019 - how to feel like you are winning
Since I returned from my vacation two weeks ago, I have lost every single chess game I have played on Chess.com. Every. Single. One. This is very frustrating because, prior to my vacation, I thought I was improving at chess. I was really starting to enjoy it. Now I hate chess and I think I might stop playing altogether.
This losing streak has done untold damage to my psyche. Every morning the sun comes up over the horizon and the dew-kissed grass glimmers with the possibilities of a new day. Then I play a game of chess and am reminded that I am a loser who is only capable of losing.
There were many weeks like this in the early days of my previous startup, Closing Folders. For a long time, my cofounder and I had virtually nothing going for us. Essentially every meeting we took ended with some form of rejection. There were days where we wondered if the problem we were trying to address was not a real problem at all and we had just wasted two of the most prime years of our lives working on something no one wanted.
When we did find success, it was slow and plodding. It often felt like one step forward, two steps back. In 2015, we landed our first big customer - but it only extended our lifespan by a handful of months. A second customer was not forthcoming.
Around that time we got invited to interview at YCombinator. They paid for the two of us to fly down to silicon valley and make a 10 minute pitch. This was very exciting. At the airport we ran into folks from another legaltech startup catching the same flight for the same purpose. A few days later we flew back to Toronto, rejected again. Meanwhile, the other startup founders made plans to relocate to the valley. Over the next few months they would receive worldwide media coverage and secure millions of dollars in investment. We'd be back to working out of my apartment with my slovenly dog.
Feeling like we were losing every day for months at a time was quite demotivating. With chess, I know that if I just keep playing, I will eventually get through this streak of losses and start winning. I'd like to tell myself that this is because I am subconsciously improving at chess and becoming a stronger player. The real reason is that, if you lose enough, your ranking falls and you get matched with worse players. Then you start to win again.
Startups are not like this. It is not enough to simply keep playing. You need to do more than just show up for work the next day. You need to show up to work with a vengeance. How can you show up to work with a vengeance when you leave work every day feeling like you lost?
The first step is to figure out what game you are actually playing. What does it mean, to you personally, to win or lose. If you don't actively do this, then you will subconsciously assume the world's projections of what winning and losing in startups means. Every time you are exposed to effusive praise about someone's achievement, you are being dosed with a vision of success for your own life. If you take a moment to think critically, perhaps there are things you feel like you are losing at, which aren't even part of the game you want to play.
In 2015, I think we were falling into this trap. If I had thought about it, my personal ideal of "winning" at that time would have been a version of the idealised capitalist narrative: (1) build great product (2) customers buy product because it's great (3) profit. Having done this, I would have struggled to connect the dots of how going to YCombinator would help us achieve this narrative. Really, the reason we wanted to go to YCombinator was that successful companies go to YCombinator and we wanted to feel like a successful company.
Had we been able to determine that YCombinator was unhelpful to us, we could have skipped the entire application process and skipped the chance airport meeting that begot the painful "tale of two startups" narrative that would haunt us over the coming months. This would have freed up a lot of time to improve our product - which is really all we needed to be doing.
The second step to overcoming the malaise of losing is to figure out what you are actually losing at substantively and get vengeful about it. Earlier in 2015, we attended a legaltech conference in New York where a large company in the space revealed they were building a very similar product to ours. What was frightening was that it looked really nice.
A core workflow in both products required a UI to combine PDFs together. It had always been completely obvious to me that this UI should work like Preview on MacOS where you can easily drag pages from one document to another. Unfortunately, having taught myself to code in my spare time over the past year, I had absolutely no idea how to do this on a technical level. Instead, I had built a terrible user interface where you had to select the PDF you wanted to insert and then type in the number of the page you wanted it to appear after in the main document. Our new competitor's demo showed a glimpse of this part of the workflow and they had replicated the MacOS Preview UI perfectly.
For a moment I felt like I was losing again, but then I was filled with vigour. I knew that I wanted to win the "best product" game and what I had seen told me that we were losing. After we got back from New York, I stared at code examples of open source drag and drop applications for hours and hours trying to figure out how they worked. It took several days of frustration but eventually it started to make sense. Within two weeks, our product also had a silky smooth drag and drop interface.
The final step to overcome the malaise of losing is to learn that the "feeling of winning" is a bit of a false idol. When you see others "winning" they come into sharp focus and you paint a picture of their lives extrapolated out from that moment. But that moment is ephemeral. Seconds later that feeling of winning fades and it is back to chasing the next win. This has been my experience on the few occasions where I've had some good news to share on LinkedIn: it's fun for a few moments while the notifications tab lights up. Then, it's back to work. With the benefit of these experiences, I try to view the feeling of winning as something incidental to playing the game well, rather than an object in and of itself.
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