Discover more from Origin Stories
"How do I know when to quit?"
Jason's story, part 2/3
“I’ve developed a personal principle never to let myself be miserable – in a job or in a relationship – for more than three months straight. When I found myself wrestling with the challenges of being CEO of Fieldbook, my startup, I often asked myself, ‘Why not just be an engineer at a tech company? It would be easier and less stressful, and I’d make more money.’
As CEO, no one but me was responsible for setting the direction or carving up the work. There were no constraints, guidance, or structure. At any moment I could be doing anything: strategy, marketing, hiring, or writing code. The weight of goal-setting fell on my shoulders.
Despite these challenges, I felt compelled to persist down an entrepreneurial path with the potential for huge scale and impact. I am very aware that my ability to live a comfortable life is due to those who came before me and struggled to bring breakthroughs to the world. While I can’t pay it back to them, if I have the ability to contribute at that level, then I feel an obligation to pay it forward.
Yet my startup was lacking momentum. My goal at Fieldbook had been to create a relational database that was simple and intuitive enough to serve small business users. The product wasn’t quite right, but it wasn’t obvious how to fix it: simplify it to lower the cost of customer acquisition? Charge a premium to onboard upmarket customers? Could I turn things around by investing more effort? How would I know when to quit?
None of these questions had easy answers. Even Mark Andreesen says there is no formula, which is one of the reasons that being a founder is so hard. In a gut-wrenching moment, I shut down Fieldbook and accepted a talent acquisition deal. I realized that as CEO, I could hit every one of my goals but the company could still fail if I had set the wrong goals. Emotionally, it was hard not to have my self-esteem bound up in the dissolution of my company.
When I clocked in as Senior Engineering Manager at the acquiring company, I expected to eventually return to the startup world. I had no idea that my side project, a blog on the drivers of human progress, would suddenly gain traction and have me considering a mid-life career pivot.”
Stay tuned for Part 2, coming next week!
Have you ever struggled with the question of when to continue, and when to quit? Share your story in the comments.