How Should A 39 Year-Old Woman Behave?

And live and work and talk and dress?

Jump in friends, we’re going for a ride.

It’s my birthday this week (not today, but this week) and I’m turning 39. The last year of my thirties! And I feel strong, I feel smart and capable, I feel young, a lot of parts of my life are in place. Still, there’s part of me that feels I need to rush and push towards something this year, this last year before I’m 40, the last year before I’m a real grown up - this is my last year to take myself only sort of seriously. My last year in dress rehearsal.

This month also marks four years since I started my newsletter - first on tinyletter, then on Substack, and I’ve dumped all of myself into it. It’s grown from a sort of silly hobby to a way for me to express myself to a fully fledged business, one that’s more meaningful than any job job I’ve had in the past. And all of it, for better or worse, rests on my shoulders. The business is me. What I have to give is me. All of this - all the ideas all of the photos all of the words and thoughts and feelings - it all starts and ends with me. It is me, this is me – I’ve made myself my own life’s work.

A lot of things I like right now - outfits that make me feel very, very good. A great Lisa Yang sweater over a Comme Si shirt, and an Ashish skirt from The Real Real, and very old Row boots (these are also pretty).

I write these letters mostly in bed at night, with my kids falling asleep next to me. Little tadpoles curled against my body in the dark. I live and feel everything and digest and share it here - because it feels good and because it means a lot to me. To do a call and response as a 39 year-old woman and hear echoes of other women hollering out of the abyss back to me. And if it starts to feel like all of these essays and everything I have to share is about doubting myself, feeling weird, getting sober, staying sober, mothering and actively being a good person in a challenging world - it’s because that’s what it’s really like. That is what I am right now, and it’s bigger in some ways than I expected, smaller in others. I’ve made a career out of myself, and doing this necessitates putting myself out there for scrutiny. I’m literally asking for it.

Another great Ashish find via The Real Real! This shirt has served me very well. The pants are Tibi (and they’re also perfect), along with these Gucci clogs, that I love so much - here’s the logo version.

But I also think it upsets people to see a woman past 35 miming the genuine effortlessness of the truly young. It’s off-putting to see a woman past a certain point trying, trying for anything – a promotion, a new hobby, trying for relevance. Cringe. At this point, you should have it, and if you don’t – pack it in. I hope you like where you are when the clock strikes midnight, because lady, the game is over!

Coralie Fargeat put this better than I ever could in The Substance, but as I creep on in years, and creep on in building this platform and my community, I feel a lot of self-imposed embarrassment that my efforts are so visible and obvious. My product is – essentially – that effort. I started writing this letter the day I left for Paris fashion week, which always makes me feel vulnerable and publicly judged - my market value appraised. I called a friend, and spiraled around about what it was that was making me feel so nervous and anxious about the trip – ultimately I realized I was trying to assign my feelings a more legitimate cause, but what it really was, at the end of the day, was that I was worried I wasn’t cool anymore (and I’m really truly not trying to get affirmation or approval right now, I just really want to talk about this). That there was something to be ashamed of because I’m putting myself out there, again and again and again, asking for your approval and your eyeballs.