The connection between luck and mistakes

Recently, I have been thinking about the connection between luck and mistakes – or approaching the question another way: how something that went right could have so very easily (and probably was much more likely to have) gone wrong.  But they spring from the same source!

Mapping out this connection started last week when I was working on a story about my mother’s logical associative leaps, the kind of thinking that improvisers (and marketing strategists as I understand it) call “A to C” thinking. This means that your brain leaps right over B, and figures out “if that, then what?” to take you right to the next level. In my mom’s case, I would say that she has “A to 3” thinking – she jumps right over into another taxonomy entirely (as she might respond: no one ever said that you had to stay within the alphabet!).  Where she arrives is usually uncanny. Often, she is dead wrong, but sometimes (just sometimes) she is scarily, often hilariously, impossibly right.  Brilliant even.  As I described it in my story, her ability to leap cognitively is virtuosic, she truly is the Mozart of mental associations. But being my mother’s daughter meant that I learned to be very aware of that moment – that moment when a leap might happen. So this means that I am just the right person to be writing a blog post about the connection between luck and mistakes because I trace them both back to that moment.  The leaping off point!!

Many cultural analysts have noted a growing trend in our culture around a fear of making mistakes, and I have been feeling it as a teacher over the past few years. More and more students want to have the instructions spelled out more and more explicitly. They are having anxiety around giving oral presentations, they are afraid to take risks with assignments, lest they get a bad grade. But I would argue that these moments feel vulnerable precisely because they are opportunities to shine.  I wish for more leaping!!!

Bringing this now to career, in a recent conversation about informational interviews, Holly shared with me that she used to sometimes come away from hearing about someone’s tremendous good fortune thinking “man! How am I going to get that luck to fall into my corner? Here’s me, I am trying to be very intentional in my career, and then this person just by fate or serendipity happened to be in the exact right place at the exact right time?!??!” And I joked about how great it would be if there were such a thing as a class in “luck-having.” But in sharing how she has come to understand luck, she said something very profound. Holly explained that she now listens differently when she hears stories about luck. Instead of hearing them at face value (and with that hint of jealousy), instead she tries to look underneath to see “what were the circumstances supporting that person that made these things happen, that helped these things along?” And then the million dollar question: “ How were they stretching themselves out?”

Reid Hoffman (founded of LinkedIn), describes this in his excellent book The start-up of You as “stirring the pot.” And also as courting serendipity and good randomness. As he explains:

There’s a reason the story that inspired the word serendipity involves exploration and journeys. You won’t encounter accidental good fortune – you won’t stumble on opportunities that rocket your career forward – if you’re lying in bed. When you do something you stir the pot and introduce the possibility that seemingly random ideas, people, and places will collide and form new combinations and opportunities. By being in motion, you are spinning a web as wide and tall as possible in order to catch any interesting opportunities that come your way (152)

And yes, I think that this will also place you in a position of possibly making more mistakes than you might if you were sitting at home in bed.  You also are much unlikelier to make someone feel envious of you (and so maybe we need to add envy and jealousy to our list of things to listen to differently as well), but I also want to ask you: which life sounds to you like it is going to be likelier to be the one that you were put on this earth to lead?

A few years ago, I had the opportunity to be interviewed for NPR. Many people told me that I was lucky to sit where I sit (at the Linguistics Dept at Georgetown University) because when the phone rings, I can be there to seize the opportunity to be interviewed for NPR. What these people don’t know is that at least 5 times before the time that I said “yes” I had said “no – I’m not an expert in precisely that.” I had been in the right place at the right time for nearly 4 years at that point, but I still didn’t feel like I was prepared, that I could say yes.

So, as Career Linguist, I want you to do three things with this information

1. Ask yourself “What are the things in my life that were lucky? What oppportunities presented themselves to me?” Were there any that I couldn’t take advantage of because I was not prepared? How could I make myself better prepared to take the next one?

2. In informational interviews, ask about luck to be sure, but also ask about mistakes. Learn to hear these as the same kind of thing as luck.

3. When you hear “and so it just happened” in stories (your own or those you encounter in an informational interview). Instead ask who did what to make what happen? Things don’t “just happen.” As Holly said: “What’s populating that “it”?  A whole history of luck is getting subsumed into that pronoun.

Retrace and populate that “it” in your own life and help others see it in their own as well!! And let me know all about it – send me your stories.  I can never get enough of these!! ☺