Feeling embarrassed when looking back at early versions of your product or career milestones shouldn't be seen as negative. It is a strong signal that you have made significant progress and that your standards and capabilities have improved over time.
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The belief that your current product is "a giant piece of shit" is a powerful motivator. This mindset ensures you are constantly seeking limitless opportunities for improvement. If you can't see flaws and feel a degree of humiliation about what you offer the public, you shouldn't be designing the product.
The primary obstacle to taking risks isn't the potential for failure, but the ego's fear of public judgment and shame. People avoid challenges to protect their image. True growth begins when you prioritize learning and feedback over maintaining a facade of perfection.
When pursuing breakthrough ideas ("10x thinking"), the process is inherently uncomfortable. It's crucial to distinguish this discomfort, which signals you're pushing boundaries, from the feeling of being wrong. Embracing this discomfort is key to innovation in ambiguous, early-stage product development.
Working with generative AI is not a seamless experience; it's often frustrating. Instead of seeing this as a failure of the tool, reframe it as a sign that you're pushing boundaries and learning. The pain of debugging loops or getting the right output is an indicator that you are actively moving out of your comfort zone.
Much like a failed surgery provides crucial data for a future successful one, business failures should be seen as necessary steps toward a breakthrough. A "scar" from a failed project is evidence of progress and learning, not something to be hidden. This mindset is foundational for psychological safety.
Top product builders are driven by a constant dissatisfaction with the status quo. This mindset, described by Google's VP of Product Robbie Stein, isn't negative but is a relentless force that pushes them to question everything and continuously make products better for users.
Rick Rubin avoids regret by viewing each project as a "diary entry"—a reflection of the best he could do at a specific moment in time. Since it was the peak of his ability *then*, there's nothing to be critical of later. If it could have been better, he would have kept working on it.
Entrepreneurs often view early mistakes as regrettable detours to be avoided. The proper framing is to see them as necessary, unskippable steps in development. Every fumble, pivot, and moment of uncertainty is essential preparation for what's next, transforming regret into an appreciation for the journey itself.
To identify how you've changed, review your calendar from a year ago. The activities, people, or mindsets that now make you cringe are the clearest signals of your evolution and updated thinking. This is a tangible way to measure personal software updates.
Early efforts in a new domain, from sales calls to content creation, will likely be poor. The key is to persevere through these initial failures to accumulate the necessary repetitions ('reps') for improvement. Don't wait for perfection to start; the value is in the action itself.
