Okay, I wrote a book.

Is this thing on?

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I finished writing my book.

Well, that might be a bit of a stretch, but I turned in my manuscript to my editor, and man, the second I hit send, it felt like a gorilla hopped off my back. Spend enough time in a constant state of stress and you begin to normalize it. You forget about it, you know. “Stress” is just life. And then the stress is gone, and the absence of that stress is euphoric.

Today is the first day I’ve had little-to-no stress in at least a year. I want to tell you about the circumstances in which I finally grinded out the final stretch of this book (which, really, meant writing the entire thing in about two weeks), but first, I’d like to give you a brief recap of the last year of my life.

Let’s turn the clock back to July 2024. A few publishers had expressed interest in me writing a book, and considering I’d spent the previous, I don’t know, three years, just writing incessantly, that seemed like an optimal next step. Lucky for me, one of my friends, Nat, had recently signed his own book deal. He introduced me to his agent, David, who I promptly signed with. David is the absolute man. Then I started thinking, “What book do I want to write?” There was so many ideas percolating in my brain.

Where to begin?

The idea that I kept coming back to was that so many young people have this overbearing fear of “not making the most of their potential,” or “wasting their lives.” And that fear manifests itself in so many ways: relationship insecurities, clinging to certain jobs out of desperation when they have no clue what they actually want to do, and wrestling with the duality of pursuing a successful career while still satiating their desire for adventure, fun, and novelty in their youth.

Being a 20-something today is fucking exhausting, man.

As a 27-year-old who had wrestled with, and, in some instances, was still wrestling with, these same questions, I felt well-primed to write my way through it. Part of my motivation was to (hopefully) help someone else out, part of it was working through my own anxieties about my own life. One publisher, Portfolio (a Penguin Random House imprint) happened to like my proposal (which is basically a small book within itself), so they decided to sign me. The day I signed that contract vindicated the 500,000+ words I’d written over the previous three years.

I almost cried. I didn’t cry, but, like, I could have pretty easily coerced myself into crying. I was ecstatic. And then I had a problem. I was wrestling with my own career anxieties: I thought I had made the wrong career choice in business school, and I thought it was too late to pivot, and I freaked out. As someone who spent a significant amount of time writing, I thought the thing I wanted to do was be a writer.

“HA! WHAT AN IDIOT!”

No, it turns out that simply enjoying blogging in my free-time does not mean that I wanted to work in media. And I wanted out. Like I really, really, wanted out. And I felt like a total fraud; I’d just signed a book deal in which I was supposed to give advice to people like 3 years younger than me on navigating their own uncertainties, and here I was, with my mind in a pretzel, as I had no idea what I was doing. Okay, sweet, now let’s inject a healthy dose of a fresh breakup a few weeks after signing the book deal as you’re speedrunning a career-induced existential crisis. Have fun writing your book!

I ran into that ex-girlfriend today, btw. She was happy for me for finishing the book.

Okay, back to August 2024. Book deal. Job freak out. Relationship implosion. Cool. One step at a time. We should probably figure out what we want to do for work, then, at some point, write a book. Given that I’d spent most of the last few years writing about businesses and investing, and I had a pretty sizable following on my own newsletter, venture capital was the next logical step for me career. It’s a somewhat typical career pivot for MBA students, but my issue was that I was trying to make this pivot three months after graduation, with zero venture capital internships or experience on my resume. I did, however, have lots of Twitter friends, many of whom happened to be VCs. So I pinged, I don’t know, like 20 people? And I ended up joining a fund part-time while I was still working at Robinhood.

Ever try writing a book while you’re working two jobs? Not going to happen.

I decided, over Thanksgiving, that this job probably wasn’t the best fit for me, and I went back to the drawing board. The next day, I saw that Slow Ventures was hiring, I applied to work for them in New York, and, in an ironic twist, I moved out to San Francisco to work for them two months later. Great. I still hadn’t written more than 2,000 (sloppy) words for my book. And starting a new job is stressful! I didn’t know what I was doing. But I had the job. Now, back to writing a book.

