Hi friends! 🍵
So: milestones. I mentioned in my last newsletter that I had two significant ones coming up. Be warned: this will be more personal, and less writing-focused, than the usual newsletter!
I find milestones stressful. I don’t like attaching outsize importance to things. I can’t totally articulate why, but it sometimes feels like daring the world to trip things up, or disappoint me. Oh, you think that’s gonna be great? Well, maybe it won’t be! In general, I do kinda adhere to the idea that happiness = expectations - reality. (Waitbutwhy has a thought-provoking article on this that I sometimes return to.)
On the craft front, I’ve also found that milestones can be dangerous, because you might obsess over them…even when you can’t really influence them. I love this post by Tobias Buckell on the difference between milestones and goals, and why you should spend more energy on the latter. In short, it helps to focus more on things you can actually control (like writing) instead of things you can’t (like winning awards, or selling your book).
He does, however, say that milestones ought to be celebrated. That’s something I struggle with. I once described it to a friend as, “It’s never a party in my brain.” I often feel fundamentally wired to downplay wins and simply move on to the next thing. If I’m to be completely honest, part of me thinks this is positive—it keeps me ambitious; I’m always on my toes, looking to the next thing. But as I’ve gotten older it’s troubled me too. I mean, I want to be able to say good job, self! without having a minor freakout or feeling like I’m jinxing myself. That should be normal, right?
I think I’ve gotten better at this, but to hold myself to it, I’d like to share some milestones with you.
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I turned 30 last week. It was a lovely day—I never have expectations for my birthday (by choice! see above!), but it was nice. Due to timezones, I started receiving greetings from friends in Manila the evening before. Day-of, I wrote for a few hours in the morning with my Boston quarantine writing crew. I saw friends from my school acapella group (if you’re curious, you can watch one of our songs here)—we gathered in a lounge, and shared some wine and surprise cupcakes my mom sent. A friend in my dorm, who is an excellent cook, made curry for me and another hallmate also celebrating his birthday. I closed out the day with a Zoom session with my family.
I sometimes see posts on Twitter where people feel anxious about turning thirty, because they feel the need to accomplish a lot by that age. Again, it’s that idea of a milestone. It’s easy to feel pressure, especially given the high visibility into others’ achievements that we get with social media. It’s hard not to compare yourself to others close to your age, or younger than you, and not think: what the hell have I been doing with my life? (Sometimes this morphs, dangerously, into why do I suck.)
I get it. Especially when it comes to achievements related to your art or craft. I mentioned my own struggles with this last December, and was surprised by how much it resonated with people.
Of course I dreamt about publishing a book in my twenties! Especially since I was lucky enough to attend Clarion straight out of undergrad, which introduced me to publishing—I found myself thinking, I should be able to do this. It frustrated me so much that I couldn’t. The years slipped by and I failed to grok the book form. If I measured the past decade against that dream, I’d be awash with grumpy feelings.
Luckily, I don’t feel that way. When I think clearly, I recognize that my life is much more than just my writing. And it is so much more productive to view age-milestones not through the lens of what haven’t I done yet, but instead by recognizing: damn, I’ve grown a lot!
The past decade was pretty bonkers. I started my 20’s moving from Manila to California, leaving behind everything I knew. I struggled with significant losses in my family. I nearly stopped writing, especially when I was about to start working full-time; a little workshop convinced me otherwise. I moved five times in seven years, learning the downside to having friends all over the globe: I am always missing someone, dammit. I braved a start-up, learned how to be a professional, and realized I enjoy product management.
To be honest, I still understand the part of me that thinks oh shit! I’m 30! How old! It’s the kid who grew up on middle grade books and anime/manga and JRPGs—like, the 19-year-old characters were the height of maturity in those! Someone over 25? Unheard of!
