Go Big.

Paul Simon plays to the crowd at Newport Folk Festival in 2022

One more story from Newport Folk:

We’d been told that at Newport, special guests sometimes show up. And then on Saturday night, Nathaniel Rateliff & The Night Sweats came out and played two Paul Simon songs in a row, and we realized: Paul Simon might be tonight’s surprise guest!

An hour later, after a half-dozen artists had played Simon’s music, Paul himself came out and played five songs with the band.

So we weren’t expecting much on Sunday night. How are you going to top a special guest appearance by Paul Simon? Brandi Carlile was expected to play with some friends. (The set was billed as “Brandi Carlile & Friends,” which made that a fair assumption.) We figured she’d bring out the usual group of indie musicians and colleagues. We didn’t realize one of them would be Joni Mitchell! And that a group of musicians would sit around in a circle and play for — and with — her.

What I loved wasn’t just that Newport brought out two icons. It’s that they found new ways to honor them. They’d clearly asked: How do we pay tribute to these legends? What formats can we try? How do we do something that’s never been done in the history of this festival?

Had a group of musicians played a tribute to Paul Simon, that would’ve been something. Had Brandi Carlile played “Blue” from start to finish, that would’ve been amazing. But instead, they somehow did something even more unexpected.

If you’re going to go big, go big.

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That was my view of the stage for Paul Simon’s set. Paul’s up there if you zoom in far enough.

The Only Time Is Now.

The truth is, I almost didn’t leave The New Yorker when I did.

I knew that I wanted to start Inbox Collective. I knew there was a market for my services. I knew that I had an opportunity to help the journalism world.

But I wasn’t sure if the timing was right.

Sally was in nursing school. She was 18 months in, with a year of classes left. She’d graduate in Spring 2020. And my thought was simple: Sally still had a few semesters of tuition left to pay, we were a one-income household, and if Inbox Collective didn’t work, we’d be a no-income household. Leaving my job to start a consultancy was a gamble, and the safe move was to wait until Sally had graduated and gotten a job — sometime in the summer of 2020.

But Sally convinced me to take the leap anyway. She reminded me that I had momentum and a clear opportunity. There was something else, too, something we talked about a lot at the time: The window for me do this was open, and we weren’t sure how long it would stay open. There was risk in leaving my job to start something new, but also risk if I waited too long and the window closed.

Now looking back, if I’d waited, I don’t think I’d ever have left to start Inbox Collective. Taking the leap to start a business is tough enough during good times, but during a recession and a pandemic? There’s no way.

It’s a reminder that when you’ve got something you’re excited about, and something you feel ready to take on, the only time to try it is now. If you wait, the window might close, and you might miss out on that opportunity forever.

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That’s a photo of me giving a talk in Sydney last year — one of many pretty amazing experiences that I couldn’t have had without taking the leap.