I tried to write after work, and before work, but that’s virtually impossible. Cool. How am I supposed to write a book? Well, if I can’t do it after work and before work, I guess it has to be a weekend project.

So, from Friday after work to Sunday evening, I would just write. It was the only way I could get 5+ hours of uninterrupted time. The benefit of moving from New York, which is just dopamine in civilization form, to San Francisco, where a “party” is seven dudes with a bunch of AI coding assistants pulled up on their monitors, is that the opportunity cost of spending your weekend writing a book drops dramatically. So I wrote, and wrote, and wrote.

But I didn’t write enough! I probably wrote 20,000 words of mixed quality in San Francisco, and then it was back to New York for the summer. The pros of being back in New York for the summer: my friends are here, the girls are prettier, the city is more fun, I’m closer to home, and I actually have a social life.

The cons? I still had to, you know, write a book.

I was supposed to go to Ibiza in mid-June. I panic-cancelled my trip, booked a 12-night stay in the CitizenM hotel in downtown Manhattan, and figured I would just lock myself in there until the book was done. And that’s exactly what I did.

The blank page is so intimidating. It never intimidated me while writing a blog. What’s 1,500 words? But a book? Those chapters are 5,000 words each, and they all have to stack, and flow, and scaffold around each other. I have this outline, which, at this point, is basically worthless, because no good book has ever followed the bullet point proposal that its author used to sell the book itself. Those guidelines wouldn’t save me.

So the blank page stared at me. “Fuck you, write something.”

And I started writing. And I wrote for, I don’t know, six hours. I read what I wrote. It made no sense. I hated it. I wanted to delete it. I grabbed a coffee. Went for a run. Back to the hotel. It’s 3 PM now. Suddenly, a burst of insight. The writing sucks, sure, but the idea, buried deep within that writing, is fantastic. So, like a sculptor chipping away at marble, I refined this mass of words in front of me. Then an anecdote from four years ago hit me. “That’s the perfect introduction,” and an analogy comes out of nowhere. And, oh, yes, that conversation with my friend from a few weeks ago really ties this chapter together. And then, I revised that. And I revised it again. And, at 11:47 PM, I hadn’t eaten anything in 12 hours, but I had a pretty good chapter.

And then I woke up the next morning, and the blank page stared at me. “Fuck you, write something.” And I did it again. And again. And I wrote three chapters, and I realized, these three chapters were so much better than the eight chapters I had written in San Francisco. I was now disgusted by the very work I was so proud of just weeks earlier. So I started revising those chapters too. I looked at the calendar: running out of time. Back to work in just a few days. I’m about to have to leave this hotel. Was the book done? No.

I flew home to see my grandparents. I should have been present, my grandparents are old. I rushed through my meals to get back to the book. “Why can’t I get these paragraphs to flow write?” I asked myself.

I drove from Georgia to my mom’s in Birmingham. She said I didn’t look too well. No shit, I lost 10 pounds in the last week. I probably should have been eating more.

My brain was a hand grenade waiting to explode. My other grandparents came over for dinner. I rushed through dinner. They were looking at baby pictures. Sick, I was cute when I was three. Back to the book.

And then I finished the book. Chapter 14, turned in. 56,000 words in 14 days. Not bad. I think I teared up a bit. That was a lot. But I think I wrote a very good book. Sure there’s still edits, a revision or two, and more work to be done. But what I turned in is, in my opinion, better than anything I’ve written on here, anyway. I don’t know how the hell I finished it, but I did. And I like it. If my goal was to write the most useful book possible for 23-year-old Jack, I think I succeeded.

God, the blank page is intimidating. But 56,000 words later, Jack: 1. Blank page: 0.

Anyway, my book comes out in a year, and I can’t wait for all of you to read it. In the meantime, I guess this means I’m blogging again. Much to come, stay tuned.

- Jack

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