When quitting is the logical decision

I went to bed crying about business once, years ago, and I remember feeling like the whole thing was fucked.

We were running out of cash, over 70 employees and their families were counting on me to find more cash, and even though the business was meeting its objectives fundraising was going terribly.

The day before it had been going well, funny enough, before the investor who had spent literally dozens of hours with us pulled out instead of offering a term sheet as he had told us he would. He explained that his partners weren't as excited about the market as they had been, and the $10m that we had been expecting to close within the next 30 days evaporated when I hung up the phone.

I knew the next step was to open my laptop and get back to work, but it all seemed pointless. We were going to run out of money, I was going to let down everyone that had believed in me, and I personally would be branded a failure and run out of town as a response. I forced myself to look up when Laura got home, and her smile turned to concern when she saw me. We talked, and because she's amazing she tried to mirror me in such a way that I could see my way out of the situation. She talked through alternative options, bright sides, everything, but I didn't want to hear it. All our options sucked. We had banked it all on one investor, which I knew was a bad idea but had somehow convinced myself would work, and now it was all going to blow up. Our business was gone, my life was over, and I wanted to crawl into a hole and sleep until I died.

So I went to bed at 6:30pm.

When I woke up, the investor was still a pass. I went through my situation logically, evaluating all the options that we had, and came to the unavoidable conclusion that we still didn't have any options. I hated that reality, but it was fact. We would run out of money, we would fail, and it would be all my fault.

I've found that there are choices and decisions in life, and the two are very different.

Decisions are what you make when you know where you're going and you're trying to optimize for the best way to get there. There is a right-est answer, so you evaluate all the data and then make a decision based on that data, trying to steer as close to the correct answer as possible. Choices, on the other hand, are what you make when there is no right answer, you don't know where you're supposed to go, there is no available data, or the data contradicts. You don't evaluate anything in making a choice. You make choices based on gut (said differently: based on nothing), and if someone asked you why, you might be able to spin up some logic in support of that choice, but you'd know it was made up as you said it.

At that moment, sitting in my kitchen with everything telling me to simply pack it in, I made a choice to keep going. All the available data said we were screwed, and I maintain that the correct decision would have been to stop, were I evaluating data. If I had done a pros/cons list the piece of paper would have tipped over due to the weight of ink on the Cons side.

But I chose to keep going.

Three months later we'd secured follow on financing from a new investor just in time, and from that were able to launch the 2.0 version of our product which leads the market today. None of that was possible sitting at my kitchen table looking at the data, but all of it happened because I chose to keep going despite its impossibility. We reached second base not because we knew how to get there and were skilled navigators, but ultimately because we were willing to step off of first base despite having no idea if second base really existed.

Running a business means making thousands of decisions every day. You succeed or fail based partially on your ability to make those decisions with a high degree of accuracy. But running a business also means making at least a handful of choices, and in those moments every successful entrepreneur has consistently made the choice to keep going.

In the words of a mentor of mine, Chelsea FC Avram Grant:

If you persist, you may succeed, or you may not. But if you quit, you ensure you will not succeed.

Update: I went to bed crying about business this week, as COVID-19 shut down the economy. I know a lot of founders who did.