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This talk is really about rewiring what “success” means. From chasing validation, money, and outcomes to building with reflection, detachment, discipline, and community, while protecting your inner life (mental health, spirituality, relationships, and creative practice).

Somdutta Singh shares how she broke away from a “doctors and scholars” family expectation to pursue entrepreneurship, driven early by the idea of high risk, high reward but later grounding that drive in reflection, discipline, and self-awareness (influenced by Dr. Amar Bose). She describes building and exiting companies, then scaling her third venture, Assiduus, and why reflection matters: entrepreneurs often get overly attached to outcomes, opinions, and rejection, which can derail decision-making and mental health.

She speaks candidly about depression during a high-growth phase, despite strong financial performance, triggered by culture not scaling, relationship strain, and the illusion of “work-life balance.” Therapy helped her reconnect with self-worth, stop chasing validation, and return to what made her whole: spirituality and music. That inner rebuild reshaped her ambition: success became less about personal wins and more about creating leaders, enabling wealth for the team, and impact.

On leadership, she names non-negotiables: clarity, passion + prudence, and kindness. She discusses the hardest CEO decisions of letting people go when they don’t scale with the company, while keeping relationships intact through an alumni network. On women in leadership, she highlights an uncomfortable truth: women often don’t support women enough, shaped by years of insecurity and trauma, but change is possible through intentional investing and community-building. She closes with OPM learnings (listening, unlearning, community) and advice to her younger self: stop chasing, love yourself more.

Here are the Top 10 Takeaways from the conversation:

1. Reflection is a competitive advantage: it reduces over-attachment to ego, outcomes, and rejection—and keeps you focused on “why.”
2. Execution needs humility: hire people better than you; vision isn’t enough.
3. Detachment isn’t apathy: care deeply, but don’t let setbacks define you.
4. Mental health is real and common: treat depression like any other health issue—get unbiased help early.
5. Numbers aren’t the full scorecard: revenue/profit can rise while culture and inner life collapse.
6. “Balance” can be a trap: entrepreneurs may need integration, boundaries, and support systems more than perfection.
7. Return to non-transactional anchors: music, spirituality, sport, art—these stabilize the builder.
8. Leadership non-negotiables: clarity, passion + prudence, and kindness (skills can be taught; character is harder).
9. Hardest CEO move: letting loyal early teammates go when the company outgrows the fit—do it with dignity and continuity (alumni mindset).
10. Stop chasing validation: your definition of success must come from within; self-love fuels sustainable ambition.

Books:

1. Many Lives, Many Masters 
2. Atomic Habits
3. The Hard Thing About Hard Things
4. Zero to One
5. Bhagavad Gita
6. Works of Swami Vivekananda