Be Lucky
Being lucky is just about the best thing you can do for your career, but it never struck me as great career advice.
“Be lucky” is not just flippant, it’s actively unhelpful. Randomness is by definition what we don’t control (unlike work ethic, skill, self-confidence, empathy, and all those other traits we can develop.) It’s tantamount to telling someone there’s nothing they can do. But… opportunity plays such a large role for all the successful people I know, I wasn’t comfortable leaving it out when people asked me for advice.
Vegas gave me the inspiration for what to say. I enjoy playing blackjack (with the disclaimer that I expect to lose money when I play — it’s paying for entertainment, just like Cirque tickets.)
Blackjack has a pretty small house edge — meaning, if you play perfectly, the casino will beat you only a little bit more than half the time. “Playing perfectly” is the operative phrase — most people don’t. Some of the most important decisions come down to maximizing your winnings when your luck is good and minimizing your losses when the luck is bad. And those end up being good career principles, too.
One of the best blackjack plays is to “double down” when you’ve been dealt good cards. Some players are scared to double their bet size, but if you don’t, you’ll dramatically reduce your expected outcomes — you’re handing money to the casino.
From a career perspective: you can’t control when the good opportunities will come along — but when they do, don’t pass them up! As Eric Schmidt famously told Sheryl Sandberg: “If you’re offered a seat on a rocket, don’t ask what seat. Just get on.” You can’t control when or whether you’ll get offered a seat on a rocket, but it’s not just a question of accepting the seat — it’s what you do with it. When I joined VMware in 2003, I had no idea that it was about to kick off 4+ years of exponential growth. But as the company took off, I worked as hard as I could to have as big an impact as I could, and my responsibilities grew exponentially, too.
One important coda to maximizing your good luck is that you have to notice when good opportunities come your way in order to take advantage of them. Unlike “being lucky,” “noticing lucky opportunities in your vicinity” turns out to be a learnable skill. Learn it!
At the other extreme, we have the most unpopular play in blackjack: surrender. It’s a bit like folding in poker — instead of hitting or standing, you exit the hand without playing, “surrendering” half your bet. Used on bad hands, surrender significantly improves player outcomes. But most players who scrupulously play every other rule in the book ignore surrenders. If I had a nickel for every blackjack player who told me “you don’t win the hands you don’t play,” well, let’s just say my cumulative lifetime blackjack earnings would be a much more robust number.
The fact is, if you have a losing blackjack hand, you are better off walking away with half your bet than none of it. And so it is in life. When you’re in the wrong job, the best career move you can make is to walk away, and spend your most precious resource (your time) on something with a better payoff.
As humans we are prone to a cognitive error known as the “sunk cost fallacy.” Blackjack players hate surrender because they don’t want to walk away from their ante. Humans hate quitting jobs because they’ve worked so hard and invested so much.
In my first job out of college, I had an important realization: sometimes you can end up on a team or a project or a situation that is screwed up, for any number of reasons. Let’s call it bad luck. Sometimes you can do something about it. I have an over-developed sense of responsibility (or perhaps hubris), so fixing what was broken was always my first instinct. When I ran into problems that were too big for me to fix, I felt upset and betrayed. This stuff was messed up — why wasn’t my boss solving the problem? Or the execs? Why wouldn’t someone take responsibility, the way I would in my work? It was unfair.
Then one day, drinking coffee in the break room, I had an epiphany: unfairness exists in the universe. I can’t control it; I can and should try to fix it, but if I fail, I still have two choices: I can stick around feeling like a victim, or I can leave. Leaving may come at a big cost, a cost I may not want to pay. If I don’t, then I’m making a conscious tradeoff to be here and thus in a sense I did choose the conditions. This mindset was liberating, because it meant that I always had agency.
Once I realized I had the choice to quit, I realized I had a lot of other choices, too, that had previously seemed inaccessible to me. I could change teams, projects, job function — I had nothing to lose if the alternative was quitting the company. In the end I got the best of both worlds: I switched projects, and later went back to my original team with a mandate to solve problems that had seemed so intractable to me earlier.
Going back to the career impact of luck — sometimes you can’t control aspects of your environment. Your company is going under, your team is dysfunctional, your skills and effort are a bad match for the work, your confidence is shot. At moments like these, your sunk cost fallacy is likely to kick in. You are likely to think you have to stay committed because you’ve already invested so much. But if you want to maximize your overall outcomes, walking away needs to be in your vocabulary. You need to choose to leave an environment that makes you feel small, even if it means starting over.
