some things I learned this year about love and work

+ sub $100 things that improve my quality of life

1. I still love writing on Substack. I was looking at this today and thinking: how fortunate am I?

   

   I know there are lots of bigger Substacks out there, but I feel so incredibly lucky to have 31020 of you hanging out in my little corner of the Internet. All my life the thing I spent my time doing (happily, for free) was reading and writing and analyzing relationships and feelings in my own unstructured way. And I never thought in a million years it could be a job. I still feel every day like I’m getting away with something.

2. Everyone has to figure out what works for them.

I still panic all the time about the precarity of my career. Is the book I’ve been working on for four years any good? Will I run out of things to write about tomorrow and have to shut down the Substack?

The hardest part of doing Substack as a business is, in my opinion, incentivizing paid subscriptions. Even though my total subscriber count has grown very steadily ever since I first started writing on Substack, the amount of money I make from subscriptions has plateaued. I think I don’t personally do a great job of being like “Okay, here’s the separate, different content you get for being a paid subscriber.” I also suspect some of it is subscription fatigue: most people don’t have the bandwidth or the budget to pay for 20 Substacks.

I know people do a lot of different things to make it work. For instance, Anne Kadet, one of my favorite Substackers, doesn’t paywall any content: she just asks people to pay for a subscription to support her work. I love her Substack, I’m so grateful it exists, and I will be a paid subscriber until I die.

I’m still trying to find a model that works for me. Which brings me to:

3. Everyone should be doing more experiments:

As you may have noticed, I’ve tried a lot of things this year. We did:

• four workshops

• many, many meetups in cities ranging from Sydney to Boston. I only attended two in person, but I was hopefully spiritually present at many more Bookbear Express meetups

• two rounds of matchmaking

• one accountability group

Thanks to Rishi for kicking it all off by doing the workshops with me. And thank you guys very much for being part of all of it! This feels like the year I went from a person writing into the void to a person who has met and hung out and befriended many people in this cool little ecosystem we inhabit together.

Every time I would post a Typeform this year I would literally be quaking in terror, like no one’s gonna sign up! No one’s going to want to come! But people signed up and came. I am aware they didn’t have to.

It’s so cool to me that not only do I get along incredibly well with you guys (I am friends with many people I met because of this blog!!) but you get along with each other. Which again brings me to:

4. For me, helping people find love is the most gratifying thing.

Platonic and romantic love, of course. The thing that makes me believe in Bookbear Express as a project more than anything else is all the people who’ve told me I had something to do (?????) with them meeting their partner or close friend. That’s crazy. I can’t explain how incredibly awesome that is.

It’s funny because I never really saw myself as a “community” person. Up until the past year or two, I’ve primarily hung out with people one on one, and identified as someone who felt quite awkward in groups. But it turns out that I just love love and really love people falling in love and group events really help that happen faster. I now identify as firmly pro-parties and pro-community events. You live and learn.

5. Work and love are both really important to me.

Even if I had infinite money I don’t think I would change anything about my life. (Okay that’s not true. I would buy more clothes. But I really love my life!) I think much of that is because I am so fulfilled by my work. Sometimes when my personal life feels quite chaotic I have less energy for writing and I always notice after a couple weeks that I’m really bothered by that—I’m happiest when I’m writing a lot. Writing gives me a sense of agency and freedom that I need and crave.

At the same time, my life could never be complete without friendship and romance. I’m always encouraging people to be more serious about relationships because—like, that’s what it’s about, that’s what life is about, and I think it’s such a shame that people don’t necessarily recognize that their friendships can absolutely be the backbone of their lives if they put enough into them. We don’t live in a culture that tells us we should be investing more into our friendships. But I really think it’s critical for our health and happiness.

5. It’s not about who’s right and who’s wrong, it’s about being ready to move forward

I used to get really hung up on this in conflicts—who wronged whom, who should reach out first, all of that. Then I had this revelation that it doesn’t matter. It doesn’t matter if my ex was more in the wrong or I was. It doesn’t matter if my friend was too sensitive or I was too callous. What matters is whether I want to continue the relationship and what kind of dialogue we’re able to have about our feelings. I’m the kind of person who still thinks about everyone I’ve ever been close to. But that doesn’t always mean I need them to all still be in my life. Understanding who I still want to be close to in the present moment is the thing that unlocks what I should do next.

6. We don’t decide who we fall in love with

It’s okay if it doesn’t make sense. Not everything needs to make sense. What matters is 1) Does this person love me back? and 2) Can we find a way to be kind and supportive to each other?

7. Writing 30,000 words in a month can feel really good

I wildly enjoyed my writing accountability group and am already excited for the next one. I hope some of you guys will join! I use this concept of “going under” and “coming up for air” when it comes to periods of intense creativity—sometimes I need to just dive in and write a thousand words every day. Other times I just need to read and walk around and not write very much for a couple of months. Coming up for air helps me be more comfortable in the water.

8. Your work persona can help a lot in your personal life

What’s helped me most in anxiety-inducing social situations, weirdly enough, is having an attitude of “I’m just showing up for my job.” Whenever I’m doing a meetup or a party or a workshop or a talk and feel myself panicking, I take a deep breath and tell myself that I’m just going to be “professional”—which to me means staying calm, saying whatever feels true in the moment, and being attentive to other people’s needs. It really helps me stop obsessing over my own neuroses and channel my most composed self. I’ve noticed that learning to do this in work situations helps me stay calm when I’m fighting with a loved one or freaking out in my own bedroom. It really seems to be a transferrable skill.

9. It’s possible to be in conflict with someone and not freeze up

For a long time, i.e. my whole life, anyone I cared about being mad at me would make me spin out. It didn’t matter if it was minor or major, it didn’t matter if I knew we would resolve it—I would freak out if I realized they were unhappy with me. It felt like I had fucked up and would be abandoned, even if intellectually I knew I would be totally okay. Over time, I trained myself to behave in a relaxed manner (no weird texts! Give the other person time to cool down!) but my internal experience was still tormented. This has been the first year where I’ve been able to be in conflict with someone and actually feel okay about it. I think it’s because I’ve just had more practice disagreeing with loved ones and experiencing rupture and repair. I no longer view conflict as a existential threat to a happy relationship.

10. Everything is about decreasing tension.

I did a podcast with my friend Jackson recently and he asked about the origins of Bookbear Express. I guess relatively few people know that I set out intending this to be a Substack about mindfulness. Turns out I find mindfulness impossible to unpack compellingly, but it still guides every aspect of my writing and my life. Five years ago I was tense and anxious pretty much all the time. These days, I’m able to be present for much more of my life. My external life got drastically better because my internal life did.

Relatively inexpensive things that I use all the time

This is not so much of a gift guide as a list of things that I use all the time and think everybody should probably own.

1. Hanes boys’ t-shirts.

The best white t-shirt I’ve ever owned. You can get a five-pack for $10. I own 10 of them and I get them in a L.