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Faye Penn

@fayepenn

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Former: NYC’s official career guru. Now: Exec coach to creative geniuses. Wanna talk about your work or business? I do!

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POV: You got invited to the glorious wedding of @originalamericantreat and @timdonz on Saturday and this is the dress code. Tips welcome! Especially for the MWAW (AKA mensch with a wrench, AKA Joel the hubs, a man otherwise disinclined toward sequins and glitter.) by @fayepenn

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4 months ago

Drop-off day for our @fortlewiscollege Adventure Education major, kicking off with a five-day, first-year camping trip in the San Juan mountains. Whole lotta feelings, mostly excitement that our city kid is charting his own course. Also that we get to visit him here. taken in Durango, Colorado by @fayepenn

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a year ago

June 2025 was a busy one! Two graduations, one speech, a jewelry drop, one prom, one conga solo, 100 years of PSJC, a Prospect Park mega-picnic, new garden offerings, a cute cat and a Berkshires sunset. I was inspired by @lorileibo to do a monthly roundup and while I’m still figuring it out, it’s really nice to take stock of the happy moments. by @fayepenn

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a year ago

No bad vibes can survive a blossomy spring stroll in #ditmaspark and #prospectparksouth Brooklyn. Highly recommend a visit! taken in Ditmas Park, Brooklyn by @fayepenn

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a year ago

🎉🎂I don’t know why it took me so long to find the words for Sami’s (now belated) 14th birthday, except that choosing from 37,000 photos of a very cute and fun person isn’t easy. Somehow, being a teen in a tough city hasn’t diminished Sami’s kindness, compassion, self-awareness or moral clarity — nor her enthusiasm for our mom-daughter silly dances or trashy TV nights. Happy birthday to one of the loveliest people I know. 🩷 by @fayepenn

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a year ago

Happy 17th to the life of the party: our dynamic, funny, magnetic, ever-evolving son, @im_ezt. May you never stop moving, growing, creating and making us laugh. L’chaim to a fine young man with a big heart, a beautiful spirit and a killer right hook. ♥️ by @fayepenn

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2 years ago

Guys is this legit? by @fayepenn

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2 years ago

🌿A year ago this nice family from Bensonhurst adopted some pavers we were giving away. The next day, as thanks, the dad brought us a container of Vietnamese basil.

I looked around the yard today and noticed that Joel, my excellent gardener husband, had turned these little sprouts into eight flourishing plants (not counting the ones that sprouted up between the stones.)

There’s an unsubtle metaphor here about what can happen a year later when you plant seeds and nurture them consistently along the way. Kind of amazing.

But also, does anyone need any purple basil? 🌿 taken in Ditmas Park, Brooklyn by @fayepenn

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2 years ago

The Jewish news has been mostly crappy for a few months, but here’s something super fun: Borscht Belt Fest is back in Ellenville this summer, July 27 + 28. I’m a proud board member of this new cultural org that celebrates the history of America’s vacationland, the cradle of standup comedy, mamboing yentas, Black athletes doing the rounds to build their profiles and even a trans resort or two. 💄

You’ll hear a lot more from me on this — tickets now on sale! See @borschtbeltmuseum for details. taken in Ellenville, New York by @fayepenn

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2 years ago

Oops this posted too quickly! Happy 21st to our extremely witty, taste making, high standards having, good values exhibiting, excellent clothes wearing, BS calling, piss taking, family appreciating, clever bar spitting, irreverent, artistic, self-aware, no moped having a** son Zeke. We are proud of you and endless entertained by you. We love you! L’chaim! by @fayepenn

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2 years ago

So I completed the 100 executive coaching hours required for certification and want to thank the folks who have enlisted me as a thought partner while they figure out what’s next.

Shout out to the leaders facing soul-sapping complexity who find a way to move from dread to strength and clarity. Props also to people seeking new opportunities who keep their hustle and creativity alive despite inevitable letdowns + headwinds. And big ups to the founders: shit is hard but you all find a way.

Respect and gratitude to my colleagues, teachers and mentors — turns out that coaches are pretty great people. I had some hang ups that coaches would be flaky or woowoo and maybe some are, but mostly I’m meeting really impressive people who want to deepen their impact in all kinds of ways. I can say for sure that I would never not have a coach if I could afford one. And it happens that I know a bunch of super smart and affordable pros who are building their practices in a range of industries—happy to make connections if anyone’s looking.

One more thing: I’m not doing barter as a mainstay anymore (unless you have a villa in Capri) but a really fun part of this process was bartering coaching for other services. It’s such a great way to swap brain cells and build relationships. Everyone wins! Ok if you’re still here thanks to you too. by @fayepenn

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3 years ago

“I have your back, sweetie, and I always will.”

My mother, who would have been 94 today, told me this a few weeks before she died on 8/9. I admit that it unsettled me at that particular moment, but I’ve started to get it.

She may not pick up the phone anymore, but she gave me a reserve of strength that I tap all the time: when one of my kids is having a tough go, when I’m questioning my professional path, when I feel overwhelmed by life’s complexities. She thought I was smart, funny and interesting — “some dame”in her adorably archaic parlance, so right or wrong, that’s the story I’m sticking to. Plus I am hoping that some of this badassery is hereditary. (Exhibit #2: her mom, a “Yiddish Cowgirl” from Saskatchewan.)

So thanks for having my back, Mom. If it’s not too much trouble, please send a sign — any idea where that leather trench might be? 😘 by @fayepenn

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3 years ago