Some things I enjoyed this year:

1. Clarifying my edge. I got a lot weirder work-wise this year. My edge in investing has always been with what I call Moths at the idea-stage, which means I spend as much of my time as possible trying to understand the strangest people I know. Conversely, fundraising this past year meant a significant portion of my time was spent with normal people. I did not enjoy this nearly as much, but did learn a lot from it; I got better at telling my story, sales, and putting my foot down.

2. Coaching. The way I work with founders involves asking a lot of questions, connecting the dots, and reflecting them back at themselves. It’s honestly more like coaching than anything else. Through hundreds of conversations, I’ve developed a better sense for what questions to ask and at what time to ask them.

3. Being Tom’s wife. Marrying Tom was without a doubt one of the best decisions I’ve ever made. The united force we create together is something I’m in awe of and feel like I’m still getting to know. What stood out about our wedding was the warmth and genuine love in the air. It was a macro version of what Tom and I share. So much of my growth over the past year personally and professionally has been with the help of my husband. I am beyond lucky to have Tom.

4. Weekly rituals: walking to Arizmendi for pastries, post-mass brunch with friends on Sundays to discuss our weeks, occasionally hosting people over for parties.

5. Calling people and actually showing up to events. I’m still skeptical of events but there were enough occasions that something good came of them that I’ll give credit where it’s due. I’ve been fully converted on calling people vs texting.

6. Morning pages. I can always tell that some probably-not-great emotions are brewing when I have nothing to say to the page in the morning.

7. Crafts. I got into cyanotype, jewelry, and a bit of leatherwork this year. This next year is going to be about pottery, more jewelry, and finally getting good at sewing.

8. Depop, Poshmark, and Facebook Marketplace (the thrifting trifecta). I sold most of my closet this year and replaced it with better quality, more practical things that I now wear everyday. I finally accepted that I will always love technical wear.

9. Apples. I have put in the 10k hours of eating them and am an expert in all the varieties. The secret is to know what they should feel like when you squeeze them.

10. Rhododendrons. And other flowers that grew naturally where I grew up. We’ve had a lot of bouquets in our home this year and it’s made me a very happy girl.

11. Blue Lights and Landman (TV shows). Cop show and a western. Both have excellent acting and loads of drama, which is why I keep watching.

12. Sentimental Value and One Battle After Another (movies). Recency bias but yes both were as good as the reviews say. Sentimental Value will make the girls cry and One Battle After Another is just a really good romp, boy-friendly to boot.

13. Dijon, Kuomo, Jamilah Berry, Leif Vollebekk (musicians). All made it on my Spotify wrapped, all really excellent in their own way. This is my song of the year.

Thank you to Tom McCarthy for everything. His annual note can be found here.

Ever since getting married, most of my attention has been on my friends. Being fully loved long enough to trust the love is here to stay raises the question: what do you actually want to do, given you don’t need to prove yourself? I’ve long believed that my purpose is to make beautiful things and love my people dearly, but it took a sizable life chapter shift to help me actually reorient my days around that belief. I notice now how my motivation slumps immediately whenever I feel disconnected from either goal.

I suppose what I’m saying is that my ambition is no longer an ambient mystery to me. Instead it lives closer to my heart, directly tied to core beliefs I hold about the world. The kind of rumination that used to fuel the writing I do here feels far less necessary to ground my sense of self, partly because so many of the conversations I once had in my head now play out in far more interesting and unexpected ways with my friends.

The main commonality tying all my friends together is how incredibly individual we all are. None of us are pulling on precisely the same threads, yet we all share a way of going about the world that I can best describe as meticulous, curious, and deeply kind. Vocation is a topic we discuss often — the idea that each of us was designed to work on specific things in the world that we must first do the work to reveal to ourselves.

In many ways, this is the opposite of the Silicon Valley thinking that surrounds us — which sees humans as interchangeable workers rewarded most highly for extremely uneven development. Precocious spikiness is what gets you noticed in the world of startups, so it’s no surprise how many competitive people become razor-sharp, functionally turning themselves into tools tailor-designed to solve specific problems.

But that’s obviously no way to live? Or at least, it’s definitely no way to live long-term. All of my favorite people contain all manner of superfluous, silly, and soft parts that make them so much more than a tool. One of the greatest joys of my life is being able to behold those parts and watch as their confidence in their own uniqueness grows. To say that I am consistently inspired by my friends would be a gross understatement — more accurate is that I am constantly being reminded how lucky I am to be shaped by the wonderful people around me.

Links

• Will raising venture sell my soul? (essay)
  I’m trying out a career advice column :)

• Direct and indirect by Josh of Greenlea Lane (essay)
  A great example of rigorous writing about a qualitative subject. This oral history of the venture capital greats is another good example.

• Rewriting the California Ideology by Nadia Asparouhova (essay)
  An examination of the ideologies that underpinned early Silicon Valley and their evolution over time. Nadia’s new book Antimemetics is also excellent!

• Marriage and Philosophy in George Eliot and Søren Kierkegaard (essay)
  Close study of the meaning of marriage as seen by Eliot and Kierkegaard.

