Dear Wonderful Readers,

I am sitting in the airport, grumpy with myself. I’m in Terminal 2 at Heathrow in London. For such a massive space, this place is oddly quiet. There’s only the shuffling of footsteps and the thumping wheels of carry-on suitcases.

When I go to the airport, I often feel inspired because, in the most physical sense, I am going somewhere. But I don’t feel inspired today. Twelve hours into my travels, I’m incredibly jet-lagged, and I’m also stuck in a funk. I’m about to turn 30, and yes, I’m lamenting about my “writing career,” or my lack of it. A sluggish sense of dread has been hanging over me for weeks. It’s the lack of momentum. I quit my full-time job almost three years ago to become an author and a writer, and things have been going okay. Recently, I even drafted my second book. But nothing sensational is happening.

Perhaps I’m more worried about this than usual because I’m about to visit my family. My mother has very high expectations of me. She’ll never admit it, but she wants me to be very rich and very famous. As famous and rich as possible. Not only am I neither of those things, but I am also far less rich than I would have been if I had just stayed in my boring tech job, even if I would have remained deeply, paralyzingly unhappy in the process.

I remember how uplifted I used to feel when I was in this exact airport. I remember flying back to university in America and listening to the podcast How I Built This with Guy Raz, specifically the Airbnb episode. That story gave me a sense of possibility—that external pull, that demand; that someday, I could be “successful” also.

So, I connect to Heathrow’s WiFi with a fake name and a fake email address. I whack on the episode. I’ve still got three hours to kill before my flight to Derry (which will later be canceled). The podcast episode begins to play. The inflections of Guy Raz’s familiar, measured voice captivate me. I am caught up in the catchy music and the suspenseful sentences. Joe Gebbia, one of the co-founders of Airbnb, speaks to me through the void,

“It was not a smashing success at all…It was completely demoralizing. Like, 2008 was the worst year of my life…Because you’ve put so much into this thing, like, there was nothing else going on in my life except this. And to put it in front of very credible investors, the guys who had picked the Googles and PayPals and YouTubes of the world, and for them to look you square in the eyes and go, “Well, this is weird, I’m not investing in this.”

This episode was recorded in 2017, about seven years ago. We now know how the story plays out, as Airbnb recently celebrated reaching 2 billion lifetime guests. Yet as I relisten to his words, the podcast episode strikes a new chord with me.

I gaze drearily into the high ceiling above me, which is framed by purple and gold fairy lights and the odd wreath. I am reminded that in Airbnb’s story, really smart investors and even their close family members and friends didn’t see the company's potential. Not even the founders themselves understood what Airbnb was or what it was going to become at points in their own journey. I chewed on some Haribo sweets from WHSmith as an insight sank in:

Even really smart people are wrong about stuff all the time.

I sat up a little straighter in my hard, plastic seat, which I had found impossible to sleep on. Maybe I’ve been wrong these three years about how success can even happen for me. Maybe I’ve been approaching my life too rigidly, with too much structure. Recently, microdosing on magic mushrooms has helped me see that my solidified weekly work patterns are holding me back. My problem is that, from all the fancy schooling I’ve had, I was told that I’m a smart person, which has made me believe that I make smart decisions. But if I think I’m smart, well, that means that I could be just as wrong as the investors who turned down Airbnb. And I’m not just wrong about predictions of the future. I could be wrong about anything because the truth is that I have no idea what aspect of my work, if any, will lead to my success or why. I don’t know what part of my work will resonate most with people. In fact, many of the pieces I write that I think are going to resonate with the most people actually don’t. There is no way for me to know.

I watched this clip of an interview with Adam Grant that describes exactly this. He says,

“…the more brilliant you are, the worse you are at recognizing your own limitations.”

Describing myself as brilliant is a stretch; arrogant is more like it. But what is the antidote to my arrogance? Inc magazine contributor Jessica Stillman paraphrases Grant:

“What’s the antidote to this kind of overconfidence that’s so common among smart people? A stiff dose of humility.”

Hah! Humility. Well, now that I think about it, I do have a favorite wrong prediction in mind about commercial success for you that demonstrates this. And the story of it goes like this…

About ten years ago, my sister and I were home for the holidays, and she brought her friend from Cambridge University over for tea. Joscelin, her friend, was this thin, nerdy guy. He told me that he was studying music and starting to play some gigs in London. Curious, I asked him if he could share some of his music with us. I don’t remember much about what he played, but all I remember is that it was ultra-modern, disjointed, and weird. As I listened to it (or tried to), I thought to myself,

“This guy is not going anywhere. He should go back to studying music academically because he’s never going to make it.”

But then, fast-forward about a decade. A couple of months ago, I was scrolling through Instagram. I was watching an Instagram Reel of Vanity Fair when they interviewed Margot Robbie and Florence Pugh, and then…

“Joscelin? What the f**k!” I said aloud to no one.

Except that his name is not Joscelin anymore. His stage name is Jerskin Fendrix, and he was in the Vanity Fair video because he composed the music score for Poor Things, starring Emma Stone. So, the guy who I thought would remain a totally unsuccessful musician forever (sorry, Joscelin) has now been nominated for an Oscar for Best Original Score.

The moral of this story is that I have no f*****g clue about how the world works, especially when it comes to commercial success. As I continue to listen to how the potential investors in Airbnb failed miserably, sitting in the middle of this airport, I realize something: I must embrace the fact that I can be totally wrong. I must embrace the fact that I don’t have all the answers, and many of the answers that I think I have are totally wrong.

This message from “the universe” has been coming to me in more than one form. Just last week, I was walking down the street when I passed a tiny piece of paper on the pavement. I knew from its shape that it was from a fortune cookie. Not my fortune, but one that, apparently, I was meant to stumble upon. It said,

“Ideas you think are absurd will lead to your success.”

I took this photo of it (above).

You see, no matter how smart we think we are and how great the decisions we believe we are making are, we need to leave a giant space open in our minds and our hearts. A giant space where we accept that, much like the very smart investors who turned down Airbnb, we may simply be wrong. We may even be wrong about most things. And this is a good thing if we believe it. Once you’re aware of your own limitations, you can start to entertain ideas that you think will not work out. Because the truth is that neither you nor anyone else in the world knows if they will or not. Only time will tell.

So, what have you been wrong about? And what could you be wrong about right now? Leave a note in the comments.

Lots of love, and enjoy your weekend!

Tash

💌 ✍️

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