The period after a major achievement, such as selling a business, doesn't always bring relaxation. Instead, it can create immense internal pressure to "crush life" even harder and over-deliver for new stakeholders. This can lead to a surprising increase in stress and anxiety.
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Selling a business often triggers a period of depression. A founder's self-worth is deeply intertwined with the daily grind and pressures of their company. When that is removed, they experience a significant loss and must redefine their identity outside of their work.
The romanticized idea of "passive income" is a myth. The speaker posits that the amount of money one earns is directly correlated to the amount of anxiety and stress they can handle. High achievement comes with an unavoidable and significant mental and emotional burden, a cost often hidden behind the narrative of hard work.
Hitting a major revenue goal can feel meaningless if it leads to burnout. This form of "success" simply replaces corporate constraints with entrepreneurial ones, creating a new trap that you've built for yourself.
Despite selling their company for nine figures, founder Cass Lazaro reveals she suffered from PTSD after the sale. The intense pressure of growing to $50M ARR in three years, marked by 14-hour days and neglecting personal health, left her nervous system 'fried.' This highlights the hidden, long-term mental and physical toll of startup hypergrowth.
Despite having the funds, a majority of founders regret making large 'trophy' purchases right after selling. The sentiment that 'the things you own end up owning you' holds true, as these assets add new responsibilities and stress during a major life adjustment.
Shift your definition of success away from external markers like titles or salary. The ultimate professional achievement is waking up on a Monday genuinely smiling and without anxiety. This makes personal well-being the primary metric for your career, regardless of your income or status.
A major struggle for accomplished professionals is the internal conflict between their identity as a "stone cold high achiever" and their current lack of motivation. This cognitive dissonance—knowing you should be achieving but not feeling the "juice"—is a key psychological hurdle when past success eliminates original drivers.
Achieving external markers of success, like a multi-million dollar exit, often fails to provide a sense of accomplishment. Instead, it can lead to feelings of emptiness, anxiety, and imposter syndrome because internal self-worth was tied to the struggle, not the outcome.
After selling his company, the founder experienced six months of bliss followed by a period of feeling useless and lacking purpose. This 'valley of shadows' is a common but rarely discussed phenomenon where accomplished founders struggle with a loss of identity and intensity, ultimately driving them to build again.
Reaching a long-sought-after career milestone, like a specific promotion, can unexpectedly lead to depression and a sense of aimlessness. The "chase" provides direction, and without a new goal to replace it, you can feel lost, like a dog that has finally caught the car it was chasing.