• Crossing the cringe minefield by Cate Hall (essay)
  Gateway drug to going down the Jungian shadow work rabbit hole (A Little Book on the Human Shadow is good if you want more).

• The tensions of staying too long by Haley Nahman (essay)

  “From a practical distance, achieving public success scanned to me as belonging, which is ironic, because what I’m talking about is actually separation: an elevation of my own standing above the crowd. This must be one of the most common misapprehensions about fame, while somehow also being the most cliché.”

• Lorde in conversation with Martine Syms (interview)
  I love listening to women who are shamelessly themselves speak candidly. Also good in this way: this interview with Maggie Rogers and this profile of Miuccia Prada.

• Epic Systems (MyChart) by Acquired (podcast)

  Both boring and impressive. Very aspirational for founders who want to retain control of their business and sustain a maker (not manager) schedule.

• The Empathy Exams by Leslie Jamison (book)

  Fascinating collection of essays on how our empathy thwarts us.

• Swag by Justin Bieber (album)
  I listened to this constantly on our honeymoon and felt like it was made for me.

Parting thought

“She was explaining to me that I had won nothing, that in the world there is nothing to win, that her life was full of varied and foolish adventures as much as mine, and that time simply slipped away without any meaning, and it was good just to see each other every so often to hear the mad sound of the brain of one echo in the mad sound of the brain of the other.”

— The Story of a New Name by Elena Ferrante

Nothing has caused a bigger shift in how I feel about my friendships than marriage. Planning a wedding is a massive forcing function to both clarify who your true friends are and immediately ask them to do big things for you (like fly to the other side of the world). I realize now that asking for big things was exactly what I needed to do to gain a great deal more confidence in the community of wonderful people who love me.

Friendship has historically been a big area of anxiety for me, mostly because a) I didn’t have many authentic friendships growing up, b) I’m in an industry where the term “friend” has no meaning at all, and c) it took me a long time to learn the difference between a few good chats with someone (excitable, often unearned intimacy) and true friendship (requires effort, not without friction). I’ve consistently shied away testing the depth of my relationships for fear of judgment or rejection.

It’s strange to realize how my past confusion about relationships directly benefited my career — motivating me to mine my brain for thoughts to share with strangers and maintain loose ties with powerful people for no real reason other than the attention. What I craved at the time was a group of people who loved me, but it took me many years to realize this, much less find it. I’m very lucky to have this now, and know it.

We’re getting married in two days (part one of two ceremonies). I’ve been listening to this song on repeat and feeling every emotion under the sun. I’m incredibly excited and also totally terrified. It scares me to my core to lean on anyone else for fear of their growing to resent me for it over time, yet I continue to lean all the same. Tom was the first person to show me that this was possible. My friends followed shortly after. A recurring thought: I hope I never take this stable, rooted sort of love for granted.

Links

• Interview with Hunter Walk
  My friend Hunter asked me a few questions and I answered :)

• Bill Gates by Walter Isaacson (interview)
  Honestly just impressed by Bill’s funky and fun rebrand.

• Neil Mehta profile (profile)
  The ever-elusive man behind Greenoaks — he strikes me as the epitome of the “finance bro with a dash of Engelbart” archetype.

• Building a seed stage venture firm by Roger Ehrenberg (guide)
  The best high-level firm-building blueprint I’ve come across.

• Would you rather have married young? by Lillian Fishman (essay)
  Predictably, I liked this a lot. It prompted me to reread Sally Rooney’s third book, which stands up! Good exploration of the choices young people face in modern relationships today.

• Critics, fans, and subjects with Tavi Gevinson by Rayne Fisher-Quann (interview)
  Fav tid bit is this quote by Tina Fey: “Authenticity is dangerous and expensive.” Also in this corner of the internet: Lena Dunham has a Substack now.

• The Weight of Glory by C.S. Lewis (essay)
  An antidote to competitive striving culture.

• Sandy Liang’s Normal People Ireland guide (guide)
  As a part-time Ireland travel guide right now, I highly rec this guide for the girls.

• Saturday Night by Jason Reitman (film)
  Frenetic and funny, puts you in the room with them. More interesting backstory on the SNL audition room here.

• 2000 by Joey Bada$$ (album)
  This album feels like it transports you to another space and time.

Parting thought

“How to not be a perfectionist:
People are vivid
and small
and don’t live
very long”

— Molly Brodak

The past few months I’ve felt a gradual yet marked shift inward. Building the “right” life for myself post-college was something I experienced a lot of anxiety and despair about that only recently started quieting down, three years later. My life today feels decently settled and deliberately chosen in all the areas that matter — revealing to me the painstaking truth that I’m the only person who can make sure I actually enjoy it.

