Starting a Company Feels Like You Are Unemployed

I have had numerous friends and family members negatively affected by the shakeout at Zenefits, so I was hesitant to write this post, but this quote from Parker Conrad, the founder of Zenefits, is a key one that I wanted to reflect upon.

“When you start a new company, it kinda feels like you’re unemployed,” Conrad told Axios shortly after his Demo Day presentation. A program like Y Combinator can motivate and bring structure to a founder’s work, he added.”

I couldn’t agree more about the unemployment bit. At the beginning, even with great co-founders, starting a company is a mental challenge and feels a lot like unemployment (save for all of the hard work you are doing). No paychecks. Sparse email traffic. No direction. Limited accountability. Total schedule flexibility. Also, answering the, “What do you do?” question at social gatherings can feel awkward, especially if you allow doubt to creep into your mind.

I’m not sure that structure through a program like Y Combinator is a silver bullet, though. Sure, it certainly greases the skids and makes life easier during a tough time. But ultimately, I have found the most helpful thing during the start-up stretch is a clear sense of principles and focus, as well as a robust set of opinions (loosely held, of course) informed by experience and reinforced constantly by speaking to the smartest people you can find to offer their insights. I have found this combination helpful to (1) stay motivated, (2) have a clear sense of what you will and won’t do as firm, and (3) rapidly adjust your thinking on #2 based on others’ feedback, but not by taking feedback wholesale or blindly.

As things get busier and the “unemployed” feeling fades due to increased email traffic, principles and focus remain critical to allocate time. Why is managing time so important? Because time costs money and both are in short supply during the start-up phase. So whether bootstrapping or venture-funding your business, managing time and priorities carefully seems to be the best way to go from feeling unemployed to over employed. 🙂