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 process of striving for a financial goal often provides more meaning than its achievement. Upon reaching the goal, some people experience a "meaning vacuum" because the guiding purpose is gone. This often necessitates a difficult but crucial period of introspection to discover more intrinsic and sustainable motivators.

Many founders treat their startup as a temporary vehicle to an exit, which can lead to an identity crisis after they "win." A healthier approach is to build a company as a "way of life"—a system of activities you want to engage in for the long term, regardless of specific outcomes.

Unlike professionals who move to similar roles, entrepreneurs enter a vulnerable "in-between time" after their company ends. Their personal narrative was tied to their last venture, leaving them in a "weird wasteland" while figuring out what's next, a period that is often overlooked.

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.

Melissa Wood Tepperberg challenges the common entrepreneurial goal of building a company to sell it. After experiencing investor-led growth, she realized her true desire was to continue doing the work she loved, not to cash out. Founders should define their own "North Star" beyond a lucrative exit.

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.

Lyft's co-founder describes his post-exit journey not as a victory lap, but as a three-month period of relief followed by feeling lost. The transition from an all-consuming role to unstructured time is a significant psychological challenge that a margarita-fueled vacation can't solve.

The day Poppi's acquisition closed, co-founders Allison and Stephen Ellsworth had a huge fight. This highlights the often-overlooked emotional and vulnerable side of a business exit, which can be as stressful as it is exciting, reminding founders that major business milestones are also major life transitions.