Early ventures that failed weren't seen as setbacks but as low-cost learning opportunities. This perspective, framed by his grandfather's high-risk business, eliminated fear and built foundational skills with minimal downside, making eventual success more likely.

In a corporate setting, a PM might build a feature because an executive wants it. As a solopreneur, you personally absorb all financial and time costs. This forces a raw, unfiltered evaluation of business viability and opportunity cost for every decision, a muscle often atrophied in large organizations.

Instead of "burning the ships," treat potential career changes as experiments. By starting a new venture as a side hustle without financial pressure, you can explore your curiosity, confirm it's a good fit, and build a "safety net" of confidence and proof before making a full leap.

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.

To accelerate growth for talented individuals, give them responsibility where their failure rate is between one-third and two-thirds. Most corporate roles are over-scaffolded with a near-zero chance of failure, which stifles learning. High potential for failure is a feature, not a bug.

The designer initially felt her career stagnated from being the only designer at companies like Descript. In retrospect, this "lone wolf" experience was critical training. It forced her to develop frameworks and decision-making confidence without peer feedback, enabling her to single-handedly own the massive Comet browser project from day one.

After a startup fails or you exit, dedicate time to writing a detailed, private postmortem. Critically analyze interactions, decisions, and outcomes. This exercise helps transform painful experiences into a concrete set of operating principles for your next venture.

When you build a tool to solve your own problem, the worst-case scenario is that you have a custom solution that improves your life or work. This makes every project a success on some level, reframing the concept of failure and encouraging action.

To avoid developing bad habits, solo builders should simulate a corporate environment. Set artificial budgets, conduct real demos, talk to external users, and establish deadlines. This forces the discipline that traditional product management constraints provide and makes the experience transferable.