Jenny Douglas
55, Prospect Heights, Brooklyn and Elsewhere 

For the most part, I like being older because there’s so much more to work with! I far prefer a rich history of choices well and poorly made to all that glittery blankness that lay ahead of me in my twenties. It’s good to have arrived at who I am.

What do you do for work?
For my bread and butter, I buy (and sometimes renovate) investment properties in the Hudson Valley; I own a cabin in Margaretville and a multi-family building in the village of Catskill and—together with my dad—another multi-family property in Hudson. To each of these, and to my garden apartment in Brooklyn, I welcome a mix of long and short-term renters.

Growing up in Tokyo of Canadian parents, I struggled at times with not feeling like I was from any one place or belonged to any one tribe. Over the years I’ve slowly managed to turn those early worries inside out, and now find ideas of home and belonging to be largely portable and largely inclusive. (And this feeling generally extends to the guests who show up at my various doorsteps.)
Being a late-in-life real estate entrepreneur has granted me the freedom to engage other pursuits that matter to me. In recent years, I’ve served as the Story Consultant for the Netflix documentary series Daughters of Destiny, turned my brownstone into a pop-up arts salon called The Brooklyn Cottage, hosted once-a-month meditation evenings for anyone in my community wishing to “walk through the unlocked front door,” been a TueNight storyteller, created a “giving circle” with a noble tribe of Woolfers called Woolf PAC (which over the course of its 1.5 year life-span issued grants totaling more than $40,000 to progressive not-for-profits) and, when I was feeling lonely after a divorce, designed a workshop for others like me called Grief and Gratitude. The workshop has been attended to date by over 250 women, and I continue to offer them regularly—through, out of my home, and lately in collaboration with TheWoolfer.

I’ve recently enrolled in a several-months-long end-of-life course at The New York Open Center and just this week secured a desk for myself at The Center for Fictions Writers’ Studio—because there’s a piece of writing (I’m afraid to call it a b-o-o-k) that’s been nipping at my heels for a while now and I’d like to see if I finally have the courage to, yes, go there.  (Oh and I’m a Woolfer mod!)

Tell us about your life as a Woolfer.
I’ve been a Woolfer since the group’s earliest days when none of us could have imagined what we would go on to become. Since that time, members have:

  • Directed me to the perfect pair of toenail clippers.
  • Shown me extraordinary kindness when my parents were both really sick and I was weeping into my phone at JFK.
  • Supplied me with friends to meet in far-flung destinations.
  • Explained the value of a high-yield savings account.
  • Become lasting and excellent friends.

Wherever I go Woolfers are in my back pocket. It’s hard to ever feel truly alone with you there.

Last great book you read?
I’m late to the party on this one, I know, but I’m knee-deep in Donna Tartt’s The Goldfinch (and am 15% ambivalent and 85% intoxicated).

Greatest new discovery?
I met Kent Shell in the summer of 2014 and nearly bailed on our first OkCupid date due to online dating fatigue. Five years later, he still feels like my favorite new discovery.

I never skip dessert.

Favorite quote?
“What you can plan is too small for you to live.”
—David Whyte

Tags : WOW
The Woolfer Newsletter Team
Stephanie Staal and Nina Collins have worked together and adored each other since 1994 when they were both babies in the world of book publishing. Stephanie is a lawyer, journalist, & author of READING WOMEN, and Nina is the founder of "What Would Virginia Woolf Do?" Hillary Richard is also a lawyer and co-host of the Raging Gracefully podcast. Sidney Morss is a recent NYU grad and the youngest member of our team.

1 Comment

  1. How did I miss this? Jenny Douglas, you radiant being, I cannot WAIT to read your book (no presh). Love you xo

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