How I’ve Learned to Handle the ‘Trough of Sorrow’ as an Entrepreneur

The “trough of sorrow” is not limited to the startup community.

Jessica Donahue, PHR
6 min readOct 18, 2021
How I’ve Learned to Handle the ‘Trough of Sorrow’ as an Entrepreneur
Photo by Ron Lach from Pexels

Last year, I quit my full-time job in the middle of a global pandemic to become an entrepreneur. In some ways, the life of an entrepreneur was exactly what I had expected it to be. While they’re certainly not easy, the long hours, lack of structure, and pressure of controlling my destiny were all things I expected.

What I didn’t anticipate was spending so much time in the “trough of sorrow.” I hadn’t anticipated just how emotional the journey of an entrepreneur could be.

The “trough of sorrow” is a term coined by Phil Graham, Co-founder of Y Combinator. This particular trough is not so much a physical place as it is a headspace.

Branded initially as an issue unique to startup founders, the “trough of sorrow” has been described by Forbes as the “deep period of malaise that can sometimes follow a significant setback, at a time when you most need to be focused.”

Source: Andrew Chen, Partner at Andreessen Horowitz

It’s the period of time following a burst of innovation and adoption when the novelty and…

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Jessica Donahue, PHR

Fractional HR & People Ops for Startups & Early Stage Companies