But then I passed those ages and realized, hey, I’m still here. In fact, I’m still a compelling character (lol). There’s another part of me now—wiser, more forgiving—that knows 30 isn’t old. (I’m sensitive to the fact that some of you, dear readers, are cringing at the very thought of 30 being old, and like—I’m sorry. I know, it’s ridiculous. I don’t really have a defense for it. It’s just a whole thing with my generation, I think?)
There’s so much more I want to do, and much more growth to be had; what better way to honor my twenties than to be proud of how they’ve shaped me?
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I’m writing this email on the eve of my graduation from Harvard Business School. It’ll be a Zoom celebration, and I won’t have my family physically around me. Like other 2020 grads, I won’t be wearing a cap and gown—but still.
When I’m wearing my Isa-Yap-the-writer hat, I don’t talk a ton about graduate school. Or business, or tech, or product management. These are all things that I’ve lived and breathed for the past several years but somehow, they seem to occupy an entirely different world than my writing. I know that’s actually not true, because nearly every writer I know has a day job, and several do in fact work in technology. It’s a shame because it would probably help if we all talked about our other careers more, and how stressful it is to balance writing with it—but I digress. Topic for another day.
Back in 2015, I was deciding between applying for an MFA in Creative Writing, or an MBA. They’re two very different degrees. I researched both and talked to friends who were enrolled in such programs. I decided based on two factors: (1) I was witnessing issues in my company/professional career where the value of an MBA was apparent; (2) MBAs are more time-bound in terms of students’ ages. MFAs have pretty young cohorts these days, but it seemed like the kind of thing I could go for later on, if I still wanted it.
The MBA was never a sure shot for me. I told myself I’d only attend if I got into one of the best schools; that way, I could justify the extreme cost. I first applied in 2016 and failed to receive a single interview (at least for MBAs, the interview stage basically indicates you’re 50/50 for acceptance). Crushed, I had to ask myself: do I really want this, or do I just think I do? Am I running away from something? Am I making a practical decision against my will? I needed to make sure my heart was in it if I was going to apply again.
Ultimately, I decided to give it one more try. I spent 2017 working on applications and keeping it together at my day job—and yes, I did sacrifice writing that year. But it worked out, and luckily I managed to recover my writing (story for another time!). In a few hours, I get to say that I graduated with an MBA from Harvard.
It’s a weird thing, being a Harvard student. For me it’s like a birthday-jinx…too much pressure, or whatever. It went against a lot of my instincts to ever mention it, but I realized trying to downplay it comes off as even worse flexing, usually. The way I’ve reconciled my complicated Harvard feelings is to recognize that it’s a privilege I’ve received, enabled by several other privileges. If it makes me feel uneasy in any way, then the best thing I can do is to use that privilege well; make something of it.
You may be wondering what I think, now that I’ve finished the two-year program. Whether the tradeoff was worth it. What it was like. I’ll keep it short by saying that more than anything, I feel grateful that I had the chance to come here. I met wonderful and inspiring people, I learned a ton, and I even got to develop my creativity and writing toolkit in interesting ways. Finishing is bittersweet. I’m going to miss my classmates, and I do genuinely love being a student. But I’m also looking forward to what’s next, in whatever form that will take.
If you’re also graduating: congratulations! What a strange time to be heading on to the next thing, huh? Good vibes for whatever’s next. I’m rooting for you. And to those not-graduating: hugs, regardless. 2020’s been so bizarre, so please do find things to celebrate, however big or small. 😌
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I mentioned two milestones in my last email, but actually, an unexpected one came up since then: my book now has a cover and a title! 😭 In my brain, I knew I had one coming since I signed the contract, but I don’t think it really hit me til I saw this.
The art is by Filipino-American artist Alexa Sharpe—you can see this illustration and more on her website.
I’ll talk more about the book in future posts, but in the meantime, you can preorder it here. 😊
Thanks for reading! I’ll see you in two weeks, where I’ll be talking about how the zero draft didn’t work for me. If you liked this, feel free to share it with others, or sign up if you haven’t yet. And if you have a writing-related question you’d like me to answer, leave a comment below.