A young entrepreneur asked me a great question the other day, “What are some things you learned later in your career that you wish you knew earlier in your career?” I didn’t have a great answer at the time, but of course it got me thinking. There are a few key lessons I have focused on these past five years or so that weren’t part of my thinking early in my career. I’m not sure I would have cared for these thoughts back then, but I thought I’d share them.
Be comfortable being uncomfortable.
Most of the great things in life are hard. The circumstances that lead to great accomplishment are often uncomfortable — strange and new, out of your comfort zone, and filled with challenges. Getting your mind programmed to be comfortable in the midst of challenge, conflict and uncertainty brings you great benefit. You won’t shy away from the conflict or uncomfortable conversations often required to influence outcomes. Your mind becomes in control of your body. In physical challenges, your mind usually quits before your body does because it is opting to avoid discomfort. It tells you your body is failing before it actually is. Take control of this and get comfort around the fact that many situations in life are not comfortable, but you can still handle it. Hang in there. Be in control.
Develop an expert point of view earlier than the consensus.
By the time everyone agrees on something, it has already happened. You can’t innovate ahead of the curve unless you see a future that most others don’t yet see. You also have to be right about it, but not every time. You can change your view about the future when you see evidence that it won’t happen the way you thought it would. For me, I first try to become expert on something by going super-deep on the topic, learning everything I can about it, talking to many people about it, and using the technology or product in question as much as I can. Once I do, I usually find that many of the people talking about it aren’t truly experts. In fact, I believe many of the loudest voices are often the most wrong.
I remember in 1996, John Markoff, then the most senior and well-respected technology writer at The New York Times, called Microsoft’s Active Desktop, “the most fundamental change to personal computers since the machines were invented in the 1970’s.” To me, this sounded like not just silly hyperbole, but a fundamental misreading of where things were going on the internet. Given his vaulted position at The Times, many people believed Markoff and accepted his view that Microsoft would dominate the next phase of the internet. As we all now know, Active Desktop was an inconsequential product and a failure, and more than fifteen years later, Microsoft is still struggling to be consequential on the internet.
I work to develop my own point of view about where things are going. I work to validate that by looking for data or evidence. Then, if I feel passionately about it, I try to bet on this outcome. And in many cases, my point of view is different than most others. This gives me confidence that I might be on to something (or just be totally wrong). Consensus scares the heck out of me. Really loud voices tend not to be right. My job, as both an entrepreneur and a venture investor, is to beat the consensus long before it happens, but to be right that it will.
Be fact-based in your observations and beware of confirmation bias.
We live in a world filled with data, so use it to make observations. Don’t live life purely on your gut. I gain confidence in my point of view by seeking out research or data that supports my hypotheses. But I force myself to be open about the data I find, knowing that we have a psychological tendency to seek out data which confirms our preconceptions. In short, be honest with yourself about what you observe and challenge your point of view.
Figure out what you are good at and depend on it.
Are you great at reading people, generally right about their capabilities? Are you an astute observer of markets and trends, usually right about who will win or what will happen? Are you a product savant whose obsessiveness with simplicity produces outstanding experiences? Are you a natural leader, able to convince a room full of people to follow you into an uncertain future? Are you an outstanding sales person, able to convince people to part with their money? Or, are you a total introvert who wants to avoid interaction with people but can architect a massively scaleable web application? Maybe you are a mixture of these things? Knowing what you are good at and building your undertakings around that is a quicker path to success. Yes, you can improve in all areas of weakness, but certainly engineer the game to play to your strengths.
Be self-aware, know your short-comings, and find mentors.
We all suck at plenty of things. The only way to get better and to level-up is to first recognize our own limitations and to work with experts to teach us. Self-aware people recognize their short-comings, are not afraid to talk about them, and seek out experts to teach them how to improve. Asking for help is not an admission of weakness. It’s the path to improvement.
Big companies are slow, do not innovate and are unwilling to self-cannibalize.
When I was younger I thought this might be true but now I have seen it happen over and over and over again. Sure, there are exceptions, but in general, startups can move very quickly and innovate on the home turf of large incumbents. As organizations get bigger, executive pay structures often do not encourage companies to cannibalize their existing business even when they see a new technology coming that may impact them. And power is more fleeting these days then in decades past. Do not be daunted by the presence of large incumbents when you can capitalize on a technology shift and catch giants flat-footed. There are too many examples of this common cycle of disruption working time and again.