Lesson 2: Why Teshuva Feels Stuck

Video Summary

🎯 Core Idea

Teshuva should work better than it does. Year after year, we find ourselves wrestling with the same struggles. In any other area that truly matters—whether business, therapy, or health—we demand tangible improvement. Shouldn’t we expect the same from our avodas Hashem?


🔍 Why This Feels So Frustrating

In business, employees are held accountable for measurable results. In therapy, clients want to feel better and see progress. Yet in teshuva, many of us don’t feel that same forward motion. Something about the way we approach it is holding us back.


🧠 The Big Insight

We need to simplify our approach to teshuva.

Frum-from-birth Jews often complicate things with our heavy mix of obligation (“Hashem commanded it”), guilt and shame over past failures, pressure to compare ourselves to others, and fear of the Yom HaDin. Baalei teshuva, by contrast, often approach it as a life upgrade—a personal choice, a beautiful and empowering transformation. They do teshuva because they want to, not because they feel forced.


⚡ The Real Secret

Lasting change doesn’t come from endless reminders, obligation, shame or guilt. 

Sustainable growth comes from choosing a goal so meaningful to us that it naturally stays in our awareness.

We succeed in life when we pursue things we believe will upgrade our lives—a teen desperate to get a driver’s license, a professional earning a degree, a parent building a business for their family. These goals aren’t easier than teshuva, but they feel worth it. The same principle applies to spiritual growth.


💡 The Takeaway

Teshuva becomes sustainable when we simplify our mindset, reconnect to what we love about Torah and Hashem, focus on the joy and beauty of living our best life, and

See teshuva as the natural expression of becoming the person we dream of being


🛠 What’s Next for Us

The real question we need to ask is: What kind of life do I truly want? When that vision becomes clear, teshuva flows naturally—as a by-product of upgrading our life and returning to our truest self.


📚 Where This Is Going

This seminar is built around The 3 Habits of Highly Successful Yidden—a Torah-based adaptation of Stephen Covey’s world-famous model for personal transformation. You’ll learn how to craft a personal vision, live with integrity to that vision, and create real momentum in your avodas Hashem.


🎬 Coming Up Next

In the next lesson, we’ll explore the authentic Torah definition of teshuva—not as repentance, guilt, or shame, but as alignment with our deepest self and with our Source.

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