burnout. And almost always, they knew that they should do something different. They just couldn’t bring themselves to do it.

Why?

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The Entrepreneur’s Predicament

Years earlier I read a book on relationships called Getting the Love You Want by Harville Hendrix. In it, he introduced the idea of psychodramas unconscious scripts we reenact in relationships to heal old wounds or validate familiar beliefs. And I began to wonder:

What if entrepreneurs are reenacting psychodramas through their businesses?

We recreate familiar dilemmas over and over subconsciously choosing the same type of partners, or hiring the wrong type of employee, reliving the same leadership dynamics, the same self-sabotaging behavior because, at some level, our psyche is trying to resolve something.

While the big loops - like my ‘build and bounce’ routine - become visible over time, the real damage often happens in the unconscious moments of the day to day:

The daily decisions. The knee-jerk reactions. Actions that feel right—because they’re familiar—not because they’re effective.

This is what I now call The Entrepreneur’s Predicament:

We experience real pain. We sense the need for change.

But we’re running patterns that keep us from doing what needs to be done to get different results.

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From Stuck to Free: The 3 Forces at Play

Let me name these:

1. Pain Points: These are the symptoms, the moments that wake us up: burnout, resentment, broken systems, team dysfunction, missed milestones. They’re the signals that something isn’t working.

2. Psychological Pitfalls: These are the patterns that underlie the pain. They are subconscious scripts we act out—ways of thinking, deciding, reacting, or avoiding that have been shaped by history, fear, identity, and ego.

3. Practices: This is the way through. This is the lever we can actually pull to change things.
   

   Over time, I began noticing what was within my control that could help me disrupt the cycle. These became my core approach to breaking patterns and finding more fulfillment—in work and in life. They are simple—Not easy—But they work.

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The 5 Practices of Entrepreneurial Freedom

Each of these is a discipline, a way of being. They don’t just fix problems. They rewire the person facing them.

1. Talk to Yourself - The Practice of Reflection

Self-awareness isn’t automatic. It’s a skill worth developing. Whether it’s meditating, journaling, walking, conversations with a friend or mentor—this is how we make the unconscious conscious. This is our feedback loop. The mirror we hold up to ourselves. And like mirrors, we don’t always like what we see, but this is our prompt to dig deeper, not avoid the discomfort. That’s your gold. That’s your growth edge.

2. Let Go - The Practice of Humility

As entrepreneurs, we’re trained to bend the world to our will. It’s literally in our job description. So cultivating surrender can feel contradictory—if not downright impossible. The consequence is that we are constantly in fight or flight mode and that is not a good place to be long term. Letting go doesn’t mean losing, it doesn’t mean apathy. It means acting from a place of safety. There is profound power in calmness that follows. It’s where real strength lives.

3. Make Things Happen- The Practice of Creation

Am I giving you mixed messages? No. It's just that the order matters. When you haven’t Let Go first, Making Things Happen feels stressful, frustrating, and un-gratifying. The path is riddled with resistance. And it rarely feels worth it. But when you practice Making Things Happen from this new place, it feels fulfilling, surprising, and delightful. The default mode shifts from hustle to flow—where action comes from purpose, not panic.

4. Connect With Others - The Practice of Belonging

Success is sweeter when it’s shared, but isolation is one of the most common experiences reported by entrepreneurs. We think no one gets it. When things get tough, we think we have to go it alone. We don’t. This practice is about letting people in—not just so they can help, but so they can thrive with you. Your family, your partners, your team—they don’t just want you to succeed. They want to belong to what you’re building. And you don’t just want support. You want to share the journey.

5. Keep It Simple - The Practice of Clarity

Complexity has a way of creeping in. Opportunities multiply. Ambitions grow. More and more things call for your attention. This practice asks: What can I remove? What actually matters right now? What’s stealing my focus? Keeping things simple is a true art form worth mastering. Simplifying isn’t dumbing down. It’s subtraction with intent. It’s a path to clarity, not compromise. It’s carving away what doesn’t serve you—so you can prioritize what matters.

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What These Practices Have Done for Me

These practices didn’t just help me fix my business. They helped me grow into the person I was trying to become all along. Through them I learned to live more fully in the present. To enjoy the act of building. To let go of the noise and follow what matters.

Because of them, I’ve built things I’m proud of—without losing myself along the way. I’ve found joy again. Shared the journey. Focused my energy. Protected my peace. And not just in business—in life.

I’m more grounded. More open. More free.

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An Invitation

So that’s the Entrepreneur’s Predicament. And those are the 5 Practices to get you started on your journey. The path to freedom isn’t a sprint, and it’s not a secret formula. It’s a series of small, intentional shifts. It starts with seeing your patterns, then practicing new ones.

That’s what we’re doing here at Routine Rebel. And if you're stuck—but ready to move—you're not alone. We're here.

So ask yourself:

“What would happen if you stopped playing out the old script—and wrote a new one instead?”

The next move is yours.

—Stavros

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This isn’t just a content series. It’s a movement to redefine what success means—and we’d love to have you with us.

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This is the first in a 7-part series on The 5 Practices of Entrepreneurial Freedom. In the next article, we’ll dive deep into the first practice: Talk to Yourself—and explore how reflection can unlock clarity, resilience, and momentum.

Follow along in this series:

• Article 1 - The 5 Practices to Escape the Grind (and Reclaim Your Life)

• Article 2 - Talk to Yourself

• Article 3 - Let Go

• Article 4 - Make Things happen

• Article 5 - Connect With Others

• Article 6 - Keep It Simple

• Article 7 - The End of Old Patterns. The Start of Your New Story.