If you asked, I’d say that right now I’m focused on living well and loving my people dearly. I also want to do good work by becoming hyper-discerning about when to push myself and when to rest. I’ve noticed that feeling in flow and like I’m being led by something greater seems to be a special byproduct of getting this balance right. To sum up this pursuit, I’d say it feels a lot like chasing light in a metaphorical garden. What this intention looks like for me:

1. Revisiting all my childhood hobbies (and taking classes regularly with friends)

2. Creating the colorful nest (aka my own apartment) I dreamed of when I was a girl

3. Making Friday a weekend day and Saturday a workday (a self-employed pleasure)

4. Slowly constructing a closet of carefully collected and deeply researched pieces

5. Having a walking commute and taking my walks in the sun extremely seriously

Links

• Larva learnings (essay)
  "At the stage I invest, I’m selling my viewpoint to founders in the form of a small check, and I’ve found that the weirder that viewpoint is, the more interesting I am to the type of outlier people I want to back.”

• Casual Viewing by Will Tavlin (essay)
  A history of Netflix and the Netflixification of the entertainment industry.

• The Carrier Bag Theory of Fiction by Ursula K Le Guin (essay)
  Fascinating “retelling of the story of human origin by redefining technology as a cultural carrier bag.”

• Principles by Nabeel Qureshi (list)
  I emphatically nodded my way through my read of this list. His point on being specific hit especially hard right now — granularity is gorgeous.

• Kim Kardashian, mogul, tells us her money story (profile)
  A peek inside the pocketbook of an impressively commercial woman.

• Pregnant With One Child and 295,233 Words by Molly Young (essay)
  One woman’s account of becoming wildly creatively productive while pregnant. Motherload and Splinters were two other recent accounts of early motherhood.

• Michelle & Trae Stephens interview (podcast)
  I adore honest interviews with couples who each have equally interesting careers. Nadia & Delian Asparouhov’s was also great and I’m actively on the hunt for more.

• Bon Iver Glastonbury 2009 full set (video)
  I’ve listened to this too many times to count, it just never gets old.

• Beauty Sleep by AB001 (song)
  A song that sums up the feeling of being able to lie and rest peacefully.

• House by Nobuhiko Obayashi (film)
  If you’ve already exhausted the Lynch catalog, I offer this surrealist masterpiece for consideration (and Rubber, for that matter).

Parting thought

You do not have to be good.
You do not have to walk on your knees
for a hundred miles through the desert repenting.
You only have to let the soft animal of your body
love what it loves…

— “Wild Geese” by Mary Oliver

I got engaged recently :) and keep getting asked the question of how I knew he was the one. My answer is simple: he saw me fully from the beginning, made me feel deeply safe, our dynamic felt like play, and I truly believe he’s the best person I know.

Love has changed me a lot. I used to be an incessant ruminator, convinced I could create the outcomes I wanted if I just plotted and planned the world (and more accurately, myself) into submission. The past few years have been a process of learning to trust and nesting in myself. Lesson #1 was learned over our first dinner. I’d never felt so ambiently accepted before — a special sort of admiration without possessiveness. That acceptance then morphed into mutual adoration, followed shortly thereafter by complete love. He showed me that he didn’t want to own me by helping me see all the ways I was the one trapping myself. All of our “steps forward” didn’t feel like steps at all — we were already there, just now with a label applied.

I’m afraid I can’t offer much concrete advice on love. Marry your best friend? Translate your mind to the internet and always answer thoughtful DMs? Maybe just this: becoming the most specific, shamelessly you version of yourself by being around someone else and their experiencing the same is something well-worth waiting for.

Links

• Powerhouse by James Andrew Miller (book)
  If you’re like me and come at this topic more from the angle of being curious about CAA’s early culture, I think this read is better than the more popular Michael Ovitz book. The inverse of this industry domination story is perhaps Selling Sexy by Fernandez and Sherman (on the rise and fall of Victoria’s Secret).

• Didion and Babitz by Lili Anolik (book)
  I’ve been reading way more books than blogs lately and it’s largely because there are character study stories (like this one) that would be done a great disservice by summarization.

• Impro by Keith Johnstone (book)
  An incredibly dense book by the father of the "yes and” mindset (review here).

• The Artist’s Way by Julia Cameron (book)
  Part therapy and part creative coach — this book is just as good as everyone says.

• Liquid vs. illiquid careers by vaishnav92 (essay)
  I always thought it was strange to let anyone else, much less a job, dictate what skills I should be focused on developing. Nowadays I frame it to myself as: for me to get better at any skill I’m not interested in, doing so needs to in turn unlock my ability to focus more of my time on the things I actually do want to get better at.

• How feminism ends by Ginevra Davis (essay)
  My favorite part of this is the beginning’s vivid description of what it can feel like to occupy a female body.

• Rejection isn’t personal by Heather Havrilesky (essay)
  A very good pep talk in written form.

• Birthday letters by Evana (essay)
  I loved how this piece was structured — the wisdom of a crowd of writer’s words.

• Siqi Chen on pitching (video)
  Siqi is a master at this and gives great explanations of many of the more counterintuitive fundraising social dynamics and dances.

• When You’re Near by Quinn Oulton (song)
  This song feels like a hug!

• The Moosewood and Tassajara Cookbooks (recipes)
  I’ve been getting back into baking and these two cookbooks are my bibles (and a clear sign I was raised by total hippies lol). No one ever suspects either are veggie!

Parting thought

What can I do but be a cat? Perfectly and unselfconsciously a cat. Thank god for the miracles showered on me.

— “Are you Somebody?” by Nuala O'Faolain