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

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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 excitement of whatever you’re working on starts to wear off, and you find yourself metaphorically hurdling toward the “crash of ineptitude.”

Kyle Wong, Founder and CEO of Pixlee, says that:

“Getting back on the momentum train after you’ve suffered a setback, like the loss of key team members or the realization that your target customers aren’t satisfied with the current iteration of a product that you’ve spent months developing, can be difficult and demoralizing.”

Some never make it out of this place. But by sitting in their discomfort and chipping away at the challenge at hand, others successfully climb their way out.

Now that I am over a year into my entrepreneurship journey, I can confidently state that the “trough of sorrow” is not limited to the startup community.

On the contrary, it’s something that every business owner faces at one point or another, and some…

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Jessica Donahue, PHR

Fractional HR & People Ops for Startups & Early Stage Companies