Why we fail: a lesson from startups

I recently filled out a job application that had a few required questions that you had to answer in order to successfully submit your application. Don't you hate it when they ask you to do anything beyond submit your resume? I know that I do! As a result, I usually won't bother to continue filling out the application--unless it's a genuinely job at an interesting company. In this case, I did just fill out some answers for a relatively interesting opportunity and one of the questions they asked was about the difference between companies that fail and those that succeed.

As I was reflecting on what to write, I was struck by the similarities between the ingredients that lead to success and failure for both startups and individuals. One of the main reasons that startups fail is because they work on the wrong things, whether they're fundraising instead of building the product or hiring people with skills but poor EQ, they're making poor use of their limited time and resources. This is usually due to poor leadership where management doesn't pick the right set of things to work on. I've seen this happen in cases where the management team can't work together and actually pick what next product or direction to work on. I've also seen leaders who like to rely on their "gut intuition" instead of looking at the data that says otherwise. This is also relevant for us as individuals. When we think about whether or not we are "succeeding" in life, this is often a reflection of how we're spending our time and resources. If our goals are to be healthy and lead a life filled with joy and purpose but we're wasting away at a sad office desk job that we hate, well, we're by default failing because we're not working on the right things.

Another example I sometimes see with startups is that they decide to go all-in on a specific solution or direction without having tested a hypothesis first. Perhaps there's a low cost, low risk experiment they could run to validate whether or not it makes sense to invest more. One of the challenges for us as individuals as we experiment across various domains of our lives--like finding suitable work or a spouse to commit to--is that it's hard to balance trying different things and taking the leap of faith to make a commitment. When you're dating, how many dates are you supposed to go on before you make a decision about whether or not you like someone, or how many people are you supposed to date before deciding to commit to one person? For individuals, there are many low-cost, low-risk ways of trying new things but in some ways it's a lot harder to make a decision, because our emotions are a significant player in the decision making process. For startups, it could be easier to make a decision if you're using objective key metrics and data points to inform your thinking.

On the flip side, what makes startups successful? Definitely the people, but also a culture of accountability. While it's not always fun to work for a company that is crazy about setting goals and tracking them religiously, it does create a different environment than those that are a free for all. Similarly, if we're thinking about finding success as individuals, being disciplined and mindful of our actions as a means to achieving our goals is a significant driver of whether or not we will be successful. If my goal is to be healthier by exercising, then actually making sure I go to the gym or find other ways to move throughout the day is critical. If I always make excuses or find reasons why I can't go, then I won't achieve my goals. This is one of those things that is easy to forget about, but if you're like me and have worked at a startup where there is zero accountability, you'll start to miss it even if you were never that into rigid work goals.

While companies and people are certainly not the same, it is interesting to think about how we can apply the things we've observed and learned in one context to another. Thinking about why I am where I am right now is directly linked to the fact that I spent my 20s working on a bunch of different things, trying out different roles and workplaces, without ever having found one that felt like it could become home. I've gathered a lot of data about what doesn't work and in the process have been able to also assess which things I do want to prioritize. For me, career is certainly a hot-button subject with lots of emotional factors in play, but taking a step back has been able to given me some space to be objective about what has worked and what hasn't. Sometimes, when we're in the midst of the chaos it's hard to see things clearly, but hindsight is 20/20, so let's make sure we're taking the time to reflect, process, and learn.